yes, you are awkward … and yes, it’s okay

by Alison Green on February 15, 2018

I love awkwardness — my own, other people’s, all of it. There’s little I enjoy more than dissecting a mortifying moment with a close friend (“What do you think they were thinking when that came out of my mouth?!” “They must have been so baffled by why you said that!”) or even speculating on hypothetical mortifying moments that haven’t even happened but could (a friend and I have spent entire meals laughing about the prospect of embarrassing things that haven’t even happened to us yet). It’s probably no coincidence that I write a blog that frequently trafficks in the embarrassing situations of others (like accidentally hugging your CEO in the office elevator, or spontaneously biting a coworker).

So I was beside myself with excitement when I found out that Melissa Dahl, the editor of New York magazine’s Science of Us, was writing a book about awkwardness — Cringeworthy: A Theory of Awkwardness. I recently got ahold of an advance copy and it is AMAZING, and she was nice enough to give me a copy to give away here (more on that in a minute).

Cringeworthy delves into when and why we feel awkward, and how we can move past it. You’ll learn about why it’s awkward to mix two groups of friends, where secondhand embarrassment comes from, and how to fight off a cringe attack — and there’s a whole chapter on awkwardness at work! (I’m interviewed in that chapter, and it’s probably my favorite interview ever.)

Melissa writes with candor and humor about her own experiences of awkwardness — and she seriously sacrifices for her readers by intentionally putting herself in awkward situations so that she can explore them in the book. She reads her teenage diaries live on stage, she does improv, she tries out a Tinder-like app for friendships, she makes herself network, and she has a hilarious account of her session with a professional cuddler (which she, quite understandably, sprints out of).

I love this piece from the intro and think it sums up the entire credo of the book: “The things that make you cringe are usually the things worth sharing, because they can help others feel less alone. … It’s an understandable reaction to flee the situation that makes you cringe, but what if you could teach yourself to tolerate it? You could, maybe, learn to use the empathy as a portal to compassion, for other people and for yourself. Looked at in a certain light, cringing becomes a worthwhile feeling, an emotion worth exploring, not avoiding. Little humiliations can bring people together, if we let them. The ridiculous in me honors the ridiculous in you.”

This book is the book I always wanted to read! I want you to read it too.

To enter to win a free copy: Leave a comment describing the most awkward situation you’ve ever experienced or witnessed at work. I’ll pick the the winner at random (or rather, a handy WordPress random selector plug-in will). All entries must be posted in the comments on this post by Friday, February 16, at 11:59 p.m. EST. To win, you must fill out the email address section of the comment form so I have a way of contacting you in the event you’re the winner.

And if you don’t win this giveaway, I hope you will buy yourself a copy. If you like this blog, you will like this book.

* I make a commission if you use these links.

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{ 1,261 comments }

{ 1,261 comments… read them below }

    1. Ask a Manager* Post author

      Also, a reminder that entries need to include your email address in the email section of the comment form if you want to be able to win (otherwise I won’t be able to contact you to tell you that you did!). If you forgot, you can leave a reply to your original comment that includes it. (As long as you put it in the email section and not the comment itself, only I can see it.)

      1. romana*

        I was working with a male coworker and he’d pulled two foam spacers off a motherboard. When I was cleaning up the floor around my desk (I was kneeling) I looked up at him and said “Do you want these two soft squishy things?” I was not holding the spacers – still not sure what they’re really called.

        Same job, different incident: I’d decided the elevator was a good place to adjust my bra. The doors opened before I was finished. My boss was standing on the other side. He forgot where he was going.

        Same job; I was finishing up an install for a professor and I went to leave but suddenly couldn’t work the door handle. He came up behind me and politely showed me how it worked, as I was leaving I tripped over two plastic chemical buckets that were in the hallway.

        I still work there, believe it or not.

      2. Marti G*

        I wore dress pants and a blouse with a cardigan so I would feel comfortable and professional for a presentation. The awkward time came after when I removed the cardigan. I had walked to my desk to wind down and another manager came over to tell me how well I did. He also stated that I would make a great representative for the company and department. I was flattered and thanked him. I went to the rest room to freshen up and realized that the shell I wore underneath the blouse had created a static cling, and completely stuck to my body! I ran to my desk to put the sweater back on and still do not know what he actually saw. Awkward and a learning lesson I will never forget!

        1. Worked for Scrooge*

          Thanks for hosting this contest!

          The most awkward work situation I’ve had is a very odd company owner giving all the staff a Christmas gift of a roll of pennies. This was over 10 years ago and I still laugh wondering what the heck he was thinking.

          The awkward part was watching other Co-workers react. None of us knew what to do.

    3. Cajun2core*

      IMHO, the “duck club” letter writer should automatically win and get a copy of this book. Heck, her story should be in the book!

    4. spaceygrl*

      I meant to write this the other day when there was a question about clothing malfunctions or something like that…. I was about 25 and in a meeting with two very senior people: my boss, the VP and the CEO of the company. My boss and I were sitting in chairs in the CEO’s office facing his desk. I was explaining something and didn’t really notice, until later, that the CEO was hunched over his desk staring down at the spreadsheet I had prepared. My boss started talking and looked at me and his eyes grew wide and he looked down and then back up and kept talking. I was like “that was weird” and so I looked down and my v-neck shirt, which would normally be completely appropriate had gotten stuck on my fuzzy bra and a whole boob was sticking out of my shirt. Luckily, I was wearing a sweater I could pull around without having to adjust my shirt. That made me realize why the CEO wasn’t looking at me. I never wore the velvet bra to work again.

      3. TeacherOffTopic*

        I just Googled velvet bras. I had no idea they existed, and I’ve had boobs for almost half my life now!

    1. Snark*

      Sorry, got excited there. So, my most awkward work-related moment occurred when I was working alone, late at night, in my lab in grad school. I was very focused on my work, bent over a piece of equipment I was trying to fix, and I felt a hand land on my on my shoulder. I was dating a labmate of mine at the time, and she had a habit of giving me little pats and squeezes as we moved around the small space during the day. So I said, “hey, sweetie pie,” gave the hand a smooch, and realized that it was male and hairy.

      It was awkward with my advisor there for a bit.

        1. Snark*

          I guess he was just trying not to startle me while I worked with his expensive lab thingy, but….yeah, regrets were had by all.

          1. Hey Nonnie*

            I dunno about you, but an unexpected shoulder squeeze while working alone (or thinking I am) would achieve the exact opposite effect.

            I actually don’t startle easily — I have good hearing when it’s quiet. But I also have intense focus when concentrating, which tunes everything else out. If you DO startle me, you bloody well better duck, because there WILL be flailing and anything in my hands will probably smack your face.

        1. Specialk9*

          I dunno, I feel like that’s what you get for touching coworkers. It’s not exactly normal to just grab someone’s shoulder.

      3. bb-great*

        NOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO (by which I mean YESSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS this story is AMAZING)

      5. ggg*

        This is good.

        My advisor was known for putting his foot in it, especially with female students. I will only tell my own stories:
        When I told him I was getting married, he said, “I think I should probably hug you. Should I?”

        Also when I finally graduated he said, “Well, we never thought we’d get here, did we?”

    3. Danger: Gumption Ahead*

      Back when I worked in private industry I handed my coat to the CEO as I walked into the Christmas party. There were 3 doors, 2 of which had coatroom clerks taking coats and one of which has upper management shaking hands. I had no idea what the CEO or the CFO looked like, so I walked through the upper management door and handed over my coat. Everyone had a laugh and it ended fine, but I was teased for at least a year after that

  3. Emi.*

    Well, I once had to listen to a coworker tell me about how much he and his friends wanted to watch Romeo+Juliet as teenagers, so they could see Kate Winslet shirtless. So that was pretty awkward.

  4. MuseumChick*

    Most awkward situation at work: When, while alone in the museum I worked at the time, a homeless man with mental health issues decided the day was to hot for clothing and processed to remove said clothing in the middle of our parking lot just in time for a visitor with his young daughter in tow to see.

  5. NYC Redhead*

    I work with philanthropists, and I was trying to say that a well-established nonprofit in our city was known for doing good but not pushy outreach, and I said, “XXX always touches their donors appropriately.”

    1. CoveredInBees*

      I worked at a nonprofit for a CEO who was not careful about talking about “touching” donors as in being in contact with them about our work and their interests. She also repeatedly talked about not being dressed when what she meant was “dressed up”. I was on a call with her and a prospective funder when she mentioned that she and I weren’t dressed. I jumped in to clarify she was referring to casual Fridays but I’m pretty sure I could hear the poor guy blushing.

      The funniest was when an attorney (thankfully, not me!) said, “Thanks, I love you too.” to a judge. He was distracted and said it in a way like he was ending a phone call with a loved one. The funniest part was that it took the judge a few beats to notice. I am certain that there was nothing going on between the two of them but they were very careful after that.

      1. Higher Ed Database Dork*

        My old boss was really bad about saying “touching the students” – we were a para-IT helpdesk at a university and it drove me nuts!

        Also the concept of “nudging” is huge right now in higher ed so I keep hearing people use “nudge” and “touch” interchangeably and it’s just always bad.

      2. chocoholic*

        I live in near-constant fear of telling an interview or some work contact that I love them. It is how I end most phone conversations with my husband.

        1. the gold digger*

          I have never said, “I love you” to my boss, but in heated discussions, I have, more than once, yelled, to my boss, who does not have the same name as my husband, “[Husband’s name], you are driving me crazy!”

          And he has called me by his wife’s name by mistake.

          1. Anonymoose*

            Ha!

            I have called a few (!!) bosses ‘Mom’ when trying to explain something while I’m frustrated.

            Habits – they kill us, sometimes, don’t they??

        2. Wombats for All*

          That happened with one of my new bosses. When I said um in response he had an “Oh Crap not again” reaction. Then he told me to never tell his wife as she’s convinced he says it to everyone else more often than to her.

          As an old mentor of mine used to say there are worse things to say than I love you.

        3. Princess Consuela Banana Hammock*

          My coworker used to do this often, especially at the end of the day or when she was distracted. It was usually after she’d finished talking to her fiance, and I always felt fremdscham for/with her.

      3. DG*

        Oh man, I’ve done the “I love you” at the end of a call with a co-worker before. Luckily, it was someone I was friends with outside of work, but I did laugh and turn bright red after it happened.

        1. Anne of Green Gables*

          My boss has done that to me more than once. I don’t think he realized it and I never said anything. I’ve heard him on the phone with his wife and know’s it’s the ending to the conversations with her. I laugh on the inside, though.

      4. Golden Lioness*

        I did this to my boss. It was my day off and he needed to contact me about an emergency at work. Before I hung up I said “see you tomorrow, I love you!”

        he was a cool guy, and teased me mercilessly about it.

      5. mrs__peel*

        My job involves participating in legal hearings via telephone. Although I haven’t said that (yet!) to a judge, I have heard all kinds of accidental/ inappropriate/ hilarious things on the phone during those.

        One of the doctors I work with has a talking parrot, who loudly announced “HI, BIG BIRDIE!” to a judge when she was on speakerphone for a hearing.

      6. PhyllisB*

        Bees, this is not an awkward work story, but talking about your CEO saying that she wasn’t dressed made me think of my mother. She says three things that crack me up. First one: “I couldn’t answer the door, I don’t have my face on!!” (No make-up.) “I went running outside to catch the garbage truck and realized I was standing there with just my feet on!!” (Barefooted.) ” I can’t go yet, my hair’s all over my head!!” (A big mess.) My sister and I always tease her mercilessly about these sayings, but I’ve found myself saying them from time to time.

        1. Daisy Avalin*

          My family (dad’s side) has always used ‘feet or ‘feets” to refer to shoes or socks, i.e. “We’re leaving in 5 minutes, go get your feet on!” My daughter argues with me now when I say it, because “I’ve already got my feet on, can’t you see?”, but she does find her socks/shoes to put on.

    2. TheAssistant*

      I worked for a fundraising director who encouraged all of the fundraisers to “love up on the donors”. She said it constantly. “Can’t ever love up on them too much!” “Have we done enough loving up?”

      She had this folksy charm that was disarming, even to a person (me) who is normally immune to that, so it was more funny than awkward. But I always hoped that nobody else slipped in saying that to an Actual Donor.

      1. Ruffingit*

        I have a boss now who says we’re going to “love on” our clients. Dude, you’re going to have to pay me A LOT more for that! ;)

    3. Elemeno P.*

      My former boss was so excited about an email he got to send once. He had to send an update about the teamwork on a new building that was going up. He wrote, “The erection is massive, and the whole team is trying to finish it off.”

      He knew EXACTLY what he was writing and it was hilarious.

    4. Jadelyn*

      I mean, if the alternative is touching your donors inappropriately, maybe touching your donors appropriately is actually a good selling point?

  6. Amber Rose*

    My boss was treating a supplier and ended up pinching his nipple because she thought it was funny to see him blush.

    That was so awkward I got second-hand embarrassment just listening to the story (it happened before I started here).

    1. Amber Rose*

      As for personal experience, how about the discussion of which Christmas tree ornament looked more like an… object of an adult nature? When we were decorating the office last year. Actually I’ve experienced more uncomfortable conversations but I don’t know how to explain them without moving into language that probably won’t make it through the filters.

      2. Amber Rose*

        I mean yeah, sort of. You have to understand that she’s been working with this guy for over a decade and they are relatively close, and they were drinking at the time. It was still crossing the line, but it was one of those crossings that is shrugged off as long as it doesn’t happen again.

  7. Marillenbaum*

    When I worked in college admissions, it was probably the time that I read an application essay about how the student in question had laughter-based incontinence, and how she was grateful for it because it meant she had so much to laugh about. Rule of thumb: keep bodily fluids out of your college applications (see also: the student who wrote their essay about contracting herpes).

    1. GetYaGritHeeere*

      I actually cringed reading that. The second hand embarrassment I’m feeling for both of them is so very strong.

    2. Todd Chrisley Knows Best*

      I’m really curious to know if they made it in or not. I’m assuming not, but I’m curious all the same.

    3. Competent Commenter*

      I don’t know, to play devil’s advocate, I feel like that student was showing that she had a medical condition she couldn’t control, and that she’d made peace with it in a graceful way at a very young age. How many people can say that? I agree I wouldn’t have recommended she pick this subject, and maybe the essay was written badly, but the topic itself seems like it has some strengths. If she’d been describing her hemophilia and how she coped with it, that would have been fine, right?

      1. Anonymoose*

        I agree (the first essay). Especially if she could tie it into what she wanted to study, I think it could be an excellent essay topic. Not all of our challenges are going to be pretty, I think holding that against her is actually small minded.

        Now, the second story…ya.

      2. Ani are you okay*

        If you are going to ask every student to describe a struggle they’ve had to overcome, I guess you will get ridiculous stories from the kids who have relatively easy lives.

  8. Mr. Programmer*

    I used to work at an American division of a Japanese company (this is relevant). I was able to get the job, partially because I studied Japanese at school, so even though it had lapsed some, I understood some of what was going on.
    One of the Japanese members of my team was on a conference call with Japan, which went well until the end. As he was hanging up, he was saying goodbye to people and when he should have said “Sayonara, Oka-san”, he ended up saying “Sayonara Okaa-san” (very minor intonation difference, but enough). Those of us who understood Japanese just stopped and stared at him as he turned bright red. Everyone else around just kinda looked around, asking what they missed.
    What he meant to say was “Goodbye Mr. Oka”. What came out was “Goodbye, mother”.

    1. EddieSherbert*

      That is extremely unfortunate… hahahaha. I’m dying from the second-hand awkward of these stories!!

    2. Amber Rose*

      Ahaha, that reminds me of an article from my favorite author who recounted the time he was trying to give an inspiring speech to his Japanese associates and mixed up the word ninjin with ningen.

      In other words, he told the room that they were all carrots, instead of people.

      2. Cherith Ponsonby*

        It’s particularly funny / confusing because “nin” and “jin” in context can both mean “person”!

        I studied Japanese intensively at primary school (long story) and when I was in first grade one of my language teachers used to tease me by calling me silly things in Japanese, and I’d pretend to get mad and deny it. So this one morning I met him in the corridor on the way to assembly and he said “Ohayo, ringo-chan” (“good morning, apple”) and I said I wasn’t an apple, and he apologised and said I was a ningen. And my Japanese vocabulary wasn’t really that big at the time but I was pretty sure he’d called me a carrot, so I loudly and indignantly replied “ningen ja nai desu” – “I’m not a person!”

        Some years later a different teacher was going over slang terms for one’s parents, and told us that while otousan and okaasan did indeed mean father and mother, they were childish to use in speech and you would generally use chichi and haha respectively. So overachiever me, knowing very well that you can often put an o- at the front of a word to make it formal, piped up with “so in a formal situation would you call your dad o-chichi?”

        No, no you wouldn’t, as the teacher managed to explain after a few minutes of uncontrollable giggling. Turns out o-chichi means boobs.

    3. Serendipity*

      I lived in Japan for a year when I was a teenager. When I was new and still learning Japanese I tried to make friends by giving my schoolmates compliments.

      Yeah, I mixed up ‘kirei’ for ‘kirai’ and ‘kawaii’ for ‘kowai’ .

      Turns out that instead of saying ‘you’re petty, I like you’ I was saying ‘you’re ugly, I hate you’.

      Much embarrassment.

      2. BeenThere*

        I studied Japanese from grade 8 to 12 and was lucky enough to visit for two weeks during that time, one week with host families in a rural town with Mt Fuji a short drive away. A dear friend of mine was also on this trip, upon seeing mount fuji on thenhorizon whilst on an outing with the family happened to also mix up kirei and kirai when she tried to exclaim how pretty it was. Her host family were initially horrified and she was confused followed by utter mortification! Fortunately sumimasen is one word you get drilled into your vocabulary when learning the language.

    4. the gold digger*

      Another Peace Corps volunteer in Chile once asked a waitress for a kiss instead of a glass – beso/vaso.

      I told the people at the bakery by my office that I was from Texas – that place with a lot of cowboys. Or bones. You know. Huaso/hueso.

      1. Emi.*

        Oh golly, I have a cousin who went out to buy chair cushions in Germany, but he only knew the word “Kissen,” which means “pillow.” Buuuut he didn’t know it as well as he thought he did, because he went up to the poor saleswoman and asked for “Kuessen,” which means “kisses”—“but not for here [pointing to his cheek], for here [pointing to his bum].”

        2. mrs__peel*

          There’s a whole thing about this in Jerome K. Jerome’s book “Three Men on the Bummel” (where he and his two British pals are touring Germany). It’s hilarious.

      2. Countess Boochie Flagrante*

        Oh god, I feel this.

        In college, I took Japanese and Spanish classes back-to-back. They were on very different levels — I was in 100-level Japanese and then 400-level Spanish — but my brain was very not good at differentiating what word went with what language. (In my defense, there are a lot of crossovers, especially in the two-syllable category. Casa/kasa, taco/tako, etc…)

        Well, in Japanese, if you’re searching for a word, one of the fillers you use is ‘ano.’ It’s the equivalent of ‘um.’

        It also mean things in Spanish. Things you don’t really want to just randomly drop in conversation with your professor about Ibero-Moorish architecture.

        (For those who don’t know, ano means anus in Spanish.)

        1. Todd Chrisley Knows Best*

          I spent most of this post trying to figure out what was so wrong with “year”, so I’m sure my Spanish teacher is sending a death glare at me from miles away since I forgot about the differences in having an accent or not. Language is hard.

    5. doubleblankie*

      too funny. Reminds me of when we had a Chinese delegation visit us, quite a high level one. I speak Chinese but it gets really rusty if it’s been a while.
      And I accidentally starting talking about how they had arrived at Hitler airport instead of Heathrow airport. They were very polite about it and pretended not to notice…

    6. JKP*

      Reminds me of when I was at a fan convention, standing in line waiting for a celebrity autograph. The lady in front of me was Deaf with an interpreter. When it was her turn to get an autograph, the celebrity tried to be gracious and tried to sign probably the only ASL they knew: “Nice to meet you.”

      Except they actually signed “Nice to f*ck you.”

        1. Cherith Ponsonby*

          Check out Adam Hills (Aussie comedian) – I can’t google right now but in one video he explains “F you and F the lot of you”, and in another “F you and the horse you rode in on” :)

          1. JKP*

            Thank you for that. His bit on sign language was hilarious. (Even if American Sign is different than British or Australian sign).

      2. J*

        I have a friend who’s an interpreter and her husband made that mistake when meeting one of her clients! Luckily the client thought it was hilarious.

      3. phyllis b*

        This reminds me of a story I read in Reader’s Digest. A mother was taking a sign language class because her daughter was deaf and the instructor was showing them obscenities that they wouldn’t know. Later she and her daughter were talking and she threw a couple in to see if her daughter would pick them up. Her daughter told her to go wash her hands with soap.

    7. overcaffeinatedandqueer*

      That reminds me of what happened to my poor friend on an exchange trip to Costa Rica!

      Her Spanish was good, but still only high school level, and she did not know slang and connotations. Out for breakfast, asks waiter “Usted tiene huevos?” (Eggs).

      He got an evil grin and replied, “siiii, tengo huevos graaaaandeeess!”

      It turns out that “huevos” also means, um, the thing that male pets lose when you neuter them, and that particular way of asking “do you have” is more meaning do you, personally, have, rather than does your shop have.

      1. Specialk9*

        Yeah, similar thing with saying I’m hot (as in warm) on Spanish. Nowadays I just say that I have heat, because I came remember in the moment which ‘to be’ verb form means hot vs horny.

    8. Corrupted by Coffee*

      When my husband and I started taking Japanese, we had to introduce ourselves to the class. When he stood up and said Hi, my name is —–, the teacher burst out laughing. It took him awhile to regain his composure, at which point he informed the entire class that my husband’s name meant “diarrhea” in Japanese.

    9. Veronica*

      A friend of mine was studying abroad in a Spanish-speaking Latin American country. Apparently the word for “to shower” and the word for “to douche” are very, very similar. Yep, she announced to her whole host family that she was going upstairs to douche.

    10. Middle School Teacher*

      I was living and working in Poland. I spoke barely any Polish. My friends and I were looking for the movie theatre. I said I would ask a hot dog vendor for directions.

      The words for “excuse me” and “I invite you” sound very similar in Polish. So instead of asking politely for directions to the movie theatre, I asked him to come with me. I didn’t live that one down for a while.

    11. Chameleon*

      When I was in college, I had taken one semester of Japanese and had managed to pick up a few words here and there outside of class. A friend was hosting two exchange students from Japan and we were having lunch together. Excited to show off the tiny little bit of the language, I offered one of them a bowl of rice in Japanese, “Meshi wa ikaga desu ka?” They looked at each other very confusedly.

      I hadn’t realized that while “meshi” is a word for “rice” the more proper term for rice you are eating is “gohan”…and I also had lengthened the first vowel, making it “meishi.”

      I had offered them a bowl of rice as my business card.

    12. Bluesboy*

      I once confused the word ‘pompelmo’ and ‘pompino’ in Italian.

      ‘Pompelmo’ means grapefruit. I wanted to ask the nice lady in the market what she charged for grapefruit. Unfortunately I asked what she charged for a pompino. Which means oral sex.

  9. Detective Amy Santiago*

    We had someone on our team give her notice because she was looking for a better work/life balance. It was common for us to throw a going away potluck in those type of circumstances. The day of the potluck, we got her to the conference room on some other pretext and she stood in front of the room awkwardly and told us that she wasn’t actually leaving now because she was going to be moving to a different position with more flexible hours.

    1. Merci Dee*

      That’s when your co-workers just smile and say, “So . . . yay on your new, more-flexible position! Let’s eat this delicious food to celebrate!”

      1. K.*

        I can totally see myself saying “Well … let’s eat!” to break the tension in that situation, and start passing out plates.

  10. Undercover Commenter*

    My manager told our team (a mix of women and gay men) that we were such awesome employees we all deserved vibrators.

      1. Snark*

        I can’t tell whether I hope he meant something else, or whether I will luxuriate in the secondhand awkwardness of knowing he actually meant that. Either way, A++ five stars would cringe again

        1. SusanIvanova*

          Maybe we’ve found the one person who believes those ads that show suspiciously shaped “massage devices” being used for backaches and other body parts.

          2. Working Hypothesis*

            Actually, they do work for some genuine massage purposes. I’ve recommended them to clients who have chronic migraines or tension headaches — only women; I don’t think I could bring myself to recommend going out and buying a vibrator to a man, no matter how bad his headaches were. But I’ve never yet had a female client who didn’t either already own one, or know where to get one easily, so I will occasionally suggest applying one to the painful area of the head, and it usually helps.

  11. Alex*

    On my first day at Old Job, I was running an errand for my director and went to fetch documents from someone else. I left their office and quickly turned around not realizing a large concrete column was there and body slammed into it. I was flushed, flustered and embarrassed and left quickly. I ended have having a hairline fracture on my cheek and it hurt to smile for about 3 weeks afterward. Never told anybody about it!

    2. overcaffeinatedandqueer*

      I was at the Mall of America with my church youth group once, and my friend and I had gone to the Barnes and Noble to pick up a Series of Unfortunate Events book. It had just come out, and being huge fans, we read while walking around with the rest of the group.

      Until I crashed into a pillar. My friend then crashed into ME, because she had been behind me and looking to me to keep us on track. Youth director helped us up while trying not to laugh, and said that one of us should read aloud so the other could look where she was going.

  12. Mayor of Llamatown*

    A new coworker was introducing herself during a web conference. She went into great detail about her son’s relationship with his wife, how they had courted instead of dating, and went into great detail about what that meant in terms of intimate activity. I never found out exactly what others’ reactions were, but I was cringing all over.

    3. paul*

      You win. or I hope you do; I’d hate to see the story that beats this!*

      *that is a lie, I would love to. So long as I’m not involved.

        1. Aurora Leigh*

          They don’t always hold hands. Depends on the couple. Sometimes side hugs, sometimes no touching period.

        2. Time Traveller*

          Back in the 90’s, I endured a two hour lesson on the benefits of avoiding premarital handholding. Chastity was very important to the adults around us.

          The theory is that when you are married, you will know that your spouse will never cheat on you, because you can think back on those days when you still loved each other and how in spite of that you were able to exercise restraint and not hold hands, so you can know for sure that even if your spouse comes to love someone else, they won’t hold hands with them, either. I don’t know why it took two hours to say all that, it wasn’t very complicated.

          I think it’s just a way of trying to find certainty in life where there can be no such thing. People want to think they can know for sure they’ll be safe instead of having to trust, but modesty isn’t some kind of magic spell that will ward off heartbreak.

          1. Working Hypothesis*

            And honestly, if my spouse fell in love with somebody else, whether or not they’d held hands would not be the most urgent issue on my mind.

      2. Daria Grace*

        Courting normally tends to mean intense oversight from parents/other authority figures and little to no physical contact

      3. Mayor of Llamatown*

        Pretty much what everyone said already, but it was explained to us that courting meant no sexual intimacy (yes, in those words) and that after a year he gave her a promise ring, and after another year he proposed.

        I don’t judge how others manage their relationships or what they think is right/moral. I just don’t particularly want to hear about it. Especially about someone else’s son who I’ve never met.

    5. Emi.*

      Whaaaaaat

      I had the opposite problem–one of my coworkers telling me about his son’s romantic woes, which apparently cannot be adequately explained without the line “And that’s how I found out my son wasn’t a virgin anymore.”

    6. Rebecca in Dallas*

      Haha, similar story though not nearly as cringey!

      We had a new employee starting in our department, so a coworker (Arya) and I offered to take her out to lunch. Arya and I didn’t work all that closely together, but I’d been around her enough and she is pretty friendly. Well we’re doing the usual get-to-know-you small talk with our new coworker, coworker asked Arya if she had kids. Arya said she had a daughter that had just gone off to college and then for some reason went into a very long explanation about how she had wanted to have more kids, but her husband didn’t and they gone back and forth for years about whether to have more kids… It was just so personal to go into all this detail to someone that she just met! I was cringing so hard and I could tell our new coworker was just thinking “What have I gotten myself into?!”

  13. MovieMaven*

    While sitting in the corner of a room, prepping for a client meeting, my friend witnessed the owner of the business pace into the room and begin a passionate self motivation ritual [ie. “you can do this sh**, you’re the f***ing best, now get out there and win!”]. And then he left – my friend froze as if he was hiding from a T-rex… thankfully he lived to tell the tale.

    1. EddieSherbert*

      Ohhhh that poor guy. Haha!

      Makes me think of that Friends when Ross is dating the daughter of Rachel’s boyfriend, and ends up hiding under the man’s bed and witnessing his “pump up speech” in the mirror….

      1. Detective Amy Santiago*

        It also happened to Jack on 30 Rock! He accidentally had his mic on and a whole room full of people heard him psyching himself up.

        1. Veronica*

          I was just rewatching the whole run of 30 Rock, and I had to skip that episode. It made me cringe so hard I just couldn’t bear to watch it again.

      2. GetYaGritHeeere*

        I was picturing Dwight Shrute when he was in the stairwell doing karate and hyping himself up. Also, that T-Rex comment just paints the picture so perfectly!

    2. Damn it, Hardison!*

      Or on 30 Rock when Jack was giving himself a pep talk in the bathroom before a leadership speech, but didn’t realize he was already on a live microphone.

    3. JokersandRogues*

      For creepy psych-up, Sexy Beast has a scene with Ben Kingsley’s character screaming at himself in a mirror.

  14. Always Awkward*

    When I was 23 I was promoted into a leadership position. My then boyfriend (now husband) had been on that team for several years. To be upfront I asked my boss if my relationship would cause problems with my new role. He paused and thought a bit before telling me that no, it’s still okay because we don’t supervise the same department or work together in a way that would be impacted by a relationship. He went on to explain that really in this role I could date anyone at the location I wanted to except for him. He and I would just never work. I think he saw me start to laugh at the thought (he’s considerably older and shorter, and less active than I am and I was 23!). Seeing my almost reaction he made a comment about having a very busy dating life anyway. He’s still my boss several years later.

  15. Andy*

    last week I was coming down with flu but I didn’t know it yet
    and a coworker (several rungs up on the ladder) come over to compliment me on something particularly polite I had said moths earlier in an awkward situation.
    It was a very nice compliment.
    Due to my as of the time not yet recognized illness related loopiness I responded to the lovely compliment with the following expletive: Well MuthaFurkER, thank yew.
    So, in response to a very nice compliment on a polite thing I said I washed myself in irony and answered in an exceedingly impolite manner.
    I am still mortified.
    Deeply.

    2. Competent Commenter*

      I oh FEEL you! I’m on day 15 of the illness that’s going around my work (not the flu but really debilitating) and I have been really loopy. Just been observing myself making strange choices, hoping nothing I do causes any long-term problems!

  16. Wannabe Disney Princess*

    I was walking into the office. Had my purse. Lunchbox. Coat. Everything. Unbeknownst to me, someone had spilled some water right in my path. It was like my own personal patch of black ice. I didn’t just slip. Oh, no. That would have been far too dignified. I flew. Not quite like an eagle. More like a drunk pigeon. FACE FIRST. My purse soared to right (still thankful it didn’t injure or kill any passersby) and my lunch went careening to the left. Once I was wheels down, I confirmed that I was uninjured and alive. My pride, however, was desperately hoping the embarrassment would kill me first. I finally gathered myself. Picked up my stuff. And faced the stunned faces of my coworkers as I limped back to my desk.

    1. Reba*

      Watched Olympics women’s downhill skiing. When they wipe out those beautiful valkyries can go a loooong way penguin-style (on their bellies).

        1. LizB*

          Solidarity! I ate it hard in front of my coworkers in the parking lot the other week trying to kick the accumulated snow boogers off my car. My legs went straight out from under me, I shouted “WOOP!” really loudly and landed flat on my back. Then I got the knees of my slacks wet trying to stand up as quickly as possible.

          Then there was the time I had a similar wipeout crossing the street right before the light turned… and the time the sidewalk was only partially covered with ice, but I managed to slip on the icy bit with my left foot and land on the bare concrete with my right knee…I may not be cut out for living somewhere with icy winters, but I persevere.

          1. Penny*

            LizB literally that exact thing happened to me down to the position you fell in (2nd paragraph)! I was on campus crossing a road between sides of the campus & of course people were waiting at the light where i fell. Glad it was dark so i didn’t have to see their laughter. Of course i continued on to watch a movie in class for extra credit, so i only had to sit there through Lord of the freaking Rings in horrible pain. My knee was bruised for months.

        2. Detective Amy Santiago*

          I fell over a construction sign in downtown Chicago.

          I’m pretty short, so I was trying to walk under it. I didn’t realize that the two vertical metal poles holding it up were connected by a horizontal metal bar that was just below my knees. I took a couple steps forward and was like “why can’t I move” and the next thing I knew I was practically upside down.

        3. Nolan*

          In my last year of retail I fell down the stairs at work twice in one month. The first time happened in my home store, my heel got caught as I was going down, right leg folded beneath me, arms extended to the walls, left leg splayed out in front. My left shoe flew off my foot and my smartphone flew out of its holster, both ended up at the bottom of the stairs while I managed to hold myself after a couple feet. When a coworker rushed to the bottom of the stairs to make sure I was okay I exclaimed, “is that my phone!? Is the screen cracked!?”

          The second time was at another store I was attending a training in. It had snowed, and I was wearing wellies. I’d just bought a coffee, took one step down and on the second step my foot shot out from under me and I flew down the remaining 20 or so on my ass. The coffee exploded everywhere. When I got up and went into the conference room, the trainer and other attendees just stared at me like it was nbd, and left me to clean up the mess by myself. That store was only 15 min from my apartment, but I never set foot in it again.

          2. Petunia*

            I slipped coming down the stairs at a conference last fall – just the last couple of stairs – and fell over. The friend walking with me was totally horrified and tried to haul me up but he’s not a large guy and it was a lot of effort partly because I was laughing like a loon.

            He was worried for the whole rest of the conference. It must have been a surprise to see me just go over like that.

        4. overcaffeinatedandqueer*

          I once fell on some glare ice on my way to a college class while clutching a very hot coffee!

          Didn’t even try to save myself. Backpack weight pulled me slooowly down as I skittered and flailed. I had just enough time to decide what to save from impact.

          Fall forward and save laptop and homework? Nope. Fall straight back, no attempt to catch self, with coffee holding hand straight up in the air like an Olympic torch bearer.

          It felt like I broke my back, but I saved the coffee!

          1. Specialk9*

            Laughing so hard at this mental image. I would love you forever just for this. Like, hey, let’s be best friends, coffee saver person.

        5. Adlib*

          Was salting my driveway Sunday after a mild ice storm. Managed to steadily slide down the middle while salting. Later I wiped out while standing almost still. Nobody was out, but I wish my doorbell cam had picked it up!

    3. Nita*

      Ouch! Your description is epic though.

      And that reminds me, my husband flew into his office once! But first, he flew into a truck. His office was in a bit of a windy neighborhood, and one day he comes out of the subway, and a gust of wind just picks him up, and he goes flying through the air right at the truck, Superman-style, with the arm outstretched and all. He’s a big muscular guy, so I wouldn’t have believed it, but he’d called me freaking out that if the wind could pick him up, I should NOT LEAVE THE SUBWAY unless I’m hanging on to something.

      Frankly, a small part of me was disappointed when I got off at my stop and found that the wind in my neighborhood doesn’t pack the same punch… flying sounds kind of awesome even when it ends with a bruise.

      1. Working Hypothesis*

        When I was a kid, the local carnival was held on a weekend which featured a ginornous, and very sudden, windstorm. Everything closed down and we were all sent home when the wind began to pick up. It was only about three blocks to my house, but I flew almost a block of that before I managed to snag hold of a passing lamppost and haul myself back down to the ground!! After that, I kind of crawled along the building line for the last block, terrified that if the wind picked me up again it might not put me down till I was over the river.

        I admit that, once I got hold of that lamppost and could afford to stop being terrified, it *was* pretty cool to have experienced flight, though. I’ve done the indoor skydiving things they have a few times, and it’s actually very similar, so if you want to find out what it’s like, I recommend those.

    4. JB (not in Houston)*

      I have so many stories of my falling down in front of people. Once in law school, I stuck my feet on the rails of the chair, then leaned over to pick up a pen I had dropped. My heels had become stuck on the rails, and so when the chair started to tip over, I couldn’t put my feet down to stop it. I was in the front row. The whole class got to see my chair fall sideway with me sitting in it.

      Another time I had my hands full of books as I was leaving a building, so I decided to use my foot to press the button to automatically open the door. Although I’d done this many times before, I guess because I was wearing boots with heels and had a heavy backpack on, I started to tip backwards. To stop myself from falling, I slammed my foot back down to the ground. All that accomplished, though, was to stick my leg straight into the paper recycling bin next to the door. So I fell straight back, leg in the bin, taking the bin over with me. Fortunately, I guess, the backpack absorbed the fall, so I wasn’t hurt, just really embarrassed.

      1. Legal Beagle*

        The recycling bin is just the perfect cherry on top! I’m a huge klutz, so I sympathize.

        I was sitting in a folding chair at a friend’s dinner party. I dropped my fork, leaned over a bit too far to get it, and the chair slipped out from under me and dumped me onto the floor. I was also 12 weeks pregnant but wasn’t telling anyone yet, so I just silently freaked out for the rest of the party. (It wasn’t a big fall, but I was a nervous first-time pregnant lady.)

      2. Free Meerkats*

        Since this wasn’t at work, I’m asking Alison to pick someone else if the algorithm chooses me.

        This was back in the 70s, a friend had bought a new Honda 450 motorcycle and we were all outside the barracks looking at each others’ bikes. He offered me a ride on it and I swung my leg over and, since it was already running, off I went. What I didn’t notice was that my pant leg had gone over the kick-start lever when I got on.

        Being the (I thought, with the stupidity of youth) suave young man I was, as I rode up to a light that happened to have a car with some attractive females in it sitting there waiting, I decided to be really cool and come to a stop before I put my foot down. So I came to a full stop and went to put my right foot down, only to discover it wasn’t going to move that way.

        You remember the tricycle guy on Laugh In? That was me. Came to a stop and promptly fell over. Needless to say, I didn’t impress the young ladies in the way I intended. And I had to buy a new turn signal for the friend. But of all the injuries, my pride was hurt most of all.

    5. justsomeone*

      Your description of the event is so well done I’m sitting here chuckling audibly to myself, partially because I’ve also slipped in a glorious manner and if I can’t laugh I’ll cry.

  17. Sarah*

    So a woman I worked with was super excited to be pregnant and expected all of us to be equally excited. She decided to throw herself a gender reveal party at the office (presumably after having one for friends and family? This part was unclear) and sent a department-wide email asking us all to meet at 3:00 that day. Now, 3:00 was a bad time for my team specifically as we had daily 3:15 deadlines, and it was pretty common for us to miss the start of birthday/anniversary celebrations each month so we could hit our KPIs. But she came around and did everything but physically lift us out of our seats – she would not start the “meeting” until we were all standing around.
    She then had her friend from another department walk up with a bunch of blue and pink balloons and started popping them one by one until she was left with a blue balloon and she was shouting, “A BOY! I’m having A BOY! Aren’t you so excited? Isn’t that great? A BOY!” Everybody just stood around awkwardly while she talked at them about how excited they must be for her and how proud her husband was.
    By the time this whole charade was over my team had missed their deadlines and screwed up our KPIs for the week. On the plus side, we got to teach everybody about assignable cause variation by highlighting the dip and circling it with a note that said “Surprise gender reveal party”.

    5. Falling Diphthong*

      I have actual children, of all the major genders, and don’t remotely understand gender reveal parties. Unless the context is “We want to eat simple carbohydrates, and this is the second-week-of-February pretext. No, Neal, no one cares whether you are actually pregnant. Just hand out the cupcakes.”

      1. Falling Diphthong*

        Also, the symbolism of popping the balloons is really freaky. Like reproductive Hunger Games.

        1. Rebecca in Dallas*

          This is the part I can’t stop laughing at! Like someone just popping balloons and everyone jumping each time. My coworkers must think I’m a loon.

  18. MsMaryMary*

    I once made an expansive sweeping gesture and smacked one of my direct reports in the face.

    One of my friends was having a one on one with someone she managed, and he told her that he was a little anal retentive when it came to certain parts of his jobs and he was concerned it might cause problems with his coworkers. “Oh, don’t worry,” she said, “I LOVE anal!”

    2. London Calling*

      Oh, have done that but to a total stranger who staggered back in surprise, no doubt wondering why this idiot she’d never met before was socking her in the jaw.

    4. JB (not in Houston)*

      I have (lightly) punched my sister in the face before while putting on a coat, and then again later the same day when trying to show someone how it had happened in the first place.

      1. Mabel*

        I did this once on the subway while taking off my backpack. I accidentally smacked the woman right on the temple and knocked her glasses halfway off her face. I felt terrible, but she was amazingly gracious.

    5. Lily Puddle*

      On two separate occasions I have smacked the person sitting at the table behind me in a restaurant while making an expansive sweeping gesture. But at least it wasn’t someone I worked with, so I didn’t have to see the poor folks I smacked every again.

      1. JaneB*

        I hope nice threw my scarf back over my shoulder and hit the thing behind me. It wasn’t a person. It was a seven foot tall cheese plant, which fell onto our table. How w to attract a lot of attention…

      2. BF*

        My boss was in a meeting where the general made a big gesture and knocked his chewing tobacco spit cup into the lap of the admin assigned to take notes. My boss didn’t know generals could apologize that much! The general gave her the rest of the day and the next day off and he would clear it with her boss. And she was to send him the cleaning bill and if the outfit couldn’t be cleaned to send him the receipts for any replacement items.
        I was impressed she didn’t throw up on him because I find that stuff disgusting.

    7. Lily Rowan*

      This isn’t that embarrassing, but it literally just happened in my last meeting — I was laying out a couple of options and said, “I go both ways.”

      Really, self????

      1. London Calling*

        Sometimes you have to wonder if your brain and your mouth are in a conspiracy to make you look as bad as possible, don’t you?

    8. palomar*

      I was in a departmental meeting once when our CFO said something about being really anal retentive and an older coworker piped up from across the room, “Oh, anal’s great! I love anal!” It’s been at least a decade but every time I think about it I laugh so hard I see spots. Bless her heart.

    10. Alex the Alchemist*

      In my community choir in high school, one of my friends was putting on her robes and accidentally elbowed one of the choir’s littlest members in the face. The kid’s response? “It’s ok, my mom does that all the time.”

  19. Lady By The Lake*

    I interned for a firm where a Very Important Person (think former President or VP of the US) worked. As a treat for the interns, we had a meet and greet with the VIP and he went around and asked us all where we had gone to college. I went to a famously artsy school. When he got to me and I said the name of my college, he said, “Oh, Artsy School. I knew some Artsy School girls. Is everyone still running around the woods naked, or did you do actual work?” It is thirty years later and I am still at a loss as to how to respond to that in front of sixty strangers.

    1. Detective Amy Santiago*

      Even though you said this was 30 years ago, I am choosing to believe it was GWB who said this to you because that mental image is way too funny in my head.

        1. she was a fast machine*

          Same here; I’m picturing Clinton 100% and half the room being utterly swept up in his “charm”

      1. AMPG*

        I went to Wesleyan, and there aren’t any woods nearby, so it couldn’t be. Now, if he had referenced lying on the hillside stoned out of your gourd…. :)

        1. Dee-Nice*

          Eh, there were copses of trees and verdantry around. Maybe “woods” was used loosely. Nudity certainly abounded.

        2. Dylan Is A Lady*

          I went to Wesleyan, too. The graveyard is an excellent spot for shenanigans, but the tree cover is scant.

          Sarah Lawrence, on the other hand…

            1. Lady By The Lake*

              That was the other thing that was really awkward. We DID run around in the woods naked. But I also had an excellent education. The knowledge that what he was saying was true only added to the awkward. Added my email.

              3. Working Hypothesis*

                I spent a summer at Bennington, when I was in high school. Gorgeous place, and we did a lot of running around in the woods, but we were warned explicitly to keep well covered because of poison ivy! I didn’t know that poison ivy only targeted those under 18…

        4. Elemeno P.*

          Oh my god, I went to Bennington too! I was thinking that it sounded like us, but then thought, “Nah, that’s too obscure.”

          We did still run around naked in the woods when I attended.

        5. Elizabeth H.*

          I knew it was Bennington!!! Immediately! I was going to ask “But DID you” then read the rest of the comments :)

    4. Sue Wilson*

      My response: “The workload was intense, but it sounds like you remember Artsy School fondly.”

    5. Anon.*

      Can relate. Went to school that was known for having a “Tent of Consent” and other sexual/hippie events and it somehow seems to always be the first thing people ask about.

  20. EddieSherbert*

    At a previous job, an Assistant Product Manager was giving a presentation to a large group (including their boss’s boss) for some new regulations at one of the job sites (construction), and one of their friends that was out on another job site sent them a Lync message… and you know how the first few words pop up in the corner of their screen? Yeah, it said “sup, my n*****”. Projected on this absolutely huge screen. The APM moved fast, so it was only there a couple seconds, but almost everyone saw it. And the people that didn’t see it were very quickly filled in. And their boss’s boss didn’t say a word, but was literally just red in the face (rage? embarrassment?) glaring daggers.

    Both the APM and their friend were called into HR. They were not fired (whew) and I don’t know what the consequences were.

    1. Sarah*

      Oh man!

      I was hosting a webinar and usually have my Skype set to do not disturb when I’m doing that but it didn’t work this last time, so my COO and the director of our billing team saw a message from a coworker pop up that just said, “So, I’m f***ed.”

      1. Arjay*

        Yes, do not disturb is a necessary precaution. I have a friend here who is in a lot of meetings and one day I had a lot to vent about it. I started it off with “Are you alone?” :)

        1. EddieSherbert*

          For non-work related stuff, I always send “hey!” on its own… and then my actual message in a second message. So only the “hey” pops up. Just in case.

          …. and I literally do that because of what happened in this meeting! Haha

    2. Damn it, Hardison!*

      I am so happy that Skype doesn’t have that problem. I’ve seen a few embarrassing things pop up in the past, usually along the lines of “WTF, X is an idiot.”

    5. Rebecca in Dallas*

      Once I sent my husband a g-chat message. “Are your coworkers still being super annoying?” You guessed it, he had his computer projected to show them something.

    6. ChrysantheMumsTheWord*

      This reminds me of when I was remotely making a very important presentation.

      I was in our office with several high level execs, the owner, VP and director were on-site with the prospective client and we were connected via webcam, etc.

      During my part of the software demo I mis-typed the word SHIP which was projected on the wall in both locations. I kept talking while seeing the looks of horror at the client site, while I tried to quickly fix my error. Unfortunately, on my end the person sitting next to me loudly gasped and then laugh-shouted “HA!” before dramatically clamping their hand over their mouth.

      I was mortified and those that were at the client site never spoke a word of my gaff when they returned which just made it worse. We didn’t get the client but I have no idea if it had anything to do with me.

    7. zora*

      I was not projecting, and this was more a “Huge Work Mistake Do Not Do” than an ‘Awkward Moment’, but I was at BEC mode with a coworker, while she really thought we were BFFs. She was IMing me all kinds of things that were the exact reason I was so frustrated with her, and I switched to another IM window and sent a whole long rant about exactly why Circe was “such a jerk and it’s driving me crazy!!!”…. Yup, I hadn’t switched windows…………….

      It was super bad, and she was so angry at me, and we had to have lots of “Talks” about my feelings for many many weeks. I felt really bad for hurting her feelings, but honestly, she was causing me lots of work related problems. But from then on I am SUPER careful about ever putting vents about people in writing EVER.

  21. LibraryGnome*

    I was 19 years old and working as the manager of a spa. Part of the massage therapist interview process is giving the management team a massage to demonstrate their techniques. This super buff, blond, surfer-dude type is practicing on me and I ask for my glutes to be worked on, as they are a problem area for me. He proceeds to take the sheet, pull it back to fully expose one cheek, and uses his hand to wedge it down my crack. Needless to say, that is not a normal draping technique and clients would have definitely came to me over that… We hired him, but he got a lot of draping training before he was allowed to work on clients. Definitely the most awkward day of work ever.

    4. Working Hypothesis*

      Oh good grief. I’m a massage therapist and I am absolutely cringing in professional mortification for that guy!

      If I were dealing with someone who wasn’t a regular client — especially in a job trial — I would work glutes through the sheet and not undrape at all. With a regular, if there were actual reason (there usually isn’t), I might fold the sheet back so part of one cheek were exposed, but you fold, not wedge!

  22. CatCat*

    Oh man, this book sounds amazing. I already feel secondhand embarrassment for the deliciously awkward tales that must be contained inside. I want to read it and I don’t! (But I will!)

    Awkward work situation: I had a boss who had surgically implanted her foot into her mouth. In one memorable moment, a staff member on the team shared that her son and daughter-in-law were expecting their second child (and her second grandchild) so she was thrilled. Boss: “Haven’t they heard of birth control?” Oooooooh… sooo much pained looks around the room. None of us could believe she just said that.

    1. Detective Amy Santiago*

      This just reminded me of the time when our manager was diagnosed with breast cancer and pulled us into a meeting to tell us. One of my coworkers blurted out “are you going to have to get your boobs cut off”.

      She got called into HR that afternoon.

      1. Countess Boochie Flagrante*

        Oh my god, that sounds like my mother. Not work related so I’m not sharing the gruesome stories, but she’s very prone to saying the first thing that comes to mind and it’s painful.

    2. Amy Farrah Fowler*

      Omg… My dad is the worst about stuff like that. Not in a work situation, but pretty much every time someone announces a pregnancy, he says “don’t they know what causes that?”

      “Yes, dad. Everyone knows what causes that.”

  23. Boy oh boy*

    My boss got a haircut I thought was incredibly unflattering . It was a mullet with lots of spiky layering that made his small, angular face look almost rat-like. (This was in 2008-ish and mullets were pretty much a reviled joke by then, so he couldn’t even use ‘it’s on-trend!’ as an excuse.)

    I saw him and could not control my look of horror. It was obvious that I thought it was terrible, he was clearly offended, and I couldn’t look at him properly for the rest of the week… he even ‘joked’ that I didn’t like it in a meeting but he was not happy. I have rarely felt so awkward/ashamed…

    1. ChrysantheMumsTheWord*

      I had a former supervisor see my new haircut and reply, “Did you do that on purpose?”

      1. Blondie*

        Once I thought I would try a new hair color (one that was supposed to wash out in 6-12 shampoos). It was light golden brown. I was golden blonde. The resulting color was auburn. Let me tell you, it did not wash out in 6-12 shampoos. (And the color never completely washed out. The result, though, was a nice ash blonde.) When I walked into work, one of my managers asked me “What did you do to your head?”

        1. Yikes!*

          My colleague came to work one day with a tight perm (it was the early ’90s), and a second colleague saw her, and blurted “Lisa, what did you do? You have to go right back to the salon and DEMAND your money back!”

  24. Casuan*

    At ThemePark, an older man asked me something & I laughed because he was mimicking one of the Characters. Then I realised that he had a voice-box & that was his voice. And then my horror grew when I saw the number tattoo on his forearm because this man had been through traumatising events & by laughing I wasn’t doing my job at the Happiest Place on Earth.
    Thankfully he was gracious about it!!

      1. Casuan*

        ummm… Thanks?
        30 years later & I still can’t forget this man. The snapshot of that moment is permanently seared in my head.
        Actually I’m quite grateful to this gentleman because after all of about two minutes this encounter helped me to become more aware of others & not so quick to jump to conclusions.

  25. Who the eff is Hank?*

    My first job out of college was in an office where almost all the walls were made of glass. I was walking into a conference room for a meeting but instead of going through the doorway I accidentally slammed into one of the very shiny and undetectable glass panel walls. The sound was magnificent as the glass cracked all the way down the panel from where I’d hit my head. Also, this was an all-hands meeting, so literally every person in the office saw this happen.

    3. Who the eff is Hank?*

      Replying to include my email in the comment for Alison’s drawing. But I’ll give everyone a bonus embarrassing story to make the comment worth it.

      My current job is at a nonprofit that works with children. My boss sometimes brings in doughnuts for the kids in the morning and gives anything leftover to the staff. Last week I went into his office to give him something and saw an empty doughnut box on his desk. In feigned disappointment I said, “What, none for us?!” but he thought I was being serious. He had such a sad look on his face and apologized for not bringing us doughnuts and then I had to apologize and explain I was kidding. I felt so bad for making him feel bad.

    4. Ruth ok*

      There are couple of shops that clearly have this problem regularly and have actually stuck signs on the doors to warn people. I don’t know why they can’t just add a few frosted stripes or something.

      1. hermit crab*

        We recently had some of those little frosted stripes installed in our office, because people were walking into doors. They’re apparently called “distraction marks”!

      2. zora*

        Our office is all glass walls and doors, part of the design is big red dots on every panel of glass, one at eye level and one at knee level. So, you can tell when doors are open.

        That said, I have still bumped into the glass once, but it wasn’t hard enough to break the glass, thank goodness!!!

    5. Reba*

      You know how they have those decals to try to prevent birds from crashing into windows? The one’s I’ve seen are most often bird shaped. What would be the decal shape for clumsy humans?

      1. beanie beans*

        I’m picturing how in cartoons the human cutout of people are so distinct when they run through a wall. :)

  26. Alison Read*

    I owned a produce business – sampling was encouraged. I was talking to a husband and wife and handed her a double cherry, she ate both and I told the husband (because I’d already grabbed one for myself), “Here, you can have my cherry.”

    1. LAI*

      Ok this one isn’t work related but I had to share: in college, my boyfriend and I were attending a football game and had gone to get snacks. I bought nachos that came in a little cardboard box. He got a hot dog. As we were meeting up with all of our friends, I noticed that he had his hands full and said “do you want to put your hot dog in my box?”

      1. SocialMonster*

        My first day on a new job in a bar, I was being trained by the owner. He offered me a piece of bubble gum. I declined by saying “no thanks, I swallow”. His reply was “I think you are going to fit right in here”

  27. bluelyon*

    I , as a customer in this scenario and being slow on the uptake, made a comment about not recognizing the cashier with her clothes on…….

    She was a lifeguard at the pool I swam at – I had only ever seen her in a swimsuit.

      1. bluelyon*

        Conveniently I was a 14 year old girl….she was not much older and 15 years later we remain friends

    3. Original LG*

      I was a lifeguard in college. I guarded the senior swim hour, where everyone over a certain age could swim for free. I ran into one of my regulars at my parents church and he exclaims, “Boy, Original LG, you sure look different with clothes on!” In front of my dad…and the pastor!

    4. Veronica*

      A secondhand story, about a friend of a friend who usually wore a Scottish kilt as part of his ordinary clothing. One day he decided to wear trousers, and a co-worker announced “Bob! I didn’t recognize you with trousers on!”

    5. Clewgarnet*

      I used to live in an old-ish (early 1800s) house that had been (badly) converted into four flats. One of the flats was occupied by some serious stoners, who never thought to block their smoke detector before lighting up at 2am. The smoke alarm was one that automatically called the fire brigade, who then had to go through the entire building to confirm there was no fire. I regularly opened the door to them in my nightwear.

      One day, I was walking down the street and the firefighter who usually came to my flat was collecting money for charity.

      Of course, with a huge grin, he said, “I didn’t recognise you with your clothes on.”

  28. paul*

    Went to work feeling OK; worked a few hours, took lunch. Ate lunch at a sandwich shop.

    About an hour after getting back I was feeling *awful*.

    Went to ask my boss if I could go home and threw up all over her office while asking.

    2. Future Analyst*

      Oh God. This is one of my worst nightmares. I can barely handle vomit, but the thought of vomiting near colleagues makes me ill.

    3. Coalea*

      This is not work-related, but your story reminded me of a time when I was in elementary school and feeling unwell. For whatever reason the nurse wasn’t there that day, so the principal let me lie down on the floor of her office with her blazer tucked under my head as a pillow. Needless to say, I vomited all over it. Also, she was a nun, which somehow made me feel even more awkward.

      1. MsMaryMary*

        My mom taught first grade for many years. On the very first day of school she told the kids that they didn’t need to ask to go to the bathroom if they felt sick, they should just go. She still routinely had sick children come up to her and say, “Mrs M, I don’t feel so [vomit]”

        1. Rebecca in Dallas*

          In fourth grade, I asked our PE coach if I could go to the nurse’s office because I wasn’t feeling well. She thought I just wanted to get out of running laps, so she told me no. Guess who puked all over the gym floor?

          1. Elizabeth West*

            I was in time-out in the library in fifth grade (don’t ask–my teacher was abusive) and felt really bad. I asked the equally awful librarian if I could go to the restroom, but she said no, you’re in time-out, stay put. So I sat there, feeling sicker and sicker. A moment came where I knew everything was going to come up and I lunged out of my chair, ran into the hall, and promptly chundered all over the place. We were right outside my classroom and I heard one of the boys say “Splat!” I turned around and did it again, leaving two huge puddles on the floor.

            They called my mum and I went home for the rest of the week. I kind of wish I’d upchucked ON the librarian.

    4. Partly Cloudy*

      My vomit story is so bad I try never to think about it. Out of town conference with my boss, I accidentally got really drunk and my boss and the bigwig vendor we were hanging out with had to help me back to my hotel room and essentially put me to bed. After helping me throw up in the trash can. Several times. I’m leaving out a lot of details both for anonymity and because it still makes me extremely cringe-y to relive this memory.

    6. overcaffeinatedandqueer*

      High school bio. I had started my period and it was really painful and heavy. I wasn’t bleeding through clothes, but I felt like absolute shit.

      Raised my hand and said, “Excuse me, Mr. S, can I-” CRACK. Fainted across my lab stool.

      1. Windchime*

        This happened to me at work when I was a teenager. I had fainting spells due to severe anemia. I thought I was better so I went to work at the dime store. One minute I was behind the counter; next thing I knew, I was sitting on the floor and my customer had come around to my side and was on the phone with the owner (his number was posted by the phone). It was really embarrassing; the boss had to come and spell me and my mom had to come pick me up.

    7. Lefty*

      Oh, paul… same here.

      Except that I vomited directly onto the shoes of my boss when he kindly tried to open the door for me… the man was wonderful. I apologized and tried to grab some paper towels- he reminded me that he had 6 kids at home and had been through worse. I was mortified, but he was so kind, it made a huge difference in the way I saw him after that!

    8. Escapee from Corporate Management*

      This immediately reminded me of…

      Flounder: “I can’t believe I threw up in front of Dean Wormer.”
      Pinto: “Face it, Kent. You threw up ON Dean Wormer.”

    9. Former Border's Refugee*

      My very first day at my very first job (at a movie theater), I was so anxious I didn’t eat all day. I keeled over from low blood sugar while taking tickets, much to the movie going public’s dismay.

  29. Mickie D*

    I am usually the awkward one so saying I witnessed it is not really accurate. My current job – which I have now been at for almost 5 years – had a bad start. I had worked at a dream job and the owner decided to close. As a result, I found this job. And I cried for my entire first week as I was SURE I had just tanked my career for the rest of my life. I told everyone – unconvincingly that I had allergies – but I was crying all week. They were not sure I was coming back on Monday it was so bad. But I did and 5 years later – love it here. Awkwardness happens.

  30. Js*

    During our board meetings one year, my boss (who has been single for as long as I’ve worked for her) was chatting with a group of co-workers in a lobby. One of the the co-workers says to her, out of the blue, “I haven’t seen you in a while, are you pregnant? When are you due?” To which my boss loudly replied “Nope, not pregnant, just FAT.” Cue horrified looks from everyone else as they go silent and start to back away and scatter. The inquiring person looked like they wanted to die, and after sputtering a few apologies also fled the scene.

    3. Accidental Analyst*

      I had something along the same lines. I’d just finished a training session for new contractors. On of them came up to me and asked if I was pregnant. I said no. She insisted. I said I was bloated. She insisted again. Told her nope just ate something I shouldn’t have. Now wish I had of said yes it’s a gas baby

      2. Elizabeth the Ginger*

        WTF. Bad enough to ask a first time. But it’s about a hundred times as rude to double down and insist. What possible good outcome could insistent-lady be imagining? “Oh my gosh, person I just met, you must be right! How wonderful! Thanks for helping me find out I’m going to be a mother!”

      1. ggg*

        I WAS pregnant. 8.5 months. Someone thought it was useful to tell me, “A couple people were wondering how you got so fat. But don’t worry, I told them you were pregnant.”

        1. LSP*

          That’s a pretty risky thing to say to someone 8.5 months pregnant. You’re liable to set off a crying jag or trigger Hulk-level pregnancy rage.

    5. Partly Cloudy*

      Co-worker 1 had been pregnant and was also overweight (both pre- and post-pregnancy). Co-worker 2 asked her “when are you due again?” Co-worker 1 replied “I had her three months ago.” I was standing right there and it was so awful to watch.

      3. Rebecca in Dallas*

        Similar thing happened to my dad. He asked my mom’s coworker, “When are you due?” “Eighteen months ago.” Ouch! Almost three decades later, he will not assume a woman is pregnant unless she is in active labor. And even then, he’d probably still not ask.

      4. Witty Nickname*

        I had someone do this to me 4 months after my first was born. A few years later, when I was very obviously pregnant with my second, she asked me the same question as we were walking past each other in a hallway. And I acted like I had no idea what she was talking about and just kept walking.

        (I mean, I was really really obviously pregnant and not just overweight. And when I had random strangers stop me in the grocery store to ask when I was due and then act really surprised that 1) it was still 2 months away, not the next day, 2) no, I wasn’t having twins, and 3) and no the baby is not a big boy but a girl who is measuring right on track, I didn’t really mind because I knew it was obvious. But that woman really irritated me. Heh)

      5. Little Orange Nail*

        I have triplets. It destroyed my figure, so even though I am back to my pre-pregnancy weight, my belly is still kind of pregnant-shaped, and probably always will be. I have on several occasions had someone see me with my kids and say something like, “Triplets?! and one more on the way?”

    6. strawberries and raspberries*

      I did this to someone once. (Told them I was just fat, that is.) That was my wake-up call to change my diet.

    7. MsMaryMary*

      When I was 17, I asked a customer when her baby was due. She was not pregnant. In my defense, she was buying a onesie.

      So at least I learned that lesson at 17.

    8. Rebecca in Dallas*

      A coworker and I were in our break room chatting while we got coffee. She was wearing an empire-waist dress and telling me about a baby shower she had hosted over the weekend. This poor guy comes up, hears her talking about the baby shower and says, “Oh, congratulations! When are you due?” Soooooo awkward! I kept assuring her he’d only asked because of the baby shower talk, but she was still really upset about it. :(

    9. Lissa*

      lol, I know I’m not supposed to have sympathy for the asker in these situations because it’s a rude thing to ask, but as someone with a bad brain to mouth filter I always feel so embarrassed/bad for both people.

    10. Elim Garak*

      This happened to my aunt in the elevator at a hospital maternity ward. She never comments but thought that’d be the one safe place to do so. It turned out the woman had an abdominal tumor and she was visiting her sister who just had a baby.

      It is never safe.

    11. Ermintrude Mulholland*

      I love your boss.
      This happened to me a few days ago, probably making me the subject of someone else’s Most Awkward work story. I was in a shop buying a scarf and was cheerfully asked by the cashier when my baby was due. I loudly said “Oh no, I’m not pregnant, that’s just the result of eating too much food”.
      Whilst I feel I dealt with it quite well, and admittedly had just eaten a very large breakfast, it still stang and even more so given that I was standing about 3 feet away from my husband and our Three Month Old Baby

  31. Crystal*

    Several years ago, I worked on the overnight stock team at a national retail store and we had only started carrying groceries a couple months earlier, so we weren’t that used to putting things away yet, and it came on a different truck. One morning, the store was about to open so the entire time was scrambling to stock the freezers on the floor. I was reaching in for a box and one of my co-workers was attempting to get the attention of our team lead, and called his name several times. He was low to the ground and I thought it was strange that he was pretending to not have any legs while doing this, so I stupidly said, “Hey Jason – a legless employee is trying to get your attention.” Jason looks at me with wide eyes and says, “I can’t believe you just said that!” I was confused, until I looked down as the employee came into better view and I saw that he literally had no legs.

    He was an amputee.

    I was mortified and apologized profusely, but he laughed it off. Eventually we became friends and I met his girlfriend, who referred me to the job that I’ve now been at for over a decade.

    6. Thursday Next*

      Some comments are sooooo out there they can circle back to innocence…it was obviously clear you were not trying to be a jerk!

  32. Lore*

    We publish a lot of romance novels at my job, many of them shading into the erotic. I (straight woman) was once having a conversation with my direct supervisor (straight man), in his office, about the new season list, which included our first male/male historical romance. Then our department head (gay man) came by and stood in/unintentionally blocked the door while the conversation gradually shifted into other works of contemporary fiction featuring male/male romances. And sexual partnerships. And explicit sex scenes. And menage sex scenes. And yet somehow none of us could steer the conversation back to safer waters, and Dept Head kept blocking the door, and this went on for like ten excruciating minutes.

    1. Lore*

      Oh, and here’s another one:
      I’m a long-term temp who occupies a teeny tiny office. My colleague, also a temp, comes in to tell me some piece of scandalous work gossip before a meeting and slams the door dramatically to do so. We then try to leave for said meeting with our mutual boss…and the door won’t open. We have to call the boss and ask her to come let us out of my office. Which, btw, is teeny enough to be uncomfortable with two people locked in it because most of the floor space is needed to swing open the door.

      Then she can’t open the door from the outside either. She calls security with their master keys, thinking we’ve somehow accidentally locked it and the lock is jammed. They can’t get it either. She ends up having to get a locksmith to take the handle assembly off the door entirely from the outside.

      It took about an hour and a half. Fortunately the boss thought it was hysterical, and my friendship with the coworker survived a period of basically sitting in each other’s lap on my desk chair because we were expecting the door to fly open at any moment.

        1. Elim Garak*

          Honestly if I were a sitcom writer I’d be mining this thread for gold. You could fill a few seasons with these stories.

      2. Adlib*

        I got locked in a conference room during my last business trip. The corporate office had just switched floors due to remodeling so everyone was still learning the quirks of the new floor. The conference rooms had giant doors that were motorized and closed in from both sides. My team member and I had been working facing away from the doors with them open. My coworker got up to use the restroom or something, and it was taking her a while to come back. Then I heard a knock. Turns out the doors had closed on their own when she left, and I didn’t notice. She thought I had closed them for a call or something. She went to get maintenance, and they locked the doors open. I need to ask her if they finally fixed them!

        1. Itsa Me*

          I didn’t witness this, but we had a client visitor at a site location not in the US. They have security badge readers to open doors going both in and out. If you don’t swipe on your way in, the badge reader won’t let you out. The visitor had not swiped his badge entering a training room, and everyone else in the room left but he stayed behind because he needed to make some phone calls. He was trapped in the room until someone came back to let him out! I suspect this couldn’t happen in the US because of fire codes, but it was crazy!

  33. TotesMaGoats*

    Big event at work with big wigs from our city police department. Kicking off a major partnerships. Lots of money involved. President of my university was there. Everything looks great. My boss walks around the corner to say good morning and….

    Same exact suit-seriously
    Same hairstyle (french twist)
    Same jewelry (black pearl dangle earrings)
    Same shoes

    We just stare at each other because it doesn’t help that we are both the same height and hair color and body type. Then we laughed and resolved to always check our closets before big events but that wasn’t the only matching outfit we had. Did I mention there were pictures to be taken in all our twinning glory?

  34. sparty07*

    After a few margaritas at a welcome dinner, I said one of our VP’s was the CEO’s whipping boy. Meant to say it along the lines of when the CEO needed an answer, he turned to this VP even if it wasn’t in his official responsibility/wheelhouse.

  35. Rincat*

    I don’t really have a single, grand awkward moment, but I used to work for a boss who was so much like Michael Scott, it almost made me cry sometimes. Some awkward moments:

    – When I was pregnant the first time, he asked me how I was doing/feeling as I was heading towards the bathroom. He then realized where I was going and said something like, “Oh go pee! That’s fine! Not that you need my permission!…I mean I’m not interested in that!…I mean…” and kept backpedaling (while I needed to pee really badly!). This was in front of a big group of coworkers.
    – He plugged his daddy blog often, sometimes in meetings with clients and execs.
    – Once he was carrying around a pink travel mug and desperately wanted people to notice it – he would stand in someone’s door and clear his throat and take a big, obvious sip. When we didn’t ask him about it, he said, “Oh, this pink mug? It’s my wife’s, ha ha! No other clean mugs today. Not that I’m too insecure in my manhood to use a pink mug.” My coworker and I were like….wtf? Who cares?

  36. NoMoreMrFixit*

    I have a couple of embarrassing stories from my days working tech support in higher education.

    1. Had a helldesk ticket to look into a problem for a user who wasn’t returning my calls for more info. After a few months I left him a polite message that since I had yet to hear back I was closing his ticket. The next day I walked in to see his black draped photo in the main lobby. Seem he had been on the waiting list for a transplant and died before a donor could be found.

    2. Walked into a classroom later in the day to discover a pair of students passionately getting it on in the middle of the room. I stepped back, closed the door and marched back to my office. Managed to keep a straight face until I sat down at my desk, at which point I cracked up laughing. Best part was a couple of my coworkers were taking a night school class in that same room! I suggested they sit closer to the window than the door.

      2. NoMoreMrFixit*

        force of habit. Been calling it that so long I automatically type that instead of helpdesk. I could probably write books on why they deserved that nickname but better to leave those memories suppressed! :-P

  37. ZSD*

    I would love to win this book!

    I wish this were a funny story, but it’s really just simply awkward: back when I was president of my grad department’s student organization, we were in the middle of having elections for the next year’s leadership when a student from another culture just went on way too long (by American standards) in talking about a problem she had with a professor and asking the candidates how they would help her. What she was doing was probably fine in her culture, but from an American point of view, it just wasn’t something to be brought up in that context, and we were all looking at each other wondering how to bring the meeting back on track without offending her. Unfortunately, I as president completely failed to step up, and eventually another student stepped in and suggested we table the discussion.

  38. Namast'ay in Bed*

    A coworker of mine was heating up a microwave meal and walked away while it was cooking since she could hear the ding from her desk (small office with a kitchenette). Well apparently she accidentally hit an extra zero on the time (think 50:00 minutes instead of 5:00) and after a while smoke ended up pouring out into the entire office. We all had to evacuate while the fire department showed up, but the real kicker was that our office was attached to a hotel and the entire hotel had to evacuate as well.

    We were all laughing about the absurdity of it all, but my poor coworker was dying a thousand deaths as we heard all of the hotel guests complaining and speculating, and then laughing as the firemen carried out the smoldering microwave.

    2. Rebecca in Dallas*

      That exact thing happened to me once! Luckily no hotel needed to be evacuated, but yeah, not my proudest moment.

      1. Cherith Ponsonby*

        That happened to a coworker of mine too, complete with clouds of smoke emanating from the kitchen and one of the fire wardens standing in the doorway making sure no stickybeaks got in. The evacuation tone never actually sounded, so all of us had to sit at our desks attempting to work while the alert tone just kept going and going. After a while we all decided it was close enough to lunchtime that we could just head out.

        As far as I’m aware the culprit never fessed up. (No, it wasn’t me.) But one of the microwaves and both of the toasters were gone by Monday.

      2. Alex the Alchemist*

        Similar thing happened to a friend of mine- She was making Easy Mac in the school lunchroom microwave. Unfortunately, she forgot to add the water before she hit “start.” No evacuation involved, except for the smoking microwave.

      3. Melody Gloucester Pegasus*

        Ha! I did something similar with a combination printer/copier/fax machine at my last job–punched in a fax number when the machine was still set to copier. Fortunately I realized my mistake before anyone came in and demanded to know why I was making like 555,654,321 copies of some inane piece of paperwork.

  39. Arts Marketer*

    For fans of awkwardness I must recommend the podcast Motified! Adults reading their childhood diaries/poetry/writing in front of an audience. It’s endearing and cringy and glorious!

    2. Nines*

      Good call! I adore Mortified! It really is brilliant! The live show is also ridiculously good if you ever get a chance to go!!

  40. Anony*

    My most embarrassing work story was from when I first developed epilepsy. We had a very shaky old projector that would sometimes strobe. I had a seizure in front of everyone and afterwards I cried. I wasn’t embarrassed by the seizure but by the crying.

  41. Saturnalia*

    Oh, just that time I was trying to walk past a group of men on the open stairs, and one of them turns around and gropes the hell out of my breast. I’m choosing to remember it as accidental but the lingering awkwardness (+feeling violated) ruined my day.

      1. Annie Mouse*

        I watched someone discussing that with the female politician involved (yes, it was Jeremy Corbyn’s awkward hi-five attempt!). She was asked if he really did hit her in the chest and her response was along the lines of ‘do you think that would have been my reaction if he had?’ Apparently it was the camera angle and he never actually made contact.

  42. DaisyC*

    I once asked my new grandboss (a guy in his late 50s) if the newly displayed, framed portrait of a baby girl on his desk was his granddaughter. His face deadpan, he said, “That’s my daughter”. Why oh why did I say that?!?! Arrghhhh. Nerves.

  43. Sabine the Very Mean*

    I wish I could revel in my awkwardness and others’ awkwardness but I am genuinely mortified by my own awkwardness and watching others be awkward. Does anyone else feel this way? Does anyone else relate to feeling so embarrassed that you can barely sit through an episode of I Love Lucy? Someone tell me what that is about!

    1. Countess Boochie Flagrante*

      Oh man, you are not alone! I’ve usually heard this referred to as “embarrassment squick” — but watching someone be awkward, even fictionally, practically nauseates me!

      1. fposte*

        Yes! I’m sure there are sociological reasons for it, but it kind of fascinates me as a phenomenon. It’s also funny that if it’s strangers, an awkwardness seems to make them want to talk more to each other even if it’s not about that–suddenly everybody’s keen to share their opinion on the weather or something.

        1. College Career Counselor*

          Fremdschamen! 2nd hand/vicarious embarrassment. One of the reasons that I find it difficult to watch Seinfeld or Curb Your Enthusiasm, or “There’s Something About Mary.” (I walked out of that one) You see the mistake happen, and the rest of the episode/movie is just a cringe-fest.

          1. SarahKay*

            I’ve always avoided “There’s Something About Mary” due to my suspicions that I would find it too embarrassing – clearly I was correct to do so!
            Fawlty Towers is my huge squick; I loved it so much as a kid, but by the time I was 15 or so I just found it unwatchable because of the awfulness of watching Basil Fawlty head deeper and deeper into the most cringe-worthy situations.

    2. Amber Rose*

      Secondhand embarrassment. I suffer it acutely. I’ve been known to leave the room during shows for this reason, and I have on occasion covered my eyes while reading.

      1. JB (not in Houston)*

        Oh, yeah, I do a lot of fastforwarding because I just can’t handle it at all.

        It happens sometimes when I’m in court when another lawyer is flailing in front of a judge. I just have to look down and take furious notes on something else (like a grocery list) so that I don’t have to pay attention.

      2. Merci Dee*

        I absolutely love the movie “Dirty Dancing”, but I absolutely cannot watch during the scene when Baby carries the watermelon into the staff party, and then Johnny’s trying to teach her how to dance. The squatting back-and-forth that she attempts at first is just painful to behold.

      3. JeanB in NC*

        I don’t really feel secondhand embarrassment when reading, but boy do I ever feel it with TV or movies! I can’t watch I Love Lucy at all – same with My Crazy Ex-Girlfriend. I really tried to watch it, but I didn’t make it through the second episode.

        1. Amber Rose*

          I mostly get it with reading comics, tbh. Although a well written novel causes it too sometimes. And it’s silly because I’ll be sitting there, hands over my face, reading through my fingers and feeling awful when realistically I could just… not read that bit. xD

        2. Elizabeth H.*

          I started watching My Crazy Ex-Girlfriend and I really like it, but it is hard to watch because it’s me. It’s way too much ME. It honestly seems plausible to me that I might move across the country to “accidentally” be neighbors with the guy who got away.

          I actually almost did this in that I had been casually dating someone long distance for about nine months, and had been thinking about trying to move there, so I was constantly looking for jobs in my field and in the habit of browsing job postings. Then he met someone local and broke it off. I was idly looking at the job postings in his city out of habit, a pretty cool job came up and after much internal debate I decided to apply to it anyway.

          I ended up getting a phone interview and an in person interview where I flew down there for it. I agonized over whether to tell him about it or not but didn’t. I know I was SUPPOSED to run into him in a mortifying way . . . but unfortunately for story telling purposes, didn’t. (I didn’t take the job because of salary mismatch – but might have otherwise) I had a fantastic time there anyway and all turned out really well. But I still find My Crazy Ex Girlfriend hits WAY too close to home!

      4. eternal teapot*

        SAME. I will watch or read any kind of actual torture or gore, but the second a character sticks their foot in their mouth, I’m out.

    3. Snark*

      My own awkwardness fills me with the urge to crawl in a tiny hole and never emerge. Other people’s is fascinating and delightful – not in a “I shall laugh at your pathetic social skills” way, but in a sympathetic, “oh, I cannot look away, I am cringing in sympathy my poor fellow traveler” sort of way.

      1. fposte*

        Though when I read the ones on here today, there’s an interesting division between ones that give me secondhand cringe and ones that don’t. I totally get why the latter would be embarrassing in the moment, but they’re mostly so mild and so harmless in the larger world that they don’t feel like a humiliation.

        2. Ex-Academic, Future Accountant*

          Mine are very individualized. I love Seinfeld and Curb Your Enthusiasm, but can’t stand bad singing (of any kind — I currently have a neighbor who’s always singing to herself, in an apartment building with very thin walls, and I have to blast something on my headphones to stop myself from being able to hear it). I can’t watch I Claudius or anything else involving speech impediments, because it hits too close to home vis-a-vis problems I myself have. (I read the book in a state of low-grade cringe, and appreciated it, but could not get through the first episode of the TV series at all.)

          I even got called out on my secondhand embarrassment once. Back when I was a PhD student, I was at a conference presenting a paper. My advisor, “Peter”, wasn’t there, and I didn’t know anyone else at the conference (it was a very small conference), so at one of the receptions, I was awkwardly standing around with a bunch of people, including one famous scholar I’d never met before, “John”. He turned out to be the type of guy who “gives people a hard time” as a form of humor.

          I’d introduced myself to these people as a student of Peter’s — he was well known to many of them (smallish field). Someone told a story about being at a conference with Peter many years ago, which involved some confusion because Peter had a backpack that looked identical to someone else’s. Then someone else told a story about *losing* his backpack, at a different conference. So John said “Maybe Peter stole your backpack,” calling back to the first story. And then he and this other guy started riffing on it, coming up with some crazy hypothetical story about Peter stealing the backpack and doing various things.

          For some strange reason, my face is apparently very red by this point. So John, noticing this, says to me: “Why are YOU embarrassed? We’re making fun of HIM, not you.” Well, that didn’t make things any better…

          And that’s how I came to like John Doe, author of Famous Papers X and Y, a whole lot less after meeting him in person.

    4. The Ginger Ginger*

      I can’t watch all the TV talent shows for this very reason. American Idol? Nope! Waaaaaay too much second hand embarrassment. And if I start second hand cringing at any other kind of show? I am off the couch like I’ve been shot out of a cannon. I cannot handle second hand awkwardness in visual media format. Reading it here? Yeah, I can laugh (or skim), but I can’t sit through a tv show or movie like that. *shudder*

    5. Interviewer*

      I can’t watch Ben Stiller movies, because that guy loves to be embarrassed, and I can’t stand to watch it happen.

    6. Anonymeece*

      Yup! I have the same problem. Anytime a second-hand embarrassment scene comes up, I close my eyes and cover my ears. I found out years later that my dad and brother do the same thing! I’ve never been able to sit through: I Love Lucy, Will Ferrell movies, or a bunch of other popular entertainment.

      Interestingly, I’ve read that this is actually a sign of empathy, and not only that, but when people who do this are seeing something embarrassing, it registers in your brain the same way physical pain would.

      So it’s not a bad thing! It just means that you feel someone else’s embarrassment more acutely than others might.

      1. JeanB in NC*

        That’s interesting about the brain thing! I will mute the TV when there is secondhand embarrassment – it doesn’t seem to bother me to watch it if I don’t have to hear it.

        2. hermit crab*

          Ha, I’m the same way. I generally avoid sitcoms and sitcommy movies entirely because I am so sensitive to the secondhand embarrassment thing, but if a situation pops up that I can’t watch, I will sit in front of the TV saying something like “blah blah blah oh Character don’t do that la de dah noooo” until it is over.

    7. Sara*

      I used to leave the room while watching Gilmore Girls with my college roommate and she’d have to tell me when the awkwardness ended. I can’t stand cringe humor.

    9. Murphy*

      Yes, I can’t endure some awkward humor. Neither can my husband. We were watching something recently and he just got up and walked to the kitchen going “AH! I CAN’T!”

    10. Jules the 3rd*

      yep, that’s me too! I can’t watch “Something About Mary” and similar movies because it is physically uncomfortable both at the time and in the future.

      This actually is a part of my OCD – my ‘obsession’ (instrusive thought) is often some embarrassing flashback. And I do mean flashback – I get all the same physical reactions I did the first time around.

      1. College Career Counselor*

        I see I am among my people! Couldn’t watch “After Hours” or large parts of “A fish Called Wanda” that everyone else thought was great.

    11. kible*

      I definitely get it while watching things (anime, movies) or reading it in comics/pictures, but not as much when reading things that are just words. It’s weird. I guess being able to picture it without using my imagination is what hurts.

    12. This Daydreamer*

      I’m in the same club. I mean, I’m okay when people are sharing a personal story for a laugh, but you couldn’t pay me enough to watch the average romcom.

    13. Elizabeth H.*

      Interesting – my boyfriend has this so intensely that he cannot watch any sitcom at all. I once tried to get him to watch a few minutes of Broad City and he eventually RAN OUT OF THE ROOM. He’s an extreme case (he has lots of other uniqueness-es about what he will, aka wont, watch or read) but I totally get this.

  44. shep*

    This was more networking-related than strictly work, but still absolutely mortifying. I was talking to a friend-of-a-friend acquaintance at a party who had a similar graduate degree in writing, albeit from different schools, and spent a good three or four minutes eviscerating one of my old undergrad professors. (He was an absolute jerk, incredibly condescending to me, didn’t think I could write, and the department head–who was very complimentary of my work–even asked me later if I thought he graded fairly and what my impressions of him were (spoiler: NOT GOOD).)

    When I was done, she said, “Oh. He was my mentor during my grad program. He picked me especially because he really liked my work.”

    I’m not normally a blusher, but I flushed so hotly and prickly and tingly that I’m sure I was bright red.

    Still doesn’t change my opinion of the professor, but GAWD I was mortified.

  45. Countess Boochie Flagrante*

    God, awkwardness is the worst thing for me. I suffer from severe embarrassment squick, to the point where I even have to turn off movies/TV shows if a scene hinges around someone being horribly awkward. Full-body cringe.

    Tragically, this doesn’t save me from having terribly awkward moments. I’m the queen of mis-clicking on things, and while I’ve not had a reply-all nightmare (yet! knock on wood!) I accidentally hung up on a very angry financial advisor when I was still in training, when I meant to put him on hold… because he’d asked for my supervisor! It had been a contentious call where the FA was asking me to bend the rules for his high-value client — and since I was so very new, I had no idea which rules were bendable and which were extremely rigid. (As it turns out, the one he wanted me to bend was a rigid one.) So it escalated, with him telling me in very profane detail how my line of business was the worst, how we were all idiots, how he wasn’t going to have his client inconvenienced by some little b***h… you get the idea. And finally, finally demanded my supervisor.

    I said, “Okay, I’ll get him, please hold.” And clicked “disconnect” instead of “hold” on my call toolbar.

    (In my defense, they were right next to each other and I was profoundly rattled. Still!)

    Well, he blew up my manager’s phone immediately — which my manager wasn’t answering, because the moment I realized what I’d done, I raced to my manager panicking at how hard I’d just screwed the pooch.

    End resolution: the client didn’t even care, the FA was being a gigantic tool, and I didn’t actually get disciplined! Just told “hey, try not to click wrong buttons, but you were 100% correct that you shouldn’t do that without speaking directly with the client and this guy’s manager is going to hear about his attitude.”

    1. paul*

      I hate the rise of cringe comedy; I physically can’t watch it. It’s absurd that it gets to me so much but I’ll literally find myself screwing my eyes shut and/or with my hands over my ears…never figured out why it does that.

      Also, our CISCO phones at work have the transfer, end call and hold buttons all right next to each other. Horrible UI.

      1. Countess Boochie Flagrante*

        Personally, I’ve always felt that it relates to some degree to levels of empathy — when you can read a room clearly, it’s painful to see someone stomp through in total oblivion. Admittedly, though, my sample size is a bit small :)

  46. Jilly*

    The most awkward thing that I experienced at work was the aftermath of an awkward event. One day at work I got an email with the subject line “A hug, a rejection, and a goodbye”. Basically an independent contractor sent a company wide email to explain that he had just been fired. Per the email he had been focusing on honoring his emotions and if he needed a hug he wasn’t going to deny himself. And apparently he decided he needed a hug and gave a guy in the bathroom a hug. Completely unsolicited. Said hugee was very, very, very introverted and possibly on the spectrum. He was very good at his job and very helpful, but it was absolutely understood that you emailed him your request – you didn’t go talk to him. And under no circumstances did you make him shake hands, much less hug. So the Hugee went straight to HR and complained and they fired the contractor immediately. When he went to get his personal stuff from his desk, he wasn’t escorted and had time to send this email justifying his actions. The email was quite detailed and completely oblivious to any wrong doing on his part. The OMGs were audible around the office (of about 300 people I think). And many of us started forwarding the email to our personal accounts because sure enough, once senior management got wind of it, IT deleted the email from the server and everyone’s work accounts. 15 years later, if I see someone from that job and say “a hug, a rejection, and a goodbye” they burst out laughing. Unfortunately I lost the email. I had forwarded it to my hotmail account which beginning in 2007 I kind of abandoned and only checked 2-3 times a year so I missed the fact that it was going to disappear. . .

    1. Future Analyst*

      Wow. This is so awful for the hugee, and so hilariously misjudged and oblivious on the part of the hugger. Glad the company fired him, but surprising that they didn’t escort him to make sure he didn’t hug anyone else!

    4. Rebecca in Dallas*

      Who hugs somebody (unsolicited) in the bathroom?!?!?! I’m not on the spectrum and I’d probably be running to HR, too!

    5. Countess Boochie Flagrante*

      Please tell me the huggee was just washing his hands or something, not using a urinal at the time…

  47. Sofia*

    Not all that awkward but probably a sign I shouldn’t be reading this website at work: in an email I called my manager Fergus.

    Her name is not Fergus.

    1. Detective Amy Santiago*

      And that’s when you desperately hope your manager doesn’t read this website (even though it sounds like she could benefit).

    2. Jesca*

      Haha I once kept texting my boss and referring to him as Patricia. That was not his name. He is a man with a male type name. I had been working with him for 2 years. I don’t understand myself.

    3. SusanIvanova*

      The VP of Engineering at my smallish company decided to make people move offices for no reason other than he had the power to do so. Coincidentally, it was shortly after the Dilbert cartoon where Wally brags about controlling cubicle assignments and calls himself “Lord Wally the Puppet Master”. (The 1995-04-20 strip on dilbert dot com). So someone referred to our VP as “Lord Fergus the Cubicle Master”, somehow he picked up on it without getting the reference, and he _signed off on emails_ that way.

  48. Mrs. A*

    I can’t wait to read this book! Here’s my story: My husband and I had been trying to have a baby for years (we now have a gorgeous 1 year old) and had decided to seek fertility treatments. One day, I was walking out of my appointment and who do I see walking down the hall towards me? One of my coworkers! We had always been friendly but definitely weren’t on that intimate level. Our eyes met and both of our mouths dropped open. I was embarrassed and then curious and then excited (because infertility makes you feel super alone). I grabbed her hand and enthusiastically said “Let’s talk later!” And then was kicking myself, maybe she doesn’t want to talk about it, ugg we work together and now I know something extremely personal…… Anyway, that super awkward moment turned into a lovely friendship and we now have regular play-dates with our kids.

  49. The Other Dawn*

    Mine happened when I was only about two years into my career. I was working in a pretty big bank as a teller manager and many of their branches had just been marked for divestiture, meaning they were sold off to other banks because the local market was saturated; you don’t need two Large Bank branches on opposite corners. Until my branch changed hands, I had to attend monthly meetings that were for other branches of this bank that were sold, as well as other banks involved. The meeting was run by someone who was kind of a district manager and was the one to oversee the branch operations for all the branches involved. She was quite young, maybe 22 or 23, as was I. I aspired to be in her position one day and was thrilled when she asked if I wanted to go to lunch with her while she was on site that day. We went to a little diner next door. We chatted about various things and she mentioned how one day she wants to go back and finish school. Stupidly I asked, “High school?” She said, “No, college.” Since no one in my family had gone to college, including myself, and a few of my siblings as well as my parents had dropped out of high school, it didn’t occur to me that she was referring to finishing her college degree. I really wanted to crawl under the table. Luckily she didn’t let on that I’d said something really idiotic and let the moment pass.

    I’m still That Person, unfortunately. Things just come out of my mouth and I have no idea why I say them. I’ll be talking and things are going fine, and then I try to one-up myself or keep the flow going…and I stick my foot in my mouth every time.

  50. Secretly awkward lawyer*

    I once had to ask my assistant (middle-aged, moderately overweight) to please stop wearing a too-small shirt that would ride up and expose her undergarments. She told me that she knew it was too small, but didn’t want to waste money by getting rid of it. She told me this while kicking off her shoes in my office and rubbing her bare feet.

  51. Jen*

    I work at a college bookstore and we hire a lot of temporary workers for the semester start. It doesn’t pay much, so we regularly scrape the bottom of the barrel when it comes to temps. I was desperate and did a short 5 minute interview with a walk in applicant who seemed promising enough. He told me he also had a friend that needed work and their availability fit with what I needed. I hired them both, put them on the schedule, and didn’t think too much more about it. Their first day, both guys showed up (on time! yay!) but were dressed in Jamaican style with wigs. They then spent the entirety of their shift speaking in fake accents to customers about “island life” and weed. They were both white Americans.

    My boss was not impressed. I didn’t invite them back.

    2. Snark*

      I’m trying to imagine being so high that it seemed reasonable to think “It’s my first day at work! I shall put my best foot forward by putting on a dread wig and making racist jokes LITERALLY ALL DAY.”

  52. Front Desker*

    At about 2 pm on a Tuesday, my BF of two years sent me an email breaking up with me. The next person I saw was the FedEx guy who I had a semi-crush on. He asked how my day was going and I burst into tears and told him I just got dumped. He felt so bad for me that he gave me a hug! My manager sent me home after that as I was clearly too much of a mess to deal with people.

    But seriously, who dumps someone over email?

    1. Funbud*

      Well, Carrie Bradshaw got dumped via post-it note on “Sex and the City”.

      And Alison Arngrim (who played mean Nellie Olsen on “Little House on the Prairie”) divorced her first husband via fax. Seriously. You can read it in her great memoir “Confessions Of a Prairie Bitch”.

    2. Clewgarnet*

      I got dumped via /query in an IRC channel. He told me he’d just got engaged.

      Another time, I came home from work to find a Word document open on my computer, with a long-winded version of, “You’re dumped.” (We didn’t live together – he lived in a different country and was visiting for the weekend.)

  53. Flinty*

    As a new social worker I was conducting a home visit with one of my clients, who only spoke my second language, which I was a little rusty on at that point. After checking their bathroom for safety bars, I told them I would go write (my notes) in their living room. It was only after they stared at me in complete silence I realized I had accidentally told them I was going to go piss in their living room. Mortified.

    1. Future Homesteader*

      Russian? I did that to my host mother. (I told her I was practicing Russian in my bedroom…by pissing!)

      1. Flinty*

        Yeah! I think everyone learning Russian has at some point made that mistake, or the one where you say you prefer to eat food without condoms :)

        (preservatif = condom in Russian)

  54. August*

    Oooohhh my god. The most awkward experience in recent memory was when I finished up a meeting with one of my organization’s community partners, a lovely man who runs a Mexican dance-centered organization. When we both stood up to leave, he (casual guy, Hispanic, works primarily in the art/nonprofit community) held out an arm in what I (white, anxious, receives approximately 4 hugs a year from my mother and my mother alone) assumed was a handshake. Instead, he ended up sort of pulling me forward into a kind of stumbling quasi-hug, where my outstretched hand ended up in his gut, my chin was hooked over his shoulder, and my feet landed right on top of his feet. In retrospect, it probably would have been easily laughed off had I not panicked, squeaked “my meter’s run out, I’ve got to go!” and bolted from the restaurant.

    [shrug emoji]

    2. dr_silverware*

      Whew–those kinds of interactions between low-physical-contact cultures and high-physical-contact cultures are the worst for this kind of awkwardness. Even when you think there’s no cultural split between you and your friend’s family, and then your friend’s mom goes in for a French air kiss, and you’re 14.

  55. bunniferous*

    At a former job, one of the owners died. Let’s just say it was awkward when sales people or others would call or stop in and ask for her… no unawkward way to tell someone the person they insist on speaking to is dead.

    That same job, one of our florists died suddenly smack dab in the middle of corsage season. Yes, dear helicopter mom, little Johnny has to wait for his date’s corsage a bit longer since we are shorthanded….I finally had to tell a room full of aggravated people WHY we were shorthanded. Awkward!

    After that, I don’t get fazed by much workwise anymore!

    1. Not a Morning Person*

      I’m so sorry! That reminds me of a not so tragic situation, no one had died: I had an appointment with a client at one of his businesses and when I showed up to ask for him, the receptionist said, “He’s no longer with us.” That made me think he had died since we’d made the appointment! I dithered around and made some kind of confused excuse that we’d had an appointment and was there someone else and the receptionist said no. So I left and went outside to confer with my colleague (the meeting was to do some work outside on their lot). We spent just a couple of minutes commiserating about what to do since our client was apparently deceased, and then the client walked up to our van and waved at us. He wasn’t dead, he’d just moved his office to one of his other businesses. I have no idea what his receptionist was trying to convey to us, surely not that he was dead but perhaps that he didn’t work there? But he was the owner!

    2. Faith*

      Ooh that reminds me of another awkward story I’d forgotten about. At my first job, during my first or second week, I was assigned the task of calling all of the former winners of an award my organization gave out, to invite them to attend our upcoming conference. I really hated talking on the phone (still don’t love it, but I don’t actively hate it as much as I did back then), so this was already giving me a lot of anxiety. Still, I got through the first several calls OK.

      But then I called up one place, identified myself and the organization I was calling from, and asked if I could please speak to Jane. Silence, then finally, “…Jane passed away a year ago. I thought you knew that?” I was mortified and quickly explained that I was new at the job. My coworkers did know that Jane had died, but had forgotten to tell me/remove her from the list. They followed up with the organization I’d called to further explain, and there were no hard feelings or anything, but I was so embarrassed.

      1. bunniferous*

        As someone who had to field calls like that, trust me, we understand. I would have thought everyone knew about MY boss since her battle with a brain tumor had been in the paper and everything, but it happens. No worries!

  56. Petite Noob*

    I had a one on one meeting with a coworker in a huddle room. After we got through our topic of discussion, he said “Oh, Petite Noob, I knew an actress with your same name in the 80’s. I’d definitely rank her a B+ or an A-…” I had no clue what to say so I just went with, “Oh yeah…” Then he went into detail about how cute the actress was and how similar we looked.

    I promptly left the huddle room and that gentleman has never made eye contact with me since and meetings are now super awkward.

  57. Temperance*

    I’ve shared this story before, but it’s the epitome of awkward.

    I was attending Booth’s holiday party as his +1, and was prepared to do the polite networking thing. He introduced me to a couple and mentioned that their daughter had just gotten married, and I congratulated them. I thought this guy was their CEO, so when his wife whipped out the photo albums, I rolled with it and pretended to be interested in seeing 300 photos of strangers eating in what looked to be a firehall.

    She pointed out her 3 daughters, and told me how proud she was that they were all virgins and how she raised them to be pure for their husbands. She then told me how the groom’s brothers pulled her aside to let her know how her daughters were all “nice girls” and they hope to meet pure women when they get married, too.

      1. Temperance*

        The more hilarious part of it was when Booth’s friend also looked at the pictures and later yelled THERE’S NO WAY ANY OF THOSE GIRLS ARE VIRGINS

        2. boy oh boy*

          I almost never laugh out loud at stuff online but this has brought tears to my eyes…

          Who was the couple? I assume not actually the CEO and his wife?!

  58. Can't Believe I am admitting this*

    The most awkward/embarrassing moments of my life have unfortunately involved me being sick to my stomach.
    Last year I flew to Europe. Prior to getting on the flight I had two beers in the airport. Unknown to me was that this beer would not agree with me at all. Going thru the flight I kept feeling worse and worse but I kept thinking that I could make it off the plane to the airport. As we are sitting taxing to a gate – whoosh I end up vomiting all over myself and the person next to me. I ended up trying to clean myself up in the plane lav while everyone left. I then bought a complete change of clothes at the airport and continued my travel on another flight. Now before being accused of falling down or the like a person I was travelling with who also had two beers at the same place as me had digestive issues and made a beeline to the airport on deplaning. We blame the bar in the airport for not cleaning the tap lines.

    Now the other incident involved me and my future FIL but that is for a different time.

    1. Coalea*

      I was returning to the US from a business trip in Japan and found myself struck with motion sickness during our initial descent. The restroom door was locked. I searched desperately for an air sickness bag, but there weren’t any available, so I ended up vomiting all over myself and the aisle of the business class cabin. I was able to throw my blanket and pillow over the mess in the aisle, but I had to sit there, filthy, for several minutes. As soon as the plane touched down, I yanked my bag down from the overhead compartment and changed my shirt right there in my seat. The only silver lining is that none of my colleagues or clients were on my flight, so they were spared this horrifying sight.

  59. patricia*

    Lunch meeting with a prospective client (someone I already knew personally- had previously worked in his organization- now just trying to get him to hire me after I’d moved back to private practice). He invites me to walk back to his office so I can catch up with other former colleagues- it’s a couple blocks. I’m wearing my “I’m at lunch with a client and don’t expect to be walking anywhere” heels, and can’t figure out how to gracefully slip on the “I had to fly here and wouldn’t be caught dead in heels in the airport” flats I had in my bag. So I gamely huff and puff over a couple blocks of city streets, dodging subway grates and sidewalk cracks, trying to keep up with my client, who is wearing sensible shoes as men do. I’m almost there- it’s across the street- and we have to stop for a red light. I end up on the wheelchair curb cut, and just the slant is enough to unbalance me. I teeter to the right, almost catch myself, totter to the left and backward, and feel myself going down in slow motion. I can observe each leaf on the trees fluttering individually as I descend. End up falling into the street and cracking my head on the pavement. The worst is that I have NO idea how much my skirt rode up- I scrambled to my feet as quickly as possible and pulled it down- but there’s a significant likelihood that my client was made all too painfully aware of the existence of my “off to see a client” shapewear.

    Client did hire me, on the condition that I wear flats forever more around him. He brings it up multiple times a year, so I get to relive that on a regular basis.

  60. ThatOneRedhead*

    I was an RA in college and told a freshman’s parents that I hoped their hotel had clean sheets. In front of my boss.

  61. Whipped Cream*

    This was at my second ever Real Job, which was a supremely toxic work environment. We hosted an event annually for our members that was a very large amount of work, and on the last evening of the event there was usually a free bar for event attendees and organizers to go to. So the team and I are chilling out in there, and our Boss/CEO rolls in about an hour after the rest of us had arrived, already quite liquored up. The bartender of the evening had just started trying to convince a bunch of the party people to do a shot which involved whipped cream and consuming it without using your hands.

    Boss thinks this is a GREAT idea, enthusiastically encourages the team to do it (admittedly I partook because, well, I was young and unaware of what a non toxic work environment could be like). Anyway, Boss is drunk enough to start that somehow she manages to get the whipped cream on her back?? while doing this shot. And doesn’t notice for at least half an hour, during which the team and I keep snickering to each other (a large part of the toxicity was from her leadership). I was partially embarrassed for her and how inebriated she already was at a membership event, but also was enjoying some pettiness at her making a fool of herself with the board in the same room.

    1. Whipped Cream*

      email! Also I forgot to mention that Boss showed up with her hair tousled from a romp with previous past president of the board, at least according to previous past president. Ugh.

  62. IKnowRight?*

    One of my colleagues generally works an earlier schedule than I do, so we’re rarely alone in the office together. One evening a few months ago, we were the last two people in the office, and out of the blue, this person asked me “Do you hate me?” (Side note: this person has talked about mental health issues that could explain why they might incorrectly believe people don’t like them, so I wasn’t 100% caught off guard.)

    I was horrified, and pretty much wanted to leave the office ASAP. Instead, I told them no, and we talked about it in a way that I think was helpful for us both, but it was easily the most awkward situation a colleague has ever put me in.

    1. JeanB in NC*

      I mean, what can you say to that? “Yes, I hate you – every time you staple something I think there’s a bomb going off!”

  63. Horse Lover*

    Okay, so my first job was as a bank teller. The branch I worked for had 3 sets of sister-in-laws working there and they brought their family drama with them every day. One of these sister-in-laws was having an affair with our branch manager and the other side of her family vehemently disapproved.

    So, one day Sister-in-law #1 was “in a meeting” with the branch manager in his office. Only, we could all see in the glass windows they were not in his office. They were in his private bathroom. Sister-in-law #2 needed branch manager for actual work and stood, beating on his door and ranting for the whole branch (customers and all) to hear about what they were mostly likely doing in there, how SIL #1 was a harlot, details of the whole affair, etc, etc. It was painful and went on way too long before anyone was able to get her to stop and leave. Then branch manager and SIL #1 just calmly walk out of his office and carry on with their day like nothing happened.

    There were so many awkward moments there, but this is the first one that came to mind.

  64. an infinite number of monkeys*

    About 25 years ago, when I was a mere slip of a corporate shill, we had a new guy start on our floor. Word around the office was that he’d recently tried out for, I think, American Gladiator? He was athletic and had what I would later come to think of as “marketing hair.”

    One day I crossed paths with him on the way to the elevator, and looked back over my shoulder to check out his butt. He was turned around doing the exact same thing. Our eyes met. There was a Moment, but it wasn’t sexy and endearing like a romcom. It was just uncomfortable.

    I’m much more discreet now that I’m older.

    2. Montresaur*

      Ha! “… when I was a mere slip of a corporate shill” is my new favorite idiom mashup (surely there’s an official term for that kind of wordplay? Will investigate)

  65. Jesca*

    I know I posted this before, but I will again.

    I was once working at a place with a boss who kept heaping tons and tons of work on me and then complaining why my actual job tasks were slowing (ya know – that old tired story). Well one day she was going on about this while I was at my desk and I just whispered “I quit”. She asked me if she heard me correctly, and it was so awkward that she heard me that I just responded with “I quit”. AND THEN to add a touch further awkward to the mix, picked up my bag, gave her this kind of dismissive wave, and with a casual “bye” I walked out … never to be heard from again.

      1. Jesca*

        I literally did not tell anyone for years how I left this job! Not even close friends. I mean, I still don’t understand any of it. Alison, this is why I need this book!!

  66. Anonymous for this*

    This one’s not that bad in the grand scheme of things but it’s the best I can come up with right now.

    I was asking a manager in our department about our dress code and culture because I wanted to know if there would be a problem if I wore a skirt with unshaven legs when the dress code was business casual. What I meant to add was, “I don’t mind being seen as a raging feminist.”

    For some reason, my mouth replaced “feminist” with “lesbian.” Which statement is also true, but wasn’t the effec tI was going for.

  67. Revolver Rani*

    This wasn’t technically at work – it was in the Law Review office when I was in law school, which in some ways functions like a workplace (but in other ways does not). I hope it counts for an entry into the drawing. :)

    The background is, years before I ever went to law school, I had been interested in a woman and asked her out. She let me down very gently (she didn’t share my proclivities, and anyway was involved with the man she later married). She really was very kind and lovely about it – an “I’m flattered but…” sort of response that just struck me as deeply sincere. Fast forward 6 or 7 years and surprise! we are in the same law school class – a different university from the one at which we met, in a different state; just one of those funny things life does to you.

    Reader, I still liked her. Not enough to break my heart, not enough to ask her out again, but enough to make me a little stupid around her. When we both joined the Law Review staff I we ran into one another quite often, and so I had lots of opportunities to say awkward things to her – and I took advantage of them. One that I remember with a particular cringe was when she came in having cut her hair into a short style, one that was a little unusual at the time, a little throwbacky (think Audrey Hepburn pixie cut), and it was very attractive on her. I wanted to compliment her on the uniqueness of it. I told her it looked very good. And then, I added:

    “It’s not really in style these days, but it looks great on you.”

    2. Turtlewings*

      “I had lots of opportunities to say awkward things to her – and I took advantage of them.” A+ phrasing. Beautifully mortifying comment. Excellent post.

    3. overcaffeinatedandqueer*

      Awkward law review moment for me:

      Four women staffers, one dude. Someone asks for meds for period cramps, dude is feminist so doesn’t say anything. Then the women and I start complaining about periods. We are all eating leftover pepperoni pizza.

      Someone mentions how the clots are the worst, how they can be as huge as a quarter or bigger, how gross it is.

      Sole guy pushes his pizza away, literally green, and groans, “I can’t look at pepperoni right now!”

  68. LeeGull*

    Oh my gosh, I want to win but if I don’t I think I need to buy this book anyway!

    I once went for a handshake…and you know how you sort of catch thumbs and then shake? I missed his thumb. And grabbed his wrist. And then neither of us knew what to do so I just awkwardly shook his wrist and then backed away and tried to avoid eye contact. Like forever. Like I still don’t think I’ve made eye contact with this person since.

  69. Dixie Thursday*

    I was a young admin, not yet very confident or comfortable answering the phones when one day a guy was leaving a message for my boss. He gave his phone number, followed by a five- or six-digit extension number. The guy then went on to explain that he was just a “little guy” in his organization, to which I responded, “Well, for a little guy, you sure do have a big extension.” My cubicle mate, only hearing MY side of the conversation gasped loudly and I was instantly horrified at what I’d just said. I cringe to this day, 30-plus years later!

    4. Coalea*

      Many years ago at a previous job I was having problems with a database. The IT guy watched me demonstrate on my own laptop and then asked me to try and open the database on his machine to see if the same error occurred. For some reason, he had this crazy little mouse, and as soon as I started using is, I exclaimed, “wow, I’ve never touched such a little one before!” The entire IT department busted out laughing, while I silently prayed for death.

  70. JB (not in Houston)*

    At my boss’s wedding shower. My first office job after college. That job was terrible (we used to say that we all wanted to work at the company where our internal recruiter worked, but the place she described to us in interviews and where she seemed to think she was working was not at all the reality of where we worked), but that’s a story for another day. At the shower, I was sitting next to my boss, which was awkward enough. That it was a lingerie shower was also very awkward, but I could handle it. But when she opened my gift, she leaned over to hug me to thank me. From the angle she she leaned in toward me, I thought ‘oh, ok she wants to do that European thing where you kiss each other on the cheek. That’s weird,” but I didn’t want to obviously rebuff her in front of everyone at her own shower so I panicked and went with it. You can see where this is going. She was not, in fact, leaning in to do a cheek kiss, she just leaned weirdly into the hug. Fortunately I realized very quickly that she just wanted a hug, but unfortunately not until the exact moment I gave her a light, my-best-approximation-ofwhat-I-imagined-was-a-“European-style”-kiss on the cheek. I tried very hard to play it off like no big deal while simultaneously willing a hole in the ground to swallow me up. She didn’t make a big deal out of it, thank God, but I could never really look her in the eye after that.

    Years later, there was an episode of Friends where Rachel does the same thing with her boss, and I still cannot watch that episode on reruns.

      1. JB (not in Houston)*

        Fortunately, she didn’t make a big deal out of it. There was kind of a pause where I could see from her eyes she thought it was awkward and strange, but she then immediately started talking about and opening the next present while I sat there unable to hear or see anything because of the overpowering mortification. Later in the party we had to do that game where you choose teams that compete to make a wedding dress out of toilet paper. Of course my team chose me to be the person getting tp’d, which made things worse for me because the last thing I wanted was for anyone to look at me or even remember that I was there. I don’t remember if our team won, I just remember wanting to Incredible Hulk myself out of the toilet paper dress, run out of the party, and never return to work.

  71. Anonish*

    I used to work in the headquarters of a paint and sip event company. My aunt was in town from another country for a family wedding, and she and my mom were having lunch nearby so they dropped in to visit me at work. In a room full of my coworkers (and covered in paintings from our events), she asked in a loud voice, “So what IS a paint party?” I gave her a quick explanation to which her response was, “Well, who would ever want to do THAT?”

    Thanks for your opinion about how we all make our living, Aunt P.

  72. Chylleh*

    Years ago I ran into an awkward situation while working in the children’s department of a library. A young student was doing a project on taxonomy and asked an employee for books about the subject. The research eventually led to her, the student, and myself trying to find a book with the animal kingdom hierarchy chart for his project.

    The student ran off to bring a book back to his table where his family was, and another coworker came over to see if she could help. Original coworker said we were looking for a taxonomical chart, and explained, “It’s about animal classification. You know – kingdoms, phylums, orgasms, that kind of thing.” We all shared a moment of stunned silence while her face turned an increasingly deeper shade of red as she realized what she said, then all of us burst into laughter. We were just glad the student and his parent were away at the moment.

    1. Chylleh*

      Annnnd I forgot my email address in the last post. I promise this isn’t an attempt to create another awkward moment, game the system, and get two entries.

  73. The Ginger Ginger*

    Oh man, this book sounds awesome!

    My first job in highschool, I worked at a jewelry store in the mall that also pierced ears. One afternoon a very big, fit, late highschool/early college age guy (looked like a linebacker) came in with his mom. They split an ear piercing pack. I pierced mom’s ear, then the guy’s ear. Easy peasy, cleaned the piercing, gave them the whole memorized spiel about care, and called it done. Guy stands up from the piercing chair so they can go pay and PASSES OUT. Hits the floor like a load of bricks, takes down an earring display, the whole shebang.

    I didn’t feel awkward myself as I went into triage mode, busted out the smelling salts, cleared the floor, sent a coworker for a sugary drink, all that. But I still can’t help thinking how mortified he must have felt, passing out in front of his mom and this little 16 year old girl – and half the mall – from getting his ear pierced. Poor guy. (Of course, now I understand all about vasovagal syncope, because I’ve brushed up against it myself a couple times, but man, the sympathetic cringing is REAL.)

    2. zora*

      [raises hand] Vasovagal syncope over here!!!! I super know how that guy feels!! ;)

      What’s funny with mine is, if it’s just me, I’m fine. But seeing someone else get ‘stuck’ is way more likely to make me pass out! So, in his case, it would have been because my mom was there, not because I was getting pierced. It’s so weird and so much harder to explain!

    3. JDusek*

      That happened when I was 10 years old and my aunt took me to get my ears pierced for my birthday. Afterwards, we went to Hallmark in the mall and my aunt saw me fainting and caught me. Took me to sit down and I threw up.

    4. The Ginger Ginger*

      Mine isn’t even needles necessarily; I’ve had some issues with it when waiting for procedures – like getting my wisdom teeth out or when I had a cyst removed in an outpatient surgery. There’s something about getting a jab while ALSO stressing out just waiting for the procedure that lays me out. Blood donation? Flu shot? Totally fine. Leave me alone to stew about impending sedation then come in and stick me with the IV? I better be horizontal or I will find my way there in spectacular fashion.

    5. Adlib*

      Been there. I used to have this reaction every time I got a shot or had a blood draw. It finally went away when I had multiple tests for some health issues I was experiencing which led to a spinal tap. After that, no weird reactions to needles. I’m so relieved!

  74. CoveredInBees*

    I worked at a nonprofit for a CEO who was not careful about talking about “touching” donors as in being in contact with them about our work and their interests. She also repeatedly talked about not being dressed when what she meant was “dressed up”. I was on a call with her and a prospective funder when she mentioned that she and I weren’t dressed. I jumped in to clarify she was referring to casual Fridays but I’m pretty sure I could hear the poor guy blushing.

    The funniest was when an attorney (thankfully, not me!) said, “Thanks, I love you too.” to a judge. He was distracted and said it in a way like he was ending a phone call with a loved one. The funniest part was that it took the judge a few beats to notice. I am certain that there was nothing going on between the two of them but they were very careful after that.

    1. Revolver Rani*

      I worked with an attorney who once said “okay goodnight, love you” to a partner (meaning, a partner in the law firm) at the end of a phone call. She had been working hard all day taking a deposition, and was tired, and had called the partner from the airport to debrief, and just kind of automatically signed off the call the same way she would to the person she lived with.

  75. Languages Are Difficult, Okay?*

    My boss had the entire team over to his house for a dinner party. At some point I — the youngest person there, the only woman, and the only non-native speaker of the relevant language — am telling a story about my day, in which a moderately-famous older gentleman had become mildly annoyed at me over something trivial.

    My co-worker chokes on his drink. “This guy did WHAT?!”

    I repeat what I said, which I thought translated to “he was mildly annoyed at me.”

    Dead silence, followed by nervous laughter. I look around, and everyone was blushing.

    Eventually, someone explains that the phrase I was using didn’t mean that the guy was annoyed at me. Instead, I had just announced to my entire team that a moderately-famous older gentleman had performed oral sex on me.

    1. 2ManyBugs*

      You were reaching for “chewed me out” and missed, right? That’s the only colloquialism I can think of!

  76. The future will be better*

    I work in a profession that involves frequent use of rented company vehicles… Due to medical reasons, I had VERY heavy periods. I once realized I bled through my work clothes, and drove back to work to make sure the truck was okay… It was! But imagining explaining that to my (male) boss was one of my cringey work experiences, and I believe we all need to talk more about periods.

    I also casually chatted with an office boss like he was a fellow on worksite guy once (casual language and likely some cursing), because my old phone showed the wrong number. Eek!

  77. Kadi*

    I have so. many…. but, the worst for me still is when I was 9 months pregnant. I sat in a chair across from my boss’s desk. My legs always had to be sticking out to the side a bit to make room for my belly. She kindly pointed out that I had somehow unknowingly split my maternity pants at the crotch – and my white underwear were clearly showing through my black dress pants. Awesome. Maybe that’s more embarrassing than awkward?

    2. Close Bracket*

      Ooh, visible underpants stories! One day on my way out of the office with my hands in my trouser pockets, I passed passed a coworker walking the other direction and gave him a cheery “Good night and have a good weekend.” He didn’t respond, but he did a very small double take. I thought nothing of it until I got to my car, got in, sat down, looked down, and saw that my fly was all the way open and my red underpants were like a shining beacon framed by my black slacks. I had a moment of mortification and then laughed hysterically. I knew he would never, ever say anything to me about it and promptly put it out of my mind.
      I actually felt a little bad for him bc I am a woman and he was a proper Syrian guy. He was probably more embarrassed than I was.

      1. Cate*

        I can’t recall if this happened to my friend or if he was relating a story about a colleague, but whoever it was he learned the hard way to only wear black boxers when playing the Phantom (in Phantom of the Opera, on Broadway) when his trousers split and he had to do the entire final scene with red boxers on display through a knee-to-crotch hole.

  78. VelcroShoes*

    I went to France to work in a museum/post-office (It was a very unpopular museum of the postal system in the morning and a fairly successful post office in the afternoons. I was sent by my mother in a misguided attempt to instil in me a love of French culture – it paid off in that I now have a deep seated desire for brie when posting things and can swear broadly about stamps in perfect French.)

    On the first day, the other women who worked there offered for me to go out for the lunch break. I was an anxious teen (and now an anxious adult!) so I politely declined and hid inside to read my book and eat my packed lunch. The two women smiled at me (French-ly…?) and started nattering away in fast French as they sauntered off for a (very long) lunch break, locking the door behind them.

    1 hour 30 later they returned and life resumed as normal. But in that 1 hour 30 I’d discovered dusty old museums of the post office are kind of terrifying and I desperately wanted to be outside in the sunshine. Particularly when a large dusty model of a French postal worker from the 1940s crashed over with no encouragement… It was spookier than it sounds! I made a decision to bite down the awkwardness and tell them the next day that I wanted to go explore.

    So the next day, as lunch rolled around I took my heart in my hands and prepared to tell them I wanted out… Except, without asking, they simply left. And locked me inside. Staring balefully out at the summer weather, I was well and truly trapped inside without any lunch whatsoever. And the pattern repeated every day for the next two months (luckily I got my weekends off). By the end I had learned to pack my lunch.

    Awkward an encounter as that was, the worst moment was when a visitor tried to visit the museum during lunch. Seeing me haunting the inside like a pale chubby English ghost, they could NOT understand why I wouldn’t let them in (the French are passionate learners of postal history, clearly). He spent a good 10 minutes staring through the glass door, trying to gain access to my carefully held treasure trove of knowledge. He became really quite frustrated with my apparent lack of willingness to share my dusty prison, as I stared awkward and blank, unable to communicate my complete lack of keys.

    If only he’d known how pleased I would have been to swap.

    2. Eye of Sauron*

      This hands down is the funniest story I’ve heard/read in a long time.

      THANK YOU! I really needed it today :)

      1. VelcroShoes*

        Maybe they thought I should just give my life for the sake of French postal history… There might have been a fire exit, honestly it was about 15 years ago so I can’t remember!

  79. beanie beans*

    I can’t wait to read through all of these later! Here are my two most awkward work moments:

    1 – Boss stops by my desk while I’m struggling to get my hand unstuck out of a Pringles can.

    2 – I was listening to a webinar so I decided to french braid my hair into two braids while I watched. As soon as I finished one, my grand boss stopped by my desk for a chat about a project. We had maybe a 5 minute conversation and rather than unbraid the braid, I sat there through the conservation with one side of my head braided and the other side down.

    1. ggg*

      Once I stopped by the desk of an admin at work, as she was taking out a weave. There she sat, talking to me, in the middle of the work day, with half a head of hair and a trash can full of weave remnants.

    2. Boy oh boy*

      Pringles can just made me snort on the train because the awkwardness is so relatable and the mental image is so funny.

  80. LittleRedRidingHuh..?*

    Oh my, where to start?

    Let me tell you about that time when I decided to look cute in work, and for the first time in years, wore a skirt – only to tuck it into my underwear by accident after using the bathroom…and then walking back to my desk in front of our CEO giving a tour to potential clients. And if that wasn’t already enough, one of them remarked in a very matter of fact tone that it was very unusual to see a full moon this time of the day. Cue to me excitedly running to the window and asking: Oh wow, really? Where?

    Thankfully my CEO had a good sense of humour, gently told me about the “situation” and kindly let beet-red faced little me go back to work. I couldn’t look him in the eyes for quite some time and never wore skirts to work or elsewhere again.

    3. Detective Amy Santiago*

      I once had a very kind woman chase me down in the hallway outside the restroom to let me know that my skirt was tucked oddly and not covering my behind.

      1. AvonLady Barksdale*

        I am still mad about the time a co-worker DIDN’T tell me about my skirt tucked into my Spanx. Still mad. It was about 8 years ago and she wasn’t a very nice person anyway. I vowed to always say something, gently, even if it’s awkward.

        1. Clewgarnet*

          I once ran up an escalator at a railway station to tell a total stranger that her skirt was split.

          I didn’t tell her that a group of men had been following her through the station leering. We were ‘coincidentally’ going to the same platform, and they stopped following once she had company.

    4. Murphy*

      I got a dress stuck like that in the bathroom once. Thankfully, there was another woman in the bathroom washing her hands at the same time and she said “Um, I think your dress is caught on your sweater.” I realized what happened and said “Thank you for not letting me go out like that!” I’ve gotten over it, but I don’t really know this woman and I felt awkward for a little while after.

  81. StillBlushing*

    Imagine me… young, mid-20’s year old female, having a good day.. just cheerfully walking down the hallway at work and swinging my arms a bit (I don’t remember why, but clearly I was having a good day!). My older male supervisor is walking towards me… unfortunately my swinging, cupped hands happened to intersect with his body at the exact moment and I ended up CUPPING HIS GENITALS! I honestly think I couldn’t have done that if I was trying, but yep.. I managed to do it. He kept walking, I stopped with a look of horror on my face and he just said “no no” and kept going. Yes, I now keep my hands close to my body at all times!

  82. Sarah*

    A manager in our department was about to go on maternity leave and a card was making the rounds. I didn’t know what to put in it (about 20 people had already written “congratulations!”) so I wrote “well done!” Still cringing 5 years later.

      1. Live and Learn*

        I like it! When I was 8 months pregnant my husband and I went to a concert at a small local club. We were sitting at the back of the venue chatting with (VERY drunk) strangers at the next table over and they somehow didn’t notice my condition until I stood up to go to the restroom. When I stood, the drunkest guy yelled out “Wow! Congratulations dude, your seed is strong with that one” while pointing at my husband.

  83. Kate*

    I was at a kickoff meeting for a new project where I would be working with woman I had never met before. There were only about 5 of us in the meeting, her and I plus 3 other colleagues, and at one point she started giving me these weird looks from across the table. Like she kept motioning with her eyes, and I kept thinking, “What the hell is wrong with her?” Finally I look down to find three (THREE!) of the buttons on my shirt had come undone, so basically my bra was just out there for the world to see. Luckily, the other three were so wrapped up in discussion that they didn’t notice me rush to fix it. We only had one other meeting after that, and then I guess that portion of the project died, but we are bonded for life now.

    1. Samiratou*

      Oh, this reminds me of an awkward-for-all moment in a meeting once. Woman leading the meeting across the table from me had a button come loose so she was showing a bit of bra, if viewed from the correct angle (which pretty much all of us were because we were sitting to her right or right-ish and the projector screen was to her left). I sat there trying to find a way to bring it to her attention that wouldn’t draw MORE attention to it. She noticed after a couple minutes and chastised us (gently) for not letting her know and both I and the woman next to me protested that we had both tried to think of a way to let her know but couldn’t come up with one. Table was too big to nudge her under the table, she was presenting so no quick IM, she was looking at the projector screen and not at us for a Significant Look, and she was kind of on a roll so there was no lull to do a quick throat clear and clothing adjustment to try to let her know. Literally the only way we could have let her know was to interrupt “Hey, J, your button is undone! You might want to fix that!” which would have been as bad or worse, I think.

    2. boy oh boy*

      Oh no. This reminds of the worst wardrobe error I’ve made.

      So it was quite hot in the office. No air conditioning. There were nine people in a tiny conference room for 12 to 18 hours a day working on a huge project. We run small fan that does very little, we buy ice cream, drink cold drinks, etc. It’s nasty but just about okay.

      One foul, baking hot day I start getting PMS, which makes me super sweaty and I start feeling like I’m being roasted alive. I fan myself, have some cold water, and finally take off my thin button-up cardigan, leaving my vest top. It’s not ideal, but not obscene, and everyone’s too tired and sweaty to care, right?

      Nope. When I pop to the bathroom a day later, I realise my vest top is kind of translucent, and all could see my nice bra with a pretty pattern of cherries on it.

      I cringed like hell, threw that top out and wore thin silk/cotton blouses for the next three weeks.

  84. Eye of Sauron*

    I have 2, one mine and one related to me by my boss.

    1. Mine: I was running up a public but out of the way flight of stairs one day, I should note that I took these stairs daily and had never seen another person on them in the 2 years I worked in this building. As I was careening around the corner late for something I crashed into a man who was also in a hurry running down the stairs. Of course he had a handful of papers that exploded all over the place plus a two men flanking him from behind that crashed into both of us. My lunch was launched all over the stairwell. As you can imagine it was quite the chaotic scene. Once the papers settled and we all helped each other stay standing, I finally looked up.

    Hello Mr. Governor! Why yes, I had just crashed into the Governor of our state. Seriously, what are the odds?! Worst part was is that I got into trouble for returning late to lunch. I didn’t even bother to try and offer my excuse, who would believe it. I think I mumbled something about tripping in the stairs.

    —
    2. We’re at a large 500+ person expo put on by my company for our customers. I’m talking to my boss who is wearing a horrified look on her face and oddly a different suit than she had been wearing in the morning. She pulls me aside and tells me this tale.

    “I was at a lunch meeting (catered burrito bar) with Teapots inc. and Fergus our account exec that handles the Teapots inc account. All of a sudden and without warning Fergus spews/throws up guacamole all over the two people sitting next to him and me! It turns out he was choking on the guac and his body expelled it*. It was awful, it looked like the scene from the exorcist. Guac was hanging from one of the client’s long hair. I had it all over me and had to change”

    *He was ok after he dislodged the guacamole but it was a serious situation

    1. Eye of Sauron*

      Oh wait… I remembered another one. (seriously I’ve been trying to forget it).

      I was sitting in a conference room talking to one of the contractors assigned to my project. There was another guy in the room with us who worked with me at my company. Anyway, I was sitting next the contractor, and had taken a big gulp of water, right as I had a mouthful and I was going to swallow, a stealth cough came out (I had been getting over a cold) and spit the water straight in to his face.

      OMG I was mortified!

  85. Reanis*

    During a department meeting while we we standing in an echo-y space, I internalized an earth-shattering burp. To my horror, this did not muffle the sound. I furiously tried not to blush as my co-workers slowly deduced it must have been me (a relatively small woman). And I had a serious urge to whistle nonchalantly like a cartoon character.

    1. The Photographer's Husband*

      Hey, you’re not alone. My wife (also a relatively small woman) out-belches me (a somewhat large male) in both frequency and volume on the regular. She then calls out any humble belching I attempt as ‘gross’.

  86. PugLife*

    I had a phone interview a few months ago that was….. okay. There were two people on the other end and I’m not great on the phone to begin with. There was a lot of stopping and starting and talking over and “oh no, what were you saying? go ahead”. Plus it was a seriously last minute interview – I heard about it from a friend, applied, got a call THAT DAY for an interview the next – so I was not especially prepared.

    I ended this fairly awkward interview by saying “So, I can’t quite tell… are you offering me this job?”

    In my defense the interviewer’s verb tense was very much “these are the things you’ll be doing, we’ll want to talk next week about XYZ project…” which I realize is easier than saying “the person in this job will” but UGH.

    I got the job but it took a few days before the feeling of “oh god I want to die how could I have said that” went away.

  87. Squirrel!*

    A co-worker at my previous job was really weird–she would loudly talk to herself (like, full conversations where she would be two people talking), yell at her phone for ringing, yell at her computer and strike it; just a lot of general awkwardness. But the time that takes the cake is when she got so upset with herself for doing something wrong (no one knew what it ended up being), that she started slapping herself in the face, loudly and repeatedly. And we were in an open office. And we were all sitting in a 15-foot radius around her. She probably slapped herself a good dozen times, then went back to work. No one said a word.

    2. Squirrel*

      And a personal story I just remembered after reading someone else’s similar story: I tripped and fell over a camera cable at a company-wide meeting (I was unhurt though). I’m talking literally every single person in the company was there, they had even bused people in from a satellite office in a city an hour away to make sure everyone was there for it. Not only that, but I fell down *in front* of another camera. And I was holding a plate of food, which went everywhere and some people got hit by it. A very nice woman came over towards me to help, but all she did was pick up the food I dropped, put it on the plate, and then hand the plate to me as I was trying to get up off of my knees.

  88. Kitkat*

    Not sure if this counts, but several years ago I was having a coworker over to dinner for the first time, and wanting to impress her, I decided to make some deep fried plantains, also for the first time. When she texted me to let me know she was about to arrive, I was obliged to text her back that I had overheated some oil, set fire to my kitchen, and forced my entire apartment building to evacuate. Then one of the firetrucks broke down and that shut down the whole block for several hours. Since I couldn’t get to my car, my coworker took me to Walmart to get cleaning supplies, air freshener, and wine, which we then drank together in my smoky apartment when we could finally get back in. It actually totally bonded us and she is now one of my best friends, but at the time I was completely humiliated.

  89. LemonLime*

    I think I told this story here once, but the most awkward work moment I had was a job I only lasted in for a single day.
    It was advertised as an office assistant for a guy who worked out of his home. I expected to help with paperwork and such, but my first day he set me a bunch of personal tasks, like folding his laundry, scrubbing his toilet, ironing his shirts, and making his lunch. The moment I knew I couldn’t handle this anymore was when we sat down to lunch (the one I had cooked) and he reached for my hand to hold as he said grace. I was so taken aback I let him hold my hand for a good 30 seconds as he prayed.
    That night after I got home I emailed him that the job “wasn’t a good fit” and I never went back.

  90. Dealtwiththis*

    I still cringe about the time that I hugged my CEO. I was hosting my first big work event and he showed up to support me. For some reason, I was so relieved that the event was going well that I finally felt like I could let my guard down and was happy that he was there to support me that I just….hugged him. Ugh. I hope he has forgotten about it.

  91. Sunnyside*

    I’m a college admissions counselor and I mostly work with high school seniors. My office has a desk, but there’s also a small table with a few chairs so that I can have meetings with families. My desk chair is the hydraulic kind on wheels that also tilts back. One day, I was wearing a brand new skirt for the first time to work. I had an appointment with a student, a young man who was probably 17 years old, and he was there without his parents. I brought him into my office and I sat in my desk chair and then rolled over to the meeting table, and as usual the chair dipped back a bit. No problem, just zoomed and readjusted. For the rest of the meeting, the student was very distracted. He had a hard time keeping eye contact, I had to repeat questions, he kept losing his train of thought. This isn’t that unusual – these sorts of meetings are often the first time that a student has to engage as an adult, so I just plunged on ahead. I wrapped up the meeting and walked the kid out , then came back to my office and saw a single OB Tampon laying on the ground. It had fallen out of my shallow skirt pocket when I tilted back! Poor kid was sooo embarrassed! And what I thought was an inability to make eye contact was actually him repeatedly looking at the tampon sitting in the middle of the floor!

  92. A Bag of Jedi Mind Tricks*

    At OldJob, my co-worker showed us an email he’d received from the Wife of another employee that he counseled. Seems the email was clearly meant for her husband as she went into GREAT detail about their wonderful, romantic, night before. Ha. my co-worker responded with a “Um, I don’t think you meant to send this to me”. The wife wrote back, “Oops”. That was pretty Awkward.

    1. JB (not in Houston)*

      Once at one of my old jobs, somehow a coworker’s long email exchange with her boyfriend along these lines got sent to the entire company. Out of sympathy and secondhand embarrassment, I did not read them, but a LOT of people did. I felt so bad for her, and I always wondered how it happened because for the life of me, I cannot figure out how you can try to reply to an email and accidentally email the entire company instead.

      1. Not a Morning Person*

        Not me but a coworker: Her husband emailed her an appointment for her Outlook calendar for a date to have some “fun times” at home. He was apparently both funnier and more graphic in his description. He didn’t make it “private” and since we have shared calendars, many staff saw this on her calendar before she noticed and made it private!

  93. a story I tell all the time*

    At my old job, we had a small “New York deli” cafeteria on the campus, Mikey’s, run by a sweet guy, Mikey. I ordered a bagel, as Mikey handed me that bagel, he said, “Enjoy your bagel!”

    I accidentally said “You too!” in response. This didn’t bother me–I was feeling jolly–and I decided to play it off with a little joke. So I added, “Haha, I mean, you can’t enjoy MY bagel…”

    Unfortunately, it wasn’t a real polished bit, and I tend to mumble. So as if my bad joke wasn’t bad enough, Mikey said, “What? ….Oh, you were talking to your bagel.”

    I left immediately and never returned.

    1. Murphy*

      My husband worked at a movie theatre and said when he would tell people to enjoy their movie people would constantly respond with “You too!”

      1. a story I tell all the time*

        Oh yeah, I do it all the time and it doesn’t embarrass me…I just shouldn’t have doubled down :D

    2. DecorativeCacti*

      Reminds me of the time I got to the ticket counter of a movie theater and when they asked what I was there to see, I said, “A movie!”

      1. smokey*

        DecorativeCacti, no offense to anyone else but for some reason this made me laugh the hardest out of anything submitted so far!

  94. Looselips*

    I was leading a meeting to plan a museum opening, and I was successfully suppressing my annoyance with everyone in the room. Until I referred to the ribbon-cutting as a ribbon-cunting. Ten years later I still avoid that phrase!

  95. Bolistoli*

    My old boss was leaving “by agreement” (fired), and we were having an awkward going away lunch for her. At the lunch, in front of soon-to-be old boss (and everyone else at the table within earshot), the big boss and her “favourite” employee joked about how tough it was going to be for “favourite” to do all her work AND do everything she needed to do to prepare and interview for soon-to-be old boss’s job! It was horribly awkward, unprofessional, and frankly, disgusting. “Favourite” is now my boss. We had quite the horrible clique in those days.

  97. JoAnna*

    The most awkward moment I probably had at work was the day I told my (now former) boss in a private meeting that I was expecting my fifth child, and he blurted out, “I’m going to buy you a box of condoms!”

    I just said something like, “We wouldn’t use them anyway,” because ew, dude, none of your business what my husband and I use for family planning. And I think he realized how inappropriate that was because he quickly congratulated me and then changed the subject.

    Second runner-up is the time that company’s controller, who was acting HR (and terrible at it) since the company hadn’t yet hired an actual HR person, ushered the entire company (maybe 40 of us) into a conference room. Apparently what had prompted this meeting was that an employee had been caught watching YouTube videos during work hours (as far as I know, they were innocent ones — work-appropriate, although not work-related) and had been fired as a consequence.

    She proceeded to literally shriek at us at the top of her lungs about how terrible it was to use company computers for personal use, and if anyone was caught doing so they’d be fired immediately, etc. She screamed at us for about 10 minutes while we all just stood there awkwardly.

  98. k m*

    A temp colleague at my first gig out of school had to be sat down by the temp agency and told to wear deodorant. That means the managers noticed and routed to them to deal with… I guess that’s easier than dealing with it yourself!

  99. Errrrin*

    There are so MANY, but a recent goof was when I was describing the collection of resources the library had about Haitian history and instead of saying “Hurricanes and Earthquakes” I said “Hurriquakes.” I then started laughing but the student just stared at me. ¯\_(ツ)_/¯

  100. Seal*

    At my first full-time job many years ago, one of our part-time employees had put in his notice. He came in on his last day with a long piece of crumpled toilet paper hanging out of the back of his pants like a tail. Apparently everyone was so embarrassed on his behalf that no one would make eye contact with him or anyone else in the office. No one, including me, was able to muster up the courage to tell him discretely that he might want to check his pants. Much to everyone’s relief, a few hours into his shift he finally went to the bathroom and came back sans toilet paper. Despite the fact that it was a bit of a gossipy office, no one ever spoke of that particular incident – it was so awkward that it never became part of the office lore.

  101. Snowglobe*

    I was about two more NYU’s pregnant with my second child, and I hadn’t yet told anyone at work. I was a little self-conscious that with this second pregnancy my stomach seemed to pop right out; it seemed noticeable—to me. I was wearing a new dress, not a maternity dress, but with an empire waistline. A manager from another department saw me in the hall and said “New dress? Cute!” My immediate response was “Thanks, I’m pregnant!” In my head that made sense, but I’m sure she was wondering why I made such an announcement at that time.

  102. rubyrose*

    It’s a tossup.
    1. I had been working third shift for several days, covering for someone. My manager and I had a meeting in the morning with a potential client. I fell asleep in the meeting.

    2. Interview for which I was flown in. I took my jacket off because it was warm. Did not realize until after the interview (which included a tour of the facility) that my blouse, while lined in the front, was not lined in the back. I went through the entire interview with a sheer blouse back showing. Did not get the job.

  103. Lucky*

    Well, there was the time I was setting up files for my judge’s afternoon jail calendar – bail and other hearings conducted via video link to the jail – and heard someone clearing their throat, looked up and realized the camera was on and I was broadcasting to the jail AND that the video camera had just been pointing down my blouse. Yep, I pretty much flashed a room of 30+ inmates.

    And

  104. Aleta*

    I’m actually glad to say I don’t have any terribly awkward stories, but closest was back when I was a bike courier. I had just started using clipless pedals (so where there’s a cleat on your shoe and it attaches to the pedal via a spring mechanism), and hand managed to remember to clip out at every traffic light on my way into work. Until I rolled up to my store, try to dismount, and forget to clip out. I fell over and collided with my coworker’s bike propped up against the side of the floor to ceiling front window, knocking that down to! Both our bikes were fine, and I only had the bruised pride of my first Stupid Clipless Fall right in view of all my coworkers.

    1. Kate*

      Oh man. I did something so similar to this last summer. I had actually clipped out with one foot, but then ended up falling to the other side at a crosswalk with a huge line of cars on either side and a restaurant across the street where a lot of cyclists would stop to grab a drink, so basically in sight of the maximum amount of people allowed in that location. I’m pretty sure the next four cars to drive through the crosswalk first stopped to ask me if I was OK. I had been using clipless pedals for like 5 years at that point and hadn’t fallen since the first week I got them, so my ego was mightily bruised (along with my body). I like to think of it as the time the pedals needed to remind me whose boss.

  105. Dylan Is A Lady*

    I’m a comic book artist who does corporate consulting and design on the side and use to temp in medical clinics. So I’ve manned convention tables at regional comic book shows AND led 8-hour meetings in C-suite conference rooms AND checked people in for their appointment about their persistent anal leakage. This means I’ve seen a…very broad awkwardness spectrum.

    My favorite, though, still has to do with one fact: I’m a woman, but my first name is usually read as male. At comic conventions, I stand behind a table full of my work, in front of a banner with my name on it, with a nametag on…but some people still fail to make the connection that I might be the artist. The patriarchy harms us all, etc.

    Thus I had the pleasure of standing behind my table, listening to two dudes pore over all my work and discuss it in brutally honest detail, not two feet away from me. I was obviously just the booth bunny, right?

    It paid off, however, when one of them finally decided to purchase a book…and I cheerfully offered to sign it for him.

    >:)

    2. justsomeone*

      I read your comic!

      I also have a name that people assume is attached to a man and have experienced similar cases of being discussed by strangers to my face.

      1. Dylan Is A Lady*

        Haha, I’m sure you have bucketloads of awkward name/gender anecdotes, too! I wouldn’t change it, honestly. It’s free entertainment.

    3. kible*

      i’ve heard that type of story from like…every woman that does comics, never stops being cringe or hilarious. i tabled my first con last year and luckily didn’t have it (or the dreaded “oh did YOU draw this?”) happen to me!

  106. RJGM*

    I’m just awkward in general, so I don’t have a specific story of my own, but I’d like to submit one I witnessed for consideration:

    My husband showed up to work one day in a suit. We work together (I know), but I wasn’t dressed up that day. As we were walking down the hall together, we ran into my grandboss; she looked him up and down, then asked, “Do you have a job interview today?”

    “Nope, a funeral.”

    I will never, ever forget the look on her face as she started apologizing.

    (It wasn’t super funny at the time because, you know, funeral. But it definitely qualifies as “awkward,” and we laugh about it now.)

    2. eternal teapot*

      Oh this just reminded me of one from middle school (I guess it counts as the teacher’s work). He was a very casual teacher and dresser. One day he’d dressed up for conferences or something. In any case, it was very noticeable. A kid in front of me cracked “Who died?” at him, and very sadly, without missing a beat he said “My mother.” Kid was horrified.

  107. PB*

    Oh, goodness. I was in a meeting once, and a coworker started showing us pictures of her new puppy. We were all cooing over the cute puppy, and she told us how happy she was.

    And then she continued, saying: “but it’s you people with kids who are the real lucky ones. I couldn’t have kids. I had cancer, instead, so now I have to have dogs.”

    1. PB*

      And as awkward as this would be been anywhere in the office, yes, it was during a meeting, with our whole department. It clearly did not occur to the person making the comment that this isn’t the kind of thing you throw in among travel reports and workflow talks.

  108. GigglyPuff*

    First day of my first job at a dog kennel. The garbage bin in the outside yard needed to be emptied at the end of every shift, and during the busy summer season can get quite full and smelly. Well the only way to get it out of the yard was to sling it over the six foot privacy fence to land next to the dumpster. I go to sling it, it catches on the fence top and completely pulls one of the fence slats off.
    I was completely mortified, went through the building and all my coworkers are waiting to have the shift change meeting in the front with my manager, I confess what happened, completely red and embarrassed that I just damaged company property. Once they realized the bag didn’t split and they didn’t have to help me clean up dog poo, they couldn’t stop laughing. Not the biggest deal but I was a shy kid, so it’s always stuck out to me.
    Unfortunately it wasn’t until a few years later when one employee was hurt trying to sling it over that they finally cut a hole in the fence with a latch door.

  109. Still laughing at this one*

    Mine is short but sweet. A while back we had a huge visit from our friends up in the C levels. One of my coworkers asked a VP if they had met before…at the county lock up…In front of our CEO. Our boss looked like he was torn between strangling him or just crawling into a dark dark hole to die.

  110. Sara*

    I once went to lunch with my brother while he was temping at my office. There was one of those quick summer storms just as we pulled back into the parking lot, so we hung out in the car while it passed and listened to the radio. Somehow, I forgot to take my keys out so the radio/battery was on for the rest of the day.

    When I left at five, the car was dead and my brother was gone for the day already. I went back inside for some reason to call AAA because my cell phone was dead and my boss told me he had jumper cables in his car so he could jump it. I went back outside to open the hood and managed to lock my keys into the car before he got outside. He then waited while I went back into the office to try to call my brother or parents to pick me up, but no one was answering their phones so he drove me to their house to wait for them to help me (they lived like ten minutes away opposed to my 30 minute commute). So embarrassing. One of my directors came out during the keys locked in the car segment and laughed for a good five minutes. Took a while to live that one down.

    As a follow up, my mom then tried to jump my car but she had a small coupe and it wouldn’t give enough power. We ended up calling AAA after all that, and they showed up like another hour later.

  111. Where's the Le-Toose?*

    All the Europeans out there will love this!

    My now wife was born and raised in Ireland while I was born and raised in California. I had no idea that in Ireland, “fanny” was a euphemism for vajayjay. I thought everyone would understand it was the American euphemism for butt.

    My wife and I were on our third date and said to come over to her place and she’ll cook me dinner. As she’s at the stove I come up all playful behind her, tap her in the rear, and whisper “I’m going to slap your fanny so hard later on!”

    Her head pivots around like Linda Blair in the Exorcist. She has this look on her face like I’m some sort of super creeper, and she blurts out “what the F did you just say?!?”

    We’re celebrating our 5th anniversary this year. To this day this is still my mother-in-law’s favorite story.

    1. Borne*

      Actually, it’s not just Europeans. Only in North America is ‘fanny’ a euphemism for butt.

      In all other countries where English is spoken, it means the other, i.e. in Australia, New Zealand, South Africa etc.

  112. Liz2*

    We have safety drills for on site shooters where we are supposed to hide in specific rooms. I always pick the bathroom because it’s close and convenient. The last drill I went in and the head of my department head was coming out, I had to tell her we were in a drill and expected to stay for 15 minutes. I had never even been in a meeting with this person before.

    That was the longest 15 minutes of my life- I was a lowly admin stuck in a small space with the head of my department. I made attempts of small talk but quickly ran out of things and she didn’t pick up the ball! After 15 agonizing minutes, I was finally free to escape.

  113. with a twist*

    I was interviewing an older gentleman and he cried during our interview….twice. It was so awkward that I had no idea what to do, so I just froze. His nose was running profusely, so I eventually got it together enough to find him some tissues, but I was completely unsure how to proceed after that.

    During the same round of interviews for that position, another candidate told me about his recent battle with prostate cancer. And of course after that, all I could think about was his prostate and everything else happening in that region, which made things extremely weird. I ended up hiring him anyway because he was a good candidate, and one time he called in sick because his erectile dysfunction medication gave him a migraine the next day. You could have just said you had a headache, man. TMI.

  114. Kalkin*

    This will be nothing compared to a lot of stories, but a few weeks ago, I was in a meeting for a special “mentoring circle” program my company started. We were answering an icebreaker question: Who is your favorite fictional villain? And this poor guy — oh, it’s cliched, but yep, he was a programmer — launches into a brief paean to a character from a series of Dungeons & Dragons novels. And sure, fantasy and science fiction are far more mainstream these days, but this was not Lord of the Rings or Star Wars or X-Men — this was a relative deep cut, and quite clearly very nerdy. And suddenly it just felt like middle school: You could sense everyone’s embarrassment as he mentioned assassins and dark elves, and even though I knew exactly what he was talking about — OH YOU BET I DID — all I wanted was to avoid eye contact with him and distance myself from him as much as possible, lest the attractive women in the room realize I was a big dork too. It wasn’t intentional; it was just like a reflex from sixth grade kicked in! I honestly had never expected to feel that particular kind of awkwardness again.

    (I said my favorite villain was Doctor Doom, because he has diplomatic immunity and frequently makes proclamations about himself in the third person.)

    1. Kalkin*

      Oh! My first job was hosting at a pizza place. This woman walked up to the host stand and said, “Can you call me a taxi?” And I put on my best Bert and Ernie face and replied, “Sure! You’re a taxi!”

      She looked at me in confusion for a couple of seconds and then said, “I’m sorry — I’m deaf. Can you call me a taxi?”

          1. Elim Garak*

            Hah! I was going to ask if it was Artemis Entreri.

            I know he’s not as mainstream as Tolkien, but RA Salvatore isn’t exactly a niche fantasy author.

            1. Kalkin*

              He’s not, but he’s still outside the mainstream. Fantasy readership is pretty small, I think? When you don’t count Tolkien and the few others who’ve made it to film or TV (C.S. Lewis, George Martin, Ursula Le Guin, and that’s about it for high fantasy, right?), the fraction of the population that browses the swords-and-dragons section is low compared to other genres, IIRC.

              Someone must be working on an Icewind Dale cable series, right? They should do it, but make Bruenor a lady to improve the gender ratio. Bruenora Battlehammer.

        2. Elim Garak*

          Not a work story but tangentially related and still awkward. I used to volunteer in the RPG industry and went to Gen Con every year as part of my work. The first time I met Ed Greenwood (in a group) he got down on one knee and kissed my hand. Sweet man, but the whole experience was very awkward.

  115. Kalkin'*

    This will be nothing compared to a lot of stories, but a few weeks ago, I was in a meeting for a special “mentoring circle” program my company started. We were answering an icebreaker question: Who is your favorite fictional villain? And this poor guy — oh, it’s cliched, but yep, he was a programmer — launches into a brief paean to a character from a series of Dungeons & Dragons novels. And sure, fantasy and science fiction are far more mainstream these days, but this was not Lord of the Rings or Star Wars or X-Men — this was a relative deep cut, and quite clearly very nerdy. And suddenly it just felt like middle school: You could sense everyone’s embarrassment as he mentioned assassins and dark elves, and even though I knew exactly what he was talking about — OH YOU BET I DID — all I wanted was to avoid eye contact with him and distance myself from him as much as possible, lest the attractive women in the room realize I was a big dork too. It wasn’t intentional; it was just like a reflex from sixth grade kicked in! I honestly had never expected to feel that particular kind of awkwardness again.

    (I said my favorite villain was Doctor Doom, because he has diplomatic immunity and frequently makes proclamations about himself in the third person.)

  116. Birch*

    My most foot-in-mouth moment: I was at a conference, setting up my poster. A woman a bit older than me was setting up next to me, so we started talking about articles we’d read recently and I mentioned one written by “the Janet Smith group” (Janet Smith being the first author), which I’d really found interesting. She replies “Oh I’m Janet Smith, I like the sound of the Janet Smith Group!”

    I should have said Janet Smith and colleagues, but the last author is a big name, she’s an early stage researcher, and I wanted to give Janet credit for the article since the bigwig often gets credit for the whole lab’s work! It just came out so weird, and obviously it was humiliating to have no idea who I was talking to, especially when her name was right up there on her poster!

  117. Katie*

    I was setting up lunch with a female vendor who I’m friendly with on a professional level (I am also female). She graciously had me order something for myself even though I wasn’t part of the meeting which was a nice gesture to an admin. For some reason when she reached for something her hand accidentally grazed my boob, she apologized mortified, “oh my god i’m sorry I didn’t mean to touch your boob”. To which I responded “hey there’s no such thing as a free lunch!” I don’t know why I said that! I’m not mortified as it eased the awkwardness but it was still like why did I say that?!

    Luckily, I had trouble thinking of something which goes to show no one remembers your awkward moments as much as you do!

  118. Anonymousaurus Rex*

    Oh man, this is seriously embarrassing.
    Once, after a dinner/drinks with a client on a business trip, we got talking about some of our most interesting experiences abroad. Someone brought up Thailand, where I lived while doing fieldwork for my PhD. I mentioned some of my experience talking to sex-workers there. Somehow this ended (after a lot of awkward prying from the client that I should have extricated myself from!) with me relating the story of two men having sex on my lap at an “underwater erotica” show in Bangkok. (I am, incidentally, a gay woman). It’s not like I was drunk or anything, I just got wrapped up in telling the story (which was entertaining everyone, but totally inappropriate) and got carried away not thinking about my audience….a 50-something straight, male, ex-military defense contractor. The next day he kept making oblique references to the story. It was SO awkward.

    1. Close Bracket*

      If you are going to ask prying questions about Thai sex workers, you better be prepared for any type of story. :-)

  119. Alisa*

    I was sent to a training to become a water fitness instructor, which at my facility was always led from in the water. At the class, we learned you should properly teach from the side, and because of the height difference of standing on deck vs people in the pool you should always wear shorts. Reason being that no amount of personal grooming “down there” could provide an appropriate view in only a suit. Required materials for class? Swimsuit, towel, notebook. That was a painful rotation of about a dozen of us doing our teaching assignments with not a pair of shorts in sight!

  120. Jadelyn*

    I’ve told this one before in other contexts – namely how great my boss can be about stuff – but it remains my most awkward work moment to date, so I’ll share it here as well.

    It had been a stressful couple of weeks and a bad day on top of it, so at lunchtime I decided to go home and have lunch with my partner (who was home sick that day) just to get out of the office and spend some time with someone I knew was on my side. As I gathered my wallet and keys to leave, I texted my partner: “F*** this place and everyone in it, I’m coming home for lunch, what do you want me to bring?”

    Only I didn’t text it to my partner. I accidentally texted it to my boss.

    But there’s a happy ending here. She came out and caught me in the parking lot before I left, reassured me that she hadn’t read past the first two words because she immediately realized it hadn’t been intended for her, deleted the text while showing me her screen so I would know it was gone, and then gave me a hug and told me to go and not think about work at all for the next hour – and if there was anything I needed to vent about when I got back, to let her know.

  122. 2ManyBugs*

    A handful of years ago, I tore cartilage in my rotator cuff, and had to wear a sling to work for several weeks. I told everyone it happened in the gym, except my hiring manager, who I had a great, close relationship with. Quietly, at a team lunch, I told him it was actually a combination of Jameson and a house party where the host had a dance pole installed for exercise. (And of course, once we all got drinking, everyone decided to take a swing or two around it.)

    Unbeknownst to me, another project manager overheard this confession. After lunch, once everybody had settled into their desks and during a quiet lull, she suddenly popped up from her desk and yelled across the floor, “HEY OP, WHEN ARE YOU GOING TO TELL US HOW YOU BUSTED YOUR SHOULDER ON A STRIPPER POLE?!”

    I’m female. I work in software. It was like watching gophers, all the heads that suddenly shot up from behind their monitors, turned in my direction. I just about disappeared into my chair, and I don’t think I’ll ever fully recover.

      1. 2ManyBugs*

        She was actually very nice, and we’re good friends now! But she had that foot-in-mouth moment where she didn’t think about what she was saying, where she was saying it, or any other context – something she got better about in more recent years. :)

  123. Nepotism*

    This isn’t technically “while working”, but I got my current job through a bit of nepotism. My mom introduced me to a director in a different department at the company where she works, and I was told to apply for position X, which the director in question was interviewing for herself. When I got to the interview, she asked me how I’d heard about the job, which I thought was odd, but I told her through my mom. Then she asked who my mom was, and I realized she didn’t recognize me. As soon as she found out who my mom is, she basically stopped the interview and told me that unless god himself interviewed, I had the job. I felt so awkward for assuming that she’d recognized me from the start, and then for basically only getting the job because the director of my department knows my mom. I’m still at that job, almost a year later, and I still feel bad for the other people who interviewed who would probably have done better in this role but lost out to nepotism.

  125. Meliodas*

    I had just started my new job at a nonprofit and was meeting some of our board members for the first time at an after-hours event. I was involved in a pleasant conversation with 4-5 others toward the end of the evening when one board member raised his hand to wave goodbye. I mistakenly thought he was raising his hand for a high-five (why? I don’t know!!). Instinct took over and I felt myself reaching across the circle with my hand over my head to high-five him. I knew I was mistaken as it was happening and could not stop myself in time. I ended up in the middle of the circle with my hand weirdly pressed against his. He gave me a blank look and turned around to leave. It felt like the whole thing happened in slow motion. This board member and I now have a great relationship, but I have never mentioned our first meeting to him and he hasn’t brought it up either.

  126. Amity*

    Easily the worst one for me: We had a manager, who we all loved, whose husband passed away from lung cancer. Several months after that happened, she called my department looking for my coworker, who was on a smoke break at the time. Guess what I told her? “Oh, he’s not in the office right now, he’s out getting cancer—um, sorry, he’s on break. I’ll have him give you a call.” I was too embarrassed to tell that to anyone for years!

  127. Curly In A Cubicle*

    Oh boy. I’d applied to a reach job internally. I’d spoken with a man in the department who’d encouraged me to apply, and then I got a call from him asking for a meeting. Great! I think.

    I go to his office, and as kindly as possibly, he lets me know how much *more* qualified EVERYONE else who applied for the position was, and that he wanted to let me know because “we’re like a big family at [large educational institution]” and he didn’t want me to get an anonymous letter rejecting me.

    I managed to keep my face neutral and tell him I appreciated his time and caring. Then I left as quickly as I could.

    I would have so much more appreciated the anonymous letter.

  128. Murphy*

    I was working at a nonprofit no-kill animal shelter at the time. I was in animal care, which is part exactly what it sounds like and part customer service by answering questions and helping potential adopters visit with animals. To adopt an animal you have to apply with the adoption staff. This is a different department, and animal care is not privy to all of the rules and procedures that might make the adoption staff approve or deny potential adopters. (We were also generally prevented from asking about it, but that’s another story…)

    The place is really busy on the weekends, so it’s not uncommon for part of a family to be in the visit room with a dog and another part of the family be going through the adoption/paperwork process. I had been helping a couple with a child for a while. They were visiting with a puppy and seemed pretty nice. Eventually, the mom went up to go apply to adopt while the father and son stayed in the room with the dog. They were in there for a while and at one point the mom came back. I poked my head in and asked “Everything going ok?” The mother was crying and the father and child looked upset. She said “They won’t let us have him.” Apparently the adoption staff denied them. At this point, I was in the doorway leaning into the room while trying to make sure this puppy, who was licking my hands, didn’t run out the door. I just said, “Oh.” No one said anything. Since the puppy was already at the door, I think I said something like, “I’ll just take him…” and then took the puppy back to his room.

    I felt so bad for them. I still have no idea why they were denied.

  129. Ann Cognito*

    Working in CA, most jobs have a very casual dress code. One place I worked was no exception. It was super casual, unless you were meeting with clients. People regularly wore shorts (not short-shorts!), even the CEO, who I reported to.

    Soon after I started working there, a client meeting was being held later in the day. Before the client meeting though, there was an all-staff meeting, so almost everyone (approx 50 people) was there. I walked in just as it was about to begin, saw the CEO, who was wearing khaki pants and a nice shirt, did a double-take and said “Wow! it’s the first time I’ve seen you with pants on.” I was mortified when I realized what I’d just said.” Everyone there thought it was hilarious, including the CEO, and I still get reminded of it occasionally when I see some of the co-workers from there that I’m still in touch with.

  130. Sara*

    Oooh…I’m going to have to go with the time I was working as a teaching assistant at a preschool, and while working with one of the kids, I heard a commotion on the other side of the room. I look up to find that the teacher in the room was having a seizure and had begun to remove her clothing. All of the toddlers were running over to me to ask ‘What’s wrong with Ms. N?’. After I quickly moved all the kids to the other room, that was an awkward one to deal with…

  131. engineermommy*

    My department is so full of awkwardness that we have an award for it. Yes, an actual trophy that gets passed to whoever made the most recent inappropriate comment. My first and only win in 4 years or working here was when, during a discussion about how a coworker’s dentist wouldn’t approve of her eating some sticky candy, I helpfully suggested that she didn’t have to chew, but could just suck on it.

    So now the trophy is sitting on my desk, which prompts people to poke their head in and ask what I said to win it, forcing me to relive the moment over and over again.

  132. CV*

    This is not going to be the most awkward thing here, but was certainly distressing to me at the time. As a young professional woman (early 20s) I wore a lot of colourful button up blouses and neutral coloured pants. (Turquoise and dark grey, for example). My boss was a man in his late 40s who had the knack of showing up to work wearing exactly the same colour combinations as I. The only difference was the way the clothes were cut! It happened every few weeks. I didn’t have the money to invest in a new wardrobe, and he thought it was funny that we were “office twins” and pointing it out during meetings, so of course everyone else noticed, too!

    1. CV*

      oh, man, I forgot the other one I witnessed recently.
      My husband and I were test driving cars, and the salesman (whom we had only met about 10 minutes earlier) gets into his spiel… and somehow ends up asking my husband if he’s had a vasectomy. Husband and I ignore the question as though it hadn’t been asked. We did not buy a car from this guy.

    2. Former Admin Turned Project Manager*

      I had a similar thing happen in high school- I was wearing a sunny yellow oversized sweater, and my doofy pre-calculus teacher was wearing the same one (not quite so oversized on him, of course)! I planned to pretend I didn’t notice, but he came over to my desk, pointed at my sleeve and then his own a few times, and gave a big, doofy “check this out” grin. I heard about that from my classmates for months- Hey, K, did you buy any more of Mr. Black’s sweaters at the mall when I saw you shipping this weekend?

  133. oranges & lemons*

    This one was just secondhand, but it’s one of my most treasured memories. I used to work for an old-timey photo studio where people would dress up and have their pictures taken. One of our most popular scenes was the “bathtub scene,” basically just an old clawfoot tub that a couple would sit in together (yes this job was pretty weird on a fundamental level).

    One day, we had an unusually tall and burly customer who wanted to do this scene with his wife. Usually the tub was big enough to conceal customers’ lower halves, so they just needed to change their shirts, but this guy would clearly not fit. So to preserve his modesty, we showed him into the change room so that we could try to find something for him to wear. Since most of our men’s costumes were meant to fit over their clothes, the best we could do was a very short pair of pink, teddy bear-encrusted hot pants. He was a pretty good sport about putting them on, but unbeknownst to him, while he was still changing a massive tour group of about 30 people gathered at the front of the store. Since the change room and the bathtub setup were on opposite ends of the store, they had a completely unobstructed view of this huge tough-looking guy in tiny pink teddy bear shorts shuffling across the length of the store.

  134. Arjay*

    I know I’ve already shared about accidentally slapping my boss in the face that one time.

    And tripping over the dog leash I was using to tether my chair to my desk so people would stop stealing my chair. I had to file an accident report on that one.

    I don’t know if I ever mentioned going in for an interview at my first retail job and slipping on the floor near the shopping carts. I didn’t wipe out completely, but it was definitely a blip. I thought I might have gotten away with it until something like two years later when the assistant manager who interviewed and hired me said, “Hey, remember when you almost fell on your ass when you came in to interview?”

    And most recently, I came back to work after being out for two weeks between PTO and the flu and one of the managers walked up to me while I was talking to someone else and gave me a really awkward side hug while asking if I had a good time. He wasn’t in the loop that I’d been sick. I wasn’t contagious at that point, but it added an extra layer of awkward anyway.

  135. knitcrazybooknut*

    I worked in Human Resources at an insurance company. We had training session each week, where we flew in our newly hired employees to our home office and put them through a full week of training on all of the laws, regulations, training techniques, and everything they needed to know to sell our particular product. They were also sold on the company at the same time, so there was some wining and dining done at the same time.

    Mind you, I was in Payroll at the time, and I had landed in payroll by virtue of temping, being consistently a good employee, and knowing how to do data entry well. I knew nothing about HR. I knew how to solve puzzles and figure out paychecks and explain them to people.

    So everyone else was out of the office when a new sales agent walked in one morning in the middle of the week and had to talk to someone right now, immediately. I looked around, realized I was the only one available, groaned inwardly, and said, I’ll be happy to help you. We went into a conference room, and I realized I could smell the alcohol oozing out of his pores.

    He talked for about 45 minutes. I won’t transcribe the entire saga, or we’d be here all day. But he described in full detail the entire night, in which he and his fellow trainees were treated to dinner, a visit to a winery, and another dinner and drinks back at the hotel by the trainers and a visiting C-level executive the previous night, during which he had imbibed a perfectly REASONABLE amount of alcohol, which he described drink by drink, as if to prove it to me. During this entire explanation, he would not meet my eyes, until he finally said to me, “I am NOT an alcoholic.”

    I’m not a profiler, but I’ve dated some liars in my day, and I’m well aware that people who want to convince you they’re not lying will give you dead on direct eye contact. (Others will usually give you eye contact throughout, generally speaking.) This guy was trying to convince me, and possibly himself. His general odor was not helping his case, either.

    He then continued his story, saying that the hotel staff then 86’d him, saying he could stay, but couldn’t drink anymore. He continued to describe his behavior as perfectly reasonable, in detail. But then one of his fellow trainees set down a half-drunk beer! And said she wasn’t going to drink any more of it! He couldn’t believe it! Well, any reasonable person couldn’t let that go to waste! So he just absent-mindedly picked it up and drank it, of course! You would have done the same!

    The hotel bar staff immediately came over and told him they would be reporting the incident to his company immediately and he needed to leave the bar.

    He came to me and wanted to make sure that the company heard it from him before they called and reported him, so he just wanted to be sure I knew what REALLY happened.

    The entire time I just sat there, nodded and took notes. I had no idea what else to do. I’d give anything to have those notes. I should have made a copy. Ye Gods.

  136. Higher Ed Database Dork*

    Here’s one from early in my working life…my first full-time job out of college, I was hired at a private university to design online courses. My team was in a very small room with an open office plan, so we could all see each others’ computers. On my first day, they gave me access to the stock photo account and instructed me to make some graphics for an online course. One of the graphics was a banner for the test/quiz section. So naturally I think, “I’ll look for pictures of people taking exams,” and typed “exam” into the search bar. What popped up was dozens of photos of topless women giving themselves breast exams. Full exposure, nothing was blurred or creatively hidden. So on my first day, I gave all my new coworkers a big eyeful of boobs getting checked over.

    Thankfully they all just laughed and said the same thing had happened to them, so don’t ever just search for “exam” in the stock photo site!

  137. S*

    Once a senior manager took the whole team out for lunch (about 6-8 people). I was feeling like I wasn’t really participating in the conversation, so I was looking for an opportunity to jump in. Somehow the talk turned to the city of Annapolis, so I chimed in “I gave birth in Annapolis!” There was a *very long* silence, as no one had any response to this. Thankfully, some eventually changed the subject. I didn’t say much for the rest of the meal.

  138. Awkward Pharmacist*

    A mom came up to my pharmacy counseling window to ask for help regulating her son’s bowels. “He didn’t go for twelve days, and then when he finally did go, it was the size of a sweet potato.”

    Shortly after that, I discovered that the son in question was the hulking teenager failing to hide behind her.

    I’ve never been able to look at sweet potatoes the same way again.

  139. FlamingoFlorence*

    I was hosting a retirement party for my boss and I completely forgot to invite one person. It was an oversight, because I had him on the list, but somehow forgot/accidentally deleted his name in the “To” field. He got wind of the party and he said “Hope you have fun at Fergus’s party tonight!” and I said “Oh yeah, we totally will!!”. Then my other co-worker had to tell me, oh, Bill is actually upset at being excluded. *head-desk* I hate feeling excluded and would never intentionally do that to someone, so I was mortified. I invited Bill and I think he believed me that it was unintentional, but I felt awful.

  140. Bill F*ckin' Murray*

    I’m a woman and I work on a small, very tight-knit team. I was sitting at my desk when two co-workers came in to talk, one man, one woman. At a certain point, the woman realized that her pants zipper was inching it’s way down and she kind of pressed at it an laughed. The male coworker, thinking that she said her stomach was growling, exclaimed that that always happened to him in my office! We both just stared at him in shock with our mouths open. Then I yelled, OMG, why would you say that?! He was confused, we were confused, once we figured it all out we laughed until we cried and I’m crying now thinking about it.

  141. Eye of Sauron*

    Am I the only one that suddenly has a flood of awkward memories coming back because of this thread?

    lol… it’s hard not keep adding them!

  142. Pleading Insanity*

    I was once moderating a high-level, invitation-only, think-tank type of meeting. Because it was for a niche industry, most of the participants already knew each other, but I wanted to get everyone talking so I had them introduce themselves and tell me something they didn’t think anyone in the room knew about them. I was calling out names alphabetically and things were going nicely – a good mix of funny, sweet and impressive anecdotes. I got all the way to the Ws and called the first name “Mary White.” We all look around. Mary isn’t there. I move on. “Paul Winter.” Paul isn’t there. I make an off-hand comment, “They must be together.” The room erupts in laughter and I think, “not that funny, but good to know I have an easy crowd.” Later, one of the big shots in the group comes up to me and says, “I can’t believe you said that, but good for you. Someone had to say it.” Turns out they were indeed a couple, and were indeed together – and both married, not to each other. I was apparently the only one in the room who didn’t know that. It’s been years and I’m still cringing.

    1. TheAssistant*

      In a way, they absolutely let you know something you didn’t know about them, even without participating in the icebreaker.

  143. Lily Evans*

    I have so many, but possibly my most awkward story comes from my high school job. I worked at a big box store (like Walmart, but not Walmart) that had a bunch of teenagers working there, so of course everyone was friends and there was an incestuous tangle of inter-company dating and hooking up. Around the time of senior prom, my friend Stassi took it upon herself to find my a prom date, despite me telling her I didn’t want to go, so I didn’t care if I had a date. But Stassi was one of those people who sets her mind on something and doesn’t give up, so she started asking guys out on my behalf. The first time I heard about it, I was super embarrassed because she’d asked a guy I had a crush on, but who already had a girlfriend.

    Then it got worse. Our other friend, Kristen, had just broken up with her boyfriend, Tom, so guess who Stassi asked out on my behalf next? Yes, our best friend’s very recent ex-boyfriend. But the worst part is that I found out about this when Tom called me over the intra-store phones while I was helping a customer, and was like, “So I guess we’re going to prom together.”

    I told him that I couldn’t talk to him right then and hung up. So there I was trying to help a customer with something while processing the fact that Stassi had promised me as a prom date to Kristen’s ex, who I had no interest in. I finished helping with that customer as Kristen started calling me on my cell phone, so I went and hid in a security camera free stock room for like half an hour to talk her down from being angry at me for asking out her ex. I ended up not going to prom in the end, and somehow no managers picked up on any of the drama so it luckily didn’t affect my job, beyond the intense embarrassment I felt.

  144. Kat*

    OK, this story is maybe more strange than awkward. I don’t think I did anything cringe-worthy in the situation, but my former boss should be terribly embarrassed. However, I am certain she is not.

    Former boss asked me one day if I used the mini-fridge in our office. I told her I didn’t use it very often and was not planning to use it that day. She said “Oh good. There’s not a lot of room left because I put the dead cat I found on the side of the road this morning in there. Can you send out an all-staff email that there will be a funeral tomorrow afternoon at 3 in the garden?” I was baffled. She couldn’t have really just told me that she scraped up some roadkill on her way in to work and we were going to stage a funeral for it, could she? The conversation went something like:
    “A funeral for who?”
    “The cat”
    “Your cat died?”
    “No, I just saw this one dead on the road. Its not a cat I know.”
    “You want to bury it here at work?”
    “We need to have a funeral.”
    “Grand-boss is ok with this?
    “Yeah, I do it all the time.”
    “And the cat is in the fridge right now?”
    “Its kind of gross, so don’t go in there if you don’t want to see it.”

    I was just a year out of college and and I’d only been in the job a couple of months and pretty much everything I thought I knew about the working world was shattered in that moment.

      1. Kat*

        I soon learned she had turned part of the company grounds into a graveyard for unknown cats.

        I called in sick every time I knew she had a “funeral” planned. I mean, if you want to do that on your own time I’m cool, but I will not be a part of it.

      1. Kat*

        I did try to warn my coworker (only the 3 of us had access to that area) but he just shrugged and tossed his lunch into the fridge anyway. It was (unsurprisingly) a deeply dysfunctional workplace in so many ways. (Co-workers there loved to start conversations with, “I’m not racist, but…” which never ends anywhere good.)

    5. JKP*

      This is the best story on the whole page. I read it three times and laughed harder each time. I’m imagining someone she forgot to warn just opening the fridge and seeing the dead cat there. Also, did anyone ever use the fridge again after they found out it sometimes held dead animals awaiting proper funeral services?

  145. Not Indiana Jones*

    I have serious problems walking through doors.

    One day, I was leaving the building. The door handle snagged on my backpack strap, and as I walked forward, the stuck strap twirled me around and smacked me into the door. The door recoiled. I backed up to try to figure out what was going on, and the strap pulled the door shut smack in my face.

    I hope nobody saw that.

  146. Serendipity*

    At the end of my first week in my current professional job my manager (man in his late 50s) decided to take me (20s) and my one colleague (man in his 30s) out to lunch at a local waterfront pub called ‘the lucky shag’.

    He had to leave early for a meeting with some VIP clients, and my colleague and I stayed to finish our lunches before walking back to the office.

    As he and I walked in the door my manager looked over and asked ‘so how was the shag you two?’, in front of the VIPs who were still there waiting to meet me.

  147. Clever anonymous name*

    I was recently mortified at the funeral of a former manager/mentor, “Bob.”

    Bob had been in a C-level position and I had been his assistant. I was so grateful to work for him. He was known to be quite challenging, but we worked well together. He had such integrity and was highly respected in his field. He was also a left-lean activist who, while put together, looked the part. Many of Bob’s friends had similar looks – very much as they might have looked in the hippy days of the 60s.

    After Bob retired, I ended up as the EA for the CEO, “Dave,” who was prim-and-proper in ways Bob was not (closely shaved, always in a suit, fairly stern, etc.). I enjoyed working for Dave for about a year before changing careers and leaving the organisation.

    Bob and I stayed in touch after he retired, emailing or calling a few times a year. I ran into Dave a few times, but hadn’t seen him for years.

    Bob recently died after a long fight with cancer. His memorial service filled the hall, with hundreds of people from all walks of his life paying tribute to this great man. There were some former colleagues in their suits, but there were also many of Bob’s hippy-looking activist friends.

    I paid my condolences to Bob’s family, spoke with a few former colleagues whom I recognised, then wandered the hall looking at the displays that had been put up paying tribute to Bob. I’d occasionally chat with one of Bob’s friends who was looking at the same display, sharing memories.

    When I was standing at one display, a man started up a conversation with me. He had long white hair, an unkempt beard, a somewhat scruffy suit – and he also had a large welcoming smile and shining blue eyes. He said hello, we chatted for a while. His voice seemed familiar and I felt I should recognise him as one of Bob’s friends, but I couldn’t quite place him. We shared a few pleasantries, asking what each was up to. Mortifyingly, about five minutes later (!) as our conversation was ending, I realised it was Dave.

    Oh my gosh, I have never been so embarrassed in my life! There was nothing about Dave’s appearance that made me think it was Dave (scruffy appearance! shining eyes! such a large smile!) It was great to see him so happy and content. And yet I remain mortified thinking about it even now.

    1. Reba*

      Once at a funeral visitation I thought I was speaking to my coworker whose parent had died. He looked a little different, was wearing glasses, but I was chalking that up to grief and fatigue, contact lenses etc.

      IT WAS HIS TWIN.

  148. Jukebox Gloworm*

    I am so here for this book.
    I’m sure this is not the most awkward thing that’s ever happened to me, but here goes:
    Once when I was getting off work, my partner and I had an understanding that he would pick me up. I saw a red car that looked a lot like his, and without thinking or really looking at who was driving, I got into it. Yup, wrong car. But to make the best out of an awkward situation, I wordlessly handed him a fortune cookie message that I had just gotten that said “Hugs are life’s rainbows” and stepped out.

    1. Murphy*

      Had to cover my mouth to stifle laughter.

      If I were the guy in the car, I would tell that story to everyone forever.

  149. Sometimes Communist*

    I’d graduated with an MBA. Literally in my MBA class, we had assignments on “elevator pitches” – what to say to the CEO when you’re stuck with him/her in the elevator for 90 seconds, to get her/him to notice you and think you’re great.

    Then my first job after I graduated…. was with a labor union.

    However, as a libertarian (anti-union) friend pointed out…. the president of my labor union was “one of the good ones” who was not overpaid compared to his members’ salaries. So… what happened when I was stuck in the elevator with the (famous) president of the union where I worked and he asked me what I was working on? My mind went blank. Of course. Except for my friend’s statement…. thank goodness I did NOT say, “you know, my anti-union friend thinks you’re not as overpaid as some other union presidents!”

    Instead, my mind went blank, I said almost nothing and I just felt awkward. And took it as a sign that it was time to find a new job!

  150. Aurion*

    At a previous job, one of my duties was to collect all the cheques that come in the mail and deposit them at the bank every day. It involved maybe thirty minutes out of the office round trip and was a nice break mid-afternoon for some fresh air.

    This day, I go to the bank as usual…except when it was my turn at the teller, I…had no cheques. Turns out the large manila envelope I used (to carry the cheques and some paperwork I need to staple the deposit slips to) had a hole worn in the corner edge (i.e. not obvious) and the cheques had fallen out.

    I bolted back to my office in the hopes I’d dropped them in the hall or it’d fallen on my desk. No dice. I swore, apparently loudly enough that one of the partners noticed, and bolted back out. Retraced my steps. No cheques.

    At this point I was walking back to the office panicking and wondering how the eff I’m going to tell this story to the partners (small firm), figuring out how many people I’d have to call to tell them to issue a stop payment on their cheques, and generally catastrophizing about the shambles of my life when I got a call from my coworker. “Hey, you on your cheque run? Any problems?”

    “Yeah, to put it mildly. Wait, how did you–?”

    Turns out some passerby must’ve picked up my cheques right after it slipped out…and turned it in to the bank across the street from the bank I was going to. Some teller was nice enough to look up the company name and find our phone number and call us about the missing cheques. Since I was out (I usually picked up the phone) my coworker got the call.

    Since I was the only person without a business card and thus could not prove my employee status, my coworker had to go, armed with her business card and ID, to pick up the cheques for me. And then give them to me. And then let me go to my cheque run that should’ve happened more than an entire hour ago.

    At this point the entire office (coworker and two partners, again, small place) knew what was going on (and were laughing in good humour). AAM commentariat, my face was effing incandescent for hours.

    This never happened again, I can assure you.

      1. Not a Morning Person*

        And you’re story just helped me realize why so many cash/check bags are canvas cloth or similar!

  151. Squeeble*

    At a former job, one of the managers was famously kind of pompous and full of himself. In his spare time he taught Greek and Latin classes at a nearby divinity school, and that school decided to give him an honorary degree, I guess as a thank-you gesture. Which, good for him, but he would not shut up about it! He brought it up during multiple staff meetings, with a lot of fanfare, and gave us all invitations to the graduation ceremony where he would be getting his honorary degree. We all just sat there being embarrassed for him, a few people mumbled congratulations, and we all laughed about it later.

  152. Anonymous in the South*

    A coworker brought her 3 month old daughter in to “meet” the staff before she officially returned to work. I was holding the baby while mom used the facilities. Our executive director, who never really joined in these “meet the baby” things decided he wanted to hold this baby. Before I had time to slightly extend my arms to transfer the baby, he tried to just scoop it out of my arms. When he did, one of his fingers caught on the underwire of my bra and my breast came out of the cup. He apparently realized what happened because he reached out to pulled the cup back over my breast. It happened so fast – like in the space of 10 seconds are less. We never spoke of it, but I couldn’t look him in the eye for months.

      1. Anonymous in the South*

        I’m almost 45 and this is the most mortifying thing that has ever happened to me. He was just so matter of fact about it, like it was the most natural thing in the world to pull my bra cup back over my breast.

  153. Laura*

    I was teaching an LSAT class, and one of the examples in the textbook was about Snoop Dogg’s “Doggystyle.” It was the first class of a 2-month course, and I was trying to add in some light banter to get everyone more comfortable. I intended to communicate that I was not familiar with that classic Snoop Dogg jam… instead, what came out of my mouth was, “I don’t even know what ‘Doggystyle’ IS!”

  154. Sunshine on a cloudy day*

    I was a receptionist and had to manage phone lines/conference rooms. There were two owners/Managing Partners of the firm. I was told their names and shown their pictures so I’d know to always answer their calls/never interrupt their meetings/treat their guest with extreme hospitality.

    Day 3 on the job. I still haven’t seen either of the two managing partners. I get in the elevator to leave and Partner #1 walks up right as the doors are closing and gets in with me (just him and me in the elevator). He looks at me in confusion (there’s only about 50 people in this office so he didn’t know who I was), then says “Hi, I’m Partner #1”. I responded with “oh I’m aware”. Then my mind blanked out and we rode the elevator in silence to the ground floor. No “I’m Sunshine, the new receptionist” or “Nice to meet you” or anything even remotely polite/congenial/professional.

    I was pretty sure I was going to be let go the next day, but somehow I wasn’t. From then until the time I left, I never knew for sure if he ever figured out who I was or if he ever learned my name.

    1. Sunshine on a cloudy day*

      Runner up is the time in an interview when I answered “How are you at math?” with “Well, I’m really good with a calculator”. To this day I don’t know why that came out of my mouth. I’m actually pretty solid with numbers (in a practical/real world sense – not like advanced theoretical math – but this job just required some reporting involving sales numbers from spreadsheets.)

      I’m a super awkward person. For sure. I’ve finally just sort of accepted it and push on through. My biggest issue is my mind blanking out in very inappropriate socially-geared situations, so I now I just keep a mental list of q’s/safe subjects that I can switch to whenever I put my foot in my mouth. Might be an awkward transition, but it’s better than an awkward silence, and most people tend to role with it if I just switch and brush it off.

  155. Cate*

    I had a former colleague who, at a trade show, went out for a cigarette in a little courtyard which was visble from all sides through floor-to-ceiling windows. There was a strong gust of wind which lifted her skirt. Revealing the fact she didn’t wear knickers under her tights. In full view of the entire restaurant during lunch. To this day I don’t know if she realised we all saw, it was too awkward to ask!

    My own was during an interview, I had a horrendous cold/flu thing, but my recruitment agency had managed to get me an excellent interview so I dressed and drugged myself up and went. The first part was fine, I impressed interviewer and she asked if I had time to meet with the other person making the hiring decision. I said yes, but he wound up taking ages and by the time he arrived the cold medicine was wearing off. Halfway through the interview I had a massive coughing fit and the cough drop I’d tucked under my tongue went projectile across the room at him. I apologised profusely, collected it off the carpet behind him, and carried on. Needless to say I was not surprised when the agency later phoned to tell me I didn’t get the job.

    1. Cate*

      I, too, failed to initially include my email. So, bonus mildly awkward moment: when I was interviewing for my previous role at my current company I also did bellringing (on big church bells in a belltower) and had it listed as one of my hobbies on my CV. I’m quite short and when we got to that section the interviewer asked if I had to stand on a box.

  156. helpme*

    A few months ago there was a lot of office reshuffling at my work, and as the newest employee I got moved fairly often to accommodate new workers who were higher up on the food chain. I was prepping my old office for an incoming manager and had her office key in the front pocket of my shirt (for some reason), which I then forget about as I go about my day.

    Later on, I’m using the restroom and as I bend over to flush, the key falls out of my pocket and INTO THE FLUSHING TOILET! I tried and failed to catch it midair, washed my hands in a numb panic, and rushed back to my own office to panic text my friends to see if there’s any way I can avoid telling my boss that I just flushed a key down the freaking toilet (there was not). As I tried to collect myself, I was vacillating between a sheer, blinding panic and slightly hysterical laughter at this unfortunate situation. I still had no idea how to tell my boss what I did without sounding like a complete idiot.

    I took a quick lunch to clear my head, and who did I run into in the hallway on my way back? My boss. Of course. We had a brief conversation where I was desperately trying to seem normal but internally I was sure she could see how panicked and nervous I was, and I retreat back to my office. The consensus among myself and my friends was that there’s no way out of this without coming clean, especially since the new manager will need a key to get into her office next week, so I try to calm myself and go in to talk to my boss.

    I barely got the words out of my mouth before she burst into laughter and couldn’t stop, tears running down her face and everything. Finally, after a few attempts at collecting herself, she informed me that our admin had 4 extra keys for each office and that my story more than made up for losing one of them. She assured me that I wasn’t in trouble, and I got back to work. She told others in the department and I received a good amount of teasing for the rest of the day, but after that it was mostly forgotten. It’s been a few months since that incident, but I can still remember those panicked hours like it was yesterday.

    1. Emmie*

      You’re not alone! I was visiting a work site with a bunch of new employees. My visitors badge fell off my pants when using the bathroom. Before I could debate whether I should pull this drivers licensed sized badge out of the toilet, the automatic flush turned on and it went down the drain. I am still grateful that there was no need to pull it out of the toilet. I was worried that I’d be known as the bathroom badge lady, but I owned it. I told the receptionist right away, and got a new badge. She said it happens all the time. What a relief!

  157. Madame X*

    When I ran into a former classmate from my graduate program at an event at my alma matter. She was one of the featured speakers for the main event that day. After, the panel discussion and walked up to her to congratulate her on her work. In my awkward attempt to start the conversation, I blurted out “you look so good today; I barely recognized you!” A beat later, I apologized because I realized that my comment came off like a back-handed compliment, which was not at all what I intended! Thankfully, she just laughed it off.

  158. Steve D*

    I fortunately had a coworker who laughed both instances off and understood what an awkward goof I am.
    1) Lesson in Listening: Walking to lunch, I mentioned I was going to get a hoagie. She started talking about something, and unfortunately, my stomach took over and instead of listening to her, I was contemplating what I should get on the hoagie. The perfect dressing occurs to me and I absentmindedly blurt out “I bet it would be really good with some southwest mayo!” She stopped, glared at me in disbelief and asked me to repeat myself. Turns out she was talking about how bad her feet were hurting her and that she might have to have her husband rub them that night, to which I seemingly replied “I bet it would be really good with some southwest mayo!”.
    2) Same co-worker, different day. Sitting at the lunch table, her phone goes off. She apparently had a fresh battery and the highest setting in silent mode, and it shook the table top slightly. Before I could be stopped, I say “I didn’t know they made vibrators that strong!”
    We are no longer co-workers, but we are still very good friends.

  159. Overheard at Dinner Table*

    At a regional training. We all went to dinner and chatted. One woman states that such-and-such-a-week, she will be traveling to Napa.
    Him: Napa? Oh, I love it there! Where are you going? Vinyards? Golf?
    Her: Well, I used to live there, so I’m going back for a funeral.
    Him: Oh…
    Me: <>

    The conversation moved on…

  160. anonymouse*

    This happened at my partner’s company’s holiday party. Let’s say the company owner was named Jeanine. One of Jeanine’s relatives, Paul, who had some kind of role in the company that everyone knew was a sinecure, decided to lead us all in prayer before the meal. I already felt awkward because this company had several hundred employees, not all of whom observed Christmas religiously … then it became clear that Paul also wasn’t completely familiar with the difference between prayers and congratulatory speeches.
    “Oh Lord, we thank You for this Christmas season and the gift of Your Son, Jesus Christ. And we thank You for the blessings we have received this year and ask You to bless us in the coming year. And we also thank You for the meal in which we are about to partake. And we also thank Jeanine for allowing us to share in all of her successes. Amen.”

  161. anon in ny*

    Oooh this happened to me recently – background is that we have multiple offices in different cities and two teams that support different product lines that don’t interact much. The two teams recently had to start collaborating to support a new client so I flew out to meet the client to discuss teapots and ended up introducing myself to a colleague from this other office and who is on the other team but has worked at my company for over a year. It was really embarrassing since the client clearly knew who she was (and she was wearing a visitor tag, too, I just didn’t notice) and I looked like a dummy!

  162. OhNose*

    Story 1: I was walking down the hall at work and a coworker said, “Oh, I think you dropped something.” I look back and a panty liner, folded in half, had fallen out of my pocket.

    Story 2: I pierced my nose and was wearing a simple silver stud in it. I was having some troubles with healing, despite being diligent about cleaning it. One day, I was in an office with 2 coworkers. One of them asked if I got a new nose stud. I said no. He counters that it looks new, are you sure. I again said that I hadn’t. He looked confused. I was also confused. Third coworker said nothing. Later that day, I saw that it had started to bleed a bit and there was a ring of “red” around the silver stud.

    1. Kat*

      This reminds me of when I grabbed a tea bag out of my purse (I’m kind of picky about tea so always carry my own) and headed to the breakroom to make myself a cup only to realize I had grabbed a panty-liner instead. THEY ARE PACKAGED VERY SIMILARLY! I don’t THINK anyone noticed, but could have been a little embarassing.

  163. That Would Be a Good Band Name*

    I used to work at a call center and I hired in as entry level with a group of 25 or so people, that included a husband and wife. We spent 6 weeks in a training room together, so you got to know people. Fast forward a few years and the husband/wife had both quit within the first year, but I had stayed on and was promoted into payroll. The husband was rehired. He stuck his head in my office to say hi and of course I asked how his wife was doing. He blurted out “she’s dead”. I wanted to crawl under my desk! I had no way of knowing but if I could have melted into the floor I would have.

    1. Ramona Flowers*

      Oh god, reminds me of the time I merrily mentioned to someone that the coworker who sits beside me had a rabbit. Nope. Rabbit had just had to be put to sleep. Colleague had been too upset to mention it. I felt so bad.

    2. This Daydreamer*

      I got a lot of people asking how my sister was doing after she suddenly died. It was awkward and painful, but I would have had to carry a sign announcing the news to avoid it. It was just one of those things that happen and I always felt bad for the asker because I knew they probably felt horrible.

      Now, the guy who asked me, on Black Friday, “so, how was Thanksgiving, other than your sister dying”? He can go jump in a lake. So can the coworker who told me to smile about a week later.

  164. Erin*

    I work with (2) 20 somethings. One of the lady’s mother came into her office & started cleaning it for her. It was a sight to see. I was laughing but thinking in my mind, if you continue to do it for her how is she going to learn. Yes, this person still lives at home with her parents. I never told a supervisor.

  165. LJL*

    I have to go with most recent as my awkward moments are uncountable.

    I work remotely, and my supervisor is on another continent. So I see him about once a year face to face.

    AT our most recent meeting, I spilled a full cup of coffee all over the table where we were meeting. Fortunately I only got coffee on me, but I ruined his notebook.Of course, we had to meet for another hour thereafter! Even though he was a great sport, I wanted to crawl under the table.

    2. Elizabeth West*

      Ugh, I did that once at OldExjob when a very hot vendor came in to talk to our marketing guy. He was so good-looking and charming (he had a French accent!) that I just kind of turned into a nervous middle-schooler. I nearly drenched the paperwork they were looking at. Soooo embarrassing.

      Marketing guy must have felt sorry for me, because he didn’t even give me shit about it later like he usually did.

  166. kathyglo*

    I was working as a secretary in an office with a woman whom I liked, but who could also be somewhat overbearing and sarcastic. We had all male supervisors, one of whom (Joe) had just gotten a new hairpiece (important later…). Karen and I sat next to each other.
    No one said anything about Joe’s hairpiece, except for a few compliments. However, he and Karen began arguing one day about something involving her workload. Sitting across from her, I just continued on with my typing and tried to MMOB.
    Joe suddenly rushed out of our area towards the supply closet. He came charging back in with a broom, shoved it in Karen’s face, and yelled at her “Here’s something for you to ride on!!!” Without missing a beat, Karen said, “Oh, I thought it was a brush for your hair.”
    Joe fumed and stalked off. I wanted to bust out laughing but had to keep a straight face. Somewaht awkward, but not sure if a winner…

    1. JB*

      Oh that just reminded me of something that happened over 30 years ago and I still feel bad about it. I was talking to a couple of co-workers and I was teasing one guy about never taking off his hat, and I finally just reached out and grabbed it and HIS HAIR CAME WITH IT! I was just like, oh my god, I’m so sorry, and he left (fortunately he didn’t hold it against me). Who would have expected a guy in his late 20s to be wearing a toupee?!

  167. 2 Cents*

    I was showing the intern something on my giant screen. This intern was known for having a poor sense of personal space (definitely in the “awkward” category, not creepy). I was seated at my desk, and thought intern was either directly behind me or to the right a few paces back. Turns out, he had moved silently just to my left — and much closer than anticipated — because when I went to turn for a paper on my desk, my left hand whacked into … his person, shall we say. He said nothing, but I froze, stuttered something like “let me know if you have any questions,” then proceeded, shellshocked, to describe what happened to my coworkers (on chat) while trying not to giggle out of embarrassment.

  168. SubwayFan*

    I was working on my first major event at my new job in Very Large Corporation and had to manage a vendor relationship over an app we were building. Since the vendor was a new, hip, company, they preferred quick contact via text message rather than emails.

    I was presenting our event promotions on Facebook by sharing my screen to a group, and my husband pinged me on FB chat saying something innocuous, like “Hi Sweetie, I love you.” I tried desperately to close the chat, and managed to fire off a text to my husband saying “Shut up! You’re ruining my presentation!” Except I didn’t text that to my husband. I texted it to the app vendor. Vendor immediately shoots back “Did you just say shut up to me?!?” and there follows a lot of angry stuff while I’m trying to keep composed, finish my Facebook demonstration, and not look bad in front of everyone.

    It took a day or so of groveling and apologizing and explaining to get Vendor to “forgive” me. My husband was ridiculously apologetic about the midday chat on FB, and I have since learned to shut off everything with notifications/chat windows before sharing my screen.

    1. 2 Cents*

      If I was the vendor and got that from someone, I’d be bemused, assuming the person hit the wrong window, not offended.

      1. SubwayFan*

        That’s what I would have thought too? And I specifically explained it wasn’t meant for him too. Let’s just say I’ve never rehired this vendor.

  169. Sara Peterson*

    A few years ago word got around that the supervisor of one of the operations teams was having an affair with one of his direct reports. He was married and she was in a long-term relationship with her live in boyfriend. Rumor had it that they were having sex in the supply closets, and they would definitely go on long lunchtime runs together. Everyone knew yet they both brought their significant others to work events (summer picnics, holiday parties, things like that). It was so awkward. Eventually the supervisor divorced his wife and the day it was final they both quit. He wrote a long message on one of the meeting room white boards about how much he hated the company. They got in a van and drove to Mexico together where apparently they are still living on a farm together.

  170. KJ*

    Oh, man, I thought mine was awkward, but it doesn’t even hold a candle to some of the ones on here!

    Still: one of my employees is a kind of socially awkward guy. He’s nice enough and does a good job, but just skirts the boundaries of understood social interaction so that a lot of interactions with him become awkward. One day I was chatting with him and another employee, who was female. Female employee and I had somehow gotten onto the subject of smoking and were laughing about how ridiculous we looked as teenagers trying to look cool by smoking.

    Out of nowhere, guy employee interrupts, “You smoke?” to me.

    “Yes…”

    “I just think there’s something so sexy about a woman who smokes.”

    Cue awkward silence from me and female employee. We both kind of looked at each other and then moved on with the conversation like it had never happened. He legitimately probably did not mean it, but yeeeeaah. I was a super new manager at the time and had no idea how to respond to that.

    1. KJ*

      Oh! And not me, but I once received a phone call from my brother, who worked downtown at a very prestigious company in our area.

      HIM: What are you up to?
      ME: … I’m at work. Why?
      HIM: Oh. You wouldn’t have time to run by my house and grab something to bring up to me, would you?
      ME: I’ve got a meeting, so no. What happened?

      After an embarrassed pause, he told me that apparently he had bent over wrong and somehow ripped his pants clean open. He had tried calling his wife, but she wasn’t answering, so he had been sitting trapped in his chair for the entire time so no one would see. I felt bad, but I also laughed *a lot*. His wife did eventually pick up her phone, so all’s well that ends well!

  171. Nita*

    I once volunteered as a translator on a student tour abroad. I wasn’t feeling well that day and took a Tylenol for the headache so I could be out and about. Everything went well until at the end of the tour, I had to translate a pretty sad local legend – so I’ve got 15 college kids hanging on my every word, and just when I get to the last line I start sobbing and blubbering, and cannot stop. Ugh. I’m pretty sure it was the Tylenol… just to be on the safe side, I now stay far, far away from it if I have to do any public speaking.

  172. Fake Name for This Specifically.*

    I’m trying to describe this without outing myself too much, so some details have been changed. During installations, I will support people who are often in front of large groups of others. One of my clients was giving a very harsh speech to the group (think like, Mike Gundy’s “I’m a man” speech in regards to correcting a behavior)…but would also be giving me thumbs up signs as he went because he loved the software so much. I kept sinking down in my chair so no one would look at me.

  173. Anon for this*

    An odd overlap of friendships and collegial relationships ended me up naked in a hot tub with my boss (same sex, both hetero).

    We met eyes and kind of shrugged, then agreed later to never speak of it again.

  174. fiverx313*

    Welp, this isn’t the most, probably… that’s a rich field to harvest. But this is the most recent…

    I just started a new job as a receptionist. Last week I passed the head receptionist outside as we were coming back from lunch, and she said ‘Happy Friday!’

    Having already had about 50 mini-conversations about it being Friday with every single person going in and out of my building, my brain just shorted out and I said ‘Tastes good!’

    I have no idea why, and I’m sure she thinks I’m insane now…

    1. BadPlanning*

      I love it!!

      Have you listened to the comedian Brian Regan? He has a bit about using the wrong return phrase. Like mixing up “Take care” and “Good luck” into “Take luck.”

      1. Squeeble*

        Haha, John Mulaney has a similar one about responding to “how are you?” with “nothing much.”

    2. Elemeno P.*

      This is glorious and SO relatable.

      A couple of weeks ago, I was writing an email to two people named Dan. My boss asked me a question, and instead of “yes,” I just said, “Dan.”

      3. Ramona Flowers*

        Not my story but I have a friend who was once sneakily looking at Facebook on work time when her phone rang and caught her by surprise. She picked it up and said: “Hello, Facebook.” (She did not work at Facebook.)

    3. Rebecca in Dallas*

      Once I was on the phone with someone in another department, trying to help them figure out a problem. After they thanked me, I combined “No problem” and “You’re welcome” into “Your problem.”

  175. Jen*

    I was fairly new at the organization at the time, and we were getting an interim CEO to cover for a mat leave. I’d met this man once very briefly. A week or so later I was at our board meeting, and introducing myself to the board members, didn’t recognize him, and introduced myself to him. He shook my hand, and told me that we’d already met. I so wished I could have melted into the floor.

    1. SubwayFan*

      Similar story but the other way round: My team had just been notified of the name of our new Grandboss, Ursula, who I’d never heard of let alone met, and later that week we went out to lunch together at a place close to the office. Other folks from our work were there, and as one group was leaving they stopped to say hi to some of us. There was one lady who I didn’t know but she looked familiar and I swear we’d met at some other thing, and I said, “You know, I’m sorry, I’ve totally forgotten your name,” as we shook hands. She got a funny look on her face, and said, “It’s Ursula.” I also wanted to melt into the floor.

    2. Elemeno P.*

      I am very bad with faces so this happens to me weekly. My life is an endless sea of embarrassment.

      1. Jean Boyer*

        Oh god me too. I have to ask employees over and over what their name is. (I don’t see them often so it takes a long time to sink in.)

        1. Arjay*

          We had a regional manager who insisted on saying “Nice to meet you” to people he’d met dozens of times before. I don’t know why he didn’t just default to “Nice to see you” instead.

        2. Elizabeth West*

          Me too–some I remember right away, and some I don’t. It’s awful because then I worry that the ones whose names I can’t recall think I just can’t be arsed to remember.

  176. AlexandrinaVictoria*

    I was wearing a shirt with sparkles on a dark blue background, that I thought looked like space. Someone complimented me on it and I said “It’s my Star Trek shirt! Where no man has gone before!” Oops.

  177. Bullwinkle*

    Not my workplace, but work related. This took place in a hole-in-the-wall video store in a large west coast city about 10 years ago. I was browsing, a very unkempt dude came in for an interview for a clerk position and I overheard the following exchange:

    Manager: Why do you want to work here?
    Scruffy Dude: To get out of making porn. You have some of my videos. (note: this store had a small porn corner)
    M: Fair enough. If a customer came in looking for X type of movie, what would you recommend?
    SD: (puts head down on counter) Uhhh, ummm, uhhhhh, I don’t know. I’m really tired.
    M: Oh yeah? Been working hard?
    SD: No, I don’t work. I cultivate a lot of spiritual practices, I’m a guru. This is also my first week sober in a long time.
    M: Congratulations.

    The best part was the manager kept a completely straight face and calm voice the entire time, I was so impressed.

    1. Elemeno P.*

      That manager sounds pretty great!

      Somewhat related, an ex of mine worked in a video store in college. His favorite customers were the ones that came in for The Back Corner because they were very polite, in and out of the store quickly, and always returned the items on time.

  178. Dog Lover #1*

    I was part of a college admissions office. During an interview for a new director, the presenter was a single mother of four that only wanted to talk about finding a man, and how hard it was. We all felt uncomfortable, but managed to ask job specific questions. She was ultimately hired. It didn’t turn out well.

  179. CitiGirl*

    The one that springs to mind is the time I woke up extremely late (and honestly, hungover) one morning, and pretty much jumped into my clothes and rushed to work. I made it on time, but I hadn’t a stitch of makeup on (had it in my purse to put on at work), my hair was an unholy bird’s nest mess, and my shirt was untucked. “No problem”, I thought, as I stepped into the elevator full of people, “I’ll just tidy up in the restroom.” While riding up, I felt the unmistakable urge of gas getting ready to escape. The harder I tried to hold it in, the more powerful it became. Without going into detail, let’s just say I lost the battle, in a big way. Thank goodness I didn’t recognize anyone else in the elevator as being from my company. Turns out the crowd in the elevator was a group of potential overseas vendors destined for a meeting with our corporate heads, and all exited the elevator at the same floor as me, noses wrinkled in disgust. By the grace of god, I worked in the most remote area of that floor, and didn’t have to walk by the conference room areas (with glass walls, of course) all that day.

  180. Caitlin*

    The most awkward situation I’ve ever witnessed was a director who was the IT liaison for the department getting into a literal, physical tug-of-war with an IT employee over a printer. It was exactly what you picture, the two of them yanking the printer back and forth going “Yes! No! Yes! No!”. They were in the hallway, and the IT employee was trying to walk away with the printer because it needed to go back to the central equipment repository, or wherever extra printers live, and the director—who wanted the printer for his office—felt entitled to have this in his office as his personal, private printer. The whole thing was stunning. A thing of true beauty. They tugged back and forth on it, voices escalating, while a crowd gathered and stared in mute shock. I don’t even remember how it ended. (It will perhaps not surprise you to know that this was not the first time that Director got into a public scrum in the hallway.)

    1. fiverx313*

      haha that’s amazing… i’d be staring in mute shock, too.

      actually that reminded me of when i was working the front desk at the furniture store, and two salespeople got into a fracas over who a sale belonged to… and it went from a discussion, to a shouting match, to throwing fabric samples at each other, while the rest of us just goggled at them.

      i also don’t remember how it ended…

  181. Amey*

    Ahh, I’ve just thought of one!

    We had an automatic email that went out to our students at a certain point in their contact with us. There were some external delays in this process one year so my colleague edited the email to explain this and say ‘We apologise for any inconvenience caused.’

    English wasn’t her first language so she was maybe slightly less likely to pick up the autocorrect… This email went out for a month until I happened to have a look at it and realised that we’d been apologising to large numbers of students for any ‘incontinence’ caused!

  182. Anonymous for this one*

    Totally cringeworthy.
    We are at a training about reading data points and the presenter (in her sixties, very conservative and formal) switched slides, saying, “Now, guys, THIS is the money shot.”
    I don’t know what was worse–her obliviousness or the fact that three of us promptly burst out laughing.
    We were later called in to discuss how on EARTH we knew what that meant, since, to her horror, she had accessed Urban Dictionary and was clutching-her-pearls-appalled.
    I still laugh about that one.

  183. Kittymommy*

    I had just started a new job (about 1 mth in) where I worked for the heads of the entire organization (think board of directors with primary decision making). They weren’t on that much that 1st month since it was the holidays so I hadn’t had much exposure with them. I hit sick one Thursday night and ended up calling in the following Friday. By Friday afternoon I decided to go to a walk in clinic, w/o then decided to send me to the er (I drive myself). After being checked out at the er, they loaded me full of muscle relaxers and pain killers, resolved the issue, and discharged me. While I was still high of the meds. I go to the parking lot to text my friend to take me home, but instead text the chairman of the board a rambling, incoherent message where the only thing she could understand was that I was at the emergency room, in the parking lot, drugged up, and needed a ride home. At 11 pm. She got back with me about 5 minutes later (she had been asleep), freaking out and asking which hospital so she could come get me. That’s when I realized I had sent the message to the wrong person. My boss (and my friend) tease me about this too this day and I’m still mortified.

  184. Avocado Toast*

    For about 6 years in my late teens/early twenties I got violent PMS symptoms. They didn’t happen every time and weren’t always the same, so there was no predicting it.

    On the second week of a new job, I got hit with them. I couldn’t stand up, was throwing up in the bathroom (and in the hall), was afraid I was going to faint. I knew it would pass within an hour or so but there was nowhere for me to lay down in the office.

    I took public transportation to and from work, but since I couldn’t really walk very well that wasn’t an option…so a coworker who I had met like two days before this happened had to drive me home while I laid in the backseat of her car.

    It was MORTIFYING, has not happened since, and then I had to explain to everyone that it was just PMS and nothing at all serious.

    1. Nita*

      I feel for you! I used to get this too, and one time I almost passed out on a visit to a construction site, in front of my department head, one of the senior VPs, and the client’s attorney. They noticed I wasn’t quite myself when I tried to sit down on a pile of toxic waste. I obviously didn’t feel like explaining what was wrong, and couldn’t think of anything better than claiming I hadn’t had breakfast. In hindsight, that must have made me look very “organized” and “mature”. They were very nice about it, walked me over to a cab… and my boss also insisted on calling an admin to order me a sandwich. Somehow that made the whole thing even more embarrassing.

  185. hhwcid*

    When I worked in backstage theater, I struggled to find black jeans that a) were durable enough to withstand walking/labor/crawling around behind sets and b) fit as snugly as would be ideal. I was sitting on a stool during pre-show one day, and my pants might have been riding a little bit low in the back. One of the performers was walking behind me to get to their dressing room, and as they passed, stuck their finger down the back of my jeans (read: into the crack). They then pulled it out and nonchalantly continued walking.

    There was also the very physically fit performer who pulled down their pants backstage and insisted that we feel how solid their glutes were.

    The most awkward was when we were rehearsing a scene in which a performer picked up a jug and mimed pouring liquid all over herself. Our props person neglected to mention that the interior of the jug had just been painted…and still had wet paint inside. The poor actress ended up getting paint all over her brand new workout clothes.

    1. Dave Wheeler*

      Two Acting stories to add to your’s.
      Take 1) Acting class , doing the scene from “My Cousin Vinny” where Marisa Tomei crawls up the bed towards Joe Pesci. Doing the scene on a pull out couch (I was Playing Vinnie), actress starts crawling up gets to my knees and the couch folds up on us.
      Take 2) Actress starts crawling up we are still having muffled giggles from the first take, she says he lines and I blank, coach yells cut asks what is the problem and all I could do was laugh and say “She won’t quit smiling at me !!!”

  186. GG Two shoes*

    Alright I have a dousy. Each year, our small company allows one employee and a guest to go on a incentive trip with our agents. I was lucky enough to win! hurray! My grandboss, the president, his wife and my husband and I rode at 5:00am to the airport together. Now is a good time to mention how EXTREME on top of and organized I am generally. I really pride myself on that. Anyway, after we get to the airport I realized I left my clutch at home. The one that has my drivers license, passport, tickets, money, EVERYTHING. I’m mortified. My very cool grandboss says, sure take my car back but hurry!

    I drive back as fast as possible and get the clutch. I get back to the airport and… his keyless entry fob is no where to be found. It’s in the car, somewhere. but I CAN NOT FIND IT. My husband is calling me to say I have to get up to the gate right now, everyone else is boarding. I don’t find the fob and thus can’t lock the car doors. I get on the plane and everyone in my group (over half the plane) starts clapping. As I walk to my boss, he asks for his key and I have to say, I don’t have it. It’s somewhere in the vehicle… and then I slink into my seat and die for the rest of the flight/trip…

    Mortified isn’t even close to the feeling I had.

  187. Naptime Enthusiast*

    We had a group pizza lunch and our manager encouraged us to talk about Not Work topics. Our last summer intern was planning to study abroad the next year in a country our manager is very familiar with, so manager asked about the city he was going to, what his friends that had studied there last year recommended, etc… intern started talking about how many people got super drunk every night and came home with lots of STDs.

    Everyone in the room awkwardly pretended not to hear it and talk about how delicious the pizza was for the next 20 minutes.

  188. eating falafel rn*

    When I worked at a restaurant in high school, I answered the phone for a takeout call. The person had a deep voice, so immediately defaulted to addressing them as “sir.” The first time I did it, there was a pause, but then the person continued speaking. I then used the phrase several more times, and I noticed the customer was taking longer to respond each time and something seemed off in their voice, but I couldn’t figure out what, so I just kept on going. Finally, toward the end of the call, I asked if there was anything else I could do for them, and they paused for a long time again, and then asked me, “Do I sound like a man?” I then realized this person was very much a woman. I apologized profusely and said, “No, of course not! I just have a cold, totally my fault.” Then I hung up as quickly as possible and made sure I was not the one to greet her when she came to get her food.

    1. CER*

      My husband also gets misgendered a lot on the phone and I have been guilty of misgendering callers several times myself.. I wish there was a gender neutral version of “sir” or “ma’am” to help in situations like this.

  189. Sami*

    Swearing in front of a class of 8th graders! Yep, I accidentally said “shit”!
    Or having to explain cleavage to said 8th graders— as it pertains to rocks, not the female body.

  190. Sunshine on a cloudy day*

    Runner up is the time in an interview when I answered “How are you at math?” with “Well, I’m really good with a calculator”. To this day I don’t know why that came out of my mouth. I’m actually pretty solid with numbers (in a practical/real world sense – not like advanced theoretical math – but this job just required some reporting involving sales numbers from spreadsheets.)

    I’m a super awkward person. For sure. I’ve finally just sort of accepted it and push on through. My biggest issue is my mind blanking out in very inappropriate socially-geared situations, so I now I just keep a mental list of q’s/safe subjects that I can switch to whenever I put my foot in my mouth. Might be an awkward transition, but it’s better than an awkward silence, and most people tend to role with it if I just switch and brush it off.

  191. TheAssistant*

    In my first company, I was pinch-hitting as an Executive Assistant to an interim VP. We had finally announced the permanent VP, and the interim guy decided to make a little speech to the department (he was prone to speeching). So he’s talking about the new VP, and the department, etc. Then turns to me and says, “[TheAssistant] has been such a great wingman to me these past few months!”

    And I just died, right there. I’m now a ghost.

  192. CER*

    I work in a local government organization, so we spend a lot of time dealing with the public. My former boss was a wonderful person but she was also the queen of conversational awkwardness. One day she was talking to a customer that had just moved into the area. My boss began talking to her about moving and then said “Have you found your toothbrush yet?” The customer looked at her and said, “Excuse Me?” So my boss repeated the question, which led to the customer getting very upset because she thought my boss was insulting her dental hygiene and/or insinuating she had bad breath. My boss tried to explain that whenever she moved she always lost things or had trouble finding her toothbrush in all her boxes and so she was just trying to empathize with the struggles of moving. The customer still left in a bit of a huff and I wanted to sink into the floor in secondary embarrassment.

  193. Morgan*

    I was working at a prestigious business school while I was in undergrad. There was a woman who directed a program that I thought was just the coolest. She had the career path I dreamed of and she was just such an amazing person with an insane amount of knowledge. I was getting close to graduating and knew I would be leaving for my “real job”, and I asked her if she would be willing to grab coffee and chat about her career, etc. I’ve always been a little awkward, but she also made me nervous because I just thought she was SO COOL and inspiring. We chatted in the office, but I was excited to sit down with her 1:1. When we were scheduled to meet, she had to cancel by email due to a last minute meeting, not a big deal. She stopped by my desk a day or so later to apologize and let me know what could work for her to set up another time. As she was walking away, I said…”thanks for touching” with an incredibly long pause..and by the time she was almost definitely out of earshot, managed to say “…base”. My coworker (a good friend before and after the job) and I still laugh about it to this day.

  194. CG*

    I am sure that after I hit “submit”, many, many embarrassing things I have done will come to mind, because I think I embarrass myself with awkwardness (or someone else does it in my general direction) about once a day.

    All I can think of right now is this: my boss regularly mixes metaphors and uses words in not quite the right manner, sometimes to comedic effect. I’m trying to think of a great example, because some of them get into spit-take territory and we have to just soldier on. (Think of the Pushing Daisies episode where Olive says, “I thought masturbating meant chewing your food!”)

  195. Tammy*

    Read another review of this book recently & it’s on my wish list! Why? I’m the person who has to switch tv programs when someone is about to be embarrassed. I just can’t watch.

  196. No name plz*

    My most awkward moment? Okay.
    I live in a condo with no office for package drop-offs, so with my boss’s blessing I had permission to have my occasional Amazon binges delivered at work. Other people did it, too, but I got a little. . .casual. . .about it since the clerk in charge of mail was cool and I didn’t abuse the privilege.
    Well, I had a personal device catch on fire (YES ON FIRE WHILE WE WERE USING IT) and my husband was horrified and asked me to immediately acquire another one since they were quite nice, and we’ll just leave it at that. I double and triple checked on the “discreet packaging” of said item, and it was indeed securely wrapped when it arrived at work.
    In clear packing tape.
    I wanted to move to Mongolia.

  197. The Mango Incident*

    While in college, I worked at my school’s cafe where I was sometimes rotated to the smoothie bar.

    It wasn’t uncommon for some of the smoothie makers to furtively slip some fruit every once in a while. Obviously, it’s not something workers were supposed to do, but it happened (poor, hungry college students and all that).

    Well, this one time, on a particularly slow afternoon, I was feeling pretty audacious and took the LARGEST piece of frozen mango and put the whole thing in my mouth.

    Of course, right after I did that, someone came up to order a smoothie.

    Now this wouldn’t have been such a huge deal if this guy was like most other students: they order a smoothie, then go back to talking to a friend or texting or otherwise don’t interact. Most students may never have noticed the giant piece of mango I was trying to choke down.

    But this guy was not like most students.

    This guy kept trying to make conversation and ask questions. I tried my best to hide my wrongdoing by “mhm”ing through it but I could tell he knew something was up.

    When I was finally able to swallow the last of my guilt, I looked in his eyes and said, way too emphatically, “I am SO sorry, I should NOT have been eating that mango!”

    Awkwardness ensued. He was clearly confused why I was confessing my transgression to him, and so emotional about it. He mumbled something along the lines of, “Uh, that’s ok?”, took his smoothie, and left.

    Every time I saw him on campus after I would feel the embarrassment creep up. I’d wonder, “Does he remember me? Does he think of me as that weird smoothie girl?”

    I worked with him on something else a year or so after the Mango Incident. Fortunately, he didn’t bring it up, nor did I. I can only hope he didn’t remember that I was the same person.

  198. Partly Cloudy*

    In my first post-college job, my boss and her family were all big fans of [Popular Sports Team] and the star player for this team. My boss was pregnant when I started working there and a small group of us were having a conversation with her about baby names. She mentioned that she really liked the name [First Name of Star Athlete] and wanted to name her baby that. I laughed and asked “no, really, what are you going to name him?”

    Silence.
    A look.
    “[First Name of Star Athlete].”

    It’s not even a weird or bad name, it was just not very common at the time, at least not to 21-year-old me….

  199. Faith*

    We had a fairly new coworker and someone had somehow found out when his birthday was and wanted to have a small celebration with cake – comparable to what we did for other coworkers’ birthdays. New coworker said he didn’t want a celebration, and while most of us respected that, that one guy went out and bought him a cake anyway. He brought it and new coworker into the conference room where a group of us were eating lunch, and insisted we all sing happy birthday and eat cake. It was uncomfortable because we all knew the new coworker had specifically asked not to be the center of attention like that, but he was gracious about it.

  200. LAI*

    It was my first week at a new job, and there was an office potluck. I made a dessert. As I was sitting with my new coworkers, one of them took a bite of my dessert, then moved the rest of it to the side of her plate, looked at me, pointed at it, and shook her head slightly, warning me not to get one. I said “Oh, I made those. It’s ok, you don’t have to eat it.” I think we were both mortified.

  201. Looby*

    In my old job I was in a meeting with the Director of our institute, my manager, Gertrude, and the other managers while the director tried to explain how my role would work to everyone. The idea being that while I would report to one manager, the other groups could request my support on their projects as needed.
    The director however felt maybe he wasn’t clear enough and decided he needed an analogy:
    “Think of Looby as a racehorse, while Gertrude is her Owner, the rest of you are jockeys, and if you want to ride Looby you just need to ask the stable owner if the horse is available”
    Everyone kind of sat in silence for a moment, and as the director opened his mouth again the IT manager thankfully said “I’m going to ask you not to say anything more about horses and riding before we have an HR investigation!”
    I got a lot of horse racing emojis from my coworkers as the story got repeated after the meeting…

  202. Alex*

    I was working in a grocery store and the department manager pulled an inappropriate prank on a coworker. Everyone in the department got called into the store manager’s office one by one to tell our side of the story. After that we (including the person who pulled the prank) all had to go back to the department and work while the manager decided what to do. No one was talking or making eye contact. It was unbearably cringeworthy. The department manager got fired later that day.

  203. Legal Beagle*

    My boss kept scheduling and rescheduling a meeting with me, and I was annoyed because she didn’t even tell me what the meeting was about or why it was so urgent that we meet that day. After a few abrupt time changes, I went to a coworker and was venting about how our boss was being so inconsiderate, doesn’t she know I have things to do, she’s messing up my schedule…yeah. Boss had planned a surprise birthday party for me, and the time kept getting moved while she tried to coordinate it so the whole office (a dozen people) could attend. I felt like a huge ingrate, and my poor coworker had to listen to me complaining and pretend to be sympathetic because she didn’t want to ruin the surprise.

      1. winter*

        Agree. We had a surprise event for everyone before the holidays and people weren’t very happy about it because not knowing that it would be ‘free time’, we didn’t get a chance to plan our work accordingly. The idea was nice, but it fell kind of flat.

  204. Chinook*

    My most awkward work moment was on the 2nd day of a 2 day interview in another city. I must have gotten. The time wrong because I went shopping and missed my assigned slot for my teaching audition and showed up an hour late. I was embarrased and apologetic, so the interviewer still saw me at the end of the day but decided to tank it for me by being the worst, most dense student in the one-on-one teaching scenario. Like, literally not understanding any explanation I have on how a certain sentence structure worked. Ironically, my ability to pivot and try 5 different methods to get her to understand the concept won her over and for me the job, but it was the most awkward class I had ever taught.

    1. Chinook*

      And then there was the time my very fit colleague showed up to my classroom after hours to ask for a textbook. He had just finished up a weight workout in the school gym and was on his way home to change (housing was right next to the school) and was still wearing his workout gear where I could see all his muscles. I think lost the ability to speak and he had to repeat the question 3 times before I just nodded, grabbed the book for him and walked over to give it to him.

  205. Jolie*

    Not sure if the most awkward, but quite funny.
    Late afternoon in the office, I’m trying to pull some data out of our big creaky Access database, which keeps losing connection, freezing or otherwise spitting error messages at me.
    Boss comes in and helps herself to the office biscuit box. She makes some comment or another about craving something sweet.
    In a possibly slightly exasperated tone (the bloody database was giving me the “you lost connection” error for the 20th time in 10 minutes), I ask “Does the Internet work for you?”.
    She reacts rather taken aback. She misheard me, and thought I was asking, in a rather judgemental tone “Do you think they’re not bad for you?” (The biscuits, that is).
    I was like : Nooooooo, the in-ter-neeet ! The ruddy database keeps losing connection to the drive! “

  207. Quackeen*

    I was new in a job and heard from a coworker that she was voluntarily leaving the company. I brightly said, “Oh! On to bigger and better things?” She got quiet and told me that, no, she was actually dying of cancer.

    I have learned to just smile and say, “Best wishes to you” whenever someone tells me that they are leaving.

  208. WizzardOzz*

    I pulled up a distribution list at work one time so I can see who was on it – then make a snarky comment about each person on it in an email to a friend. Unfortunately, I left the distribution list on the email when I hit send and sent every single one of them an email with a snarky comment about the others, and about themselves.

    Fun times for the next few weeks at work…

    1. Elizabeth West*

      OMG Burn Book!

      At OldExJob, one time I was snarking about something while on hold and didn’t realize I had hit the page button. Everyone in the entire office and both machine shops heard me.

  209. Victoria Ford*

    I once left a voicemail for my boss in which I signed off with “Love, Victoria.” DOUBLE AWKWARD: I said “love” to my boss, and, uh, I used an email signoff in a voicemail. Whee!

    2. Ramona Flowers*

      You are not alone. You just reminded me of the time I forgot all the ending-a-conversation words like goodbye and eventually, after a long silence, I instead managed to say: “Well, uh, best wishes!”

  210. Foreign Octopus*

    In one of my first office jobs when I was 20, the culture was to eat lunch with your team. Me being me didn’t like that idea. I already had to sit with them throughout the day, and I needed my lunch to decompress and be by myself. Unfortunately, we were in the middle of nowhere. Literally nowhere.

    I went to my car one day but was quickly rumbled. I had to bide my time. Act casual. I integrated myself into the group like a penguin trying to pass as a bird. Head down, all’s good.

    When I’d gained their trust, I stopped attending the lunches. I took my packed lunch (and my book, of course) and I locked myself away in the bathroom – super classy, I know, but I was happy. I had a whole cubicle to myself where, if I positioned myself right, I could even prop my feet up and read happily munching on a sandwich.

    It was heaven for exactly four days. On the fifth, I used a cubicle with a door that didn’t lock properly (I didn’t realise that). There I am, sandwich in mouth, book in hand, and the door swings open and I look up to find my boss staring in at me.

    I manage a smile around my sandwich, looking not at all like I’m about to murder her, and she lets the door go. I hear her heels click as she leaves the bathroom and I contemplated drowning myself in the toilet bowl rather than leaving the bathroom.

    She never mentioned it. I certainly didn’t bring it up, but I could never look her in the eye again.

  211. Cruciatus*

    Oh boy, there have been so many I probably am not thinking of the best ones. The first one that came to mind was when a faculty member, weeks before the new semester came into the office and told me and the other front desk person that she was quitting, she wasn’t being used for her expertise in subject X and it was a hostile work environment created by M (who had just left the office-they had to have passed each other). But me and my coworker were OK and she was pleased to work with us.

    My coworker and I were NOT the ones to handle this. I got up and told my supervisor “Uh, hey, did you know so-and-so was leaving?” and I have never seen her jump out of a chair so fast to try and get more information! And by waiting until the new semester was nearly starting, this person was really trying to mess up the whole system since we had to try to find a replacement ASAP). Oof!

  212. Erika22*

    My team at my nonprofit is mostly women in their early to late thirties, so naturally we had four pregnancies last year. I’m super awkward around babies and baby-related things (and realized that before this time, I had never spent a regular or consistent amount of time around a pregnant woman before? Which is strange but anyway). One of my pregnant coworkers and I were making small talk next to the microwave, and since I wasn’t sure when her baby was due, but didn’t want to ask outright because it seemed rude for some reason, I asked, “When is, you know….” and proceeded to make a swooshing motion with my hands to suggest the baby coming out, all while making a 0_0 face. My coworker took it in stride, but I couldn’t even make my escape immediately because I was waiting for my lunch to finish microwaving!

  213. Buckle Up!*

    When I worked for a kind of a satellite government office, we were expected to keep the office open the day after Thanksgiving, even though the phone never rang, and no one else would really be working. One year, my boss tells everyone that she’ll come in, but we don’t have to and we won’t lose a vacation day. Great, right?

    I was the communications person for the office, and newspapers were still open, and my grandboss wanted a press release sent out on Black Friday about something that had happened at the Capital earlier in the week. She knew no one was really planning on working, but I lived within walking distance of the office, so she asked me to go in anyway to send it out. (I couldn’t send it out from home.)

    Late on Friday morning, I walked over to the office and found the door locked. I was puzzled, but was thinking that maybe Boss went out for just a minute to grab lunch. I used my key to open the door. I even called “hello” when I walked in. There didn’t seem to be anyone there.

    I walked down the hallway, and glanced into my grandboss’ office, to see the NAKED BACK OF MY BOSS while she obviously was straddling someone on my grandboss’ chair!!

    I jumped into my office, and waited for her to come out, since I was sure she must have heard me, but she didn’t. I turned on my computer, sent the press release, and got the hell out of there as fast as I could! As I walked down the stairs, I thought, “Maybe it was her husband, who came into the office for a taboo quickie in the boss’ office.”

    NOPE.

    When I got back to the parking lot, I realized there were only two cars there: my boss and our 19 year old intern! The pieces fell into place, as I had noticed more than a little inappropriate behavior between them, although in my defense, this was such a toxic and unprofessional working environment, and my boss was such a “mean girl” that I think I had become numb to the signs that something really and truly messed up was going on. And because of how awful my boss was to me on a daily basis, I was TERRIFIED that she would know that I knew, and that she would punish me for it. I spent the whole holiday weekend twisted up in knots, and even well after that, since I was already very stressed at that job, and this did NOT help.

    Eventually, she left, and was replaced with someone immeasurably better. The intern eventually became full-time staff, and on my last day, he came into the office, closed the door and said that he had always wondered if I was aware of him and the old boss having an affair. I told him that not only did I know, but that I had witnessed it with my own eyes. He was shocked! It was a nice was to wrap up a truly awkward situation for me (even if no one else was aware that it was awkward).

  214. hermit crab*

    My work involves both public health and public drinking water systems; as a result, there are many opportunities for embarrassment if you accidentally leave the “L” out of a word. The worst was years ago (before my time), when we apparently sent in a major proposal that said “pubic” instead of “public” on the cover.

    1. Nightmare Interview*

      At a previous job I was in charge of designing and printing paper programs for theatrical performances. One time I made a half-sheet for a one-man show that was part of the Best of the Black Box series…

      Performer Name
      *Beast* of the Black Box

      Luckily I caught a few hours before performance and had time to fix it.

      1. Ex-Academic, Future Accountant*

        I’ve heard stories from musicians about publicity posters (pubicity posters?) that left the “i” out of “recital”!

    2. Elizabeth West*

      This happened before I worked there, but a shopping paper published an ad for a woman who was selling an electric organ–the kind that had all the buttons you could push to add beats. The person who wrote the ad put “orgasm.”

      The paper had to run the corrected ad for free until it sold.

  215. MissingArizona*

    Worked at a small store with a counter and people just came up to us to purchase things. Super easy job. My new coworker gets interviewed, and hired at a different location, and transfered to my store. To get behind the counter you just move a flimsy cardboard display and walk back, well this was a big girl, and the space wasn’t big enough. Our counter was bolted to the ground, there was literally no way she could get behind the counter, and she couldn’t go over cause it was glass. I had to call the area manager for the keys to the back door that we never used. I was all of 18, and literally had zero idea what to do or say, so while we waited I just went over stock and protocol. Both of us were awkward, and that just made it more awkward. We did get new protocol with the store keys, and she was a friendly person to work with, so it ended up ok in the end.

  216. Adelyade83*

    I was in highschool and a group of us were going to an all night event for New Years. We had to drive about 3 hours to get there and decided to stop and eat at McDonalds. We also decided to ironically play in the play area thinking it would be funny. We tried to go down the slide train style with all of us holding onto each others feet. During one of the slide turns I turned oddly and my pants split. I had to spend the rest of new years in a long t-shirt trying to be delicate anytime I moved so the rip wouldn’t show.

  218. Tasha*

    Third day back at work after maternity leave, boss asks, “what is that large box you’ve been carrying back and forth” in front of several colleagues. I said, “it’s a breast pump,” kept moving, and he turned bright red. After that I could have walked out with ANYTHING and not been questioned. (This was 20+ years ago, it was a rental, and was much larger than today’s models.)

    1. CG*

      Oh gosh. I worked in an office once where you had to leave your suite to use the bathroom, and one day, my boss (male-dominated field full of socially awkward single men) loudly asked my 30-ish female colleague who was on her way to the bathroom, “why do you always carry your purse with you to the bathroom?!” Her response: “TAMPONS.”

  219. AnnieC*

    This happened only 2 weeks ago. I was mortified.
    Last year I was missed out off of the list calling out the high achievers – over 100% of quota, I also did not get the cube paperweight for hitting target. I was also missed off of the promotions list and it became a running joke throughout the year.
    Come January this year, I’m at the annual awards dinner, sitting with my business unit’s VP and EVP (from my large corporate company) and all the over 100% achievers names are called out and mine is missing again. I felt myself getting upset but thought it was in someway a good idea to say to my VP “This is nonsense, I’ve been forgotten again?! why doesn’t this surprise me. It’s becoming par for the course now. I do well and nobody cares” and he just looked at me and smiled which annoyed me all the more. Imagine my shock when 5 mins later not only was my name called out but I was given a super fancy, all expenses paid trip for 2 to Europe (staying at the Ritz no less).
    I felt awkward and embarrassed every time I saw him for 2 days.

  220. Golden Lioness*

    Oh, my goodness! So much awkwardness, so many funny (now!) moments! =P

    I come from a culture that kisses (sometimes one sometimes both cheeks). When I moved to the US and I finally started my 1st day ever at a US company, as soon as I was introduced to my new co-workers, I went for the kiss. The look of horror on their faces made blush extra red.

  221. Pick Me!*

    I was new in a healthcare-related industry and didn’t know how a particular aspect worked yet. To be fair, it wasn’t described very well. In any case, I misunderstood and thought a direct affect of the issue would cause unsuspecting women to get pregnant. Without wanting to be pregnant.

    I was horrified by this and ended up telling a coworker about it, who agreed it would be terrible to get pregnant unintentionally in this way. To add realness to the discussion, I tried to pull in another coworker, who was within hearing distance, who had just returned from maternity leave, as an example.

    “I can’t imagine being like Tina!” Long pause. “I mean, without wanting to be like Tina.” Pause. “I mean, I know she’s going through stuff and it’s hard…. Sorry Tina. That came out wrong.”

    No surprise I was spoken to by my boss the next day about being kind to others with children.

  223. N.J.*

    I’m a hugger. It’s gotten better over the years, in that I don’t often give hugs to those who don’t want them anymore, but I’ve had some cringeworthy moments. I was temping at one workplace after having worked at a very inappropriate, huggy workplace. I think it became apparent to my boss that I was huggy. I was privately working on toning it down, as I could tell it was making people uncomfortable. She was showing one of the newer interns around and stopped by my desk. Somehow they got into a conversation on hugging or something and my hugginess came up. My boss half jokingly “ordered” me to hug the intern, without knowing whether the intern would have viewed that as a violation of personal space. I cringe to this day, but my brain went into what I can only describe as a combination of hugs are nice/did she really just tell me to do this/what if she is serious?/shock/must obey/people pleaser/no don’t do it/ overload and I hugged the poor intern, who recoiled in horror. My boss then made some sort of snide coment about me really doing that and they left. I have not hugged someone at work since, even if I have to talk myself down, as it were. That poor intern never made eye contact or talked to me again and I don’t blame her. I myself wanted to crawl into a hole and die for several weeks.

    1. winter*

      Okay, but what was your boss going for there? It seems weird that they joke (?)-asked you in the first place.

  224. TCO*

    I was only a few months in to my very first post-college job when one of my coworkers was fired (or at least “counseled out”). He was allowed to leave in a really dignified way, including our customary going-away party and a kind e-mail about him “leaving to grow his own business.” (He didn’t commit serious malfeasance or anything, he just wasn’t effective at his job and even I could see that as a newbie.) I didn’t really pick up on the subtext that he was being fired, so at his party I asked him in front of everyone about his exciting new business venture. It quickly became clear that this “new venture” didn’t really exist.

  225. Kai Jones*

    I was working as a secretary; the office had study-carrel style desks raised on a pedestal with half a dozen steps (so we were all facing the center–and each other–on top of the pedestal). I turned to go down the steps and fell. I was 6 months pregnant and all the other workers rushed to help me get up. I wasn’t hurt and nothing bad happened, but it was incredibly awkward.

  226. Anastasia Beaverhausen*

    I was in my final year of undergrad, and was doing an Independent Study project with one of my professors. He called my apartment one day, and my roommate answered the phone. She thought it was my dad, so told me that’s who it was. So, like a dummy, I picked up the phone very excited to hear from my dad (this was 25 years ago, so no e-mail, cell phones, etc. and I was 4-1/2 hours away, so didn’t get to see or talk to my dad too often). I happily exclaimed “Hi Daddy!” into the phone. Awkward silence on the other end, then…”Uh, I’m looking for Anastasia?” Luckily I recovered quickly and said, “Oh sorry, I’ll go get her!”

  227. TheSoundkeeper*

    A colleague came into my office and sat in my guest chair to ask what I thought was a work-related question but was actually a request to go on a date with him sometime. I was in the middle of answering while blushing wildly, when my manager walked in with an actual work question. Said manager was not known for his appropriateness (once commented “I like seeing my employees on their knees” when watching me sort a lower bookcase shelf), so I bumbled through an answer while willing him to leave quickly and hoping that he was oblivious to the nature of the interaction. 20 years and two children later, I still tease my very intelligent spouse about his approach vs. looking my uncommon name up in a phone directory and calling me at home. :-)

  228. Joielle*

    Once, I was working with a prestigious member of my university’s faculty on a book drive. We were finally ready to launch it and he agreed to send an email to all of his (several hundred) students and contacts to advertise. I got the email a few minutes later and the subject line read, in all caps: “BOOB DRIVE”… followed quickly by a hastily-drafted email apologizing for the error. At least the book drive got a lot of buzz!

  229. Bassoon Wielding Chemist*

    My mother and I were out for a day of shopping. We stopped for lunch at the high-end steak house where I worked at the time and she had been wanting to try. As word got around that we were there various staff came by to meet my mother, very pleasant and uneventful. Then the general manager stops over and this happens:

    Me: Mom this is our general manager, Fergus Smith. Fergus this is my mother, May White.
    General Manager: (extends hand) It is so nice to meet you May, I’ve heard so much about you.
    Mom: (lightly grasps his hand, looks him in the eye) You are a good looking man!
    Me: …

  230. Elemeno P.*

    This will probably out me if any work friends read this blog, but the story is great.

    I work for a theme park. Sometimes we look at what other theme parks do so we can learn from them. A few years ago, my two (male) bosses and I went to a rival park for the day to learn from some stuff they were doing. We walked around, took some pictures, and then decided to go on some rides (why not, while we were there!). It is relevant now to state that I wear dresses to work, and my dress that day had a big, flowy circle skirt.

    The particular ride in this story is now closed, but it used air jets on the ground to make the vehicles float. I figured the jets were only on while the vehicles were in motion.

    I was incorrect.

    My ENTIRE skirt flew up to my head, front and back and sides, fabric billowing all around me. The skirt was pretty voluminous, and I physically could not gather all the fabric quickly enough. I pushed it all down frantically and then sat in a ride vehicle between my two bosses, who I then spent the whole day with.

    My underwear that day wasn’t even cute.

    1. Nita*

      I should have known not to drink coffee while reading here. Now it’s everywhere. Also, hope you didn’t get too many Marilyn Monroe jokes after that…

  231. Liz T*

    Listening to a billionaire fart and pretending it wasn’t happening is probably my most awkward work experience.

    1. Elizabeth West*

      Oh man. I keep from being nervous when meeting bigwigs or celebs by remembering “Everybody poops.” But farts are funny, will always be funny, and I don’t think I could have survived this moment.

  232. Anon for this*

    I’ve told this before here, but for anyone who missed it (and for a chance to win a book!)…

    I was working at a fairly stressful job where we semi-jokingly had asked our boss if we could have an emotional support animal. He said there were people in the office allergic to dogs and cats and for some reason seemed to think we would leave it at that. We did not. Over the course of months we discussed pros and cons of various alternatives including support emus, support goats, and support anything-we-could-think-of (surprisingly emotional support peacocks never came up). One worker even brought up having a snake, knowing that I, his manager, hate snakes to the point where even talking about them makes me cringe.

    So a few weeks later, when we had something really terrible happen, I thought I’d break up the tension by referencing the snake and getting the team to all laugh at me. Unfortunately, what I (20 years older than the rest of the team, sort of straightlaced, sort of respectable, female) very perkily said was “We’re gonna need Worker’s anaconda to get us over this!” There was a moment of dead silence and then an explosion of laughter from everyone present (so…mission accomplished?). My face turned redder it’s ever been and I took myself to hr. That’s when our hr rep lost it and couldn’t stop laughing either. I have a feeling I might still be a legend even though I don’t work there anymore.

  233. Tricksy Hobbit*

    Hi Everyone,

    We suddenly all got an email with a mandatory sexual harassment for the entire business. Of course, our eyebrows went up and our first thought was, “Who did what?”. The harassment training itself was… magnificent, in its own way. Our department was trying our best to keep a straight face when one of the slides had this cheesy video, and the takeaway was a picture on the next slide that said (and I swear I am not making this up): “Don’t get your honey where you get your money.”

    Then the trainer was trying to talk about the dangers of texting and how you can sexually harass over text, and her exact words were, “I know, it’s late, you’ve had a few glasses of wine, so you bang one out” referring to the text. The group in front of us lost it at that point.

    Sexual harassment training: a good thing. Sexual harassment training that apparently came straight out of the 1970s: not so good. To this day, my coworkers and I go into fits of giggles whenever we think of Don’t Get Your Honey Where You Get Your Money

  234. Anonymous for this...*

    Not funny awkward, just sad awkward, or maybe the world’s dullest ghost story.

    I once dated a man in another department of the company I worked for. (This was fine.) Unfortunately, he passed away from complications of medical treatment, and I was devastated. My coworkers were wonderful about it, and a few became closer friends—including one who lived near me and had 4-wheel drive, who told me to call him if I had trouble getting to work in the snow in my hatchback.

    Two years later I was snowed in, but I’d lost the helpful guy’s cell number. I figured I’d call our work number, leave a message and see if he checked his voicemail. At the time, our office had one of those directories where you could spell out the name on the keypad and it would direct to the person’s extension (let’s say the name was “Gaston”). I typed in G-A-S-T-O-N…and got my dead boyfriend’s voicemail, in his own voice (I’ll say his name was “Patterson,” so a lot of letters in common, but not all of them).

    After that, I didn’t feel like going in to work anyway.

  235. Mel*

    One time I was running late to a meeting, cup of coffee in hand. When I opened the conference room door, the meeting had already started, so naturally everyone turned towards the noise. At that exact moment, with our entire group looking at me, I dropped my coffee mug and spilled the whole thing down myself. Including my white shirt. And all over the floor.

    Luckily it wasn’t hot enough to burn me, but I spent some very fun minutes with a bright red face trying to wipe up the coffee from myself and the floor while coworkers brought me paper towels and the presenter awkwardly tried to continue the meeting.

    A close second: one time I was walking down the hallway taking a sip of water. Our VP was walking towards me and said hello. I tried to say hi back mid-sip and, uh, spit water all down my front as he watched. Like that scene in HP and the Goblet of Fire when Harry smiles at Cho and spits juice all over himself. I don’t know why I have such a hard time with beverages…

    1. JB (not in Houston)*

      Once when I’d been called for jury duty, I was sitting in the room with all the other potential jurors waiting to get called to a courtroom. I went to take a sip of coffee but missed my mouth entirely and just poured it down the front of my shirt. Fortunately I had on a cardigan I could button over it, but I couldn’t do anything about the people who saw me noncholantly pour coffee on myself.

  236. Nightmare Interview*

    This happened in my early 20s just before the interview for my first Real Job at a municipal agency.

    While waiting to be seen I used the restroom, but afterward the toilet wouldn’t flush (mechanical; not because of me). I sat there a good minute deciding if I wanted to be the candidate who didn’t flush or the one who broke the toilet. I decided on the latter and was telling the receptionist about the problem when my interviewer walked up and joined the “conversation.” Then she invited me to follow her beyond a counter-height door to the interview area. What I thought was the knob promptly twisted off in my hand; apparently you are supposed to push open. But wait! There’s more! As I’m finishing up a practical exercise, the computer I was using crashed. I just grabbed a notepad and wrote out as much as I could remember doing of this 45-minute project and had to tell them the computer died while I was using it!

    Everyone on the floor – including grandbosses and VIPs were aware of everything and giving me a variety of Looks. Some amused, some incredulous, a few sympathetic.

    As I was leaving they joked that they needed to hire me just so I could work off all the damage. I replied that they’d better prepare for increased insurance premiums. I literally started crying the moment I was alone in my car.

    I ended up getting the position because it was a public-facing PR job and performing so well during an awkward and embarrassing situation actually helped me!

  237. Folklorist*

    I was doing an apprenticeship at a highly, highly prestigious publication. At the same time, I was just out of grad school, but having a weird overlap with still needing to take my grad school exams to complete my degrees, and having a part-time job on top of it because the apprenticeship only paid $10/hr in a very high-cost-of-living city. Basically, I was working or studying 24/7 and miserable and breaking out into stress hives. One day, I had this genius idea–I realized that people (except me because I was always trying to catch up) never went into the office on Saturdays, and they really had all of these fancy couches that never got used, so it would be a great place to study! So I went in wearing my pajamas, set up my piles of study materials, and got to work in a comfy atmosphere (I couldn’t afford coffee shops because, $10/hr, and there was very little room at the tiny house I rented with 3 other people). Except, my stress-hives flared up and were super-itchy. And high on the back of my thighs. Oh, well, I was alone in the office, right? Went into the bathroom, took my pants off, and started rubbing on cortisone cream using the mirror so I could see. And then in walks the photo editor, a pretty high name in the industry. While I’m rubbing my rashy butt. She kind of stammered and walked out and I tried to explain that I thought I was alone and nobody was coming in. She was nice about it, dropped it, and never mentioned it again, but I know that I live in her mind as THAT person (and she probably told everyone else about the kooky apprentice too. Sigh.) Needless to say, I figured out other places to study after that.

  238. Jersey's mom*

    I work for a Fortune 300 Company. I do esoteric environmental work. The Company was planning a multibillion dollar project that had esoteric environmental issues. I was called into a meeting with 25+ Executive VPs, attorneys from two different firms and the VP of the environmental division. My VP was a nice lady, but not overly perceptive. At the start of the meeting, I began to have a hot flash. My skin tone is whiter than snow, and during a hot flash, I get beet red and start (very obviously) sweating from my hair roots to my knees.

    My VP sat next to me and began introductions around the room. Everyone could see me trying to unobtrusively blot the river of sweat off my face. My VP announces my name and turns to me; her eyes grew round, and she shouts out “oh my god, are you OK? Are you sick? Do we need to call an ambulance?”

    I mumbled, “no, I’m just blushing at being in a room with so many VPs and attorneys” and tried very hard to become invisible.

    1. I'll come up with a clever name later.*

      I am fair as well and while I was pregnant with my first born I worked for a medical insurance company. I was in the middle of a training class (as a student) when I suddenly became warm. It was spring, heat was still on, windows closed, pregnant…it was the perfect mix. Apparently I got very red. At times I actually turn kind of purple when I get very red, such is my skin tone. This happened during the class. The trainer immediately stopped the class without a word, went to the phone and called for medical personnel to come to the classroom. The class all kind of looked around wondering what was going on, myself included. Moments later three security/EMT guys come in and she points at me and announces that I am at risk because of my color and pregnancy. The entire class turns which makes me blush harder so I resemble Barney the dinosaur. The EMT’s check me out, talk to me, etc and I tell them I was warm and flush easy. They opened the windows, turned off the heat, and gave me some water. For weeks after my co-workers would say stuff like “don’t make her blush…she can get the officials in here without trying!!”

  239. Not a Morning Person*

    SO many awkward options to choose from!
    At one job where I was a new manager, I had a meeting with my general manager (boss) and a vendor. I had a new blazer and chose to wear it that day. So I’m sitting in the meeting where we are discussing of all things, the William Tell Overture, and I said something silly that made it sound like I thought William Tell was a real historical figure. And the vendor looked at me a little condescendingly and said something like, “You know that is not a real story; it’s a legend.” And I replied, “Oh of course”, and followed it with something about the legend, while gesturing with my hands, and noticing that the blazer still had the extra buttons attached and swinging from one sleeve and that the sleeve also had the white sewn on tag on that sleeve. As a new, youngish manager, I was mortified! Now I can laugh at it, a little, but then I still thought I should try to hide it and I spent the rest of the meeting trying to rip off the little bag with the buttons and unobtrusively tearing off the white tag. Do you think they noticed? Hmm?

  240. ValaMalDoran*

    The husband and wife owners got into a personal screaming match while having lunch in her office. He stormed into the shop, and she followed him. And kept screaming.

  241. Word Nerd*

    I have a problem of excessive mucus. I must clear my throat regularly (eh-hem, or huh-huh-hum, or a voiced cough) or I gag (extended horking sessions). The latter is awful to listen to and experience, so I engage in the former as needed. I try to keep it quiet.. but apparently not quiet enough.

    My office is closest to the front door, where the receptionist/office manager sits. One day at about 3pm she stormed into my office, slammed a bottle of water on my desk, and commanded me, “Stop that disgusting habit! Drink something if you need to clear your throat, because what you’re doing is gross!” I was in the middle of coding at the time, and had not seen her coming, so her verbal explosion hit me like a bomb blast, and I sat there stunned, watching her glare at me as she strode away.

    This is someone with whom I had been on very friendly terms (warm greetings daily, sharing details of family, kids, life experiences etc., including that she fundraised for my kids when they were going on a band trip) and I certainly would have taken even more precautions had I known it was bothering her. This is not the first time she handled things in an odd/inappropriate way (examples include: requiring everyone to stop the common office practice of bringing in baked goods for coffee breaks because she was trying to lose weight: locking up all the silverware because she felt people weren’t taking enough responsibility for dirty dishes) it was just the first time it had been directed at me.

    I waited until end of day when she was gone, and put the bottle back on her desk along with a note. I thanked her for the water, and asked her not to use that tone of voice with me again as I am not a disobedient dog or a mortal enemy to be treated like that. I also explained that it was a medical condition, and said I wished she had told me sooner that it was bothering her, and that I would try to muffle it in the future.

    She did not make eye contact when I came in the next day, nor the rest of that week. For weeks after our communication was limited to a ‘Good Morning’ and nothing further. She has never brought it up or apologized or mentioned it in any way, and I wish she would because I would forgive her. (Who among us hasn’t had a bad day, or snapped when we shouldn’t have?) We are now at the point where there is at least a professional relationship, but any closeness or friendliness is gone, and I am sad for that loss.

    1. Golden Lioness*

      Ugh! I am sorry! I have really bad allergies, and when I have bad flare ups I had people asking my manager to send me home or not entering my office. Most of them are OK after I say I have bad allergies, but there are a few… ugh!

      Its more annoying to me to not be able to breathe!

      Which reminds me of another awkward moment. This one during a meeting with higher ups on my 3rd week on the job. One of the ladies was wearing a strong perfume, so my sinuses immediately closed and my eyes watered. The congestion was bad enough, but in one loud sneeze… (sorry this is gross) I could not get the tissues fast enough. I turned my head fast and grabbed my tissues from my purse, but it was pretty obvious what was happening.

  242. I'll come up with a clever name later.*

    Oh…this one. I still cringe more than 25 years later. It’s not a good story for me, but I did learn from it. I was a teenager at my first job. I was in school, had my first boyfriend, a job, family obligations, friends, and a lot of clubs. I was burning myself out very quickly. My boyfriend’s mom and step dad had just gotten married and were having a reception to which I had been invited. My boyfriend was pretty crappy with communication and time management so didn’t tell me that there was even a party until a week before the date. I knew that I was already scheduled to work and my boss was kind of a line in the sand person when it came to the schedule – “it’s already on the schedule, no you can’t have it off!” – so even asking wasn’t worth it. I decided to call out. BUT…(here’s where it gets awkward!) back in this time before cell phones and texting we would write notes – to friends, to boyfriends, etc. It was the teen thing to do. I wrote my boyfriend a note outlining my plan to get the night off and then….I left it on the counter and forgot to take it with me. The day comes, I call out, I go to the party, life is good. Then I come back to work for my next scheduled shift and my manager pulls me into the office. She then sits there and reads me my own note (sarcastically and with too much glee, but it really was my note so nothing I was able to do). I got a write up. Two weeks later I got mono (glandular fever as it’s known in other countries) and ended up quitting the job outright, but yeah…I still cringe when I remember that.

  243. Mae West*

    On one of his first interviews out of college, my husband sat across the desk of his interviewer. All was going well until husband exhaled too forcefully which caused a noticeable boogey to fly out and land on the interviewer’s desk! He was mortified but he tried to laugh it off hoping the interviewer would find it funny. He didn’t. They stared at each other briefly and the interviewer ended the meeting. No, he did not get hired.

  244. Innocent comment turns tragic*

    I wish it were a funny one, but the most recent awkward moment to come to mind happened just a few weeks ago.

    Sansa had been trying to get pregnant for about 4 years, and finally conceived! We were all super excited for her and very supportive. She had to leave the office for an hour or so for her 12-week checkup appointment. When she came back to the office her desk mate Arya cheerily/cheekily asked with a big smile, “How’d it go?! Still pregnant?!”

    Sansa just said – “No!” and burst into tears. IT. WAS. THE. WORST. :(

    Sansa had actually just found out she miscarried and had come in to let the office manager know in person so she could explain the need for some time off. Arya was obviously horrified at her seemingly innocent friendly follow-up that ended up as a massive faux pas.

    Sansa was given our EAP info and we’ve all been super supportive, but that moment was really awkward in the worst possible way.

  245. Anonymous this time*

    My most embarrassing moment in a workplace came during an interview for my “dream job” right out of college. The company itself was a unique, up-and-coming startup, with a cool office space, progressive work/life policies, and a down-to-earth, casual culture. (Before my in-person interview, the person on the phone told me I could come in slippers if I wanted to. Thankfully, I didn’t.) There was an extremely high level of competition for even entry-level jobs and so I was thrilled when I made it past the phone interview stage and was asked to come to their office for an in-person meeting.

    Everything was going really well right up to the point where they asked me, “What is the hardest thing you’ve ever done?” I then proceeded to tell them about my recent breakup with my fiance, with whom I had been for 4 years, 3 months before our wedding. (Ugh…I’m cringing as I write this.) While I didn’t go into excruciating detail, I remember vividly how instantaneously the atmosphere in the room changed. Needless to say, I was not offered that job. Luckily, I ended up landing in a great place, but I’m still horrified every time I remember that interview.

    1. JB (not in Houston)*

      I just remembered that I once mentioned in an interview at a law firm that I’d found out that morning that my former boss had just been indicted by the SEC. As it was coming out of my mouth, I was telling myself to stop talking, but my mouth kept talking anyway. I knew I wasn’t getting that job.

  247. Taylor Klein*

    Most awkward moment I have ever witnessed at work was while working as a supervisor at a Retail store I was in the process of training in a new team member. This team member had a lady probably close to her 70’s who comes in every week and to buy her weekly supply of cinnamon rolls. She became such a regular that eventually we kept a dozen set aside for her ready to go when she comes in. The new trainee asks the lady if she needs help finding anything or if she is here to pick up her weekly supply of cinnamon rolls. The customer begins to go on a bit of a rant and start explaining how she came in for a “Personal massager” to use on date with some new boyfriend and started to ask her (new employee) questions and recommendations on what she feels and i quote “give me the best experience for my pension”. Never seen an employee go as beat red and ghost white as she did.

  248. Jules*

    There are so many to choose from.

    I was new to the organization and the team was talking about a huge sum of numbers and I was a little surprised. I am used to multiple currency but in my previous work, we are less like to make such an aggressive change to a number. Think of, working in a company with a less than 3,000 employee to an organization with 15,000. I guess it showed on my face when someone helpfully explained, oh, these numbers are in pesos. I knew we were talking in a foreign currency, I just was surprised at the aggressiveness of the change. It would be awkward to explain to her why I was surprised and so I let it go. But it was embarrassing to think that they think I didn’t realize in what currency we were talking about. It was my first senior role too. I felt utterly stupid.

  249. jnsunique*

    I work with someone who manages awkward amazingly well. It’s truly inspiring. He is the highest ranked person at our site and it is one of his tools. A few months ago, he announced in a team morning meeting that his fly zipper broke (and not to look) and we all had a good laugh, because it was of course the day that he had 2 site-wide communications meetings at which he was a presenter and would be standing in front of everyone. He’d already had one of the meetings, and was headed home to change before the next. He uses his mistakes and natural awkwardness to build rapport. There are numerous other examples, but that is such a classic and he handled it so well.

  250. Anna*

    My favorite awkward story!
    When my 2nd daughter was about 3 she had a weird speech problem where she only said the first syllable of any word. So my husband and I decided to take our 2 kids to the zoo. It was just at opening, and the elephant enclosure was the closest to the gate. We saw a crowd gathered and stopped to see why. Found out they were just bringing the elephants out. So my husband puts our oldest on his shoulders, and I put our 2nd on my shoulders so they can see over the crowd. The first elephant comes out and my darling girl at the top of her lungs starts screaming “Whore! Whore! Ma a Whore!” I turned bright red while everyone turned to stare (judgmentally) at me. One of her favorite movies was Horton Hears A Who. I said very pouring “Yes Baby, that’s a Horton”.

    2. Elemeno P.*

      I was so sad when my friends’ kid was able to say his Ls. I’d really enjoyed him pointing out clocks.

  252. Itslikelyn*

    I work in hotels and part of my job is touring people around the property to show them our event space. I was meeting someone for the first time and went to shake her hand hello… but I tripped and smacked her in the crotch (for the record, I am a female so I suppose it could have been slightly worse). She stood very far away from me for the tour… but she did end up signing with us, so at least there’s that.

  253. Bow Ties Are Cool*

    The most awkward scene I’ve witnessed is when a truly incompetent and mansplain-y contractor was literally, physically dragged out by security after being fired, all the while ranting at the top of his lungs about how we were all fools who didn’t deserve his brilliance.

    The following week, the situation took a darker turn when our building was briefly put on lockdown after he threatened to come back and shoot the place up. Then there was a police chase into the next state before he was finally arrested.

  254. nisie*

    I used to work with people with intellectual disabilities and/or autism. So many talks about body fluids and body functions.

    My worst was having a client who needed a shower and taking them to take said shower. Client prepared for shower and then realized he didn’t know how to work the shower. He came out naked and asked for my help.

  255. Symplicite*

    I was newly-wed, new-to-the-workforce (still on probation at my job), and my (then) husband and I were out grocery-shopping one weeknight after work. As we were leaving the store, I happened to run into my then-boss, and was chatting with her. In my naïveté, I had forgotten to introduce my husband to my boss. As the conversation progressed, my husband decided to introduce himself.
    “Hi, I’m . Who the hell are you?”
    Fortunately for me, she had a great sense of humour, and bowled over with laughter. And the next workday, she told me that she’d found it funny, and moved on. Thank God.

    2. Sled Dog Mama*

      My husband did this at the Christmas party this year, I nearly died. Boss though it was funny, bosses wife thought it was awesome.

  256. LizB*

    At a past job, I kept a reusable metal water bottle that had an open mouth and a separate screw-on lid with a loop built into it that you could use to hold the bottle or clip it to a carabiner or something. I was returning to my office after filling it up at the water fountain when I crossed paths with my boss and we started a conversation. I’m a fidgety person and tend to play with whatever’s in my hands, and as we were talking I shifted my grip on my water bottle to hold it by the loop of the lid and let go of the body of the bottle. Unfortunately, I had neglected to actually screw the lid back on after filling it, so the bottle plummeted straight toward the ground. I looked down in surprise as it fell, and the laws of physics being what they are, as soon as it hit the floor a plume of ice-cold water shot up and hit me full in the face. I tried to splutter through the end of what I had been saying while frantically groping around for something I could wipe my face on, but my boss just shook his head and walked away, leaving me to recover my dignity and clean up the mess in private.

  257. not so sweet*

    As a woman in my 20s, I spent a couple of years working with a group of men who had all worked together for years, paying close attention to each other’s lives and medical histories. My closest coworker there, Wakeen, got frustrated with this, especially when him declining to go for a lunchtime drink one payday because he had a doctor’s appointment turned into “Wakeen can’t drink any more because he has problems with his heart; doctor’s orders”. So when Wakeen was having back troubles, he didn’t want input from the crowd, and just took to using his filing cabinet as a standing desk to read papers and make phone calls, rather than sit down. He took me into his confidence because we had to travel together, and for a few weeks I had to do the driving while he lay down in the back of the station wagon. At one coffee break when Wakeen wasn’t present, I heard “Don’t say nothin’, because he doesn’t want to talk about it, but Wakeen has hemorrhoids.” I knew it wasn’t true and Wakeen would hate them to be spreading that rumour, so I said “I thought only pregnant people got hemorrhoids …” and someone piped up “Oh no, Jack’s had them for years and he says they’re really painful!”

    Then our middle-aged boss Fergus had to go to the hospital to have some tests because of suspected prostate troubles. He complained about the procedures quite a bit before he went, and everyone had advice or anecdotes. I spent several coffee-breaks looking down at the newspaper. Then the day he was away, people from other departments would look for him and say “Fergus not in today?” so my colleagues would all explain “No, he’s at the hospital getting a tube put down his dick.” The next day, Fergus was mystified about why so many people from other departments were coming down to our office to ask him how things were with his marriage and why he hadn’t ridden his bicycle to work.

  258. Aunt Betty*

    I accidentally set a coworker’s hair on fire!

    When I was a teenager I was a cashier at a hardware store and one day a customer left a cigarette lighter on the checkout counter. We were very slow that day so I picked it up and starting flicking it. It was empty but my job was so boring that flicking that lighter repetitively seemed like a good way to pass the time. An older woman coworker said, “Be careful! You’re gonna start a fire!” I said, “Oh, don’t worry. It’s empty. See?” Then I held it up right beside her head (WHY?!) and flicked it. The lighter chose that moment to spark up and a small piece of her hair went POOF. I was horrified and began beating the flame out with my hand!

    Fortunately for me she was very nice about it and even thought it was funny. But I was mortified. I can still see her hair lighting on fire!

  259. Dr_Danger*

    I have so many stories, but I think I’ll share the one where I most wanted to melt into the ground from second hand embarrasment. I have a co-worker who is very into running. She runs into and out of work and uses the work showers and changes into her work clothes in the morning. So far, so dull. She leaves her running gear in a bag by her desk in our open plan office. One day this bag got knocked over and her clothes spilled out. Another of my co-workers picked up her knickers from the floor and waved them above his head while loudly asking if these were her panties. My face was a picture, she didn’t seem to care in the least!

  260. Kate*

    That time when I worked at a sexual health nonprofit and we had to talk about how sexual health impacted our life this week at the start of meetings.

    I was the only unmarried person there.

    Oh boy. Do I tell the truth and get seen as a slut? Or do I lie and get seen as a prude? What do I do with the 16 stories about how people don’t use condoms with their husband because OF COURSE YOU DON’T? And the details about IUD insertion I never wanted to know?

    Even in a sex positive environment you can’t win this one.

  261. Suzanne*

    The most awkward thing at my workplace continues, yet it doesn’t affect me near as much because I recently moved offices.

    My co-worker and his fiance have almost a contentious relationship. This added to said co-worker’s hard of hearing adds up to lots of personal business overlapping. Our offices used to be next to each other, and at least once a day he would get into a fight with “Jane” over the phone. He’s already a loud talker, probably due to his hearing, and would have her on speaker. The stuff they argued about was the stupidest! I regularly turned up my music or podcast volume to drown them out. It was hard to believe that a 50-year old man didn’t get the hint that this kind of interaction was not appropriate in a professional office…

  262. DecorativeCacti*

    This isn’t my story but I have to tell it because I know it will be appreciated here:

    One day my coworkers Jane and Amy are walking out of the bathroom together. Sarah is walking by them and all of a sudden Amy is possessed by some demon and she hauls off and smacks Sarah right on the butt. Full wind up booty smack. Horrified, Jane goes, “Do you know her?!” And just as horrified, Amy says, “No!” It was Sarah’s first day.

    To this day Amy says she doesn’t know what came over her. She just saw a big butt and needed to smack it. It’s like the slap ass skit from Key & Peele.

    A couple years later after Jane had suddenly passed away, Sarah was walking behind Amy and gave her a nice booty smack. When Amy turned around, Sarah just shrugged and said, “It looked like you needed it.”

  263. Robin B*

    Years ago my boss had to let a sales employee go. After multiple chances, the sales person was just not putting forth any effort. The day after he was terminated, his wife showed up at our office with a paper bag in hand. She stomped past the receptionist, stormed into boss’ s office and hung the phone (he was holding a land line phone.) She screamed at him, “You want the food off my table? Well here it is!” Then proceeded to take 2 fully loaded hot dogs from the bag and throw them at him. The rest of us were standing there wide-eyed. (Until I called Security.) The following spring at the annual branch manager’s meeting, this boss was served a hotdog when the other meals were served. At least corporate had a sense of humor!

  264. Jeannie Nitro*

    So, this was not actual At Work, but it happened at a happy hour with coworkers, so I’m counting it as close enough.

    We all went out after work to this little tiny dive bar that my coworkers loved. Since it was warm enough outside, the giant windows all along one side of the bar were open, such that you could pull up a table next to them and sit on the windowsill like a bench, which was handy since there were a lot of us and it made it easier to squeeze all into one table. Well, I was sitting on the window bench next to this really nice guy who I’ll call Ned – sweet, friendly, had recently gotten engaged to his girlfriend who he was currently long-distance with. As everyone is sitting there making conversation, this girl walks by on the sidewalk outside, reaches in, grabs Ned from behind, pulls him backwards half out the window, plants this giant kiss right on his lips, then shoved him back into the window and kept walking. Keep in mind this is like . . .6:00pm, so it’s not like anyone should have been particularly sloshed at this point in the day. Poor guy was shellshocked. None of us really knew what to do except laugh awkwardly for a while and pretend like it didn’t happen.

  265. Kateshellybo19*

    My company has a policy against weird hair colors. I do not have a problem with this policy but do skirt the edges of it by coloring my hair a pales gray. My gray was starting to get some brassiness to it so I decided on a tuesday I would tone it and the dye it on the wednesday.

    The toner turned my hair a sickly green color. I tried everything to fix it but it wasn’t budging. The next day I was going to try and hide from my boss knowing I could get a darker dye and fix it that night. My boss saw me anyhow. I promised him it was an accident and it would be fixed by tomorrow.

    That night I had my bottle of dark gray and guess what; it turned my hair purple. Again I could not get the color to shift. I had to go into work the next day and assure my boss that I was going to see a professional that night and get it fixed.

    My boss is a nice guy but very, very straitlaced. Those conversations were so awkward.

  267. cleo*

    Hah. I have been preparing my entire adult work life for this call.

    Many years ago, at a departmental luncheon, my boss announced that she was expecting a child and would be going on maternity leave in a few months. I gasped and said “Oh No!” Audibly.

    *Quick backstory so I don’t sound like a monster – I was reacting to the idea of another maternity leave because her previous maternity leave had been disorganized and miserable. She’d been promoted to department head when she was 6 months pregnant, after the former head was unexpectedly fired, so it’s understandable that it was disorganized but it was not a happy time in my department – we were all over worked and other department heads kept circling like sharks, waiting for signs of weakness.

    I’m happy to report that her 2nd maternity leave went much more smoothly and years later my boss and I were able to laugh about my awkwardness. She says everyone stared at her in shock and dismay after her announcement (it really was a rough maternity leave) – but I was the only one awkward enough to gasp. And we did throw her a very nice baby shower to make up for our collective awkwardness.

  268. Mona Lisa*

    Oh, this sounds right up my alley!

    I have so many awkward work stories, but this was the first that came to mind:

    I was working my first post-grad school job, and my team had a lunch meeting that segued into a bit of history on the program and the state it had been in when my director took it over. She was running the department almost single-handedly, her assistant had quit, they were doing a bunch of events… and during that time she got pregnant with her daughter. I made a comment like, “Wow, I can’t imagine how you had time to be pregnant between all of that!” I was thinking of the doctor’s appointments, the researching, and all of the preparation that comes with expecting a kid.

    I can only assume she heard “Wow, I can’t imagine how had time to get pregnant” because she looked at me funnily, turned red, and said something like, “Well, we had a pre-planned trip to Hawaii, and we were there a whole week so…”

    I can’t even remember how I backpedaled out of that. I was so embarrassed and just stuffed my sandwich into my mouth so I couldn’t open it again during the rest of the meeting.

  269. Former Admin Turned Project Manager*

    I was preparing for my huuuge convention meeting, and was on my way back upstairs after having picked up a print job for handouts I needed for my session the following day. I, in the super graceful way I embody, managed to fall up the central staircase at our office (despite not having any of the typical things that would cause such a fumble- no flowy skirt to trip on, no high heels to make me overbalance), banging my knee in spectacular fashion and sending packets flying. The jolt made me cry out, and the noise attracted folks from the nearby cubicles. One kindly went to the restroom to bring me a wet paper towel to cleanse my bleeding knee and another went to the first aid kit to find me a sufficiently sized bandage. As the momentary adrenaline wore off and I began to realize how darned much I was hurting (and fighting back tears), the health and safety manager happened to walk by. As a result, HR got involved and I had to fill out an incident report, including the corrective action that could be taken in the future to avoid a similar workplace accident. I threw away my torn stockings and iced my knee for a bit, and thought to put the moment behind me.

    The following day at the hotel, with trousers hiding my very bruised knee and a smile hiding my only-slightly-less-bruised pride, I encountered my boss on the very long escalator to the meeting rooms. The incident report had gone to her, as my supervisor. While she agreed that a corrective action of “hold the handrail firmly” was satisfactory, and commiserating about how we hate the metal corners on those particular steps, I do wish I’d spent less time having to drift down the hotel sharing my klutzy stories with the second-highest ranking person in our organization.

  270. Jane*

    I was working on a control room console during an astronaut space suit test run a few years ago. These tests begin early in the morning and last several hours, so periodically we are able to take turns getting up for a short break.

    This astronaut had a television crew from his home country at the test site documenting their training experience. They were walking around in various locations somewhat at random.

    While I was in the process of standing up to take my break, I got my headset tangled up in my hair. As I turned around, I saw the camera pointed directly at me!

    I don’t really even want to know whether that particular portion ever aired, but somewhere on B-roll that footage probably exists. Yikes.

  271. JaneB*

    Another grad school one. We had some practical jokers in our tiny, over crowded office, and prank wars sometimes developed, always kept to just the people who enjoyed it – the rest of us were audience. It was really all very well judged… apart from one occasion.

    One of the prankers from a different office, A, had a habit of standing in the hallway talking to someone, but with his hand around the door holding it partly open, so from the inside all you saw was his hand, but the drafts from the corridor and noise from the stairs were very annoying, so we kept asking him not to do it and he kept saying it was just for a moment.

    One day another prankster, B, decided to prove it wasn’t just a moment. The next time the door partly opened, held that way by a clearly male hand, and As voice was heard outside leading forth about something, she got out her white-out bottles (several colours for different colours of forms – I’m old) and very delicately painted faces on all four of the available finger nails. Which was just a LITTLE awkward when it turned out that for once the door was being held open by our terrifyingly clever, socially awkward professor, who was the same height/hair colour as A and wore the same male science uniform, and who was being harangued by A… so all the clues did NOT add up. So when he did come in and realise there was something different with his hand, that was awkward. Then B tried to explain, with lots of back story about past pranks, none of which the prof had ANY idea about (his office was on a different floor, and he travelled a lot, so pranking happened when he was away. Intentionally). And when he tried to just go away and forget it all, B followed him around the building still trying to explain. Not apologise, explain. Very, very awkward. He couldn’t look at her for months….

  272. JMJ*

    Late 1980’s, I was twenty-something, working in retail. Two female customers came in, one pregnant. I asked when she was due. After some chit-chat, I asked the other lady, “When are you due?” She said “…I’m not…”

    I still think about that incident and no matter what, I WILL NEVER ask.

  273. Live and Learn*

    My first office job out of university I worked for a small company owned by a husband and wife. The male owner was teaching me about some account management work by having me attend client meetings with him to understand client needs. After one such client meeting, to which he had driven us both, he asked if I minded if we stopped at a men’s clothing store near the client’s office so he could pick up a couple of things before a work trip the next day. Since he’s the owner and he drove, I went along with it. In the store he asked me my (female) opinion on what kind of pants he should buy, which was awkward enough but when I nervously mentioned something about how the fashion styles seemed to have shifted to plainer styles (meaning, no cuffs, obviously tapered legs or pleats) he told me that men will always need pleated pants so they have room for “their anatomy”.

    My other favourite awkward moment is me causing awkward because sometimes people don’t know when to stop talking. In the last year I lost a very significant and noticeable amount of weight, before, during and after being pregnant with my first child. When people would fawn over me, telling me how incredible I looked and asking how I accomplished it, I told them the truth with a very straight face. I almost died, due to a septic infection caused by an internal organ spontaneously bursting…while pregnant. Don’t congratulate people for losing weight if you don’t know their feelings on the matter.

    1. Serendipity*

      I lost 17kg in two months due to a pulmonary embolism during late stage pregnancy and the resulting hospital stay. I hear you on the all-kinds-of-awkward conversations that ensue.
      I usually thank them for the compliment but day that I don’t recommend near-death experiences as a reliable form of weight loss

  274. TardyTardis*

    Ah, the popcorn incident! I had been at the job for three weeks when I decided to have some microwave popcorn. I have an older model at home, and five minutes is just about right for a bag to come out the way I like it. I did not realize that our workplace had a much newer model which was more powerful. I put the bag in, set the timer, and ducked into the bathroom close by.

    Results: billowing smoke, fire drill involving the entire building, and a Strong Hint to never have popcorn again, unless I brought it pre-popped. I was there 15 years, and guess what got brought up at my going-away potluck…

  275. jamlady*

    I worked as a sub at a preschool years ago in an area where the culture basically dictated that women shouldn’t breastfeed after about 3 months. As a result, most of the babies were on formula or solids, but there was a 1 year old who was on solids, formula, and breast milk. At the end of the day, we were responsible for throwing out the old formula and cleaning the bottles once the parents arrived. I was so used to throwing the formula down the sink that it wasn’t until I was dumping the one and only breast milk bottle and the mother was saying “noooooooooooooooo” (all in slow motion) that I realized what I’d done. That memory still makes me cringe to death.

  276. Cambridge Comma*

    At a team building away day type thing with close colleagues, there was some kind of trust fall type thing (but not exactly that), but we were instrusted not to touch anyone. Without thinking, I did the ‘No touching’ thing from Arrested Development. Not a single person had seen it or even heard of it and they thought I was unhinged.

  277. mc_hammer*

    I worked for a company and every quarter we had to complete compliance training. The compliance team would try to make the courses fun and entertaining with videos while talking about serious issues. One course was about having integrity. For some reason they decided to start the course with a video of someone showering and washing with integrity soap. As the course went on the next clip was of a person being approached by a sexy coworker in the storage room, the person denies the sexy advances because they wore their integrity deodorant! Then the scene cut to a video of them putting on said integrity deodorant.

    Not sure how this passed the pilot phase but as awkward as it was I thought it was hilarious. It resulted in many people around the office asking others if they showered with integrity this morning or if they remembered their integrity deodorant to ward off unwanted advances.

  278. Arbex*

    I used to be a secretary/typist for a man’s home business writing nonfiction books about various things when I was in high school. Also relevant: I’m female and was in a relationship with another female. A few months in, his wife who had mobility issues started giving me the stinkeye and being kind of rude when I’d walk in and down to the workspace. One day she asked me if I’d bring her a glass of water as her husband went to the workspace, and when I did, she grabbed my wrist and pulled me into her lap (awkward), called me a little whore (awkward) and told me I’d never seduce her husband away and that his money was HER MONEY and I wasn’t going to get ahold of it (awkward). I pushed away which kinda knocked her over, she couldn’t use her lower legs. Her husband came upstairs and saw and I was worried he’d start yelling at me but apparently she’d been doing this to previous people who worked with him as well (awkward) and he never felt the need to tell or warn me…? I quit pretty shortly thereafter.

  279. Sled Dog Mama*

    No lie this happened earlier today.
    Today is my Boss’s birthday, yesterday we decorated her office after she left, full of balloons, streamers, etc. There is a long standing joke about my boss and cakes shaped like certain pieces of the male anatomy (She’s been here 20 years and has moved up through all the levels and only became manager about 18 months ago), this has evolved into someone baking here a cake shaped like said piece of male anatomy every year for her birthday. Today she took a selfie with her cake and tried to send it to a couple of people in the office via airdrop on her iphone. She airdropped it to the two people she was trying to send it to and one unknown. It is now at least 4 hours later and we still can’t figure out who she sent this pic to, we all hope it wasn’t a patient. She’s been walking around the office bright red all day.

  280. Alex*

    I had a job once where I was sort of a “Jane of all trades” and was frequently called upon to do random tasks. My boss was also a bit strange and had strange ways of asking me to do things or explaining things to me. But I tried to go with the flow.

    One day, my boss bursts out of his office and says to me “Alex! I have a task for you! Follow me!” This was an open office so everyone else heard this. As told, I immediately got up and followed my boss, who was walking briskly in front of me out of the office into the hallway. I tried my best to trot to keep up with him…as he walked right into the men’s room.

    Fortunately, I stopped short of following him there, but I didn’t exactly know what to do next, so I went back into the office, where everyone proceeded to look strangely at me. “Where’s Boss?” someone said. And I had to say “He’s in the bathroom?” Apparently I started blushing, because everyone started laughing at me. I guess Boss didn’t intend for me to jump up and follow him so quickly, but that wasn’t clear!

  281. Beachgal*

    Ok. So this happened many years ago when I used to lifeguard during the summer. During one training, at the start of the season, I started early while in the pool. So I try to discretely go to the bathroom. I was almost there when the head trainer came running after me shouting OMG are you ok? Because he saw blood running down my leg. Everyone started staring while I ran off completely mortified. When I finally got out of the bathroom, the entire group of lifeguards had been moved to a different section of the pool and one the directors was cleaning up the area we once occupied. Add to that since it was the beginning of the season, this was my introduction to many of my new coworkers for the season.

  282. Teapot Tester*

    I work at a software company and for security reasons, everyone is encouraged to lock their laptop when they step away. It’s common for people to prank their coworkers when they leave their laptop unlocked, usually simple things like changing the wallpaper or reassigning keys. My neighbor had stepped away and left his laptop unlocked so I decided to change his wallpaper. As I finished up, I turned back to my desk, all smug and satisfied, to find he’d been standing over my shoulder for most of the time. He quietly said, “Boo,” right as I turned, and I screamed at the top of my lungs. The receptionist came running, managers stepped out of their offices, and we all laughed hysterically for a good 10 minutes. It’s become legend in the office and I am still mortified at how loudly I screamed.

  283. Salyan*

    First job. Fresh out of high school. A friendly coworker (of the opposite gender) decided it would be a good idea to give me – just me – a Christmas present. I couldn’t decide if he was just being (weirdly) nice, or if there was romantic intent, so decided to give him back the present. Only problem was, it was a personalized gift certificate to my favorite bookstore. My mom (I mentioned I was young, right?) put cash in an envelope, and I awkwardly tried to return it to him the next day. He wasn’t pleased. Threw it straight in the garbage can. And we never mentioned it again.

  284. Itsnotme*

    So in high school I worked a retail job. We kept our purses in lockers and it was my time of the month, but not my time for a break. We were allowed to use the restroom whenever, so I leave my checkout lane to use the bathroom and discover I need to change my sanitary item (conveniently in my locker). My male boss asked me why I was going upstairs when it wasn’t my break and I said I needed to use the restroom, thinking he might catch on. Well the bathroom wasn’t upstairs so he didn’t catch my drift. He prodded, and I just said “I have my period so I’m going to my locker to get a tampon”. His face said it all. I bet he never asked that question again

  285. JaneB*

    I remembered another one I need to share.

    To set the scene, I am very overweight, and I have some mobility issues. I also tend to be pretty pragmatic about dress – I’m an academic, and have a basic “uniform” of black dress trousers with pockets (which I fill with stuff), a tunic length top with some movement to it and a nice scarf. The pockets full of stuff matter, especially as I’m a bit of a magpie and tend to acquire random bits & pieces as the day goes on.

    So, late one afternoon I’m teaching in a giant computer lab. I happen to be wearing new trousers which are a classy linen blend fabric. Turns out the blend is very slippery when placed in contact with the cheap artificial fibre hard wearing fabric of computer room chairs… right in the central aisle, I was responding to a group with a query, grabbed a chair, sat down slightly off centre (carefully holding the back of the chair as I’m clumsy) and my bum slid right off.

    The chair went flying, I went down flat on my back, and the contents of my pockets attempted to escape the scene in all directions. My mobile phone even separated from its battery… so there is this almighty, attention getting no noise, as I and the chair crash to the parquet floor and about 50 small objects from used tissues to stray coins via an acorn, some hair pins etc etc, skitter away, and then I’m trying to retain a little authority as I scrabble around like an overturned turtle trying to get up without doing myself any injuries and reassuring the students that I was fine… then we had to retrieve all my pocket stuff…

    The best way to get the attention of that class for the rest of their time with us was to start sitting down, not sure if the main emotion was hope I’d do it again or anxiety, but t it was sure focused on me!

  287. mamaprobs*

    I’ve been walked in on while using my breast pump TWICE. The first time, our building manager walked in with a team of 9 other men going through a building inspection. The second time, my boss was giving a donor a tour. I put a sign on the door, at eye level, that says “In Use, Do NOT Enter”. Clearly does NOT work.

  288. PersistentCat*

    I wish I had a better narrative for this story…
    Ok, so. I was 23, just starting a new job. At this point, I had been working for 5 years, but multiple full-time jobs at a time (2012 was rough). I had never worked the office side of production, but had been in leadership on the floor for 4 of 5 years. Basically, young, but knowledge of workplace norms, with a tolerance for less than professional discussion topics. The first week. Man, my coworker that was training me…she could make me blush! She was so raunchy! She’d been there for 3 years, she was a year older than me…to this day, I sideways cringe about it. The worse part is she would pressure me to share, and ugh. I just had to laugh it all off, but one day she had a vibrator fall out of her purse. And turn on. Oh man. AWKWARD

  289. Many Hats*

    I am the Queen of Awkward; it’s my super hero power. I can make an entire room shift uncomfortably just by entering the room.

    Of course I am our Human Resources person, which may have something to do with it.

  290. So very very mortified*

    I have 2. Same boss, a couple of years apart.

    First one, we are both attending a webinar given by a supplier. For some reason, there was a lot of background noises by the attendees who hadn’t muted their phones that was really distracting. Afterwards I instant messaged my boss and asked what he thought of the session and he said he had to leave early and didn’t hear the whole thing. And I replied “Did you stick around for the hummer?” and hit send. The instant I sent it I realized what I’d typed but there was no going back. He sent the little surprised face emoticon back. I sheepishly said “Yeah, one guy was humming for like 5 minutes straight.” Then I avoided him for like 6 months.

    The next one was…worse. So much worse. We were in my yearly review. I was telling him how everyone always comes to me with their problems like I’m their mom or something (I was like 35 at the time.) He replied “Yeah, that’s weird, you don’t have gray hair or anything.” And I said “Well, not that you can see!” I could immediately tell by the look on his face that he didn’t realize I colored my hair and how he interpreted that comment. But what could I do? It’s not like I could say “Oh, not like you’re thinking, boss-man. Not “down-there.” I just color my hair to hide my grays.” I swear he cleared his throat, shuffled my review paperwork for 5 seconds (the whole time I am screaming in my head “OH NOOOOOOOOOOOOOOOOOOOOOOOOOOO!!!!!!!!!!!!!), and then we moved on. I avoided him for a year after that one.

  291. Ellen Rozsa*

    That time nearly 30 years ago when I worked for a few months as an admin for a computer whiz/government consultant who had serious academic credentials but seemed clueless to many social norms observed in the workplace. Not long after I started, he asked me to accompany him on a business errand. He was carrying a clunky desktop computer and when we arrived at his car, remembered that his keys were in his pants’ pocket. Front right pants’ pocket, IIRC. He asked me to retrieve them and after a second of hesitation, I did, and opened the car door for him. Very awkward at the time, to me. A life-long people-pleaser, it didn’t occur to me at the time to either take the computer from him (it was very heavy) or tell him to put it down on the ground and get his own keys. He wasn’t a creeper at all, just clueless af.

  292. Close Bracket*

    You might also enjoy Awkward, by Ty Tashiro. I found it particularly interesting that he was writing about 10% or 15% of the neurotypical population who scores just below the cut off for autism on the Autism Quotient (although he doesn’t address why he only counts NTs who score below the cut off and not those NTs who score above the cut off).

  293. Wendy Darling*

    When I worked for a Giant Multinational Corporation I was coming through the secured, key-card-locked door from the elevator lobby towing a flat cart stacked about six feet high with heavy boxes and, of course, as I went through the door the little door jam thing on the floor jostled the cart and sent the boxes flying all over the place, half in the elevator lobby and half in the office.

    In front of the senior VP of my division, who was about to come out the door to the elevator lobby.

    So I had to wedge the door open with my cart and frantically pile boxes back on while a security guard and an SVP stare at me. After like 15 seconds the door alarm goes off and the security guard starts yelling at me about how he needs to close the door. Meanwhile I can’t get my damn boxes to stay on my cart. And the SVP is just standing there watching the chaos.

    It was awkward for me because I was a klutz in front of the SVP, made a big mess, held him up, and set off an alarm. And it was awkward for the SVP because what kind of monster sees their underling struggling with a huge number of boxes and JUST STANDS THERE GAWKING? And same to the damn security guard.

    1. Church Lady*

      What? Neither of these men helped you, and you got scolded to boot? Unbelievable. I’ve never worked in a place where the majority of people witnessing my distress would not have helped me.

  294. Free Meerkats*

    OK, a work one.

    I was working for a hot-air balloon company as ground crew. After landing, one of the things you have to do is milk all the air out of the balloon so it fits back in its bag. One does this usually in pairs by starting at the throat (bottom), wrapping your arms around the balloon, and squeezing the air toward the vent at the peak. The first person gets much of it and the second eliminates the rest; you usually end up with your head buried in yards of nylon, working by feel. It’s not unusual to get foreign objects wrapped up as you are doing this, so you try to work them out before moving on. I was second and gathering and squeezing and I felt something large, so I started feeling around to try to identify it. Turns out what I had a grip on, and feeling around on, was what the Brits would call my coworker’s fanny.

    There was much embarrassment involved, on both sides. Not the least that I was in my mid 20s and she was at least twice my age – and my Mom’s friend…

  295. kage*

    I’m a woman (this matters).
    First internship while in college so I think I was about 20 at the time. Get asked to go on a site visit with a coworker (male probably about 40). Our office was on the 4th floor and folks typically used the stairs as the elevators were very old/slow/sketchy. I meet my coworker at his desk and we head out. Chatting/talking on the way. We go down from level 4 to level 2 and he suddenly pops into another room without saying anything. Thinking maybe it’s a storage room or another exit I didn’t know about, I follow him. Nope – it was the unmarked men’s room. Cut to lots of stammering/backing out on my part. It was a pretty awkward next two years while we both worked there…

    In my defense – A) he should’ve said something and B) the women’s rooms in that building were all locked with key-only access. It never even occurred to me that was a gendered thing until that moment and that it wasn’t that all restrooms were locked.

  296. eternal teapot*

    A humorous one: I am a coffee fanatic and my thermos barely leaves my hand. Once it’s empty, I pretty much just forget it exists, leave it in random places, and so on. Have had to return to people’s offices later to pick it up. But I teach morning classes, and one day I was talking to a student at her desk and went so far as absentmindedly picking up HER thermos. I guess I thought was mine, since it was actually still at my elbow, but a lot of mockery ensued. I still haven’t learned to keep conscious track of my mugs.

    A not so humorous one: One summer I (woman then in my mid-twenties) was teaching a class mostly made up of incoming freshmen and rising sophomores. There was a kind of bro-y and abrasive Student, and things came to a head one day when everyone was doing group work. I was moving around to check in on people, and Student decided to get my attention by putting one arm on my shoulder and trying to steer me in his group’s direction. I was so surprised that I just…sidled out and slunk away and carried on? I was looking right at a female student at that moment, and the look of cringing wtf we exchanged is one of purest moments of understanding in my life.

    I had a day before the next class to talk things over with fellow teachers, but also to move from surprise to what the bloody fuck. It was only mid-term and I felt like I had to say something to him (I am sure I gave this 100% more energy than Student did, which now just pisses me off). Well, after the next class I asked him to hang on a sec. He had a friend waiting for him, and I hoped the other kid would just take a hint and leave of his own accord. He did not. The three of us exchanged weird revolving looks for looks for a very elongated minute + until I finally shooed the friend out to wait in the hall.

    Anyway, I told Student that should never happen again, with me or anyone else. He said it never happened at all, no memory, nope.

  297. Patsy Stone*

    Many years ago, I was working the front desk in a posh resort hotel at the biggest ski resort in Canada. One day, it was pretty quiet…middle of the day, everyone up skiing, and me standing behind the desk with not much to do. I was looking out the lobby doors, when I saw a guest approaching me. Eager to FINALLY have something to do, when the guest asked me, “Hey, do you have a sec?”, I enthusiastically replied….”Oh, definitely! I have lots of secs!”…………….. cue huge laughter from the guest, and a fireball-red face from me…..

  298. Soft Gray*

    When I was a tutor through my undergrad university, the program lead would hold mandatory bimonthly meetings (you pick from 5 or so time slots). We’d watch a bit of the world’s most boring and obvious video about how to tutor effectively, and then she’d get on her soapbox and pull out the emails. The email addresses were hidden, but she’d quote emails ver betim while shaming the sender for asking a question or not knowing a rule that should be SO obvious to any competent tutors. I lived in fear of her pulling out one of mine. There’s no way the senders wouldn’t recognize their own email, and they must’ve been at one of the sessions where she condemned them in front of everybody. And I’m talking issues like someone having the gall to ask if they can record a no show for pay when they didn’t wait the full half hour for the student or for someone sending her a session info when the system was down. There were like ten every time, and she clearly just accumulated them and kind of forgot what was in the pile until she was in front of us.

    I really didn’t like working with her, and that was just the detail that cemented it. On our very first meeting, when I mentioned I was in comp sci, she commented on how great it was to have my choice of all the smart guys. I wish I’d told her point blank that I’m a lesbian. Oh well.

  299. Die Forelle (The Trout)*

    Mine is pretty minor compared to some of these! I worked as receptionist/admin assistant/wearer of many hats at a small company, and the owner of the company, Bill, asked me for a file or something that I felt he should have known where it was and taken care of it himself. There were lots of things about this job and Bill that were very frustrating, and my coworkers and I sometimes vented to each other on our company Gchat (don’t do this, guys). So when Bill asked me for the thing, I sent a chat to my coworker reading, “OMG Bill just asked me for the [file]. Why the f* can’t he get it himself?!” Only instead of sending it to my coworker, I sent it to Bill. He wasn’t a perfect guy, but was gracious about it. I remember an awkward face-to-face apology (don’t remember the details – which is fine with me), and I’ve definitely learned a lot of lessons from that job (it was my first office job and I was too emotionally invested, hence the inappropriate venting).

    1. zora*

      Yep, I did almost this exact thing, I mentioned above!! GAH, high five in solidarity!!!!! I am sooooo careful now, I never want to do that again!

  300. Beaming*

    I’m a (female) attorney and was in the middle of a trial with a senior male attorney at my firm. The transcript feed wasn’t working on his computer so he asked me to work with the court reporter to get it reinstalled. She needed to put in a cd to do this. I could see that he had something in his disc drive called “Everyone Loves Lexi” and assumed it was like a kids’ movie for his daughter. Until the (also female) court reporter presented me, with a totally disgusted flourish, a cd that featured ALL of Lexi on the cover. Clearly my coworker was using different motivation and preparation techniques for the trial than me. I was totally horrified and felt absolutely frantic that he would come in and see me holding his very pornographic movie. Or that anyone would, really. Right before some pretty critical work needed to be done by both of us. So I quickly stashed it under his folders upside down and then when he returned to the courtroom casually said, “oh by the way, court reporter needed to put in a new cd for the program and she said she left the one that was in there under your folders.” He didn’t miss a beat, just said “great, thanks” even though I’m SURE he realized even at that moment what was in there. I fervently hoped he wouldn’t think I’d seen it too, but I could not wipe that image from my mind the entire rest of the time I was at that job working with him. The worst part is that I also participated socially in an event with his wife and children so the awkwardness seeped into that too every time I saw them!

  301. Pontoon Pirate*

    OH GOD. I am in perma-cringe mode, but thankfully (?) most of my awkwardness shines beautifully through in my off-work hours. Ask me about the time in my childhood when I proudly and loudly expounded about how I’d just learned all about “organisms” in science class … in the middle of a crowded state park … in front of a group of college-aged boys who were nicely trying not to die … and the word that I used was NOT organism.

    But work! Well, once I went out into a shared, public hallway of my office building to use the bathroom and there was a man splayed out face-down in front of the men’s room. Really, less awkward and more scary/concerning, on reflection. The awkward part was me trying to explain to our temperamental VP why I needed him to go out in the hallway and talk to a possibly-dead man.

  303. Anlyn*

    Oh my god, I need this book. I have been struggling for years with how to move past embarrassing situations I’ve put myself or others have put me in. This is going to be a HUGE asset to my depression and anxiety therapy.

  304. Dismal Scientist*

    The first of many awkward moments occurred my very first week of work. I work in state government in a support capacity to a budgetary committee. My boss was taking me around town to meet the legislative members that served on the committee when we ran into a Jimmy John’s employee giving out free samples. I was so distracted by my free (tiny) sandwich that I managed to step into the same revolving door segment as my boss. Not only was I pressed right up against his back, we had to do weird shuffle steps in order to get the door to revolve into position so that we could leave. What was my genius remark to break the ice? I went with “I’ve made a huge mistake” before walking quickly, and silently back to my office.

  305. Wren*

    This is more my boss’s embarrassing moment than mine, but it involved me:

    I make custom leg braces and prostheses under the direction of a orthotist/prosthetist. In some leg braces, the thigh cuff (or the socket on most prostheses for above knee amputations,) comes all the way up the thigh and there is a small “shelf” in the upper brim where the lowest part of your pelvis (the ischial tuberosity) “sits.” My clinician was back in the fabrication lab partway through the fitting of one such brace. I asked him how it was going, my back to him, not turning away from what I was working on. He starts to say, “Pretty good, just needs a slight adjustm… AUGH!”

    I whip around in alarm, thinking he’s cut, burned or otherwise injured himself. But he just insists, “Nothing! Nothing!” to my bafflement and does not talk to me again for about 20 minutes, when he finally admits that while saying that the brace needed a slight adjustment in the height of the “shelf,” he had unthinkingly almost reached out and pointedly /touched me on my ischial tuberosity.

  306. NewHerePleaseBeNice*

    Oh boy, so many. I used to be an admin, then an educator, now a trainer.

    As an admin, I was a fast but not accurate typist, I once sent out an email in which I had not only mistyped the name of the county neighbouring the one I lived in as ‘Oxfordshite’, but I’d also mixed up some of the letters in ‘accounts’ so it read, erm, ‘acco- see-you-next-tuesdays’. Cringe.

    Fast forward a few years and I was working as a tutor, teaching a group of Chinese students. They were learning English as well as covering science, history, geography etc. I had them researching and preparing presentations on countries and varying and contrasting stages of economic development. One group chose to compare the USA, Brazil and the sub-Saharan African nation of Niger. Except they spent most of the presentation prounoucing ‘Niger’ rather differently to the normally accepted way, shall we say, and I had to intervene and explain how the addition of an extra ‘g’ was problematic… while the course director, who is British but originally from Jamaica, was in the room.

    2. Ten*

      I once very nearly sent an email to a colleague named Bobby having spelled his name as ‘Booby’. I was soooo glad I caught that!

      1. NewHerePleaseBeNice*

        Ouch – that’s brilliant. I have a colleague called Bobby and I am absolutely certain I have addressed him as Booby now!

    3. Mona Lisa*

      Oh, man, your second story is fantastic. It reminds me of an incident that happened when I was in an undergrad singers’ diction course where we were testing our skills with the International Phonetic Alphabet.

      The teacher asked one student to come to the front of the room and write the name of his favorite dessert in IPA.

      He tried to write “cake” but wrote out the pronunciation as [kak] (kawk/cock).

      The whole class laughed as he blushed and said he’d realized that he’d left out the diphthong and wanted to fix it. He went back up to the chalkboard and wrote [kaɪk], which would be pronounced not as a sugary confection but as a derogatory, racist term.

      The teacher took pity on him and suggested he come sit down again after erasing what he’d written.

  307. Red*

    Bent over and my supervisor saw my bright pink lacy thong. Thank God this was in fast food, where people got drink and high at work, can’t imagine it in my office job!

    1. AMPG*

      I was once in the kitchen getting coffee before a staff meeting; the kitchen was adjacent to the big conference room so our whole team was filing through at the time. A younger co-worker came in and bent down to get something from one of the cabinets, exposing the whole top of her red satin thong. I was the only one who saw it because she was just bent over for a second, but as soon as she stood up I said (much louder than I meant to), “Jane, you should NEVER bend over in that outfit!” Of course half the team heard, and I felt so stupid.

  308. Anlyn*

    Okay, so most awkward moment:

    Brief backhistory—I used to work at a fast food place at a teenage, with all that being a teenager entails. So, I was not always at my most mature, and we got away with things we would say and do to each other that we wouldn’t have any where else. Very important.

    Fast forward a couple of years. I’m about 19, and am temping in an oil and gas company. I’m data entry for accounts receivable; literally, just typing in figures and letting the programs add them up.

    My supervisor had an issue with her computer one day, and was on her hands and knees, under the desk, trying to fix whatever was wrong. I see her backside sticking out, and think “oh, what a funny opportunity!”. So….I kicked her. Lightly, mind you, but still….she jumped up, banged her head on the underside of the desk, crawled out and saw me grinning, and yelled “WHY DID YOU KICK ME??”.

    I was SO MORTIFIED. I think that was the only reason I wasn’t canned on the spot. To this day I wish I could remember her name, track her down, and apologize for my absolute idiocy.

  309. Sarah*

    Years ago I worked at a bookstore, and people frequently came in and did disgusting things. We kicked people out on multiple occasions for having sex in the store, and there were all sorts of bodily fluids issues.

    However, most customers who came to the store lived in some sort of blissful utopia where it was perfectly normal, if not desirable, to sit on the floor and read a book. I was kind of alarmed by it, but management was pretty clear that they considered it something to be encouraged, so the most I mustered was a “I wouldn’t personally sit on the floor” but I never told anyone not to. I figured it was honestly probably about as sanitary as sitting in the subway seats.

    One day, however, two women were walking around the store barefoot, and that was just a bridge too far for me. I told them that they needed to put their shoes back on. They challenged me a little bit on it, and for some reason “store policy” was not the first thing I thought of. Instead, I explained in great detail all the things that had happened recently that they were walking over. How we’d found two people having sex in the shelves they’d just walked by. How we’d had multiple urination and defecation incidents in the aisles. How we’d found recognizable bodily fluids in some of the books in a nearby section. How we’d had several times where people came in dripping blood and walked through the store. How you should never ever ever assume any public place is sanitary just because it sells a product you happen to like.

    When I finished this tirade I realized not just the two women but a half dozen nearby customers were staring at me with absolute looks of horror on their faces. I think it’s safe to say Amazon gained several new customers that day.

    1. zora*

      OH NOOOOO!!!!
      Wow, I just realized, when I lived in NYC, I basically lived at the big Barnes & Nobles in Union Square, I would spend most of my days there either studying or reading, or even reading books I couldn’t afford to buy. And I used to curl up on the floor in various corners ALL THE TIME. OMG, that is probably the absolute worst bookstore to ever do that in, EeeEEwWWWwwwwwWWwwwww. It was 18 years ago, but I still feel like I need to take a shower in bleach right now!

  310. Samiratou*

    I tend to block out awkward moments, but I did have one just happen now. At my desk, with my salad-from-home, in one of those containers with compartments and a little tub for dressing. Was attempting to be veeery careful opening the dresser container, and yet the lid went flying and half the dressing splattered all over myself and my desk. Hopefully nobody in my later meetings will notice. Or will at least be too polite to comment…

  311. Patches*

    First time poster. One day I was getting coffee for several people in the office. As I was holding a tray full of coffee cups, my boss’ boss came into the elevator. He was a bit standoffish and intimidating. All I had to do was stand still and then exit. I couldn’t do that. I dropped the entire tray of coffee. I wasn’t even moving. It was a mess. I saw him again the next week and he kidded me about it.

  312. SandwichGenLady*

    We had a coworker, Bill, who had lost a lot of weight and was very proud of it. He talked about it a lot, and people joked around with him quite a bit (it was all good natured.) One day in a meeting with him, me and the CEO, the CEO made a joke about his weight loss, following a comment from Bill about not being able to eat something. The CEO and Bill went back and forth a bit, and the CEO made a comment about being inspired to lose weight too. At this point, I turned to the CEO and say, “it looks like you’ve already lost weight ” (error number one, don’t comment on someone’s weight). Things went downhill from there. Bill asks, “how can you tell he’s lost weight?” to which I responded, “look at his baggy arms!” The CEO looked taken aback, and Bill then says, “did you just say he has saggy arms.” Then I begin to awkwardly backtrack (making everything worse) by trying to explain that I mean baggy sleeves, not baggy arms. Thankfully we all have a pretty good relationship and it all blew over, but for a few awkward moments, the CEO through I told him that he had saggy arms in a meeting.

  313. Ramona Flowers*

    In my first job out of college, I worked for this tiny magazine publisher.

    One day, our designer told us the police had come into the building the previous night. The way he told it, was working really late, someone saw the lights on and thought it looked suspicious so they called the police, and the police walked in through the unlocked door and found him in the gents toilets where they effectively interrupted him relieving himself. Which was mildly amusing, kinda.

    Except one of my friends from grad school just so happened to be dating a policeman. And when I mentioned that this had happened, she burst out laughing and said that wasn’t quite how it went down. Apparently they were bored and having a really quiet night (this was in the middle of nowheresville where nothing much ever happened) so two squad cars turned up with about eight cops.

    And when these eight cops walked in, they did not find him relieving himself in the urinary sense but in the watching explicit movies sense. On his own in the middle of a deserted industrial estate never expecting eight cops to walk in.

    I may possibly have mentioned that my friend was dating a cop who told me a different version of events. I didn’t elaborate. But his face was a picture…

  314. LCH*

    i worked for a non-profit theater (live performance) in nyc as a pt receptionist for the admin offices. i was only semi-trained for the job. during my orientation, a private balcony on our floor was pointed out as being off-limits. very, very rarely VIPs would be allowed out there. one day a well-known actress came upstairs from rehearsal to have a quick and private smoke. i tried letting her out on the balcony and couldn’t get the door open. she got more and more annoyed while i was sweating and thoroughly inefficient. she finally left after maybe 3 min, but it felt like forever. after this, i learned the door had a special trick to get it to open.

  315. Why does everyone ignore the "well regulated" part?*

    I work for a company that makes products for kids, especially boys. We got a new manager from another part of the company. In his introduction to us, he said he wasn’t just interested in making the specific products we make, but that he thinks we should be “Touching boys everywhere they can be touched.” And he didn’t even seem to register how weird it was to say that.

  316. Anne*

    Somehow a lunchtime conversation ended up on the topic of bras, and how they fit properly and improperly, and someone ended up diagramming the difference between British and American bras on our office whiteboard! Yikes.

      2. zora*

        They use a different size system, so the letters are different. For example, what we call a DD in the US is an E in UK/Europe. The bras themselves aren’t necessarily different, but the sizes/measurements are. ;o)

  317. FuzzFrogs*

    I had been promoted from a part-time position at another location to a full-time position at this location, but I had worked at this location before. On my first day, I had just started my lunch break when one of the volunteers approached me. She said she’d forgotten to bring her lunch, and would I give her a ride home since her parents were out of town and wouldn’t be able to pick her up until later that afternoon? I could just do it during my lunch break, that wouldn’t be a problem, right?

    I told her I wasn’t really comfortable with that and I couldn’t really use my lunch break just to drive her around, and I will be honest–I wasn’t very nice about it. I was hungry and really uncomfortable with the idea that she thought we were on the give-rides-to-each-other level of friendship.

    I found out later that what she was *trying* to express to me was that she was having a blood sugar incident related to her diabetes and *needed* to go home. A senior coworker ended up taking her home, basically because she had to either do that or let the volunteer become seriously sick.

    To this day I don’t know what’s more embarrassing–the fact that I responded so coldly to what ended up being a serious medical issue, or that the volunteer continued to try her hardest to be friends with me for the next two years, including monopolizing my time at a big work event and making weird comments about being invited along to things. (I thiiiiink she made one of these comments about my wedding, but I’m not sure.) It got so bad that I once had to hide behind some furniture at the Ikea to avoid talking to her. And honestly, it’s just incredibly awkward that I’m continually dodging attempts at friendship from a lonely young person who doesn’t understand that we would not make good friends.

    Honestly, driving coworkers around has been the source of a lot of my workplace awkwardness. I had a coworker tell me over a 5-minute car ride that she regularly looked for leftover food in dumpsters (she framed this as an ethical decision, not an economic one) and how she’d once found a dead bird in a takeout container.

    1. Ramona Flowers*

      That sounds awkward but you couldn’t possibly have known! You evidently picked up a boundary stomping vibe from her and she didn’t mention the issue so you are totally not on the hook here.

  318. Jen RO*

    This is pretty tame compared to most, I know.
    My (male) boss was visiting our office for the first time. We had worked with him for about a year, but none of us had met him before, because he’s an ocean away. My (female) coworker, instead of shaking his hand or waving or doing nothing… she hugged him hello. He was shocked and she wanted to crawl under her desk.

    1. Jen RO*

      Oh, and one from my boyfriend. He was having lunch with some coworkers when one of them announced to the entire table that her boyfriend dumped her because she had a VD. Yeah…

  319. Goldensummer*

    I was working for the town Public Works department for the summer in college. We were outside all the time, getting dirty etc so I always wore the same 2 pairs of blue jeans. One day we were out cleaning leaves from sewer drains and I was riding with a guy that I’d had a crush on since high school and an older full timer who did not like the student workers. So there are 3 of us in the pick up truck, I’m in the middle because I’m the only female. The two guys hop out of the truck and I’m left to slide across the seat. My jeans caught on the gear shift and ripped from the crotch to knee. I was mortified and this is cell phones everywhere days. I had to radio in to dispatch, have them call my mother and have her bring pants for me. While my high school crush and the full timer laughed and laughed.

  320. Penny*

    Oh these should be fun to read! So my awkward story. I’m was having a friendly chat in the hall one with one of our most tenured C-level executives who is a man about 35 years my senior. As we were wrapping up, he reached out to pat my shoulder (he’s that kind of guy, so it’s not unusual for him to do that with both men and women), but I was already turning and instead he patted my breast. He quickly apologized and I could tell he was kind of mortified since he was turning red and he’s not one to easily embarrass. I knew he meant no harm and forgave him and laughed it off, but it was so awkward in that moment. Luckily, it hasn’t impacted our working relationship and was just a funny story to tell my family.

  321. Ten*

    I don’t even remember how the conversation started, but a few coworkers of mine were talking at lunch about sleep habits: sleeping positions, number of blankets used, what type of pajamas (if any)… and a habitually-oversharing coworker at a different table piped up and announced, “Oh, I LOVE sleeping naked! It’s the BEST!!” and proceeded to go on at length to the whole lunch room about the wonders of sleeping in the nude on silk sheets.

  322. FlexitimeCanSuckSometimes*

    When I was working as a receptionist for a school after undergrad, my coworker would always come and rant/cry to me about how the other teachers were rude to her. We both worked reception and she also was the academic coordinator’s assistant, so that involved a lot of people ordering us to do a bunch of stuff and us having to pass messages on to other people. However, usually she would misinterpret the tone/gestures of the people talking to her, and that would set off waterworks. I understand she was going through a hard time personally, but it would get extremely awkward when she’d start crying and ranting to me in the receptionist area…where anyone could walk in. It was hard being sympathetic when this became a regular occurrence and people would get exasperated and short with her, which would start even more issues, and then they would complain to me about her professionalism.

  323. BatFantastic*

    At my old job, I ran a computer lab where we hired temps a couple of days at a time to test elementary school math software. The temps were supposed to let me know if they saw a problem, and I’d investigate and file a bug if necessary. A middle aged man raised his hand and told me that the program was not accepting the correct answer. I walk over and ask him to reproduce the bug. The software presented the question, 9+6= and the man clicked 17. “See? It keeps saying that’s incorrect!” I reply, as kindly and nonchalant as possible, “Let’s try it again, but click 15.” It only took a second for the realization to dawn on him, and I felt so bad. I tried to reassure him that this happens all the time and it’s always important to check that the incorrect answers work as expected too. I hope it helped. First grade was a long time ago, we can’t be expected remember all of it, right?

  324. SweetiePie*

    The time my boss saw me in make up for the first time and said in a horrified, condescending tone that I “looked like a fish.” It was just eyeliner with a green shimmer to it, nothing worth the comment other than I normally don’t wear makeup. It was awkward staring and mumbling as I rushed to the bathroom to wash it off. My coworkers agreed it was extremely awkward…and that I totally didn’t look like a freaking fish.

  325. Fiennes*

    I have written some books, and almost exactly one decade ago, I was invited to my publisher’s cocktail party for Book Expo America in NYC. As work events go, not bad. This was the 2008 primary season, and Newt Gingrich’s team had issued this unbelievably melodramatic press release. Either Jon Stewart or Steven Colbert had John Lithgow come on to give a Shakespearean performance of the release, which was hilarious. This detail is pertinent because Lithgow also writes children’s books, which were published by the same house that published my book, and so was also coming to the party.

    As fate would have it, I reached the door at the exact same moment he did. Half of my brain thought: “Leave the celebrity alone. Be cool.” The other half thought: “I love this guy’s work so much and that reading was so great I MUST TELL HIM.”

    Inexplicably, my brain split the difference, so I grinned and said, “Well, heeyyyyyy!” like you would to a good friend you hadn’t seen in a long while. Lithgow got this slightly panicked look for half a second before he replied, “Heeeeyyyy! Good to see you!” Instantly I realized that he assumed I was someone working with him through the publisher, whose face and name he’d forgotten.

    At this point, John Lithgow and I are trapped in an awkwardness vortex. He can’t admit he doesn’t know me, for fear of offending someone who’s worked hard on his book; I can’t admit I don’t know him without it coming across really, really weirdly. So we blundered through what felt like an eternity of disjointed small talk (but was probably closer to two minutes), before I saw one of my editors and could go, “oh, there’s someone I should talk to. So great to see you!” and flee. This was no doubt as big a relief to him as it was to me.

    I always liked him as an actor but have been especially fond of him ever since seeing that even the most polished performers in the world sometimes can’t avoid The Awkward.

    1. Thursday Next*

      This reminds me of the book launch party scene in the movie version of Bridget Jones’ Diary, when Bridget asks Rushdie where the restrooms are.

  326. GreenDoor*

    We were in a full-staff meeting with all managers and our director included – about 40 people in the room. I work in a political/government office. We’re extra sensitive to things like using speech appropriately and maintaining appropriate boundaries are all the more important because the press and activist groups are always watching what we do. The boss had just finished running down the list of office updates and organizational news and whatnot and asked, “Does anyone have anything else?” Our temp, who was there about 3 months and should have understood the culture by than, turns to one of the guys and says, “Roberto, I just love your teeth! Your smile is just so white and just so kind. I could stare at your smile and those teeth of yours all day! How do you keep them so white?” I never knew awkwardness was something you could cut with a knife. Someone else finally said, “Ok Marla, let’s move on” and the boss was able to recover long enough to change the subject. It was just the weirdest, most random thing I’ve ever seen.

  327. Clever Name*

    Aw, I get the secondhand cringes often! Here’s my awkward work story:

    My boss at my last job was a horrible boss and a horrible person. For some context, he was not shy about eating other people’s food. I was in the kitchen while he was looking in the fridge once and he picked up a package of cheese I had brought in and wondered aloud, “I wonder whose cheese this is”. I looked right at him and said, “It’s mine.” He put it back, a little disappointed. I was miserable in this job (and was furiously job searching) and had taken to complaining to my friends via email during the day. Yes, not cool. So one day I went to go heat up my frozen lunch when I saw my boss come out of the kitchen with a frozen lunch that looked just like the one I had brought in that day. My lunch was not in the freezer. So of course I complained to my friends that my boss stole my lunch. Unfortunately, I had accidentally put my boss email in instead of a friend (whose name starts with the same two first letters). Another friend pointed this out to me. I was horrified. Moments later my boss comes out of his office and asks about the email. I tried to play it off like I meant to send the email to him. I wanted to die.

  328. ISayDumbThings*

    I was working at Big Shipping and Copying Company. Normally I handled shipping but production needed some help and shipping was done for the night so I offered to help. I should mention that my boyfriend at the time was the assistant manager (in my defense, he didn’t transfer to my store till after we’d been dating a little while). Other Guy working that night was a good friend of my boyfriend so he knew (we kept it a secret for obvious reasons and no one we didn’t tell figured it out).

    So here’s the scene, it’s just the 3 of us, it’s later in the evening so only a couple of customers milling about and Boyfriend is filling me in on the project while Other Guy is across the store working on something else, so it’s pretty quiet. The project required folding some really thick card stock. In order to get a really clean fold you have to score it first. We had a nifty little machine some one gave the super creative name of The Scorer (this place was hell so we had very few F’s to give about anything).

    Boyfriend sets up the machine, tells me how many he needs done. Now I’d used the machine before but only with regular paper. So (without thinking cuz thinking is for chunps apperently), I turn to my Boyfriend who is also my boss and 100% seriously say:

    “Wait, I’ve never scored with anything this thick before, how do I do it?”

    Other Guy drops whatever he’s holding, gaining the attention of everyone in the store, tosses his hands in the air and shouts “THATS WHAT SHE SAID!” In a perfect mix drop moment.

    Customers stare, I stare, Boyfriend stares, Other Guy is beyond happy and proud of what may be the best possible iteration of that joke ever. I am both mortified and completely amare of the absolute hilarity of the situation. Which, of course, became a long running joke in our store.

  329. Lana Kane*

    The time a coworker decided she was going to blow off a task our manager gave her, and she decided it would be a good idea to send a chat message to another coworkers saying so – except she sent it to our manager by mistake. She got fired.

    Or the time another coworker saw a different manager disciplining an employee most people in the office didn’t like, and went to spread the gossip via chat – and accidentally sent it to the manager in question. Then the manager stomped over to her desk and in front of all of us went, “In my office. Now.”

    Be careful with those work chats, kids!

  330. Goldensummer*

    Second story: At work (on a lunch break) talking about a major medical breakthrough (double arm transplant) I said to my much younger colleague, Elizabeth ‘My husband knows my rules about my waking up without limbs from say a flesh eating disease’ She was shocked that anyone would have that conversation with their spouse and I said that it was pretty normal to discuss hypothetical major medical decisions with your spouse. Just then a co-worker entered the room and Elizabeth asks ‘Susan, what would you do if you got a flesh eating disease?’ I immediately felt the chill in the room and Susan says ‘this isn’t something I want to talk about.’ I attempted to divert the conversation and but Elizabeth pressed the subject. Susan looks at Elizabeth and says ‘That’s how my close relative died, I don’t want to have this conversation’ I have never been so mortified in my life.

  331. Linds*

    Ok so I before I tell this awful, AWFUL story I have to say that it is not only awkward but truly a horrifying and mortifying experience for me. I’ve regretted it for nearly 15 years and my biggest regret is I will never have to opportunity to apologize or share what I’ve learned from what I said and did. I say this so no one reads this as a comical story or thinks I tell it laughingly.

    Many years ago I was a portrait photographer for a studio in a department store. I was young and it was my first professional job out of school. I loved my job and a big part of it was wrangling kids and trying to get them to sit still without actually scolding or touching them. It was tough as you might imagine. I had gotten into the habit of using animals to remind them of their behaviour. So I’d say something like “Uh oh we’ve got a playful puppy on our hands! Can I see your tortoise now? Remember how they move? Sloooowwww and stilllll.” It sounds ridiculous but it worked. Sometimes.

    One day I had a family of Mom, Dad, Little Girl, and, Baby Boy. Gorgeous family, dressed up for pictures etc. LG was about 3 and BB was only a month or so. Simply adorable and I was really looking forward to their session. Everything was going great, I was really on a streak and I was getting great shots. Then I helped LG onto the little sitting platform for a few snaps of her. She was wiggling and squirming of course so I pulled out my props and said it. “Oh aren’t you being a monkey today! A silly little monkey, well there aren’t any branches to swing on in here! And I’m all out of bananas. Can you show me your owl now? How do they sit?” This is the place to point out that this family was black. And I’m white. I had just called this gorgeous little girl a monkey, with all the hurt and history that that imagery contains. Mom shot Dad a Look and left the studio with the baby. I was bewildered at the time, wondering what had just happened. I definitely did not have any idea of how offensive what I had just said was.

    Dad and I headed out to look at the proofs and as we were sitting there I’ll never forget what he said or the look on his face while he said it. “You know” he said “She wouldn’t want me to say anything, but when you called our daughter a monkey, that really upset my wife. That word is hurtful for a lot of black people.” I had a sort of realization then that what I had said might have been offensive but I didn’t really understand the gravity. I stammered out an apology, he bought a few pictures surprisingly and that was that. I was left feeling something I didn’t understand. So I googled “Black people monkey racist.” I read what it showed me. I saw Stormfront, and racist 30s cartoons. So much hate. And I felt sick over what I had said and what it had meant.

    My biggest regret is there isn’t anything I can do to make it right. I wish I could say to them that I’m sorry I turned a memory sour. I’m sorry I was just another ignorant person who wrecked your day. Most importantly I’m sorry that I am part of the problem. I’ve learned since then that words carry weight that I’ve never carried. If you fire a bullet at a bullseye and it hits a person instead, they’re still shot even if you didn’t mean to hit them. Words can hurt and I am much more measured and careful in how I speak. So I try to remind myself when I cringe at the memory that some progress has been made, some lessons learned. I’m sorry it came at such a shitty cost, though.

    1. Radius20*

      I don’t think you should feel bad. Sounds like you were young and didn’t know that it could be hurtful! You would have said the same thing to a white little girl. It does not sound like there was any hate in your heart and it sounds like the father knew this deep down, which is why he still bought the pics.

  332. Janey-Jane*

    How about the time I was asked to take part in a video to go out to donors. All I needed to say was “I believe in ORGANIZATION!” And I said to the poor video gal, who loved the organization and had worked there for 20+ years, “What if I can’t say that seriously?”….

    What I meant was, I don’t film well, and feel like I’d just say it sounding sarcastically. Not that I didn’t really believe in the organization. But I know that’s how it came across. I filmed as quickly as possible and bolted.

  333. ohroie*

    My work has a tradition of throwing a small baby shower for expectant mothers just before they go on maternity leave –
    just afternoon tea and a few presents from co-workers or friends. Once, when throwing one of these for a team member, our boss (who is known for his social awkwardness) insisted that the mother-to-be had to read the cards out loud whilst opening the presents. Some of those were written by her good friends and we’re obviously not for public consumption, but he persisted all the way through the 10 or so presents. No one felt much like celebrating after that.

  334. Automotive Engineer*

    Last summer I was lucky enough to be starting a role that was super exciting and new and really aligned with what I’d like to be doing long term. I got along great with my manager and ended up being quite good friends with the engineer I primariy worked with. I’m not used to getting calls on my cell phone for work since it’s my personal phone and I don’t typically give the number. In fact, I pretty much only talk to my family members on the phone.

    On a work trip I was in the car with my manager and I got a call from the other engineer I worked with about an issue. I talked to him for a few minutes and then said goodbye and hung up. Only I didn’t just say goodbye. I said “love you, bye” as habit when hanging up my cell phone. I didn’t even realize it until my manager asked me if I just told my coworker I loved him.

  335. the one who got away*

    At lunch with several members of our department, including a more junior colleague who had been with us for a few months at this point (I was mid/senior level). We’re telling stories about weird food issues our parents had and I mentioned that my mom used to pick out and eat only the red M&Ms until she found out that the red food dye they’d been using at the time was a carcinogen and then she switched to eating everything except the red ones.

    Junior colleague asked how she was doing now. I said she’d died of eating red M&Ms. People laughed and we finished lunch.

    A few hours later, junior colleague comes into my office and closes the door. He says he wanted to tell me privately how sorry he was that I’d lost my mom; he had also lost his mother at a young age, so this was something we had in common.

    MY MOM IS FINE.

    But if I could have been hit by a lightning bolt at that very moment, I would have gone down gladly. That poor guy.

  336. Michelle R*

    I was listening to hip-hop Pandora at work and closed my laptop without closing the website. When I opened it again in our staff meeting, the entire room heard Big Sean singing “ass ass ass ass” as I struggled to find the mute button.

  337. Not Rebee*

    When I was in college, my girlfriend and I were heading to the campus library to do some studying. I totally forget what happened in the car as we were parking, but she refused to get out of the car and locked the doors after I was already out. It was something funny, like a tickle fight, nothing crazy. Anyway, so I decided I’d be a loon and climb onto the hood of her car to make faces at her through the windshield and she turned the windshield wipers on me, liquid and all. I’ve never jumped off of anything so fast in my life! Then had to stand there, wet, while she recovered from a laugh attack enough to unlock the doors and get out of the car. Walked into the library still covered in washer fluid lol.

  338. Casual Fribsday*

    I’m 98% awkward, so I was kind of surprised to realize that it’s almost never work related. I mean, I feel awkward at work, but I don’t think the situations are objectively awkward. There was one time though…

    I work in a (Christian) church, and I once took an international phone call from a man who wanted me to repent and give my life to Jesus. Very aggressively, I might add, and while strangers getting aggressive on the phone is generally #NotMyJob, there was no one else around I could pass it off to. I engaged for four or five minutes before I hung up on him. He called back — over and over and over again. It was a long afternoon.

  339. 123*

    The most cringe-worthy situations, I swear, are always made by the same person in our office. But, recently, she outdid herself. Over a recent weekend, a manager’s brother had unexpectedly passed away and it was shared in our daily meeting. Manager was very close to all of her family and we all knew of him, some of us personally. Many of us were concerned for our manager and visibly upset. “Lucy” felt it was pertinant to note at this time, “since we’re talking about” people dying, that her niece was killed a few weeks ago. Her tone very much implied that it was even worse for her because she was killed. I am not saying that it wasn’t a horrible event or that she wasn’t grieving, but the timing, and everyone’s unsure response, left me cringing for sure.

  340. AnonMurphy*

    Oh it’s all mine. First job out of call center and retail (I was about 24, female). My (male, mid-40s) director seemed harried… I commented on how he looked stressed (unobjectionable) and when he confirmed he was, I… offered to give him a back rub. (OBJECTION!)

    After several seconds of silence in which I churned through all the things wrong with what I has just said, and seeing the dawning horror on his face, I fumbled an apology and got the hell out of there.

    As it turns out, he actually was sleeping with a coworker closer to his own age, not that it made what I said acceptable.

    This boss is also the same one who did me a kindness by telling me, in my first yearly review, ‘you got this! You do good work. If you could just stop being a bitch to everyone you’d be unstoppable’. I treasure his criticism to thus day because it increased my self-awareness haha.

  341. Darcy*

    At a former job where Halloween was a BIG deal, our legal department (yes, the one department that should have known better) dressed up as Snow White and the 7 Dwarfs. The attorney who headed the department was male, and all of the other team members were female. For the Halloween skit, the cross-dressed Snow White did a pole dance and stripped down to his skivvies. Our employee relations person was in tears, and not of joy. It was the most awkward thing I’ve ever had to watch/experience at work.

  342. Kate*

    When I was working as a receptionist, it was part of my job to oversee the meeting rooms and prepare tea and coffee for guests. It was my day off when the Chinese delegation arrived and they asked for tea. My coworkers brought them boiling water in cups and put the teabag next to it. That’s how they usually did it, so people could control how strong tea they want.
    And the meeting went on and on and when the Chinese delegation left, they complimented the tea. It turned out that they’d never figured out the tea was only half-prepared and they should’ve put the teabags in. They complimented hot water…
    As a person who has studied Far-Eastern cultures, I got second embarrassment hearing about the situation!

    1. Kate*

      Another one, this one involves me. An interview horror story:
      CEO (woman) and the hiring manager (man) were interviewing me. It was for an assistant position.
      CEO shots off quick questions:
      “Do you smoke?” No, but you shouldn’t ask. “Do you drink?” Occasionally, but another thing you shouldn’t pry. “Drugs?” At this point my eyes might’ve bulged out. Sure, everyday, do I look like a drug addict? “Do you have any tatoos?” Not that I think it has anything to do with the quality of the work I do… I might’ve been silent for too long or my face might’ve reflected my thoughts because she brought up excuses like the hiring manager wouldn’t care but she doesn’t like tatoo-ed people (what made it more awkward, that she pointed out the hiring manager is male and it might’ve been not very appropiate to bring this up with him in the room) Anyway, no, I don’t feel like having tatoos all over my body. Not that it was any of her business.
      “Also, there’s no place to buy food nearby, so the guys usually just order or bring their own. But please don’t expect to be given their left-overs to eat.” At this point I seriously started wondering what kind of people they’d hired before!

      1. pancakes*

        It’s bizarre people like this expect candid answers to such idiotic questions. “Yes, I’m on heroin. I’m a wreck without it and will need a break to get high at least twice daily.”

  343. Duffel of Doom*

    I worked for a small local retail chain, and my store was the store where the CEO and his family would shop. His wife often special ordered items, and 2 months into working there I ended up being the one to call her when an order came in. I got her voicemail, and as the tone went off I realized just who I was calling, and that my usual script wasn’t right to leave for her because she clearly knew what store it was and how to reach us. I tripped up HORRIBLY and left a bad message that probably wasn’t quite as awful as my anxiety insists it was, but I stressed for over a week about it. I was mortified.

  344. jj*

    I worked at an agency and the client services woman (we’ll call her Judy) was just an awful pill. Horrible. Terrible human being. And completely clueless as to how she was perceived by others. To this day I can’t listen to the Goo Goo Dolls song “Iris” because it was set as her cell ringtone, it went off all the time, and she’d sing along to it for as long as possible before picking it up. In our open plan office.

    The worst was when we all got accidentally copied in on an email from our client that read “Judy is a pain in the ass but I guess she gets shit done.”

    The creative lead on the account, bless him, responded “We sure do appreciate Judy’s effectiveness!” LOL

    The day she got fired was amazing, she stormed all over the office foaming at the mouth then logged in from home later trying to pull documents off the server.

  345. Sherm*

    I once had a bit of a medical malady: an abscess on my upper back. Fortunately, my doctor was close by, so one day at work, I headed out, got the abscess scooped out and bandaged up, and returned to my job. I went to a meeting where someone was doing a presentation at one end of the conference room. I was near the speaker and turned toward him, which meant that my back was faced to most of the other people there.

    After the meeting, a coworker discreetly informed me that I was bleeding! Not to a dangerous extent, but most of the meeting’s attendees got to witness a big splotch of blood on the back of my shirt grow ever larger, like red ink from a fountain pen.

  346. Barefoot Librarian*

    This happened about two weeks ago (trust me, I have a ton of awkward, foot-in-mouth stories lol).

    We were having a weird issue with the company phone lines where a call to one of the dean’s extensions was being routed to one of my employees. If he didn’t pick up, it would come to my office. Neither of us are even in the same building as the dean in question.

    Well my assistant director and I were talking about it and she started joking about our telecom guy sitting secretly having a switchboard and messing up the cables like the Lily Tomlin sketch. I went on a tangent about how I couldn’t get the image of him out of my head in a dress and a wig. After 30 seconds of me laughing and her giving me a strange look, I realized that I was making a horribly off color, insensitive joke to my TRANS boss. I wanted to sink through the floor. It was wrong on so many levels and I just let my sense of humor get away from me.

    To her credit, she replied to my profuse apologies with “it’s okay, honey. I know that your supportive.” She has so much class and I was a total jerk. I wanted to die. I seriously did.

  347. SharedDriveUser*

    In my younger years, I supported my college costs by working part-time at a local department store, in women’s wear. I worked evenings (store closed at 9 pm) and weekends, and was one of two evening ‘change cashiers’ for the store. The store was experiencing cash drawer shortages, so all cashiers had taken extra training, including some of the more common change-making scams. So it’s the Friday night before Mother’s Day, and we’ve been really busy. I finished checking out the last customer in my department at 9:25 pm; once clear, I started counting out my register. The store is pretty quiet, I’m focusing on the count, when someone grabs my shoulder from behind, followed by loud – LOUD – scream and my elbow slamming into the ribs of the … senior department manager. He’d come by to see if I needed any assistance, and said when he spoke to me, I didn’t respond, hence his hand on my shoulder. Much mortification and embarrassment for my 18-year old self, and much teasing from co-workers that weekend.

  348. RedSonja*

    I had an internship at a marine mammal training facility. Early on (first few weeks), I was skimming the leaves and other detritus out of the pool. I don’t know exactly what happened, other than I took a step and…. missed. Suddenly I’m falling into the pool. (In Milwaukee. In November. Unheated.)

    My first thought was “oh god I’m getting fired”, followed by “don’t drop your shoes or the skimmer because they’ll have to dive for them” and then “Oh please don’t let the baby sea lion bite me this fun new toy in the ass before I can get out”. I managed to hold on to both shoes and skimmer, and exit the pool with no biting. I went to the trainers’ office to report my mishap and, after they made sure I was okay, they laughed hysterically and took a picture of my cold-drowned-rat-looking self that, as far as I know, still hangs in the office to this day.

  349. Meowzer*

    Some years ago, a not particularly well-liked colleague left my company. When folks left, we used to gather in the conference room for cake and well wishes. This time, the bakery made a one letter mistake and created a funny yet terribly awkward moment, since this colleague knew he was unpopular. They missed a crucial “s.” The cake said “Good Luck From Your Friend at Teapots, Inc.”

  350. Beancounter in Texas*

    This was awkward for my coworker, not for me.

    I supervised a guy in his 40’s in the accounting department who was conservative in his values, and he might have had a small problem with me being his supervisor as a woman. We were talking about our weekends and I mentioned how I was solicited to sign up for an electric company contract and I went for it. He blurted out, “You didn’t ask your husband for permission?!”

  351. SarahKay*

    I was part of a team of six admin staff, sitting in the centre of the site workshop, processing the paperwork for teapots coming in for repair and the invoicing when they shipped out again. Our teapots tend to skew towards a primarily male workforce, although the admins, myself included, were mostly female. It’d been a cold start to the day so I had a sweater on over my t-shirt, but now it was warming up and I was too hot and need to take off the sweater.
    Sadly my t-shirt decided it was BFF with my sweater and wanted to stick together – a fact that I didn’t notice until both were up around my head!
    Thankfully I was wearing a respectable bra, but nonetheless I showed all the teapot repairers far more of myself than I ever intended or wanted to. What made it worse was that my office chair was fabric-covered, so I’d stood up to take off the sweater (so that it wouldn’t catch on the chair) thus drawing far more attention than if I’d stayed seated.

  352. Pamalamadingding*

    My cringeworthy moment bears similarity to the accidental hug. But like the Energizer Bunny, it kept going…..I worked as an admin associate/ministry assistant at a church, and as such, was friends with my pastor, as well as acting as his EA. We suffered a pretty bad sewage disaster at the church and our worship center was under a foot of sludge on Saturday at 11:30 a.m. I called him and told him that there was no way we could have services–I was pretty freaked out by the stench alone. He assumed I was over-reacting and at the end of the call after I (kind of rudely) insisted that he come NOW, he said, “OK–you win. On my way. Bye, I love you.” “OK thanks. I love you too. Bye” *crickets* Phone rings…
    Him: We didn’t just? Oh well.
    Me: Yeah um. See you soon.
    Him: Ok. On my way. Bye. Love you.
    Me: crickets (he just hangs up)
    Phone rings again
    Him: Soooo….yeah. Ted and Tracy (our spouses) will laugh at this
    Me: Yeah. Guess it’s automatic.
    Him: Ok. Bye. I’ll be there soon
    Me: Ok thanks. Love you

    8-I

    Mortified.
    p.s. We were not able to hold services the following day at the church. The bar down the strip mall however opened up and we met there. Their early lunch crowd started meandering in around 11 a.m. The sermon title was “Jesus Never Tapped Out–but *Church Name* is On Tap”

  353. Irene Adler*

    It’s late afternoon and co-worker L is tasked with answering phones. Generally, phones are very light so she’s at her desk working. I walk into her office to talk about some work topic.
    Phone rings.
    L picks up. It is Ms. HP, an outside professional contact, calling for our boss. Now, Ms. HP has a reputation of not being very nice (our nickname for her: Hell-on-wheels). Boss doesn’t like talking to her. No one does.
    I look to see if Boss is in his office. Nope.
    So, L puts Ms. HP on hold and pages for Boss. No response. As ours is a big building with very few employees, I go and walk the perimeter of the building to see if I can find Boss. When I return, L is away from her desk.
    L walks in.
    “I can’t find Boss,“ I tell her.
    “Neither can I,” L says. “I walked from the back to the front and even looked to see if his car is there. It is. And Ms. HP is still on hold. I so don’t want to talk to her!”
    L works her way to her desk. See, L has only one leg. She gets around on a prosthetic. And she’s a little slow in getting around. Understandable.
    L picks up the phone and tells Ms. HP that Boss cannot be found. Then she starts apologizing; explaining that she looked everywhere because the page isn’t heard throughout. Finally, she offers to put her through to Boss’ voice mail but Ms. HP will have none of that. So, L promises to have Boss call her back when he can. End of call.

    I asked L, “What did she say?”
    L explained, “When I told her that Boss could not be found, she replied, ‘Took you long enough to get back to me!’ “
    Ouch!
    I said, “At that point you should have explained that you only have one leg. That would have taken her down a peg or two.”
    “No, no,” L replied. “I don’t want to embarrass the woman. No telling what would happen if I did that to her.”

  354. Lois Lane*

    This might be more a case of comeuppance than awkwardness, but here goes… I was a reporter covering my first murder trial alongside a seasoned veteran who was an insufferable know-it-all who didn’t like that I was tagged to help her cover the trial. She often talked down to me, didn’t work as a team and her general demeanor was to complain about anything and everything. The trial was high-profile in our region and the courtroom was packed. There had several cases of cell phones going off during voir dire and the judge was steamed. He had warned the courtroom that if a cell phone went off, it would be a $150 fine. The trial had just gotten underway when a cell phone started ringing from our corner of the courtroom. “Who’s phone is that?” the judge bellowed. All eyes turned to our bench, which of course, was in the far corner of the courtroom, furthest away from the doors. I knew I had my phone ringer turned off because I was seriously OCD about that and had checked it a bazillion times before court, but everyone was looking at me, including my coworker. Then coworker’s face turned bright red and she began fumbling in her bag for her phone and scurried out of the courtroom as fast she could. Not only was she fined $150, but one of our competitors made sure to tweet it out to the tens of thousands of readers avidly following the trial.

  355. Alucius*

    I’m a professor who teaches ancient languages. One of them changes the endings of its verbs depending on who is the subject of the verb. Since it’s awkward to say something like “this verb is second person masculine plural,” we use abbreviations like 2mp instead. So, one class I was talking about these verbs and said something, “this is the ending that gives the verb its 2mp-ness.” (notice the last 2 syllables). Dead silence, followed by gales of laughter.

  356. Frank Doyle*

    Oh, I finally remembered one! (And I find it comforting that I can’t think of any more. I’m sure I HAVE been in super awkward situations, but I’ve forgotten them, which is great!)

    I was in my last semester of college, going on interviews to find my first engineering job after college. I drove up to this place that was . . . I don’t remember exactly where, but a 2- or 3-hour drive from school and from home and from anyone I knew, in a rural area. I’m not sure why I even went on the interview, maybe because I would theoretically like to live in the woods? I mean I live in the woods now and I love it but I came here with my husband, I couldn’t imagine, at 22, how to start a social life in a situation like that. At one point in the interview when they asked if I had any questions, I think I said “do people . . . live around here?” And they were like, uh, yes, everyone here lives somewhere. There are places to live. I just couldn’t wrap my head around how to START a life somewhere with no school or friends to use as a springboard.

    Anyway the place had like three employees total, I figured out quickly that the whole thing wasn’t for me, but I finished the interview professionally. As soon as I got into the car, I rolled down my stockings, which were held up by those sticky insides and SUPER uncomfortable. As I was pulling out of the driveway, the owner of the company came over to say one last thing and poked his head in the door and I saw his eye get caught by my weird, flesh-colored stockings pooled around my knees, which I figured he probably couldn’t make head nor tails of. That was the only interview that didn’t result in an offer that year.

  357. Traveling Teacher*

    Warning: this is gets icky:

    I was feeling nauseous and unwell one morning on my way to work and thought about calling in sick. I decided against it because of the paperwork it would entail. I got my period while teaching first period in an upper elementary school class. I suddenly felt an awful sensation in the back of my throat. I grabbed a garbage can and told the kids to open up the adjoining door to Mrs. X’s room and to tell her I was going to quickly run to the loo.

    I ran, madly, and made it just in time. Then, I fainted. I woke up, in a heap on the floor next to the toilet. I vomited again, this time on the floor. I managed to roll over to avoid the tide of yellow streaming towards me. I tried to stand but couldn’t. I was discovered some 10 minutes later, still prone on the tiles, edging away from the growing puddle of vomit. The cramps were agonizing, and it felt like I was in labor. (Now, after having been in actual labor, I can confirm that the sensations were exactly the same!) After the principal and four (!) other colleagues came to my rescue, they persuaded me to leave the cool bathroom tiles, and I went to rest on a pile of pillows in the kindergarten classroom.

    My now-husband came to get me, after a long bus ride. He half-carried me to his place where I passed out for the rest of the day and night. At one point, a doctor came (not in the US, so this is still a thing), and his conclusion, as reported by my husband, was “female trouble.”

  358. Tax Princess*

    Not a work moment, but definitely my most cringe-worthy ever:

    I was sitting in my car at a gas station, waiting for a pump to come available. An older guy, finished fueling up his car and jokingly said to me, “I’ll let you have this pump if you give me a kiss”. I replied with what sounded much wittier in my mind, “what if I just blow you one?” I hope to this day that he didn’t hear me, but I still turn red at the thought of it!

  359. Merida Ann*

    I just recently had a new coworker start who moved here from several states away. He was asking about apartments and any recommendations and I listed off a few I had looked at while apartment hunting and then added “Of course, there are also lots of 55+ apartments around here that you can look into that I don’t qualify for.” Uh… yeah, neither does he. *facepalm* He muttered something about still having a few years left before 55 and I… honestly have no idea what I said after that because I was so busy trying to sink through the floor.

  360. Insert Foot*

    I worked at a large hardware retailer in high school and college. I met a lot of fun people working there and became friends with many coworkers during the five years I spent there. In the very early days a girl I had befriended announced to the team she was a few weeks pregnant. I was probably 19 at the time and she was a couple years older. As she was telling me (privately, thankfully), I congratulated her and said “…it’s a little early to be telling people but I’m so excited for you!” WTF?! Why did I say that?! As soon as the words came out of my mouth I was absolutely horrified. She just kept talking and acted as though she didn’t hear it but to this day, 18 years later, I am still mortified I said that! Now when people announce their happy news I just say congratulations.

  361. Daytripper*

    I used to work front desk at a hotel that had an attached banquet hall. There were often weddings held there on weekends and one particular wedding had a lot of guests from out of the country (I’m in the US). One Sunday morning I was working the desk and a young woman with a heavy accent approached me and asked if I could help her in her room. She seemed frantic and I couldn’t quite understand what she needed, but I followed her to her room to see what was going on. Eventually, she conveyed that she believed someone had drugged her drink at the wedding the night before, and had purchased an at-home drug test to prove it. She had asked me (another young woman) to help her read the results. Of her urine test. So I’m there, incredibly uncomfortable, as she is sobbing and shoving a cup of pee at me so I can read the panel and tell her what drugs are in her system. It was a surreal moment of, “Is this really my life??”.
    Don’t worry, she was not drugged. She had never had alcohol before and didn’t understand that what she was feeling was just ‘being drunk’.

  362. Fabulous*

    I was very sheltered growing up in a very small community (read: white, I think there was one black family, who I didn’t know) and my college town was very similar as well. One of my first jobs out of college was at this place where I happened to be the minority, so my co-workers were mostly black and Latina. I had a couple black friends who I was talking to at lunch one day and it came up in conversation that neither of them liked pork. I proceeded to ask them (and it still makes me cringe today), “Is that a black thing?” They both just stared at me in response for the longest time. And of course I felt like I had to backtrack, because I didn’t know! And I never did get an answer either!

  363. Are You There God? It's Me, Margaret*

    This is so cringey that I won’t even post under my usual name, or add my email address.

    I got caught short one day at work with an unexpected period. I had no feminine supplies with me, so I did what women always do when that happens — stuffed a wad of TP in my underpants and hoped the time would pass quickly until I could run out at lunch and pick something more suitable up.

    I was wearing a skirt that day. And apparently not the snuggest underpants. You can see where this is going…

    As I walked back to my desk, I felt the TP wad… fall out and land on the floor. The middle of the floor, in my open seating office. With dozens of people within eyeshot.

    A big wad of bloody TP. It just sat there, for all to see. I was unsure if anyone actually saw it fall. If they did they thankfully never said anything to me.

    It sat there for some time. I was dying of shame but just couldn’t bring myself to go pick it up.

    Then I looked over again, and it was… gone.

    To this day, I have no idea what happened to it.

  364. s2mathes*

    I once pointed out that a co-worker’s bracelet had fake charms (as opposed to name brand Pandora charms) in a group situation. My intention was to point out that they still looked great, but it totally came across like I was shaming her for wearing less expensive charms! I felt bad for days, and everyone involved was embarrassed.

  365. H.C.*

    Fingers crossed for this – as someone’s who’s frequently awkward throughout my adolescence & young adult years and still occasionally awkward now

  366. CheeryO*

    Luckily I haven’t done anything too stupid at my current job, but I was constantly embarrassing myself at my first job in food service. The worst was when I was taking orders at the drive-thru and didn’t realize that I had the broken headset that was constantly connected to the speaker outside. This one woman came through and ordered a TON of food, taking forever to make up her mind about each thing, changing her mind several times, yada yada… I eventually snapped and made a huge “UGHHHHCOMEONNNN” noise, not remembering that she could hear everything I said. She said, “Um, EXCUSE ME?!” I don’t know that I’ve ever been as embarrassed as I was in that moment, and my supervisor was ready to kill me, but I thought I recovered semi-well (for a 16-year-old at least) – I apologized profusely and told her it wasn’t directed at her (lies).

  367. Life is Good*

    I was young and new at a previous job and was walking around a corner near the men’s room when a wave of really awful poop smell hit me. I started to wretch while walking and looked up just in time to see the CEO walking toward me after having just stepped out of the bathroom. He looked very embarrassed and I was mortified. I learned later that he had colitis that flared up whenever he is under stress – which was often. When I found that out, I felt even smaller. That poor man.

  368. Working Hypothesis*

    So, I’m a professional massage therapist — the licensed kind who does health care work. One of the big problems we have in my industry is avoiding being mistaken for That Sort Of Massage; the kind which gets advertised on back pages of local papers, and which involve euphemistic phrases like “happy ending.”

    Normally, I handle this by keeping my website and advertising *very* professional and using imagery which shouts ‘medical’ in it, and by making a point of what someone can expect from their massage with me, both on the website and in my scheduling conversations with them by phone or email. Every once in a while, I get someone who pushes for something that I just don’t do, and that’s always a little awkward; but they’re putting themselves obviously in the wrong by pressuring me once I’ve said clearly that I don’t do that, so I’m pretty comfortable returning that kind of awkwardness to sender.

    Except this one guy. He obviously didn’t mean to pressure; he was simply clueless. He hadn’t even seen my website, apparently — heaven only knows how he found my phone number, but he made it quickly clear that he was calling every single massage therapist within a several-mile radius, hoping to find one who would give him the kind of massage he was looking for. The sheer confusion in his voice was palpable… by the time he reached me, he’d been turned down several times and he just didn’t understand why!

    So I took a deep breath and I explained the whole thing to him. What the difference was between ‘licensed massage therapist’ and ‘masseuse’ and why he would never, ever get the kind of massage he was after from anybody with a license, because even if they might be willing (which they almost certainly wouldn’t be, or they wouldn’t have gotten a license in the first place), it would get that license yanked for good and they’d never be allowed to work again. How to distinguish between ads for licensed therapists and ads for sexual massage, and even where he could probably find the latter. I don’t actually have anything against sex work; it’s just not what I do… so I taught him how to find someone who *did* do that sort of massage as a matter of choice. He was dramatically happier and very grateful as he got off the phone.

    I figure I not only made him happier, but I probably saved several of my colleagues from the awkwardness of having to tell him no, because he was clearly prepared to call everybody with ‘massage’ in their job description in the city if he had to! But that one phone conversation was awkward enough for all of them put together.

    1. zora*

      Oh no!!!! You were very generous to spend your time helping that guy out.

      My mom has the opposite story. She was a 20-something in the 70s, had grown up pretty sheltered, but had moved to California and was teaching school in San Francisco. At some point, someone had given her a gift of a massage, or something, I can’t remember. So, she had had one massage in her life. She had a long weekend off around her birthday and was wandering around downtown Palo Alto, and saw a storefront with a “Massage” sign, and thought, “Oh, I could treat myself to a massage, that would be nice!” Walked in and up to the front desk, asked if it was possible to have a massage. The lady at the desk sort of gave her a weird look, long awkward pause, said “just a moment” and walked through the dimly-lit lobby through the beaded curtain in the doorway. That is the moment my mom looks around and realizes, OHHHHH, this is THAT KIND of massage!!!! And she turned and ducked out of the door as fast as she could!

      1. Working Hypothesis*

        Eeep! Talk about awkward — I’m not sure why, when I put in the email, it gave my real name instead of my usename here! Oh well; I’m not really disturbed about this crowd knowing who Working Hypothesis is. :D

  369. LostInTheStacks*

    I have two similar stories; they’re not as good as some others on this page, but they were extremely awkward in the moment!

    The first happened at my very first job, ever, a part-time gig working in my mom’s office. The way her job works, the office is usually only staffed by three people (the boss, the administrative assistant, and the HR woman), and the rest of the staff is traveling for most of the day. I was brought in mostly as a favor to my mom, to help with their backlog of paperwork. One day, I was in the backroom when suddenly the whole building began to shake. My first thought was that a car might have hit the building–it turned out to be an earthquake, but the office was in Connecticut, and we usually don’t get those. I froze for a few minutes, and then I went out into the main office to see what was going on… and it was totally the empty. The entire building had been evacuated, and they had forgotten I was there! I was 16 at the time, too, so my mom was rather annoyed that they had left me during a (mild) emergency.
    Then, just a few months ago, I started at an internship where I worked a few three-hour shifts a week. On my very first day (again, having spent it in a back room doing mostly independent work), I came out at the end of my shift to find the whole office was closed. There were only two people, and the office always closed for lunch. I spent about fifteen minutes dithering and wondering whether it was okay to leave on my first day without checking in with my supervisor or anything–I ended up leaving a note and then going home.

  370. Nonnymoose*

    Super awkwardest boss ever:
    I’m newly returned from maternity leave (and a first time mom):
    “So, how was labor?”
    He genuinely wanted to know. I cringe about it years later.

  371. E.R*

    In my first job i had to submit boring monthly reports to VPs and execs. In an effort to be amiable and outgoing one day I burst open the VP’s office door and proclaimed, “its that time of the month!”

  373. Immersang*

    I think the most awkward situation for me was when I was working at a small tech startup that sort of blew up. We had a founder and a Managing Director, who had a meeting one morning that resulted in a major falling out. The founder essentially wanted to kick out the Managing Director right then and there on the spot.

    A couple of my colleagues and I were sitting in the common area when the two came storming out of the conference room, yelling at each other and the founder going “I want you out of here! NOW!”, with some more heated back and forth following.

    The colleagues and I were just sitting there, trying to blend into the wallpaper and holding our breaths until it was over and Managing Director being out of the door.

  374. Booknerd*

    One of my work duties is to attend weekly Rotary meetings. I am female and most of this Rotary club is made up of older men. After I had been a member for a few months, one of the fellows decided he was comfortable enough to give the side-hug in lieu of the usual handshake greeting. To be fair, he’s a nice man and hugs everyone, in a not-creepy way. But I was not expecting him to lean in for a hug, so when I stuck out my hand, he leaned in for the hug and my whole hand and arm went INSIDE his suit jacket and kind of around his waist. SO awkward. I lurched back and for one terrifying second, my watch caught on his jacket before I was able to step back. It’s a frequent joke between us now, but I was MORTIFIED at the time.

  375. Melissa C.*

    I was interning for a music festival in a Colorado mountain town and had just arrived from basically sea-level. (Up to 9,600 feet.) I wasn’t feeling *great* due to the altitude, but as a 20 year-old I didn’t really know I could say “Not feeling well…need to go rest.”

    On my first day in the office, the staff took the interns out for lunch, and then I went to a meeting at a radio station with the festival’s CEO – in his car. On the way home (winding through mountain roads) I started to feel queasy. I ended up having to ask the CEO to please pull over so I could throw up on the side of the road! It was so embarrassing. Thankfully he never spoke of it again and the rest of the summer was a success, but I will never forget that moment for the rest of my life.

  376. Office Pooper*

    Thankfully no one at work knows this happened except me! I used to go out a lot for lunch and one day upon returning I had to go to the bathroom; it was an emergency. The closest restroom was just beyond the front desk a little ways into the main floor. I got in the door thinking I’d be able to make it, but then there was a sudden turn for the worse… someone stopped to talk to me! As soon as they left I sighed relief a little too hard, as my bowels decided they were done being held. Thankfully I was wearing a dress that day with control shorts on underneath, so everything was well contained. I was able to just toss my underwear and go on with my day. What a terrible day…

    TL;DR – Pooped myself at work.

  377. HeckandHighWater*

    I work in a blue collar industry building electrical panels for building controls. It’s a running joke between all the installers out in the field that the blueprints are… well they’re typically chock full of cut/paste errors and other stupid derps. So one day I was on light duty building a panel with my shop-buddy Andy, and I couldn’t make heads or tails of what the print was telling me to do. Andy tried to help, but was just as lost. In walks Walter who works in the office. “How’s it goin’ guys?” he says cheerfully.
    “Oh, the usual. The sun is shining, the grass is green, and these blueprints are screwed seven ways to Sunday. You?”
    Walter pauses, considering. “I’ll get back to you on that.” And he walks out of the room.
    Andy suddenly explodes in laughter and starts rolling on the floor. I inquire what is so funny.
    “Dude! Those were HIS blueprints! You didn’t notice his signature on the bottom of the pages?”

    1. Barefoot Librarian*

      OMG, that is hilarious. I did something similar once when I accidentally criticized a faculty member’s assignment. I had been working for hours with this particular student to parse the assignment and help them get their research ducks in order. That afternoon a professor causally asked how my day was going and I let lose with this triad of frustration only to have it click that THIS was the faculty member responsible for the terrible assignment LOL.

  378. Darth Brooks*

    I joined a few (mostly female) members of my new team in a small conference room for lunch. As soon as the door closed they started talking about strip clubs and how often they frequent them. The conversation quickly and without warning morphed into how many people they’ve slept with, the “sizes” of those people, and their general feelings about it. I sat wide-eyed, silently and awkwardly eating my lunch.

  379. As Close As Breakfast*

    I once had a job working for a county social services program where I spent about half of my time at the front desk. The front reception was for two different programs so there were always a lot of employees and clients around. One afternoon, a heavily pregnant client passed out right there in the lobby while waiting in line to check in with me. Of course everyone around immediately jumped into action! As the main front desk person I grabbed the phone to call for help. So there I am, receiver in hand, staring at the phone. Seconds tick by and then I yell out “HOW DO I CALL 911?!?!?” As I’m still staring at the phone, I realize the room has gone silent. I looked up to find every single person staring at me like I was the biggest idiot to ever walk the earth. So I scream, and when I say scream I mean SCREAM, “DO I HAVE TO DIAL 9?!?!?!?” This didn’t clarify the situation for most people, because 911 obviously starts with a 9. So cue more silent staring. I don’t know how long it was, probably only seconds that felt like forever, before someone yelled out that I did have to dial 9. Because, you know, dial 9 to call out… so 9911.

    I’m not good under pressure.

    Also, the pregnant client was fine. She woke up after a few minutes. The paramedics got there really quickly and took her to the hospital. She was back the next week and all was well!

    1. Nynaeve*

      This made me laugh out loud. But yes! Do you have to dial 9 to call out? Why are phones so complicated?

  380. Dr. KMnO4*

    I was at the huge summer conference for my academic discipline with my grad school advisor and the rest of the research group. Two awkward things occurred:
    1. My boss made some innocuous comment that could be taken another way. I replied, automatically, “That’s what she said”, though I caught myself halfway through saying it, so it came out more like, “That’s what she…said?”
    2. Our research group was challenged to a dance-off by a research group from a different university. They’d prepared dance moves well in advance. My boss made us learn choreography in 20 minutes (she was a former hip-hop dance instructor). This choreography included “sexy” dance moves. The dance-off was recorded and posted on YouTube.

    1. Dr. KMnO4*

      This comment has two purposes – my email address and another story I forgot.
      Myself and another female graduate student were standing around talking to our advisors (who are best friends, and both are women) when suddenly the topic of conversation changed. To something generally regarded as NSFW – the effects of aging and surgery on female body parts. The other grad student and I were sharing horrified glances, because neither one of us wanted to hear anything about the personal areas of our advisors. It was so awkward, especially since our advisors felt no shame.

  381. Jessica*

    I was on a camping trip with my department (not that weird – we work in the outdoors). We were playing a game around the campfire where a random fact was read out, the group guessed who it was, and the correct employee revealed themselves. Well, my fact was read out and guessed, and I raised my hand to reveal myself, which included my empty wine cup. The cup was not empty. The wine was red.

  382. Anancy*

    I cannot wait to read these comments and this book! Oh I still groan at my example. Me (child free) said to two coworkers (single moms) that “Dogs are harder than kids.” I was trying to say that it was harder to see Bryce Canyon with dogs because they aren’t permitted there and I completely flubbed it. Ugh.

  383. Ruth (UK)*

    While I have too many awkward situations than I can keep track of, I do have one that springs to mind:

    Around 2012, I had just finished uni and had started my first full-time job – in a fast food place. We had these overhead menu boards that rotated – they showed breakfast menu on one side and lunch on the other. So usually we spun them at 10:30 when we changed to lunch menu.

    One morning, the turned one of them halfway and told people to leave it as the light inside the screen needed changing. It was one of those long tube-shaped lights. Somehow, I missed her telling anyone this, and just noticed the screen turned halfway. So I knocked it (not too gently either) back to normal, at which point the tube-light flew out of it, and smashed. Broken glass went all over the place, including into the fry machine (so we couldn’t serve fries at all that morning!). And changeover from breakfast to lunch is usually hectic even without this.

    I full-on thought I was going to be fired (I’d only been there a couple weeks when this happened). Luckily, they didn’t fire, or even discipline me in any way. However, I did get teased about it for the next almost-2-years that I worked there. That manager always used to say things like, “can someone spin the menu boards – not Ruth – we know what happens when we let her near them” even a year after the fact…

    1. Ruth (UK)*

      ps. putting my email in seems to have caused this to include an avatar that I only ever used in a (no longer in use as of many years ago) wordpress blog??

  384. Chalupa Batman*

    This sounds awesome, thanks for the giveaway!

    Let’s see…I’m chronically awkward, but usually more in my head than in real life. Every now and then I do unplug my filter, though. Not too long ago, I had a run in with an administrator at a local school. Still steaming, I asked a coworker who used to work there what she thought of said administrator. Turns out she thought he was just wooonnnnderful. She went on and on about how great he was, then (naturally) asked why I asked. So, because I’m extra awkward when I’m having Feelings, I just told her. She proceeded to enthusiastically take his side. At that point I realized how ill advised the whole conversation was (what did I EXPECT her to say?). Instead of saying *anything* to diffuse the weirdness, I said something to the effect of “hm, that’s interesting,” then turned around until she went away.

  385. Em.*

    Well, I found out my new boss kept kosher *after* he asked me to run out to get him a sandwich before his next call and I brought back ham and cheese. I was mortified when he told me, but he was very kind about it. That was three years ago and I still think about it.

    1. Radius20*

      I don’t know why you would be mortified since he didn’t tell you he was kosher. I would be mad that he didn’t mention that fact beforehand. For example, I despise mayonnaise. I would never ask anyone to pick me up a sandwich without mentioning that fact first!

  386. Gingervitis*

    My office has an annual Thanksgiving potluck, which everyone looks forward to for the entire year. I was gearing up to stuff my face with delicious deep-fried turkey and mashed potatoes, when our receptionist sidles up to me. She says “I am just going to ask you this, feel free to tell me that it is none of my business.” Obviously, nothing good ever follows a statement like that. I am not sure how I responded, but I am fairly sure it was some type of noncommittal gesture. She goes on, in a very audible whisper and in front of the entire staff: “Are you expecting again?”. I was not, and had given birth to my eldest daughter over a year prior – which is what I told her. So far, not the most fun moment, but survivable – until her rejoinder. “Oh – I guess you just look fat today then.” Needless to say, that was the end of the Thanksgiving lunch for me. She never did apologize, but she did come to my office and offer me a cookie the next day. I still don’t know whether that was tongue-in-cheek.

  387. Jortina*

    I used to be a summer program counselor for high school students. I once walked across a cafeteria full of about 60 students who I had just met with my dress tucked in my underwear. To add insult to injury, the coworker that pointed this out to me had just been hired for a full time job with the program that I had also interviewed for and was my dream job.

  389. I'll come up with a clever name later.*

    I just remembered my most awkward, awful moment….buried so deep I forgot about it. I used to work in retail as a store manager. I am large busted – not because of weight, but because big breasts run rampant through my family. I had recently discovered that Victoria Secret had a catalog and actually had some bras that could possibly fit me. I’m sure most women will understand when I say ordering a bra from a catalog is risky because the fit might not be right but I had never had a matching bra and panty set and was willing to take the risk. Bra comes in the mail, it fits, I wear it to work. The bra had a front clasp and it was made of plastic. So there I am at work and about to start a floor move (re-setting the store layout) when a woman and her husband come in to shop. It was a woman’s clothing shop so he looked out of place and uncomfortable. She pops into the fitting room and has him wandering through the store fetching things. He comes over to me to ask me a question. My hands are stretched over my head holding something, but I am facing him. Suddenly there is an audible snap from beneath my sweater and my breasts suddenly swing apart, bouncing in opposite outward direction. He witnesses this happen, stares for a moment at my chest, shoots his eyes back to my face with his mouth open. My face is so red it’s actually turning purple. I can’t move. He makes this weird “Uhhhhh” noise, turns on his heel and heads to the fitting room. Seconds later I hear his wife giggling and then they left, her kind of laughing at him but never looking at me. It was seriously awful. I haven’t had matching underwear since. My bras now are sturdy, reliable, beige things that hold up under the pressure. LOL!

    1. I'll come up with a clever name later.*

      I make the comment about the weight and my breasts only because Victoria Secret didn”t cater to the larger ladies at the time (not sure if they do now) and I was young and more fit than I am these days. I know that other stores carry matching underwear in my size, but this incident scarred me.

      1. Megan*

        The front-clasp bras are dangerous! I had one unhook on me when I was 15 at a church activity. Luckily, I was sitting down at the time and I don’t think anyone noticed, but I had to hurry to the bathroom with my arms folded across my chest to fix it, and I was sure everyone knew what had happened and was staring at me.

    2. Amber Rose*

      Once upon a time, a kind person quietly pulled me aside to let me know my shirt was inside out. In the process of fixing it, I discovered that I’d also been wearing my bra backwards all day.

      I wonder how many people noticed the weird bulge from the cups at my back. I was younger and less busty then but still.

  390. Murphy*

    I submitted an earlier one, but I just remembered this. I feel worse about this one, but I didn’t realize what I had done until afterward, so my awkwardness was all me.

    In short, I was kind of that ugly American speaking loudly to someone for whom English was not their first language. He was a customer and he kept asking me to repeat myself, so I just started getting louder. He just started looking at his daughter when he didn’t understand what I said and she would repeat it. I thought it was weird until I considered it later.

    In my defense: a) He was an older gentleman and I thought he, like my father, might be hard of hearing so I automatically raised my voice b) he had only a slight accent and his English was good so it didn’t occur to me that maybe I should have slowed down or enunciated (I’m guilty of mumbling and/or taking too fast sometimes.) It was an accident, but I felt like such an ass.

  391. Dame Judi Brunch*

    At Oldjob, HR lady called a small group into her office to show us something special.
    That something was an enormous vibrator. That she named after a famous athlete.
    It was an interesting day!

  392. Mrs. Picky Pincher*

    I’ve got a good one.

    It was my first job out of college and I was one of two women working at a male-dominated oil company. I was essentially a glorified secretary. It was my job to greet coworkers, smile, and help them with whatever they needed.

    Well.

    One coworker took this as an invitation. One day he came to my desk, dropped a slip of paper into my hand and whispered, “Show me around your town sometime.” I was confused until I looked at the paper, which had his name and phone number on it. Mind you, this is a man in his mid-fifties asking out a 21-year-old woman (at work, who’s never expressed any interest).

    I made it extra awkward by saying, “Ew, no,” and throwing his number in the trash.

    It was super awkward to deal with him after that, but I thankfully got a less demeaning job a few weeks later!

  393. Hillary*

    A tradition at one of my old jobs was to gather everyone around in a big circle and have new employees introduce themselves. On one colleague’s first day, she’s standing in the middle of the circle, talking about her background, and suddenly her eyes roll back in her head and she slumps to the ground. She’s wearing a flowing skirt, and it comes up to reveal her thong underwear. The CEO and sales manager (both men) rush over, pull her skirt down, and she starts to come to. Apparently she has a fainting disorder and this just happens to her sometimes without warning.

    Luckily, she’s a very confident person and has not only lived it down, but she’s managed to carve out a leadership position there. She’s been there 8 years and counting!

  395. Amber*

    Oh man, *most* awkward …

    There was the time that one of the department managers asked what a glory hole was in a meeting. I’ve been thinking for a while now, and this one tops the list.

    1. Boy oh boy*

      I had to explain, awkwardly, ‘pot brownie’ to someone senior at work but yours is so so so so much worse.

  396. Professor Ma'am*

    Such a little thing but it’s still hella awkward. You know how sometimes you just choke on air/spit for no reason and go into an intense coughing fit where you can’t talk and your eyes water and it lasts a good 5 minutes? I’m a college professor and I’ve had this happen during lecture. For the first few seconds your students think you’re dying, but you can’t talk to tell them nope, just choked on air. A little bit later they realize you aren’t dying but then it’s been a long enough silence (minus your coughing) that things get super weird. Eventually you can squeak out an “I’ll be right back” and you go out into the hallway and continue to sound like you’re dying. Once it’s done you get to go back to class and keep teaching with your now weak voice…

  397. Lauren S.*

    Okay so I was at a company event with my boss, coworker, and coworkers pregnant wife. We were talking about the pregnancy, how shes feeling, etc. and the subject of baby names came up. Coworker mentioned that they had picked a name and we asked if he could share it. He told us and our boss immediately started giggling and saying “you’re kidding–that’t not the name.” (in her defense, coworker does have a habit of joking around). They went back and forth for a bit with her laughing about what a ridiculous name it was and him insisting that yes, that it what they were going to name their child, before she finally got the hint. I just stood in between them and inwardly cringed.

  398. Desdemona*

    Oh man. I remember once, a few years back, we had just hired a new VP who we poached from a really prestigious institution. After an all-office meeting, shortly after he started, I had gone back to my desk and started snacking on some popcorn. Little did I know he was planning to come by my desk to thank me for putting together a report for him and the board. JUST as he appears at my cubicle (out of nowhere), a piece of kernel gets caught in my throat. I still have no idea what he said to me (or what I said back to him) because I spent the whole conversation trying furiously not to choke and not wanting to cough like a madman all over him and my boss, who was next to him. He must have wondered why I was barely speaking and why my face was getting red and eyes were watering, though.

    Luckily, I don’t think he remembers this. But I do!

  399. General Ginger*

    I still cringe about this one on occasion, though the co-worker in question doesn’t even work at the company anymore. Coworker had left some sensitive paperwork out on her desk, realized it halfway on her commute home, and called me at the office to ask if I could please grab it and put it in her lockable drawer for her. I assured her I would, and then on autopilot, finished up with “all right, love you, bye”. I immediately realized what I said, and wanted to sink into the floor, but my coworker laughed, so I apologized and awkwardly tried to laugh it off as well. Then I went to hang up the second time — and said it AGAIN.

  400. romana*

    I’d put this in the wrong place originally – so here goes!
    I was working with a male coworker and he’d pulled two foam spacers off a motherboard. When I was cleaning up the floor around my desk (I was kneeling) I looked up at him and said “Do you want these two soft squishy things?” I was not holding the spacers – still not sure what they’re really called.

    Same job, different incident: I’d decided the elevator was a good place to adjust my bra. The doors opened before I was finished. My boss was standing on the other side. He forgot where he was going.

    Same job; I was finishing up an install for a professor and I went to leave but suddenly couldn’t work the door handle. He came up behind me and politely showed me how it worked, as I was leaving I tripped over two plastic chemical buckets that were in the hallway.

    I still work there, believe it or not.

  401. The 5th Groover*

    I work for a company that has a…very unique corporate culture. Everything has to be 100% positive all of the time. They’re big on “relationships,” “connections,” and “vulnerability.” (It’s exhausting.) Whenever opportunities for advancement open up, people lose their minds trying to seem like the most empathetic, open, vulnerable, positive, passionate person in existence.
    Of course, we have a lot of team building meetings to help further all of the above.
    It wasn’t too long ago that we witnessed what it was like when those two things intersect: a handful of promotions became available and right in the middle of a couple weeks of interviews, there was an early weekend morning, rah-rah, team-building meeting.
    People were falling all over themselves at the meeting in an attempt to stand out. They were “humbly” sharing stories of difficult interactions they turned around at the last minute, how they shared valuable knowledge they’d “learned on the fly” with other team members and created a “better experience for both internal and external customers,” but the worst (BEST) thing that happened was this.

    There exists, at our company (Teapots, Inc.), a Teapot Credo. It’s a few paragraphs of feel-good buzzwords that they print on framed posters or gift us on expensive paper. It’s important to know this exists for the purpose of this story.

    So, we are at the meeting listening to person after person describe how much they love their job and the many ways they express their love for their job, both on and off the clock, when this dude stands up and addresses the room. He stands up.

    “Hey,” he says, looking around the room at us, “have any of you memorized the Teapot Credo?” (Absolute silence.) “I have. Sometimes I recite it in my car on my way to work. It’s pretty inspiring. I suggest you try it.”

    He sits back down. The rest of us exchange glances that range from “I…doubt the veracity of that statement.” to “I swear to god if another person makes this meeting any longer by talking, I will set myself on fire.”

    The meeting lasts about half an hour more. At the end, they always ask if anyone has any questions and everyone tries to psychically will everyone else to not ask any questions so we can go home. The same dude stands up. “Hey. Would it be alright with you all if I recited the Teapot Credo right now?”

    I silently, internally groan. One of the managers even checks his watch but reluctantly gives him the floor. The dude assumes a meditative pose and begins to recite. He gets one line in and pauses. We are all watching him. He is silent. Three seconds. Five. Is this whole speech going to be this dramatic? Or are we watching him crash and burn right here? I’m overcome with the urge to laugh but the room has become deadly silent, every eye fixed on him. He licks his lips. Surely…surely he wouldn’t have claimed to have memorized the Teapot Credo…surely he wouldn’t have stopped a meeting-twice!-to let us know he knows the Teapot Credo…and then ask for the opportunity to prove he knows it…when he doesn’t…actually…know it?!

    His face is turning from pink to red. “I forgot it.” He mumbles and sits back down. We still couldn’t laugh because that is Not Positive. And deep down, everybody wanted one of the promotions. Even if they didn’t try to prove it out loud at the meeting.

    He did not get one of the promotions. (Neither did I.)

  402. Ginger F*

    I had to have dinner with the head of our agency during a conference. He was a total self-absorbed blowhard and all I wanted to do was get done so I could go back to my room to get some work done. Well, as we’re leaving the restaurant I thought he was bending over to tie a shoelace, but he was actually passing out. He slumped to the floor. Luckily there was a doctor in the house, and the manager called the paramedics. They took a look at him and decided it was probably some new medication he was taking combined with the three drinks he had during dinner that brought him down (why you would drink like that while starting a new med is beyond me). They decided not to take him to the ER. Then one of the paramedics said to me, “Are you going to be with him all night?” – thinking we were a couple and I’d keep an eye on him. I’m pretty sure I looked visibly repulsed and said, “Uhhh, nooooo.”

    I did text him a couple times throughout the night to make sure he was still alive and that was weird, too.

  403. AJ*

    False cognates are dangerous! For instance, the Italian ‘eccitata’ sounds like it ought to mean excited. It… does. It also has sexual connotations. So a friend in Venice chattering enthusiastically to a gondolier and a large group of people about how excited and aroused she was… was a moment.

  404. Chiroxophia*

    This happened when I was a couple months into a new job. My boss had a small office set up so there was a desk with a computer he sat facing and a desk directly behind him he could reach by turning his chair. The behind-desk was where he kept papers in various stacks that he would only file when the piles became really unmanageable.

    I was in his office looking at something on the computer over his shoulder and for some reason had carried in my just-filled water bottle without the top and placed it on the desk covered with paper. Of course, I knocked it over and it completely ruined lots of papers.

    His stack organization was not the best and he had no idea what was there or how important it was. I was mortified and apologizing and trying to save what papers I could, but he was really gracious and just said “well, it was probably time to recycle all of that anyhow.”

    This happened about 10 years ago and I have been permanently embarrassed about it. I actually just reminded him of it last week because I was in his office and it is so neat because he has tried to go as paper-free as possible. It was the first time it has come up after the initial incident and he didn’t even remember it happening.

  405. VermiciousKnit*

    The most awkward moment I ever had at work was when I was working an admin job at a retail store as a second PT job. One night in the back-to-school shopping weeks, a family that universally had incredibly poor hygiene came to the fitting room where I was working (if there was no attendant the admin staff had to sit there instead of the office). They had a son in his early teens who had a giant pile of clothes to try on and a few pairs of shoes.

    A few minutes later, and incredibly foul smell wafted into the fitting room lobby. Thinking a coworker had tooted, I giggled and sprayed some lysol, but the smell got worse. And worse. Said coworker began to tear up and then gag and then left to go do something else. I could not leave without backup, so I had to sit there, gagging myself and mouth-breathing as the stench grew overwhelming. Everyone else in the fitting rooms began coughing and complaining and within a few minutes all of them had bolted. It was clear from the direction that it was this kid changing clothes, and it was beyond stinky feet, it smelled like rotting flesh. I called the grocery dock to bring the fans and deodorizer they use to combat rotting food stink; but it didn’t do anything.

    I have never, ever, ever had a more awkward and sad moment than trying to pretend like I wasn’t dying in front of that kid’s family and smiling and taking the armloads of clothes he decided against when he left. We had to immediately discard all of them. The smell lingered to the point of customers complaining for days; eventually the store had to cut out and replace the carpet in the stall where the kid had changed to get rid of what must have been rotting skin on his feet. I felt terrible for him and for everyone.

  406. Business Cat*

    I’ve got two, one that was personal and one that I merely experienced secondhand.

    1) Some time ago when I worked for a local boutique, I helped my dad pick out a set of jewelry for his Valentine’s gift to my mom. True to form, she didn’t care for the jewelry, told me it “looks like something an Avon lady would wear” and proceeded to return it to the boutique *while I was working*. My (busybody) coworker looked at me knowingly and whispered “I didn’t think she would like that, but I didn’t want to say anything…” Mortified, I had to follow my mom around the store to help her pick out some replacement jewelry with my coworker in tow trying to be “helpful.”

    2) This one is a little more…heinous? Some coworkers and I were waiting on another coworker to arrive to begin a training session. He finally arrived, looking pretty down about something. We asked him what happened, and he let us know a consultant who had worked on our facility had just passed away from a heart attack. At that time, our director walked into the meeting, and the coworker asked him if he’d heard about the consultant’s death. What follows was one of the most secondhand-mortifying work moments of my life:
    Coworker: “Did you hear about Consultant? He just died…”
    Director: “From the chemicals?” (he refinished our floors)
    Coworker: “No, man, from a heart attack.”
    Director: (Pause) “So you killed him!”
    He laughed and sat down at the conference table. My coworker’s jaw dropped and we just stared at each other. The director didn’t say anything else and continued the meeting as if nothing completely bizarre had just happened.

  407. LauraMiss*

    I work as a theme park photographer, typically taking photos of guests with characters. One day we had a big group squeezing into out little bitty room, and one of those guests was on a massive rented electric scooter. The standard procedure for the attendant is to ask whether that person will be parking and standing up or remaining in the chair. So coworker asks. The guests looks at her incredulously and goes, “Really?” Turns out coworker had was running on autopilot – the guest’s legs ended at the thigh. She felt terrible about it after, poor woman.

  408. Umvue*

    Oh my god I want to read this book. Preferably on the bus, so I can create my own embarrassing moments by snort-laughing at the stories.

    My favorite awkwardness: Once when traveling for work, I was the first person from my team to arrive at a meeting, so I had to introduce myself to the client, and I got my own name wrong. For some reason I blurted out my maiden name instead of my married name, which I’d had by that point for ten years. Of course, because it was a confidential meeting with a restricted guest list, I had to correct the record. We talk a lot about classy ways to correct other people who screw your name up, but unfortunately there is no classy way to correct yourself.

  409. Oh so anon for this one*

    Our facility had a high-level visitor from the US and were asked to prepare him a presentation on our facility and ourselves as managers. Several of the managers added a note about their love of classic cars and/or motorbikes to their slides, and Wakeen asked us as a group what he could put as a hobby. Fergus suggested Dolphin Polishing, the group laughed (which both Wakeen and I assumed was due to the absurdity of the suggestion), and the discussion moved on.
    VIP duly arrived and was shown the presentation, in which it turned out that Wakeen had included Dolphin Polishing as a hobby at the bottom of his slide. Room went oddly silent, but VIP didn’t pay much attention to it which it turned out was just as well.
    Once VIP was gone, Fergus confessed he was using Dolphin Polishing as a euphemism for a man… umm… stroking himself and had assumed Wakeen knew that. It turned out most of the team had indeed understood the euphemism but Wakeen had really, really not. (For the record, no, neither had I). I have never seen anyone blush as deeply as Wakeen did.

  410. Julie*

    I was visiting a different office building with a co-worker and it had a rotating door that was huge- only 2 compartments, obviously designed for more than one person. Shortly after that I went to a different office building with a co-worker and followed them into the rotating door. This one was not designed for two people. It was several awkward seconds of basically hugging him and stepping on his heels. Afterward I stuttered out an explanation, but luckily he laughed about it.
    My second one was the first time going out for lunch with a vendor, where I was already feeling a bit uncomfortable and on edge. We got a shrimp dish which had tails still attached, but not cooked or fried or anything. Technically edible, but not intended to be eaten. I got freaked out and just took the whole thing and put it in my mouth and ate all of it. Spent the rest of the meal trying to pick tail out of my teeth while watching everyone else pull the tails off and discard them. I don’t know if anyone else noticed.

  411. Belana Torres*

    My first job out of college, and our department had a new director starting. My manager asked me to give him the tour of the building. I think my manager had a meeting and he was always trying to find ways to get me to come out of my shell a bit (I was still really quiet and shy at work).
    It was the lunch hour, so a lot of people were in the break room, so I lead him there for more introductions. Our break room was really nice, with lots of seating, a full kitchen, and large plate glass windows. On the way out of the break room, I was walking a bit ahead and didn’t notice that he failed to see there was a window next to the doorway. He walked straight into the glass window… full force. He yelled, grabbed his nose, which immediately started bleeding. My heart leapt out of me, as I quickly grabbed WAY too many napkins and started stuffing them into his face. It’s a bit of a blur. And it happened in front of most of the office, since it was the lunch hour. I felt horrible, and so embarrassed for him and me.
    Luckily, the director laughed it off, and his nose didn’t suffer any permanent damage. After awhile it blew over, and someone put stickers on the glass so it wouldn’t happen again. However it didn’t quite help me come out of my shell. :)

  412. C'est Moi*

    This is more of a sad cringe than a funny cringe. At a previous job, my boss was partially deaf and wore hearing aids in both ears. I often had to repeat myself when speaking to him, but this was perfectly fine with me since I tried to be sensitive to his disability. One time my coworker, who sits next to me, was out of office, and my boss’s computer broke, so he decided to sit in my coworker’s desk while she was gone. I was trying to get my boss’s attention to ask him about something, so I started calling his name like “Hey John. John?”

    At the same time, another coworker IM’d me something funny, so I started laughing, but it was just as my boss had finally heard me and turned his head towards me. Basically it looked like I was laughing at him for not hearing me calling him multiple times. I was MORTIFIED and didn’t know what to do or say! I just froze and wished that the ground would open up and swallow me into the deepest depths of hell!!!

    I hate myself for not thinking of something to say to him in that moment, and for possibly causing him to feel bad about himself or his disability for even one second. SO AWKWARD and still makes me cringe to this day… :(

  413. Megan*

    I can’t bear to think about all my awful embarrassing moments, so I’ll share one about a couple coworkers. One of my coworkers, Jane, decided she wanted to start doing bodybuilding competitions, so she started a pretty extreme diet and exercise program, and over the course of a few months, lost about 20 pounds, so a pretty substantial amount, but she was thin enough before that she didn’t look that much different to me. She was talking about her diet/exercise program to three or four of us one day, and Fergus came over from the next row of cubes to join the conversation, and said, “You look so much better – you look like a totally different person.” There was a moment of stunned silence, and I tried to smooth things over by telling Jane I thought she looked good before too and Fergus just sort of walked back to his cube.

  414. Runaway*

    I work for a large-ish consulting firm doing back-office operational support. At the time of my cringe-worthy moment, I had been there a few years, and I think had a fairly good professional reputation. On this particular day, I was talking with a client’s contracting officer at a large municipal organization – a very nice man with maybe a Vietnamese or Laotian accent. I can’t remember the exact spelling of his name (we had exchanged emails previously), but to my ear it sounded like he pronounced it “Long Dong.” I realize there was probably a different tonal inflection in his native language, but I couldn’t hear it.

    So, yeah… I get off the phone with him and pretty much immediately start joking with my female coworkers about this gentleman’s name, which would be bad enough by itself. But what made me wish the ground would swallow me whole was when I looked up and saw one of our (male) production division heads standing in front of my cubicle. Our cubicles had these horrible half-walls, so there was no pretending I hadn’t said it. He was pretty reasonable about it, and just said something along the lines of “Okay that’s enough of that” and then launched into whatever question he’d come to ask me, but I thought my face was going to burst into flames of shame.

    The good news is, I’m still at the same company 12+ years later, and have had a few promotions. The division head never brought it up again (and hopefully has forgotten), and we’re on friendly, professional terms. Oh – and he’s now the company CEO. I still cringe thinking about that moment though. Horrifying on so many levels.

  415. Kitty*

    So in my family, we were not creative with naming our grandmothers. I was lucky enough when i was younger to have two grandmothers, as well as two great-grandmothers. Well three of them were called Nan. So we needed a way to differentiate between them. One of them was a gardener and always gave us fruits and vegetables when we visited her. So to mine and my siblings younger minds, calling her “Nanny Potato” made sense (I was four, eldest sibling was 10). Nan LOVED it- she had an awesome nickname- apparently not many grandmothers got given nicknames. It became a thing in our family and our cousins started calling her by that as well. My Nan passed away about 10 years ago.

    Cut to Old Job one day when we were discussing family traditions and I mentioned something that Nan Potato used to do- in my head it is her name, the same way people call each other by their first names. I didn’t say “my grandmother” but “Nan Potato”. Well I have never seen people react so strongly to a name before. Countless jokes were made about it, comments were made about the level of intelligence of the people who came up with it, as well as dissing a person who would accept being named after a vegetable. Well I was highly offended that they were dissing my Nanny Potato, as well as the fact that it was me and my siblings who came up with it. Now i am awkward and not great at confrontation or asserting myself. So after a few minutes, where i was silently fuming I just looked the ring leader in the eye and said “You know she’s dead right? Is there anything else insulting you would like to say about her memory?”. Dead silence. I’m talking crickets people. I have never seen people’t faces freeze before- that is what happened. I have never seen people exit the lunch room so quickly- some left with half eaten food.

    Awkward. Some of them avoided eye contact with me for a good few weeks.

  416. zora*

    omg, I must have blocked this out, because I JUST remembered mine!!!

    I was working on a political campaign, so in other words, months and months of sleep deprivation and not eating enough. We found out one of our volunteers was a massage therapist, so we convinced her to come in and give 15 minute massages to the staff a couple of times, instead of just making phone calls. It was so sweet and everyone was excited. But, of course, my day got super crazy, and I was running late for my 15 minute time slot, and had ended up skipping lunch, and I had a really nasty knot in my back from sitting in bad chairs. So, I asked her to really work on that knot with lots of pressure because it was driving me crazy. Not a good idea when I’d had multiple cups of coffee and not a bite to eat all day!

    I totally blacked out, and tipped the whole massage chair and myself on to the floor, the massage therapist couldn’t catch me. So, it went crashing to the floor with a huge BOOM, and I come to with the entire staff, including the Campaign Manager all sticking their heads in the door saying “What Happened???” You really really do not want to be the one to bring a major political campaign to a screeching halt because you got a massage.

  417. Shark Lady*

    About 2 years ago, when I was fairly new in my department, my coworker and I were waiting for our boss to bring over the mail for our midafternoon mail drop. He was running a bit late and finally brought it over, saying “Guys, if its 2:30 and there’s no mail, come remind me. Who do you think brings the mail, anyway?”
    Like the smart aleck I am, I respond “Oh I dunno, the mail fairy?” to which my coworker goes “Do you mean the m-a-i-l fairy or the m-a-l-e fairy?” I turn bright red and want to disappear under my desk.
    My boss, who is a fairly small man, is red and barely containing his laughter. He finally manages to look at us and say, “I am very secure in my masculinity, THANK YOU.” before leaving.
    He is no longer my boss, but we are, thankfully, still on very good terms.

  418. LitS*

    Early in our working relationship, a male co-worker/friend from the midwest, proud of some DIY construction he’d done at home over the weekend, walked into our all female shared office and asked, “Hey, you wanna see pictures of my deck?” It didn’t sound like he said “deck.” We’ve been laughing about that one for years.

  419. peachykeen*

    I’d say I can think of two off the top of my head:
    (I work in a public library)

    — That time a patron came up to a fellow librarian and loudly announced they had hives on their scrotum and wanted medical advice. The entire library heard. I scuttled away to laugh hysterically in private.

    — Or the time I got on the elevator to go one floor down with a patron and that patron proceeded to get on one knee and propose marriage to me. He was serious. I was 6 months pregnant. We had never spoken before this elevator ride.

    Yeah. Good times.

  420. GiantPanda*

    Holiday teammeeting. Relaxed atmosphere, people joking around, breakfast and drinks.
    My coworkers made me laugh at exactly the wrong moment. I snorted and spit out a mouthful of orange juice all over the table.

  421. TiffanyAching*

    I worked in my college’s library when I was a student. My first semester there, around finals, I was working the last shift before winter break with a senior who had worked in the library for a few years, Andy. While our supervisor was out in the stacks, a student walked in carrying a fishbowl — with a fish in it. The student puts the fishbowl on the circulation desk and says they heard the library takes fish during the winter break (all the dorms close, so you didn’t want to leave any fish/plants there for the break, but the library was open for most of the break).

    I hadn’t heard about this policy, but turned to Andy, figuring that he’d know, as he had worked there for 4 years compared to my 1 semester. Andy accepts the fish, doesn’t take down the student’s name or information. Later, Andy goes off to do something, and our supervisor comes back. She sees the fish, is very confused, and I awkwardly explain about Andy accepting the fish from the student.

    The next semester training for new employees included the statement, “The library does not take fish.”

      1. Jemima Bond*

        Not work related but I have to add the two rules I have been forced by circumstances to lay down to my boyfriend:
        1) No treacle on the ironing board
        2) No dead badgers in the freezer

        He’s a prince amongst men but has some little idiosyncrasies.

  422. Not me*

    I worked for a company for about 6 months, thinking this well dressed, middle aged man I’d see around was our CFO. I was thrilled that he knew who I was (it’s a huge company) and would regularly chat with him, thinking I was gaining important career points.

    At the company-wide annual meeting the CFO was introduced to speak. It was not this guy. This guy was a middle manager in accounting. Not C suite.

    Oops.

  423. D.W.*

    During an internship, part of my job was coordinating with foreign embassies and legislative staff via phone and email. Well, I made a phone call to someone (can’t remember who), but was directed to their voicemail, and instead of leaving a message re: why I called; I said a prayer. That’s right. A full blown, “Dear Jesus, thank you for…”.

    To this day I don’t know where my mind wandered between listening to the voicemail box message and the beep to leave my own message. But I said a prayer and ended it with “amen” followed by an “O-m-g, did I just pray?!” I never received a call back from that person. So embarrassing!

  424. ThrowawayFakeName*

    #1: I’m in a shared office where we normally keep the door closed for noise, but expect interruptions from students. Once, when I was in the bathroom and heard a knock on the door, I went on the wrong autopilot and responded, “Come in!” Luckily, my boss did not take me up on my offer, but she and a nearby student were laughing hysterically when I came out.

    #2: At our university, student clubs often hold fundraisers at local restaurants that donate a certain percentage from the proceeds to the club. Our older, British admin wanted to publicize this and forwarded the flyer with no preamble, only this sentence: “If you are thinking of eating out then perhaps you will consider BJs.”

  425. Slartibartfast*

    My boss was a short, balding man with a shaved head going through a divorce, so he was undterstandably blue. It was a sad situation where they were both good people, but wanted different and irreconcilable things. He was talking about life and said something like “I’m short, bald and divorced, I’m never going to find someone”. I said “If it makes you feel better, I often forget you’re bald.”

    Awkward silence.

    Then he smiles genuinely and said “Thanks! I do feel better!”

  426. I Could Have Died*

    The most awkward time at work by far for me was over fifteen years ago when I worked for a major international company based in the US. I was working in a male-dominated field and as one of very few female employees in this company, I felt out of place and a tad uncomfortable to start with. Our employers regularly required us to travel abroad for company training. I joined some European and American colleagues (all men) in one of the Australian locations, and at the end of the training we all gathered for a farewell dinner hosted by our local colleagues. I was keeping to myself & quietly eating my meal, listening to my male colleagues discussing the national animals of their respective countries. The Swedish fellow mentions that they shoot and eat their national animal, the Cariboo. One of the Americans say that shooting the Bald Eagle is against the law. Without thinking, I blurted, “In Canada, we don’t eat our National animal. Beaver.”

    Immediately the European. the Americans, and the hosts burst out laughing, and the European leans over with lecherous eyes, and tells me, “Well, maybe YOU don’t!”

    Took me a full minute to clue in to what I had (totally unintentionally) said. I must have turned ten shades of red. Thank goodness the restaurant was pretty dark. The next day, I couldn’t look any of them in the eye. At the time, I wished the earth would swallow me whole. The story followed me back to Canada, too, so I had to live that down for a few months until the next embarrassing event came along. I find it funny now, though.

  427. Annon for this*

    With out reveling too much to identify myself, my boss had me to her home and proceeded to lift a blanket and show me her lipo incisions. No panties yes wee wee pads.

  428. Epsilon Delta*

    I was doing roll call at a team meeting once. I went around the table introducing everyone by name, got to my boss and COULD. NOT. REMEMBER. his name. So I just sat there verbally fumbling “and uh, uhhhh……” until he rescued me after like three seconds.

    I had worked with him for 3 years.

  429. Lurker*

    Back when I was in grad school, a group of us had arranged to meet up and go out for the evening. A couple of the undergrads from my residence hall had expressed an interest in coming along, so I walked with them to the place where we were all meeting. They didn’t know anyone, so it was up to me to do introductions.

    I went through saying everyone’s name until I got to the last person, who was my regular study partner and probably the closest friend I had at grad school. I’d known her for years. For some reason my brain just went blank, and I could not for the life of me think of her name. I still knew exactly who she was, and I knew it was ridiculous that I couldn’t think of it, but it just refused to come.

    There was a longish pause while everyone wondered why I had stopped. They all figured it out at about the same time, and there was much laughter at my expense. My friend was about equal parts amused and outraged. I apologized profusely to her, but it was still a long time before she let me forget it.

  430. Claire*

    The year (way too recently) I confused the word ‘photogenic’ with ‘camera-shy’ and used them interchangeably. I would often bow out of photos by saying: ‘No I couldn’t possibly, I’m too photogenic!’. I still cringe about it.

  431. Megan Undercover*

    I called a co-worker the wrong name. He works in a different division, and we only see each other occasionally, but I knew his name at one point and had sort of started saying things like “hey you,” because I was too embarrassed to ask his name again. Then I had to introduce him and I took a guess. It was the wrong guess, and apparently I chose the name of a co-worker that he really doesn’t like. There wasn’t really a graceful way to apologize, so I apologized awkwardly.

    This isn’t a great story, but I would love to be entered in the book drawing, please.

  432. BravoMessenger*

    One from my retail days. Was a very new associate in the lingerie department of a major mid-level department store. One evening shift a customer asked for help in finding a bra…by whipping up her top to show me a very large purple bra…

  433. Professional Merchandiser*

    I have two: I was doing a reset at a K-Mart store and could not get a shelf loose so I went to customer service to ask for assistance from a male associate. They were paged and I went back to wait. In a couple of minutes a young man came up and I told him I needed the shelf out it was wedged too tightly. He got it out for me, and I thanked him. Thank goodness, because as soon as he left, the male associate who was sent to assist showed up!! I had put a customer to work. (Cringe!!)
    The other one; I was on a conference at 7:00 a.m. one morning. The leader was talking, and all of a sudden, we could hear…snoring!!! *6 is your friend when you are on a conference call. :-)

  434. Harper*

    I was working at a retail store that had decided to downsize significantly – part of what we later found out was an attempt to artificially make numbers look extra good before being acquired by another company. It was a specialist shop, and after a couple of years of begging them to hire someone who could properly support my section (and cover when I was on my day off/vacations) – and dealing with AWFUL new hires who were totally uninterested/unsuited and promptly left – I finally had a great employee I had spent 6 months training who was obviously going to be awesome. Just in time for me to leave on my scheduled vacation!

    You may be able to guess where this is going. The store manager, who was nice but incompetent, called me into his office, where the HR person was waiting, to tell me that there were going to be layoffs, and MY job was safe because I had so much experience, but that New Employee was on the list. He said that they would be speaking to him within a few minutes but they wanted to tell me first so I knew what was going on and was reassured that my own job wasn’t on the chopping block. And then he asked if I had any questions. Naturally, I said, “Well, if New Employee is gone… who will be covering the department when I leave on vacation?”

    Store Manager said, “Oh, we’ll be training some guys from other departments! I’m sure we’ve got plenty of time to do that before you go… When does your vacation start again?”

    The bug-eyed silence from both Store Manager and HR when I answered “Monday” was definitely the most awkward moment during my time there.

  435. KS*

    Madeleine Albright was coming to the university campus where I worked in a student life office. A few colleagues and I were reading some biographical information about Ms Albright and looking at her book, titled “Read My Pins: Stories from a Diplomat’s Jewel Box.” (Apparently she has quite a fascinating collection of pins and jewelry. Who knew?) I actually said something along these lines… As we admired the jewelry, I looked at the only man participating in this conversation and said “well, I never would have guessed. So, what’s in your jewel box, Frank?” The following moments of silence were what clued me into how awkward my words had been. Oops.
    I bet Madeleine Albright never went around asking men about their jewel boxes…

  436. Katriona*

    I worked briefly as a receptionist at a nursing home after college, and when family members took the residents out I was supposed to check whether they had signed the person out at the nurses station before I unlocked the door for them. I only had one shift per week so I didn’t really get a chance to memorize all the residents’ faces (and I have some trouble in that area anyway), and a few weeks in I saw a family about to leave with a white-haired woman in what looked like one of the nursing home’s wheelchairs, so I asked if they had signed her out.

    …Yeah, that woman wasn’t a resident. She had just borrowed the wheelchair to get around while she and her family visited someone else. Fortunately she took it in stride and everyone had a good laugh, but I was so mortified I was afraid to ask that question of anyone again. Best of all the lobby was filled with regular visitors at the time, so I didn’t live that one down for a while.

  437. Hey Nonnie*

    I had been working for a non-profit as a contractor: the first two months and change I was working full-time in their office, helping them prepare for their biggest annual event coming up in mid-December. After the event and some wrap-up, the office was closed for the holidays, and then afterward I was to continue on part-time from home.

    Post-holidays there was a series of emails discussing changes to the website that would be necessary because our education director “Jane” was no longer with us. I thought it was a little weird and sudden that she’d changed jobs with what seemed to be little to no notice, but whatever. The place was really dysfunctional and Jane was smart, practical, and nice, so I figured she was fleeing the toxic environment.

    It actually took several more DAYS of this email chain before someone finally referred to the fact that Jane had been killed in a car accident while visiting her parents for Christmas. My jaw was on the floor, because I liked Jane and she was one of maybe two sane people in that organization and this was a kick to the gut. And also because not a single person in the office thought it was worth telling me this directly. Including the CEO, who was directing the website and communications changes that would be needed due to this. There was no reason for me not to be included on the all-staff email that I presume went out, since I worked directly with Jane on a lot of things, and particularly close with her on the annual event stuff that the entire office had been living and breathing the previous two months. Or, you know, say something when you’re directly emailing me to remove Jane’s bio from the Staff page on the website. But the “she’s just the freelancer” attitude won out instead.

    —

    President/owner/everybody’s boss of a tiny, tiny start up hired a new sales guy and decided that the best way to welcome him was to have everyone eat lunch together in the office and each one of us would draw and share a line graph of our lives up to this point, which was to show all of the emotional highs AND LOWS in our lifetimes. After I picked up my jaw from the floor, I said in full hearing of everyone that I wasn’t comfortable sharing those details, that I keep my private life separate from my professional life, and I wouldn’t participate. President/boss tells me that’s fine, I don’t have to do anything I’m not comfortable with. Thinking that the issue is resolved, and knowing it’ll be a few minutes before everyone else is done drawing their graphs (which I couldn’t believe they were doing, but whatever, their choice), I turned back to my computer to get a couple quick bits of work done. President/boss walks up to me and says “You can put the work away, remember you need to create your line graph now.”

    I was speechless. We’d had our conversation TEN SECONDS AGO. I had refused. He had said okay. Did he have an absence seizure or something? Brain damage to his memory centers? Did he think I was somehow not serious?

    In the end I drew a straight line, and included the most basic, boring biographical data I could think of, and nothing else. I graduated high school. I went to college. I graduated college. I moved to [city]. I started working for Boss. Nothing that wasn’t obvious from my resume, and zero editorializing on how I felt about any of it.

    I got away with that, but also had to cringe through a lunch where my co-workers were crying, tears and all, about their recently deceased dad, among other things. WTF.

  438. C*

    I worked with someone who refused to speak to me unless it was absolutely necessary for 6 months because I reported said individual to a supervisor for watching bootleg movies on a work computer after I told her to stop & she continued to do it.

    And then the company’s contract ended & we had to interview to be re-hire for the new company (doing the same job) was shocked that I was not writing a recommendation for her.

  439. Fake Name*

    I was working IT for a retail company, covering multiple locations. HR guy was visiting one store, and as he walked out of the back office, he warmly greeted a team member he hadn’t yet met. 20 minutes later HR guy goes back into the back office, discovers his laptop is missing. That team member was in fact a stranger off the street that waltzed through the propped open door and stole his laptop. HR guy quite embarrassed about being so nice to person that was about to rob him.

  440. AMPG*

    I was on a business trip to an organization that was a frequent collaborator of ours, and I went out to dinner with the executive director and the board chair. The board chair was an older man from one of the countries where cheek kisses are customary, so when we shook hands he leaned in to do the double kiss. Unfortunately, we both leaned the same way (I’m pretty sure this was my fault) and ended up kissing on the lips. He essentially pretended it hadn’t happened, but I was mortified.

  441. Starkitten*

    Most awkward work moment: I, along with several other employees from a variety of field offices, had flown into my company’s west Texas office for a regional status meeting/training event. Those of us in the event had a “get to know each other” dinner the first night, where one young lady from the host office proceeded to tell us how she conceived her second child in a hotel room in Dallas (complete with details about sexual position used during conception). We’d all known each other for less than 12 hours are this point.

  442. Melissa*

    I worked in an open plan office for a research group. The lab manager was SO COMMITTED to everyone being quiet to cultivate a “good environment for thinking”. (If a conversation went on for more than 40 seconds, she would materialise and request we take it to a meeting room.)

    Anyway. One day the lab head was walking from the tea area to his desk, a walk that went the entire length of our area, and every second step… he farted. And because of the oppressive silence cultivated in the area, everyone looked up to see who would DARE make a noise, and so the entire research group just… watched this incredibly prestigious professor toot all the way back to his desk.

    While I still cringe from the awkwardness of the moment (I’m terribly anxious, and if I had been in his position I think I would have tried to resign), he was completely unphased. He just refused to acknowledge what happened, and everyone followed his lead because he was the boss.

  443. Foot/Mouth?*

    The mail department leaves packages outside the office doors where I work. One day a co-worker had a tiny, like 3 inch by 3inch box sitting there. I walked up and exclaimed, “Wow, you have a TINY package.”

  444. The Luidaeg*

    I’m saving most of these comments to read when I’m at work on Saturday (and anticipating a quiet morning) — but the one super-awkward thing that came to my mind was when I was in my early 20s, working in a law office. I had stayed after 5:00 to help someone and was in the middle of the work, when one of the managing partners stopped by my desk. And then very smoothly asked if I knew how he could get some weed.
    I tried to be smooth, but I remember being dumbfounded and stumbled through saying no, I really had no idea.
    Because I didn’t. I drank about 2 beers a week and never did anything else. What I should have done was say, “Oh yeah, ask so-and-so tomorrow or this other person because they smoke weed and can hook you up.” I still don’t know why he asked me — maybe because I was young and it was after most of the staff had left for the day? And maybe he didn’t think it was awkward, but I certainly did. And this conversation threw me for a loop — which is hard to do (especially after someone else I worked for told me all about the weekend he had, including the sex in the shower with a woman he picked up at a bar. I somehow rolled with that one and shut him down, but the “got any weed” question rattled me).

  445. Paper Librarian*

    I have a habit of accidentally using suggestive language in the middle of a conversation. One of the most retold examples of this was from when the library’s water fountain kept getting stuck. You would push the button and it wouldn’t release so the water would keep running. I ended up getting really good at hitting the machine in a way that the button would pop out again. I would tell people that you just have to bang it in a certain way. I am sure in retrospect people were already snickering at this. But nobody pointed it out, until once when I came back from fixing the drinking fountain, and feeling victorious I declared myself “The Bang Queen.” There was dead silence, then uproarious laughter. And it suddenly hit me the other implication of bang, and I am sure I turned bright red.

  446. PubServant*

    I ran in to an old manager on the escalator. After some mandatory small talk, he said, “Oh, I heard the good news, congrats—” (Being newly engaged, I lifted my hand to show off the ring…) “… on the promotion!” (that I had gotten two months ago…!)
    Cue a lot of literal head scratching, as if that’s what I was going for all along.
    It’s been six months; I’m not sure if he even knows that I’m getting married!

  447. Jade*

    We had a little tradition in my old office of sending a note to everyone if you heard extremely bad traffic reports for the way home. A colleague sent out a note that “there was a fertility on the Monash (freeway)” instead of a fatality. Awful for the poor person who passed away, but extremely awkward for those, including our CEO, who received that email!

  448. Perpetual Student*

    I spend so much time trying NOT to think about the embarrassing things I’ve done at work …

    Warning: bodily fluids ahoy

    One of my previous jobs involved fieldwork in fairly remote places (read: I wasn’t going to be anywhere near a drugstore or anything like it until the end of the day). I miscalculated the start of my period, and didn’t have much to improvise with, but did my best through the course of the work day while climbing up steep slopes, etc.

    It wasn’t until the rest of the crew and I were back at the work truck that I realized I had bled straight through my pants … they were camouflage, but not enough to disguise what had happened. This was, of course, after a full day of hiking AND CLIMBING directly in front of the coworker I had a crush on, and there was no doubt that my miniature reenactment of Carrie’s prom in my pants was all but right in his face. He’s a decent enough person that he never brought it up, but I was mortified on a level formerly reserved for middle school.

    1. Yikes!*

      Reminds me of a time I was on a plane a few rows behind a woman who had bled all over her skirt, and the bloody part was hanging over the edge of her aisle seat for the whole flight. I was mortified for her, but was too embarrassed to go over to her and mention it. Just didn’t know how. Thank god it was a short-ish flight.

  449. Oxford Coma*

    (Note that I am female, and was about 22 when I did this.)

    I was a newbie tech in the engineering department, and did not know that Tuesdays were tour group days for customers to get a limited viewing of our R&D area. I was profusely thanking a senior QC engineer for staying really late the night before to finish some cycle testing that I needed for a rollout. I ended the conversation by saying, in a sickly sweet voice, “Thanks, daddy” and turned around with a flourish to a horrified tour group.

    Then I had to explain to a dozen strangers that the man was, in fact, my actual father. From that point on, I referred to him by his first name only…except when I got laid off two years later and cried in the hallway, where he hugged me.

  450. Alex*

    I was an administrative assistant at an insurance company, responsible for answering phones, etc. Someone called looking for my boss, and my brain worked faster than my mouth. So when I meant to say, “he’s actually not here, may I take a message?” I instead combined and mismatched the phrase by blurting out : “I is here!” Luckily the man on the phone was friendly about it, but of course other staff were at the front desk and heard the whole thing. We got a good laugh at my goof!

  451. Peanut*

    Many years ago, early in my career, I had what I thought was a good working relationship with my supervisor. He would come over to my workstation periodically, we’d chat, he’d assign me new tasks, he’d walk off. He seemed very laid-back and hands-off, which was fine with me at the time, and I don’t think I ever got any feedback (negative or positive) from him, until That Day.

    On That Day, I went into his office to ask him something about work. I don’t remember what I must have said or done to set him off as the conversation continued, but suddenly he was yelling, “I hate talking to you about anything! I’m sick of going over to your cube and you just staring at your computer while I try to talk to you. You expect everyone to be perfect and that they not make any mistakes, and I can’t deal with it anymore!!!”

    Now, I’m sure his complaints were legitimate – and I knew that I did have a habit of continuing to work while he talked to me (I grew up in a different culture and thought this was how I was supposed to demonstrate hard work, by continuing to work unless a conversation required that I look at a piece of paper or it turned out to be a longer one) – but in my defense, what he said was the first time he had brought ANY of this up.

    That wasn’t even the awkward part.

    The awkward part was when, stunned and completely blindsided, I stammered out, “Ok. What can we do to fix this?” and he looked at me and, with finality, said, “Nothing,” and turned away to look at his computer.

    I quit after that. He got in trouble with his own supervisor (because my husband at the time continued to work for the same company and told me), but even now, though I go out of my way to pre-emptively check in with my supervisors beginning at 3 months on the job to ask how I’m doing and what I can do to improve, I refuse to work long for anyone who has NO feedback for me.

  452. Hella Anon*

    There’s a chance this will identify me. It was that bad. Ok . . .

    I had bedbugs. It was really bad. I worked at a lower salary + doing good sort of company and could barely afford things. So I lived in the cheapest kind of housing I could find and it had a bad bedbug problem. I put up with it for a while, then looked for another place to live. It was so bad, I had bites on my face and couldn’t sleep at night. I had some sort of reaction to the bites. It caused anxiety and insomnia.

    Finally, I found a place I could afford and moved. This involved throwing away all of my stuff or treating it for bedbugs. And I couldn’t afford professional treatments. Just diy ones. So I put some diatomaceous earth in my car in case they had spread there, left it for a couple of days, and then vacuumed and had it cleaned.

    But what about my office? I panicked. I didn’t want anyone to know I had a bedbug problem. It was the kind of place where a lot of my co-workers had different financial situations and weren’t facing the same kinds of struggles.

    So I snuck in on a Saturday with some diatomaceous earth. I spread it strategically around my office. I came back the next day with a shop vac and other cleaning supplies. And guess what? I couldn’t get rid of it. I had poured out too much and I couldn’t vacuum it up.

    So there was an awkward Monday when people arrived to find a mysterious white powder all over my office! And I had to explain what I had done and why! I was so mortified, I started looking for another job. That was only one of the reasons, but I was so glad to leave that story behind me. Ah, the things we do when we are broke, short on sleep, and trying to keep up appearances . . .

    Oh, and I never had bedbugs again. So there was a good outcome.

  453. Orange Fizz*

    Oh no, I have one. My workplace has a time clock we have to punch in/out at, but it’s a long walk away from the place I and my coworkers actually do work in.
    One day, a coworker (we’ll call her Jane) came in with a fairly serious leg injury—it was healing, but she could barely stand. At the end of the day, I offered to punch out for her so she wouldn’t have to walk all the way back to the time clock. She agreed, so I went to okay it with the manager. I meant to ask, “Can I punch out for Jane?” but what came out of my mouth was, “Can I punch Jane out?”
    Cue the manager going, “…what?” And me, oblivious, continuing, “Yeah, she has trouble walking right now, can I punch her out?”
    Manager got what I was saying, luckily, and didn’t write me up for violent tendencies.

  454. LadyKelvin*

    Well, I didn’t have one I could think of (although I’m awkwardly embarrassed on the regular) until today at lunch, so now I can join the fun. I was chatting with a colleague while waiting for lunch to heat up and was asking her about how the work she was doing on a particularly dense R package was going because I want to use it for some work I was doing. So instead of asking her “Have you had any success with [Fergus’s package] yet?” I asked her “Have you had any sex?” I then asked her if she had had sex yet again, and then laughed and asked “How’s the work on [Fergus’s package] going?”

  455. Writelhd*

    I feel like every sit down with my boss is my most awkward moment ever because I spew too much of my frustration or naive ideas, and I always think back and cringe.

    For real most awkward, a co-worker and I were meeting with a client and the coworker had to leave early. Out of the blue she tried to hug client, thought better of it a second too late, while he totally shrunk away and thrust out a hand for a shake instead, almost like a defense. It was a thing to see. She told me later she was mortified. She was many months pregnant at the time and blames the hormones.

  456. Annie Mouse*

    I’ve got a few…
    The other night I ended up sat in the middle of a patient’s front yard because I didn’t realise there was a step behind me and when my ankles hit it, the only place I was going was the floor.

    I got locked out of a block of flats one day because the intercom broke, couldn’t get hold of my crewmate so had to ask our dispatcher to call his radio… dispatch found it absolutely hilarious.

    I frequently use the word ‘over’ in conversations with managers or dispatch over the phone, especially dispatch. That’s not an easy slip of the tongue to disguise either!

  457. Pathfinder Ryder*

    I’ve worked in children’s theatre. In one show, I was cross-cast purely because the previous actor had quit ten days before opening, the director was familiar with me and knew our communication was solid enough for me to learn the role in half the time usually given, and I was available. I am not particularly good at playing the opposite gender, but this role was mostly exposition anyway.

    During the meet and greets with the kids after a performance with a particularly boisterous holiday program in the audience, my director overheard one of the big and rowdy twelve-year-olds loudly informing another kid from his holiday program, “[Pathfinder Ryder]’s a bisexual.”

    “What do you mean?” asked my director, because while I am a lesbian, I don’t mention it to children at work, especially while still in character.

    “You know, she’s a Caitlyn Jenner,” said the kid, before running off yelling, “Caitlyn Jenner alert! Caitlyn Jenner alert!”

    I had no idea this was happening, being absorbed in my interactions with some of the younger kids who weren’t paying attention to the news and Caitlyn coming out, but my director was left awkwardly staring after him.

  458. Judy Seagram*

    I watched a coworker ridicule another coworker (not present at the time) by singing a little song, dancing around and waving her hands in the air. The lyrics, or rather “lyric”, to the song were the c-word sung over and over again.

    I kid you not.

    This was, and I hope remains, the worst thing I’ve ever seen at work.

    Luckily this person resigned a short while later, to transfer to a department run by someone she was having an affair with.

  459. Ex-Academic, Future Accountant*

    Here’s one from my old PhD-student days. We had a visiting speaker who was giving some lectures one week in the evenings, and due to an obligation on the other side of the campus, I was running late to one of them. Once I got to the seminar room, there were no handouts left. So I thought, “oh well, I’ll just copy down the most interesting bits from his slides in my notebook.”

    I ended up sitting near a guy who was a bit of a drama llama*. He and his girlfriend were both there, sitting next to each other. Seeing that I had no handout, he offered me his (presumably he’d then share with his girlfriend). I said “nah, you keep it, I’m fine.” And I thought nothing of it.

    Also sitting nearby was “Mary”, one of the students who had organized the lecture series. What she knew, but I learned only then, was that the slides were also posted online. So she had them up on her laptop. She turned to me and said “Here, take this paper handout, I don’t need it.” Not having my laptop on me, I accepted it. And I thought: Good thing I took a handout from someone who had a digital version, rather than someone who didn’t, eh? That worked out well! By this point, the lecture had started.

    Suddenly, I heard a sound nearby: Drama Llama had stood up. He grabbed his coat, which was hanging on the back of his chair, and…the best way I can think of to describe it is that he kind of flung the weight of it downwards while still hanging on to it, so as to make a loud sound. So that nobody could fail to notice that he had picked up his coat and was now carrying it. And without saying a word, he stalked angrily out of the room.

    I was baffled. The only possible explanation I could think of was that he was somehow offended that I had accepted Mary’s offer of a handout after refusing his. Which I had done out of a desire to avoid inconveniencing him! And I only accepted Mary’s handout because she had shown me that the slides were posted online, so I knew I wouldn’t be inconveniencing her.

    For a few minutes there, I felt almost sick with guilt at the thought that I had done something wrong and caused this. But I don’t know. Maybe something else was going on in his life that didn’t involve me at all. And to my knowledge, nobody ever said anything about it, at the time or ever again.

    *Another story about this guy, from a year or two before this happened: one day in January, when school was not in session, I received an email from this guy along the following lines…

    Dear Alice,

    If I offended you by sitting next to you in the last Teapot Theory seminar of the semester, I sincerely apologize.

    Best,
    Bob

    Yes, he was apologizing for some incident that had happened in early December, over a month before…which I didn’t remember, or probably even notice. I have no idea what I might have done to make him think he had “offended me by sitting next to me”. In this case, as in the previous case, I was completely baffled.

    I entertained thoughts of replying to say “I have no idea what this is about, I’m not mad at you, don’t worry” (I don’t think I’d even interacted with him enough to be mad at him about anything), but I didn’t know how to word it adequately, so I just never wrote back. It was probably the right decision, in retrospect, to simply not engage. But I wish I’d saved the original email — it was just so bizarre.

    1. Hey Nonnie*

      The devil on my shoulder would have been telling me to reply back to his email with “I’m sorry, who is this?”

  460. The Lion's Roar*

    I tried to block this from my memory as I felt like the worst person in the world and still do each time I think about it.

    I worked part time at a drug and alcohol treatment facility years ago. The counselors would give clients assignments that they would need to complete as part of their treatment plan. One day, the clients were at the gym while a few were sitting around working on assignments. I heard one client giving the other client answers to the assignment. (These assignments were individualized so there were no wrong or right answers.) I told them the needed to separate. They each were adults and they could read and write their own answers. (Ugh, just slap me.) The client writing the answers informs me rather embarrassingly that he could not read. I did not believe him. (I heard lots of addicts excuses and believed this was just another. Still, shoot me.) When we returned from the gym, I checked his file. It stated in his intake information he could not read. I felt like the biggest pos ever. I also had to document and inform the other staff of this predicament. Everyone cringed with me but said I should just think before I speak. I felt so bad, the rest of his stay I worked with him to learn how to read.

  461. RetiredLibrarian*

    Stories…

    This one happened to my predecessor in my last job. On her first day, she was coming out of the staff bathroom and had left her skirt tucked into the top of her pantyhose. Of course she immediately ran into the director. I’ve heard this story many times but I’ve not heard what (if anything) he said to her.

    Another one that happened to my newest employee. While in training mode, I took her through the break room and told her that normally, anything on a certain counter was food to be shared when people brought something in for that purpose. The next day, another manager had left his pizza there intending to come back for it and she took a piece assuming it was up for grabs. Again, I don’t know what he said to her but she was mortified and I felt very bad for her since I had told her that counter was for shared food… and it usually was just not that day.

    One that did happen to me but fortunately was not observed. I managed to miss a step climbing on the bookmobile and fell into the gap between the vehicle and the deck, with one leg dramatically over my head, in a skirt. Luckily I was not injured (if I did that today I’d probably break a hip.)

  463. Banana*

    I work for a very large university, and sometimes they have these HR classes that we can take with things like “How to handle conflict in the workplace” or some such thing. It looks good to sign up for one of these every so often, so I did.

    I think this one was something like “leadership in the workplace” and at some point, we were paired off to discuss some questions with each other. The woman who was my partner seemed a bit hesitant so I decided to plunge right in and give my answers to the questions, like the A student I am, and then figured she would reciprocate. I did not know her at all–she was from a completely different department than where I worked.

    When her turn came, she said she had no answers. She then said that she could not be a leader, because everyone in her department was against her. She admitted she’d only signed up for this class so that she could out of her horrible office, and that she was pretty sure she was about to be fired. She then started crying.

    For some reason, I felt panicked, which really put emphasis on my A student mentality, so through her tears, I kept trying to nod, smile, and be nice, while also trying to bring the conversation back to the questions we were supposed to be answering. “Oh, I’m so sorry, but can you relate this to leadership?!” This was probably the wrong thing, but I had no idea what to do and I’m not good when strangers start crying!

  464. MsVader*

    My male coworker and I were walking to lunch and my arms tend to swing. Well – they swimming too far and I accidentally grabbed his crotch. Not sure who was more embarrassed!

  465. Joie De Vivre*

    I used to present part of new hire orientation. One day, I had a small group of new hires who were all ex-military. When I was going over the company benefits, they started to giggle. Ex-military men don’t usually giggle.
    I’d been using acronyms for our disability plans – our corporate office had even used the acronyms in the benefits presentation I had to use.

    So, every time I said STD benefits (for short term disability), they thought I was referring to Sexually Transmitted Disease… benefits.

    Not my proudest moment.

  466. Kitty*

    Sorry I thought of a better one

    So at Old Job, two co-workers were dating but keeping it on the down low. Well they thought they were anyway- if you want to keep your relationship quiet, how about you not have “private time” in an office environment where there is an open door policy. You could always tell when someone had witnessed it- the rushing down the hallway, the bright red face, the rushing to be absolutely anywhere else. And in the days that followed, the avoidance of the workers and the particular office.

    The couple moved in together and started car pooling, got engaged and pregnant (but weren’t telling people about baby yet- one of those “we all know you’re pregnant, but we’re too polite to ask type of things). Cut to the two of them talking about something they had done on the weekend. One of the workers apparently had never been told because cut to him asking why the two of them were spending time together when the female was engaged. Didn’t her fiancee mind? Seconds of silence and awkward glances before someone corrected him. Oh but wait it got better. He proceeded to ask what happened to the guys ex-girlfriend and weren’t they living together and hadn’t they been together for like 10 years? He also proceeded to ask how he could be engaged to co-worker after a few months, but had never asked his ex of 10 years? The kicker- he told him that in this day and age, you didn’t have to marry a girl just because you got her pregnant. Well that’s one way to have a pregnancy announced

    The only time in my life i have prayed for a lightening strike to take me and whole room full of people down.

  467. schwa*

    I once went to read in my car during a break. I got in the passenger seat and leaned the seat back and started to read. Students at recess saw me and assumed I was a toddler locked in a car. They tried to call out to me, but I was in full book mode. I Looked up to see both principals and a coworker walking towards my car very worried about this supposed small child locked in a car alone. I was pretty mortified about it at the time (I find it hilarious now).

  468. Random Geek*

    Most awkward work situation, was when an employee was getting divorced at work and it was quite an ugly divorce. She ended up being served divorce papers at work but refused to accept them, and refused to allow the clerk serving the papers to leave so she literally stood in front of the door and blocked the entrance and there was a crowd standing around. I was leaving a meeting at time and walked into this with everyone else. I hadn’t clued in and this employee had a tendency to make jokes and pranks, so I assumed it was something like that and said, to everyone, “meet our new security guard and our new policy is that you can check in but never check out”. I realized about ten seconds too late. After escorting the meeting attendees to a different exit, I started to walk back, but heard the saddest scream and she started literally wailing there. The director had stepped in and taken the notice and pulled her into a room to talk to her. She left shortly after that.

  469. Adjuncts Anonymous*

    I sliced part of my left index finger with a guillotine-style paper cutter two weeks ago, and it just wouldn’t stop bleeding. I felt really awkward leaving work with a wad of paper towel on my finger. I didn’t fill out an accident report because I felt like it was my own stupidity, but I ended up in Urgent Care about 4 hours later because it was still bleeding. Let me tell you, silver nitrate cauterization hurts like [expletives deleted for the polite AaM readership]. My students have commented on the bandage, but none of my colleagues seem to have noticed.

    This is the most awkward work situation I have been in that comes to mind quickly. I am glad that the judging is random and not based on hilarity of prose.

  470. double spicy*

    Oh wow, I have so many awkward things to choose from. Years ago, I was driving to a job interview that was far away (probably about an hour). I decided to drive wearing sneakers, since I thought it would be more comfortable than my pumps. Unfortunately, while en route to the office, I realized I had inadvertently left my dress shoes at home. Fortunately, I had adequate time to stop at a department store along the way and buy a pair of dress shoes. I still made it to the interview on time, and changed out of the sneakers with minutes to spare before my start time.

    The interview itself was extremely confusing. I was interviewing at a pediatrician’s office for a social worker position. The person who interviewed me couldn’t tell me how many hours a week the job would be (it was part-time), what a day in the position would look like, or what the responsibilities would be. It was essentially as though someone told the practice that it was a good idea to have a social worker, but they lacked any sort of understanding of what social workers do, or how to hire. Needless to say, I did not get offered the position. I have since described the experience as what it would be like if I had been corresponding with someone through online dating, met up in person, and my date asked, “Wait, you’re a woman?!”

  471. Different Name Because Awkward*

    I have three:
    (1) I was wearing a pair of leggings that didn’t fit well under a dress. They started sagging and riding down as I was walking to an important meeting with a colleague and I didn’t have time to duck into a restroom and fix them. They ended up taking my underwear with them and came to a rest right under my behind, so I spent an entire meeting with C-level execs with my bottom completely naked under my dress. No one knew but me, but I was so embarrassed the whole time.

    (2) On a work trip I went swimming in the hotel pool alone and long story short a guy joined me in the pool and eventually tried to invite me to his room to have sex with him.

    (3) Not work per se but I my husband belongs to a hobby organization that attracts mostly old white men. I went to a club meeting with him and saw an elderly lady there and went up to her and started to excitedly exclaim how great it was to see another woman there. Fortunately someone interrupted me and called him David. He was not a woman. It was only cringe worthy to me because I kept thinking about how it would have played out if I hadn’t gotten interrupted, but I swore I was never going to assume anyone’s gender again.

  472. DG*

    Whoo boy…Ok. I’m cringing just thinking about this one.

    My second job out of college was working in the administrative office of a small non-profit. I was a project associate, which basically meant I was the Executive Director’s right-hand person. At the time, we had a Director of Development who no one liked, and wasn’t really effective. There were only two other people who worked out of our office, so we were a pretty small team.

    One day my boss called me into her office, and told me she was going to be firing the Director of Development, and I needed to keep it confidential. Since we were such a small operation, we didn’t have security to walk her out or anything, so for the next week I needed to come in early and stay late to scan her files into our system in case she decided to destroy anything on her way out. I said okay and started that week. It took me a full two weeks of this to finish, but I normally came in earlier than the rest of the staff so no one noticed that I was there extra early.

    On the very last day, I came in early to finish up the task. The office was very casual and carpeted, and so I would frequently take off my shoes to make myself comfortable while I was there for such long days. I finished up scanning the files, feeling immense relief that I was done and wouldn’t have to keep this weird secret for very much longer. I walked back to my desk and I hear the front door open, and the Director of Development came in and went to her office. All of a sudden I hear her call my name. I approach her office and she says, ‘Why are your shoes in here?’

    I had taken off my shoes *in her office* and had completely forgotten to go back in and get them. I turned red, stammered something stupid about needed a file from her office, and went in and got them while she stared me down. She was fired later that day and I’m 100% certain she made the connection and figured out what I was doing in there. I still cringe thinking about it to this day.

  473. TeacherOffTopic*

    I am going to preface my awkward stories by telling you that however you react to these vignettes is normal and okay.

    So, I moved back near home due a family crisis and went through a few jobs. At one, I was working alone with a new coworker, we were chatting and getting to know one another and I mentioned how many sisters I have. It’s a Cheaper By the Dozen type amount, so my coworker was shocked. “If I was a father with that many daughters,” she said, “I’d probably be comatose!”

    The family crisis I had moved home for? My father was in a coma. (My coworker was mortified, but I thought her coincidental word choice was actually pretty funny.)

    It was MUCH more awkward when a volunteer found out about it, and repeatedly insisted to me that my father was “a walking miracle.” I still wonder whether she has any idea how comas work.

    (In general, I came to learn that it is hard to know what to say to someone who is going through a hard time, and it’s okay to admit that you don’t know what to say exactly when expressing sympathy. And, if you’re going to say the wrong thing, at least make it SPECTACULARLY wrong. When Dad died and I posted about it on social media, a friend commented, “So dirty for your loss” – thanks autocorrect! – and it’s become something my siblings and I still say to each other as an inside joke.)

  474. Ming*

    One day I left the office to get some food (on a different floor) and as I was heading back up, I saw a colleague heading for the lift and cheerfully waved hello.

    I returned to the office to find out that while I’d been out, he had been fired on the spot for social media shenanigans.

  475. Harvey P. Carr*

    I have Asperger’s Syndrome and have for much of my life been clueless to many of the social cues “normal” people take for granted.

    So when I was transferred and was introduced to the boss of my new work location, he said “How are you?” I told him that I have diabetes.

    I had no idea at the time that “how are you?” was an expression and not an actual indication of concern for your welfare.

    And then there was the time when I was walking in the hallway when someone heading in the opposite direction said “Hi.” I didn’t know the person and walked past her because I thought she was greeting someone walking behind me. But there was no such person; she was indeed saying hello to me. A simple misunderstanding, you would think.

    This person apparently had a very thin skin because she took it as a personal snub. As time went on she made snarky remarks toward me whenever I was around. Ironically, if she was hoping I would be her friend, her smart-a$$ comments weren’t exactly doing anything to endear her to me.

  476. Visharoo*

    I’m a teacher. One of my students licked me in the middle of a grammar lesson. I teach middle school…

  477. loose leaf*

    Ahhhhhhh so many to choose from!
    We had a GM who was kind of hilariously innocent and clueless about innuendo, who said all kinds of awkward things at awkward times (he was from a different country / culture so a lot of things didn’t quite translate) but the best one was probably this:
    a few of us were in the kitchen, and a coworker (Steve) was making tea, which he did quite frequently. GM observes him and says “you make so many cups of tea, you must keep a teabag behind your ear! You should be called Teabag Steve!”
    We all avoided eye contact with each other until GM left the kitchen, at which point we completely lost it. This was about 4 years ago, and Teabag Steve is still known to a few of us as Teabag Steve, and he still keeps the teabag stuck on his monitor that was placed there that day.

  478. Alex the Alchemist*

    I currently work at the circulation desk of my university library as a student supervisor. On my second day of work, I accidentally set off the security system. How, you ask? My supervisor said to get there at 11:45 so we could open the library together. It was 11:45, I figured he had already gone in and I had my own set of keys, so why not just go on in? I heard a tiny beeping sound, but it was so faint I didn’t really pay attention to it. Well, turns out I should’ve and the Department of Public Safety showed up. Fortunately, my supervisor showed up soon after and cleared the air (we did have to file a report though, whoops).

  479. Sarah*

    I was once frustrated with my boss and he was walking away from me, in the workplace in which there were patrons, and called after him to get his attention: “Dad!” It just exploded out of me. It did get his attention, but oh, my God it was embarrassing. He’s nowhere near old enough to be my Dad and I had never, even as a child, called anyone else Mom or Dad.
    And speaking of jumpy people, a co-worker walked right past me in a hallway and I did not see her (I have no idea how because she would have only been a foot away from me) so she said something and I screamed so loudly the director came running out of her office thinking someone was being attacked. Scared the bejeesus out of the co-worker too. Had to take “attention to detail” off my resume too.

  480. CAndy*

    I used to work for a large supermarket chain. We had a great store and a great atmosphere, for some reason things just clicked for a few years.
    Early in 2010 we had a new Clothing Manager, Jane. We’d all been in since early and naturally we phoned Jane to make sure she felt part of the team and was with the rest of us for breakfast which we used to take at about 10. I think it was the Store Manager who phoned her.

    Everyone is sitting chatting and Jane pipes up to say she has noticed some problems and some things she’ll need to be able to deliver a clothing sale that corporate had scheduled to start in about three days on the Thursday.
    Someone at the table says, “Well, why don’t you call Mary, she’s the Clothing Manager in the store down the road. It’s only 5 miles away. We always help them with stuff and they always help us back.”

    Jane says, “Oh my god, I’d rather die than ask that bitch for help, she’s the most useless and annoying POS of a woman I’ve ever met in my career.”

    Silence all round the table.

    The Store Manager says he’s got some things to do, gets up and leaves. This gives someone else the chance to explain to Jane that Mary is the Store Manager’s wife.

  481. Elim Garak*

    When I was in college I worked for the Theater department’s costume shop. We were doing a Union show that semester, which meant we were contractually obligated to provide underwear as part of every actor’s costume. The designer sent one of the Grad students (a lovely young woman from Eastern Europe; She was fluent in English but it was not her first language) to the sporting goods store to buy undergarments for the male actors.

    About an hour later we get a call to the shop from the now panicked grad student. She said she told the clerk that she needed to buy a dozen strap-ons, but he wouldn’t help her. She and the clerk got more and more flustered as she insisted she should be able to find the strap-ons there and at a certain point he just shouted at her “Ma’am, this is not that kind of Dick’s!”

    We’re all rolling at this point, as the shop manager tries to stifle her laughter and explain to both the student and the clerk that what she was looking for was a dozen jock-straps, not strap-ons. The student, fortunately, had an excellent sense of humor and was able to laugh about it shortly after she calmed down.

  482. Millie M*

    My best awkward (but funny) moment happened many jobs ago. Our IT person used to get some fun giveaway-type things, and one time he got a set of juggling balls. One of my coworkers and I were checking out the JUGGLING balls. Someone else walked by and asked what we were doing, and I blurted out, “Playing with Jeff’s balls!” I realized what I said when it was halfway out of my mouth and too late to stop it. Everybody laughed, but I’m not sure how Jeff would have felt about people discussing his balls at work.

  483. Questioning*

    This story pops to mind – was on a business trip with a few other people, long ago, as the most junior employee, and we stopped for lunch at this one restaurant. Two of the men (one being the boss) were playing this flipping coin game (forget the rules, they had some detailed rules). They started in on the waitress, demanding that she play the game with them with a loonie ($1 coin). They kept in on her for the whole time we were there, explaining the rules to her, telling her how fun the game was, how amazing, etc, etc. She finally caved and brought out a coin, flipped it, and immediately lost. They kept the coin.
    Plus side was at least they stopped bugging her about it at that point…

  484. Questioning*

    OK, so this wasn’t at work, but it’s very awkward and I was reminded of it from another comment.

    After my father died, we had a memorial service for him, with a table at the front with some pictures and memorabilia, as well as a nice wooden box with his ashes. My cousin was talking to me at one point, and said that she was looking at the table, and she know why there was the model Volkswagen Beetle and some other items, but wasn’t sure about that wooden box – was there his military hat in there, by any chance? I just blurted out “no, it’s Daddy!”, and then reassured her that no, I definitely wasn’t offended by that, it was funny.

    And then, after the service, a friend who’d missed the service came over to see my mother and I. I was telling him that story, and got to the point where there was a table on the front with things on it, but couldn’t bring the word to mind (looking for something like memorabilia). He helpfully tried to find the word for me, and said “hors d’oeuvres”? My mother and I laughed so hard we couldn’t speak – she actually had to leave the room, she was laughing so hard – and the poor guy is sitting there, saying “that was the wrong word, wasn’t it?”, while we tried to indicate that he shouldn’t worry.

  485. oldbiddy*

    I was on a faculty interview at a boston institution of higher learning. It was my first faculty interview ever. I had graduated from a different institution located nearby. We were at dinner, having drinks, and started gossiping about other people in our field. Somehow the talk turned to a couple who had been at my former institution, who had gone through a divorce and married their affair partners, who had previously been married to each other. (It wasn’t al at once, I think one pair had an affair and the other pair comforted each other) Pretty juicy stuff for a science department. 3 our of the 4 people had left my graduate school before I got there, so I didn’t know what they looked like.
    Anyway, the people interviewing me were talking about it and I interjected “It’s not like xxx(the one person who I knew) looks like a Playgirl centerfold” when I noticed one of them start to gesture frantically at me to shut up.
    One of the other people involved in the complicated spouse swapping situation was sitting at the table across from us. Needless to say I did not get that job.
    Years later I found out that the person sitting across from us definitely heard us, and assumed we were “rude Harvard grad students”

  486. M*

    Most awkward situation at work: my shoes disintegrated on my commute in and since I was an intern, I didn’t have any money to replace them. I ended up being offered someone’s workout sneakers to wear the rest of the day and back home. Unfortunately no one asked her and she didn’t discover it until she returned to work the next day to not having her gym shoes.

  487. Elizabeth West*

    This isn’t nearly as bad as some of the others, but it was still very embarrassing. About ten years ago, I went to a job interview on a very dry, windy day, which had kicked up my allergies. The interviewers were two women, and while we were talking, I sort of had an allergy attack–which manifested itself as a horrendous coughing fit that just would. not. stop.

    I asked as best I could if water was available and one of the women took me into this small break room. She poured me a cup of water, I drank it, and we went back to the interview. They looked at me with their lips curled as though I were a bug.

    I didn’t get the job. I also never went anywhere ever again without a water bottle.

  488. JKP*

    My first year as an RA, the 2 week training before school started consisted of a lot of worst-case scenario training, like rape counseling and dealing with O.D.’s and suicides, CPR training, plus a visit to see the rehab and detox facilities. Really intense stuff.

    So the first day all the new freshman finally arrive and move in, they show up to their first dorm meeting all excited to start their new college life, staring up at me their RA who is supposed to just give them some basic freshman orientation information like where to get their laundry cards and how late the cafeteria is open.

    I burst in tears and beg them all, “I just want you guys to be SAFE!”

  489. I Coulda Been a Lawyer ;)*

    I was sent to the cafeteria to fill coffee orders for VIP customers meeting with my boss & management in a conference room. While I was gone they set up a slide projector, turned off the lights, started the meeting. I returned with 10 coffees on a tray, coworker opened the door, and on my second step tripped hard over the power cord across the doorway. Threw 10 hot coffees at the richest guy in the room, hit him in the head with the tray, then landed on top of him. Not sure how we didn’t lose the customer.

  490. Undine*

    I don’t know if this is my most awkward moment, but it is fairly unique. I was a cutter for about twenty years, starting in my teens. When a younger sibling died, I packed up everything sharp in my apartment — from Chinese cleavers and kitchen knives down to nail clippers — and gave them to a friend. After a while, I thought I was better and got the box of knives back. But a while later I cut myself again, two long scratches on the cheek. I was able to pass them off at work as cat scratches, but I felt terrible — my cat was the sweetest ever and the only time he ever scratched me was once in a blind panic when I picked him up to get him away from a dog. Anyway, I packed up all my knives again and brought them into work and put them in a drawer in my desk. Cue the day when a coworker came to my cubicle to ask for something, I pulled open my desk drawer, and he saw all the knives. He said something like,”Wow, I’m never going to contradict you!” I don’t even remember what I said — I may have said something about not wanting them in my house at the moment. God knows what conclusions he might have drawn from that.

    That was the last time I cut myself.

    1. Old Admin*

      ***hug***
      Simply hugging you for your strength (even if it was fueled by embarrassment :-D ) to stop hurting yourself.
      ***more hugs***
      Well done.

  491. copperleafsong*

    Me and colleague went out for dinner and a beer after work on a Thursday. We ended up drinking two bottles of wine, champagne and gin n tonics. I had not eaten since lunch the day before (a bad habit of mine). The next day when I came to work, I was able to stay only a few hours, since I felt so ill that I threw up when running to the bathroom. This lead to a trail of throwup from my work station to the bathroom, and also all around the bathroom.

    Fortunately we are manufacturer, of among other things, cleaning agents. So I cleaned the spots of throwup effectively. The cleaner did the bathroom. I must of traumatised his trainee as he was showing a substitute of his how to do thing.

    I received a lot of questions of if I was feeling. Being blasé about it, I told them the truth.

    I was teased by my colleagues about if for months.

  492. New Bee*

    I brought my kid to one of our school events, and right before the program started, I smelled something rank and said, “Whoo [Kid], smells like you might need a diaper change!” The smell dissipated after a few seconds so I turned to my coworker and said, “Sorry about that, it must’ve just been her gas.” Said coworker later confessed to our other teammate that the SBD was her! (And she still doesn’t know I know, heh.)

  493. Cristina in England*

    Once in a former job, I went to the break room fridge to find that someone else had taken my container and used it. The fridge was relatively empty and it was easy to see my container was the only one of its type. I was annoyed but I just took the other person’s stuff out of my container, put it in a dish in the fridge, cleaned my container and put it in my bag.

    20 minutes later my team lead came storming into the work area. “These f$&@ing people! Someone took my food and left it in a dish!”

    Apparently someone had cleaned out the fridge and tossed a bunch of stuff without telling anyone (before or after). Apparently mine had been tossed and I had the same container as my team lead. Whoops!

  494. atma*

    Yes, please, I’d love a book!

    We were going through outsourcing of IT operations and support and me and a colleague, let’s call him Fergus, were offered positions with the new company. So this wasn’t exactly an interview but more an introduction, between him and me with our two team leaders, general get to know each other, but in a work related way. Fergus was also not a very impressive coworker OR technician, he was actually rather difficult to get along with, didn’t do stellar work, and were sometimes disappearing when he should have been doing work.
    Fergus then proceeded to list enough work for someone to ave worked the last 50 years, and ended it all by saying “I heard from some friends that [Previous company] had some problems with their IT structure and processes so i decided to start working there to sort it out”
    And I’m standing there , smiling politely, biting my tongue to not burst out with an actual description of his work, because really, that would probably make them think it’d say more about me than him. No, he wasn’t a stellar technician at the new place either.

  495. GenericGen*

    I once worked as a manager in a small store. One of my subordinates was just terrible at her job and I recommended she be fired. I was in the store when the owner fired her, and we were all aware of what was happening. As she left, she said she would like to stay friends with everyone and it was very awkward as no one liked her.

    As we were getting back to work, here comes the fired coworker again. She said she forgot she had parked in the back that day and was going to walk through the store to the back door. This she did. A coworker and I looked at each other and she said, “I know it’s a bit of a walk to go around the outside from the front to the back, but if I had just been fired, I would have gone to the extra trouble to avoid that weirdness”.

  496. Jackie*

    Of course my moment had to happen at the work Christmas Party of 2001.

    A few months earlier I finally had my long awaited/ desired Breast reduction. My ” new and improved” set was quite spectacular IMO. 20 yr. old bOObs on a 40 yr. old body and I was thrilled! One of my friend co- workers helped me shop for a killer dress. Black with a sparkly skirt and the top portion with a very low scooped neckline with fitted sleeves. The kind of dress that bra straps would show if you wore one. Needless to say there were no straps interfering with my look.
    I was single at that time so I cabbed it downtown to the venue. I always used the same cab driver, and he told me my debut look was amazing! – he had known about my surgery.
    The party was fun. It was hosted by the private anesthesia physician group that employed me. There was staff from 3 different hospitals in attendance. Towards the end of the evening I was sitting at one of the tables by myself. A guy came over and took a seat near me exclaiming ” I’ve been trying to say Hello to you all evening!” Well, gee! Who wouldn’t want to meet me and my “girls” ?! Naturally my newly acquired body confidence fueled by wine was positive this guy was trying to pick me up, and I was a little miffed that he had waited so late to make his move.
    So I gave him a coy come hither side look and said ” Let’s cut to the chase here. Just who in the hell are you anyway!?”
    He said ” I’m Dr. $$$$$”.
    I thought for a moment because that name sounded familiar. Then with growing horror I said ” Oh. I think that’s the name that signs my paycheck.”
    He said ” Why yes it is. I’m the CEO of the anesthesia group.”
    Completely embarrassed. He was only trying to make sure he had greeted everyone there.

    I met my boyfriend ( now husband) a few weeks later. Cue to several months later at the 2002 Christmas party. We entered the venue and the CEO was there greeting all the arrivals. I had to introduce him to my boyfriend. I nervously started by saying ” Dr. $$$$ I don’t know if you remember me, but …” and before I could say another word he clasped my hand , laughed, and said “Oh J**** I definitely remember you!” ( cringe)

  497. rhababerbarbara*

    Okay, here we go:

    I once worked as a live-in-nanny for a family who also had a puppy of whom I took care during the day. To get the pup house-trained / on a schedule poop-wise, we would keep a journal and write down who took him outside at what time, and whether he peed/pooped/both/nothing. Also, I would send the mom texts to update her on what I was doing with the kids.
    One of my first days there, I took the dog out in between some errands and wanted to let her know I hadn’t properly walked him due to a busy schedule. So I texted her “Hey, just came home, pooped – was a little runny but otherwise fine. Didn’t have much time as I’m going to pick up the kids next, so I couldn’t clean up properly and we’ll have to walk [dog’s name] later.” I didn’t even notice that I had forgotten to put the dog’s in the first part of my message until she texted back “uhm… okay, hope you’re fine. please see a doctor if you feel you’re having digestion issues and also, which toilet should I avoid until you come back to clean it up?” Of course I let her know that night it was about the dog’s poop, but I was embarrassed nonetheless (and she thought it was hilarious, btw).

    Another awkward moment happened like 9 years back when I was interning at a big company (in my mom’s department – thank god it never came out). I was super tired, so during ‘breakfast break’ (9-9:15) I decided to close my eyes while my supervisors went to the break room. As usual, I expected them back by 9:15, at which point I would have certainly woken up. However, I didn’t wake up until 11:30, when two of them came back discussing lunch plans – the third supervisor was already sitting on his computer, and I don’t know for how long, but of course I felt embarrassed and didn’t want to be the sleeping-intern-daughter of Jane on the third floor. I later asked him why he hadn’t said anything and he responded by saying he felt like I worked hard for an intern and I had earned a nap… Well, thanks I guess? Needless to say, I never ‘closed my eyes just for a couple of minutes’ ever again.

  498. Delphine*

    I’m in Belgium, in Wallonia.
    In the laboratory, there is this general expectation that you will greet your coworker (or any other person) any first time of the given day that you meet them. Yes, with a cheek-kiss.
    I have had colleagues upset because I did not interrupt their discussion to greet them…and thus was impolite.
    I’m quite introvert, and sometimes get fed up to cheek-kiss someone that I do not really know. Especially when no other person that was with me at the moment is also able to tell who this person was…
    So one day, at lunchtime we are the usual group around the coffee machine. A woman arrives, and start to say Hello and kiss everybody.
    When she arrives to me, I ask “who are you ?”.
    She stops in her track, and present herself. She’s a new colleague in another service.

    It’s been a few years, she always hesitate before kissing me when we met in the hallway.

  500. Grad schooler*

    At an old job, I was working while going to grad school part time. My manager was really supportive about me moving up in the organization–which was amazing! Except at the holiday party when we were standing in a circle with the CEO and other top execs and her way of communicating that she thought I was a strong employee was to say, “Jane is getting her MBA and then she’s going to leave us”

  501. SartyParty*

    One of my co-workers is pretty awkward is general, but the situation that really takes the cake is when one of our mutual co-workers was pregnant. Awkward co-worker congratulated her when she announced at a staff meeting: ‘Congratulations on the fetus in your womb!” It stopped the room. And what’s worse, besides being gently corrected by the pregnant co-worker numerous times to please call the baby, ‘the baby”, she started every morning by asking her how the fetus was doing that day. Yeesh.

    1. Tassie Tiger*

      I…hm. That’s–hunh. I’m in awe that your coworker can continue to “gently” correct. I think I would be in HR complaining by day 3 of that.

  502. RogueVirago*

    (Not sure if this is open to commenters from the UK, so here is your notice that I am from the UK!) What follows might not be the most embarrassing workplace moment, but it is certainly the most recent…

    Yesterday, we had a leaving do for a colleague in the office canteen. I popped down and a table was already laid out with snacks and goodies for everyone, and presents for my colleague. In pride of place in the middle, was a large My Little Pony made out of chocolate. So, naturally, I said: “Oh look, it’s Pinky Pie!”

    I got a lot of bewildered looks. It turned out that the chocolate Pinky Pie was a joke, because colleague had a tendency to have at least one children’s toy under her desk at any one time for her small child. Nobody else knew the names of the ponies in My Little Pony, and I had just outed myself as a grown adult who watched the show. People then brought it up to all the newcomers, and everybody found it hilarious. Only one person questioned me, at which point I automatically responded “IT IS A DELIGHTFUL SHOW IN A WORLD THAT IS HARSH AND CRUEL.” I didn’t even mean to say it, it apparently is just my kneejerk response to people wondering why I watch My Little Pony.

    I’d only just lived down the time I forgot to take my dinosaur hat off before I got to the front door at work. Alas.

    1. Old Admin*

      Hey!
      I have a Furry hat I love to wear – it’s made of soft fluffy material, it’s camo (!) colored/patterned, it has cat ears sticking up (one frequently flopped over in the cutest way)… I’m a serious looking very grown up lady with blazing red hair…. why are you guys staring at me?? ;-)

  503. Itsa Me*

    I work at a call center and the supervisor stations on the call floor are up high so that the team leaders can see the people at their desks. I was about 8 months pregnant with my third child at the time and I was sitting in a tall chair at one of the desks. I’m 6 ft. tall so it wasn’t difficult to get into the chair. My son was moving so I arched my back a little bit to relieve some pressure on my ribs, and the back of the chair fell completely off. Fortunately I didn’t fall out of the chair, but it made a loud noise as it dropped to the floor at everyone looked at me.

  504. L*

    This happened at an office gathering for me, as I was leaving the department for a new job. I didn’t interact with many of my coworkers a lot and mostly kept to myself. I think my direct manager knew about this and would have just left things alone, but the department head said, trying to be nice, who would like to say some things they remembered about working with me, or something like that. There was dead silence. I didn’t really care, but I could tell others felt awkward. So then one of my coworkers who’s really nice and happened to have her cubicle on the other side of the wall from mine, said how she would remember me/was impressed with me as she could always hear me typing away very fast a lot of the time. And that was it. I am a very fast (and apparently loud) typist so it was true, but still very awkward that it was all anyone had to say.

    More recently I wasn’t the subject of the awkwardness, but it was almost worse. A vendor we did business with had asked to take our project team out to lunch, so we had a variety of people thrown together who don’t always interact so it was a little awkward to begin with as not everyone had met each other before (some of the project team does more behind-the-scenes work so would never have met the vendor or the business clients the project was for, who were also there, before) and one person definitely has a slightly off sense of humor and another isn’t afraid to bring things up that you might not usually say at work. Somehow it came up that the vendor, a taller man, had previously done work in a country one of the team members was from, where people tend to be shorter (and this team member is on the shorter side) and he mentioned something about how he stood out there. The team member made some sort of joke about himself and many others in his country of origin being short and brown. Next it came up that another person, J, had recently moved to a town where a third person had grown up, who said there tended to be a lot of people from that country in that town. So J said, well, I’ll fit right in there then since I’m short and brown too. While that was technically true it still felt really, really awkward to me since I was the one who basically brought all these people together and I don’t think the vendor expected a normal conversation about his travels to go in that direction at a business lunch.

  505. Trillion*

    Oh man, awkwardness. The reason a lot of us can’t watch the Scott’s Tot’s episode of The Office.

    One of the the most awkward moments I witness/experienced at work was at a Women’s Network meeting at my previous company, Teapot Industries. A guest was brought in, the CEO of a competitor who was one of the very few women in leadership in the industry. She gave an excellent talk about believing in yourself and breaking through the glass ceiling.

    Afterwards, our (male) president stood up and gave a rambling speech about how there’s no glass ceiling here at Teapot Industries and how the ladies just need to apply ourselves more. This was a company that had 0 women executives out of 10.

    He’s an ex-pat so I try to assume the best and chock it up to a language barrier. But oh man, seeing the stony faces of the ladies (including our guest) was so awkward.

  506. Linda Evangelista*

    When I first started dating my partner, I was just getting used to calling him “babe”. Often. Very often. So often that I accidentally called my colleague babe. Neither of us have acknowledged it to this day and I sincerely hope he forgot all about it.

  507. Tammy*

    So, I’m a transgender woman (I’ve talked about this in comments before) and I transitioned on the job at a technology company years ago. My transition was announced to the company in a series of team meetings, but not through all-team emails. I took a week off of work when I transitioned – partly to ease the transition visually for my coworkers, and partly to give me time to take care of tasks like changing my name on my bank accounts and driver’s license. I got to discover all of the people who had been absent the day of the team meetings, because almost all of them ended up in my office looking very confused during that first week. But the most awkward part was one woman who I knew casually. I rarely saw her, but that first week back I managed to bump into her in the restroom 5 days in a row – and it wasn’t until Friday that she asked me “should I still call you (very masculine old name)?”

  508. Elizabeth H.*

    Embarrassing moment I can think of, that happened just this winter – I got cut off from ordering alcohol at a super fancy art opening reception at my work. I wasn’t drunk, and I wasn’t on the clock, they just apparently have very strict rules about how many glasses of champagne they can give out? I think I got cut off from glass #4. The bartender said “I have to give you just water for now” which was totally embarrassing. But worse, I interpreted that literally as meaning for now, so I tried to order another glass a little later while I was chatting with the director of business development for the university, and was refused a second time. I spent the rest of the night obsessively worrying I seemed inappropriately drunk, and feeling so indignant that I, an employee, wasn’t getting special treatment from the bar staff. My boss, whom I love, sneakily ordered me another glass of champagne before she left, as if I were an underaged kid. I still feel embarrassed when I think about it!!

  509. ProjectManager*

    I’ve worked for my boss, who is also my mentor and my friend (more about that later), for 4 years now. He’s a terrific leader and manager and I’m fortunate to have the job I do – he supports my professional development, helped me get my PMP certification, and lets my explore my professional strengths and passions even when they aren’t really part of my job – which is as his executive assistant. Finally, about a year ago, even though he really didn’t want to lose me, he gave me a reference for a job out of state that I was considering relocating to for family reasons. Anyway, this is for context as we’ve had a few awkward moments due to the dynamics of our boss/mentor/staff/friend relationship. So, every year at Christmas we exchange little gifts. This year, I was short on time and ran into a bookstore trying to find something appropriate. I grabbed a little book of quotes about friendship, leafed through it, thought it would do and took it back and wrapped it up. As I was wrapping it up, I noticed that some of the quotes were of the BFF type of friendship, much mushier than our professional friendship. I debated for a few minutes, then gave him the gift anyway. We were off a few days for Christmas, while I really stewed and second-guessed giving the gift. The first day back at work was super-awkward all day – we both completely avoided talking to each other other than necessary monosyllables on work topics. The next day I apologized for my “bad mood,” so did he, and we never spoke of it again.

  510. Vancouver Reader*

    I used to get really heavy periods when I was young. One summer I was working in a downtown office, and so of course, downtown means lots of people.e I was dressed in what I thought was a pretty outfit, matching skirt and top. At the end of the day, I walk up quite a few blocks to get to the bus stop. It wasn’t until I got home that I realized I had stained the entire back of my dress. And the pattern on the skirt was striped, not a swirl of colours, so the blood stain was very obvious. Hopefully no one saw it, or if they did, they certainly didn’t tell me about it.

  511. Oh no*

    I have, to my eternal mortification, accidentally farted. In a very quiet, very open-plan office. Mercifully, no one commented and I tried to “play it off” by making other noises but I will never forget the shock and complete desire to melt into the floor.

  512. AI*

    I was working nights in a fast-food restaurant as a university student, and had a young man come through my drive-through lane to order just a soft serve cone (about 50c). I recognised him, but I wouldn’t say he was much of a regular, per se. After paying at my window and collecting his receipt, he drove straight past the window he was supposed to pick up the order from. Not five minutes later, he drives back up to my window, hands his receipt back to me with his number on it, and a note saying “call me”, and drives off yet again without saying a word… Leaving me feeling very awkward indeed! Several days later this same customer somehow tracked me down on Facebook (not any easy task given my privacy settings etc, but I do have a slightly uncommon first name which was on my name tag at work) and tried to “add” me. I don’t think he had any clue how awkward (and almost threatening!) his actions were. We hadn’t even had a friendly conversation, the only interaction he’d ever had with me was when I took his order, so I was simultaneously confused and worried about how he could be interested in pursuing me the way he did.

  513. ggg*

    Almost forgot the guy who was called upon to describe a new family leave plan at a large meeting, but who was clearly not prepared to do so at that moment. He stammered around for a while awkwardly and the last thing out of his mouth was, “Oh, and it could be for adopted babies. Not just regular babies.”

  514. Queen of the File*

    I have had my share of cringeworthy moments at work, but this one was just so poorly-timed and unexplainable that it is probably the one I’m most embarrassed about.

    I was struggling in a finance job that had social and professional norms that were much more rigid and conservative than what I was used to as a, let’s say, “quirky” arts student. As I walked in the door to work first thing one morning, my longsuffering CEO and CFO called me into a meeting–just the three of us–to go over some specific expectations, including several points about my appearance (no more colourful socks, do something about the hair frizz, etc.). I was taking notes and trying to at least appear to take the feedback seriously and gracefully, while being somewhat confused and dejected on the inside. I took a big sip of my coffee as they were giving me advice on professional behaviour, and just at that moment my brain completely short-circuited. My mouth popped open with a “shhhhpok!” sound and coffee drooled out, down the front of my white blouse, all over the notes I was taking. They just went silent, and so did I. You could see the words “this is a lost cause” written all over their faces. How do you even explain something like that??

  515. Awkward Lurker*

    The CEO of our (large) company sent an email announcing that a new corporate location would be opening in a state that is far warmer than our state. There was no communication about what departments, if any, would be moving there. A new hire (3 weeks into the job) on my entry-level team emailed him back directly saying they would be interested in moving to the new corporate location. He, very nicely, emailed the new hire back to let them know that this is really something they should talk to their manager about.

  516. Nines*

    I had started my first day of my first internship and was super excited and super nervous. I had gotten new fancy work clothes and was pretty happy with the outfit I had put together. I didn’t have a log-in yet so I went to a bank of some public computers on my break to check email and this old lady that was the attendant looked at me and said “I don’t know if you want to use these computers in your condition” (apparently because they were filthy or something). I just stared at her confused until I realized she meant because of the *pregnancy*… I was NOT pregnant. Though had certainly gained weight in the last year, so definitely was entirely mortified. I still kind of hate that women…

  517. LadyProg*

    I’m a woman in programming, so there have been maaaany awkward situations happening with me and around me, of course. But I guess the winner is when I was still an intern and I asked for a week off to have surgery done, which was a breast enhancement surgery so I didn’t tell it right away to my boss – he didn’t ask, if he did I would have explained (not in the US and a lot more sharing personal details is normal and I was totally ok talking about it anyway). He okayed my absence for a week, I went on to have my surgery and recover for a week at home, and next week I’m back at work, no problem. He sees me on my desk by myself (everyone else is out for lunch) and thought to ask how I was doing since I was gone for a week, if I had recovered well from my surgery, I say I’m fine, thanks! So he goes “what was your surgery again?” and without even blinking I just go “it was breast enhancement!”. OMG he turned red, didn’t know what to say, pretty much just excused himself and left! Later another coworker (which is also a woman and actually knew what I had done) told me he went to talk to her and how embarrassed he was for asking :P

  518. Old Admin*

    Well, we recently had a fire drill in our office building, in a very serious conservative indusrty..
    Everybody filed out in an orderly fashion ans assembled in the parking lot in the freezing cold.
    I had grabbed my backpack and jacket and left, too. To understand the rest of the story – I’m a fairly tall and broad shouldered lady.
    Outside, the CEO was shivering in a thin formal shirt. I already was wearing a heavy sweater, so I went to him and gave him the jacket (easily his size), joking that a CEO down with a cold would cause company expenses. He gratefully accepted and put it on…

    … when he turned around, I saw to my horror it was my jacket from the Las Vegas Star Trek Exhibition, with a huge picture of Klingons, the Great Hall, spaceships embroidered on the back, with the nice touch of “Long Live The Glory”, “Today is a good day to die” etc. added to it!!! Smiles appeared in the band of colleagues waiting outside…

    I apologized profusely after we went back in after the fire drill, explained I had not been trying to trip him up etc.
    He accepted graciously, and said: “Just one thing..” (I cringed) “…the jacket suits me, doesn’t it?”

    :-D :-D

  519. Berry*

    Oh man, thankfully nothing too much springs to mind so if I’ve done anything super embarrassing I’ve forgotten it.

    I did have a recent phone interview where the hiring manager after describing the position and answering my questions did a “I’ve been talking for a while” and while I meant to have a positive “It’s been very helpful” comment, instead I just said “You’ve said so much!”

    Was able to quickly follow it up and laugh it off, but definitely red faced for a moment there. (And then didn’t get the job because I was underqualified, oh well.)

  520. Elizabeth*

    Ha. These are all great.

    Mine: I had a back injury for a while and was applying a topical cream similar to icy hot in the mornings before work to help me get through the day. The first day I did it, I emailed my husband about the cream, talking about nice the tingling sensation was and that I could still feel it after several hours of work. Except for I did not email that to my husband, I had instead clicked the wrong email to reply to and sent the email to a manager of another group. He politely emailed me back stating he thought the email wasn’t meant for him. I couldn’t look him in the face for months.

  521. bohtie*

    My very first day at my current job, my boss was introducing me to my coworkers, and he mentioned that one of them had just come back after a lengthy amount of time away.

    Instinctively, I responded, “Oh, nice! Did you have a good vacation?”

    He very politely informed me that it was medical leave for a terrible car accident.

  522. Allison Sobel*

    I was in a meeting last October with my boss and a group of people from a variety of teams. My boss was 8 months pregnant. As the two of us walked into the conference room, a woman I barely know said; “So will you guys be out on maternity leave at the same time?” I was so surprised I just started sputtering: I’m not pregnant. My boss kindly tried to divert attention by talking about her own plans and then changing the subject.

    The irony was that i was/am pregnant. But it was the first trimester and I hadn’t told anyone yet. It’s my second child and I was already starting to show. I ended up telling my boss the next day because I felt like it must be obvious to everyone.

    I also reached out to the woman who made the comment. She told me she didn’t think I looked pregnant, but that she had the psychic ability to tell when people are.

  523. Dave Wheeler*

    In my 20s and 30s I had a very varied job history. I was attempting to become a full time working actor so I took a lot of jobs with odd hours, little oversight and working alone as much as possible for the sole purpose of focusing on my acting career. One late night, managing a gas station I was alone, caught up with my paid duties and was spending the night working on character voices, this particular night the voice was Barney the lovable drunk from The Simpsons and the prose was Hamlet,” Angels and ministers of Grace defend us!” I was in the bay of the station (better acoustics) with my back to the store/register. I completed the scene and was awarded with a loud and confused sounding applause. So focused on my character I didn’t notice the BUS of tourists that had pulled in only to find they were being treated to a strange roadside theater production .

  524. Little Orange Nail*

    I had been training a couple of my coworkers, and got to the step where I explained that you had to export a report as a pdf, except what came out was that they should “pdficate” the file, which sounds both preposterous and crass out loud.

  525. NotReallyKarenWalker*

    My C-level supervisor has been on very thin ice during the past 18 months, mainly due to his conduct towards my team, so we’re all intimately aware of how bad things are.

    Just a few weeks ago, after another series of incidents, he called an all-hands meeting of our department including lots of other C level folks. He was forced/marched into the conference room by his supervisor and announced his structured “resignation”.

    As he pretty plainly let us know he’d finally been canned, I very loudly blurted out “Congratulations! That’s great for you!”.

  526. Government Lackey*

    I recently sent a text about my intern’s awkward attempts to log into her computer (she just kept restarting the CPU and the screen when the login box came up)… to her (was trying to secretly giggle with a co-worker about “kids these days”). She bravely said from a few feet away… Uh, I think you sent me a text meant for someone else.

  527. Jemima Bond*

    Once upon a time I was sitting at my desk, in a standard fairly robust office chair with five castors on a pedestal; you know the type. Quite hefty and hard to tip over. Turns out that if you lean far enough towards your colleague’s desk/screen to help him out with something, those chairs do eventually tip over and deposit you on the floor. This took place in the middle of a large open plan office, with a resounding crash and probably a yelp of alarm on my part. Colleagues froze in horror until, from my supine position, I declared, “Gravity, thou art a heartless b****!” Then they laughed, which was fair enough really.

    And a bonus non-work falling-over story. I was returning from Paris where my then-boyfriend had taken me on a romantic weekend. We alighted from the Eurostar at St Pancras station which for the non-UK readers is also a large intercity and commuter station so at 7pm on a Monday evening there were plenty of people around to watch mishaps in the main hall. As we said our goodbyes and prepared to depart to our respective homes, then-boyfriend decided on a whim to go for a full-on Hollywood style leaning-back kiss. This did not end well. Unprepared, I overbalanced and crashed to the floor, bashing my elbow on my wheelie suitcase on the way down and taking my paramour with me, and we ended up in an ungainly heap. As I picked myself up, a man walked over and asked if I was alright, muttering something about wondering if I was being mugged – an unlikely supposition, considering then-paramour very much looked his part of a respectable off-duty army officer with a velvet-collared overcoat complete with poppy, but I appreciate his chivalrous intent and metaphorical shining armour/white charger. As I, blushing and much embarrassed, confusedly assured him I was fine and the gentleman involved in the crash was my boyfriend, I realised that the would-be knight was in fact Liam Gallagher, of popular beat combo Oasis (very famous in the UK, not sure about the US though?). This somehow made it worse, I suppose because even more people were looking, so it was a thoroughly mortified Jemima that scuttled off to the tube.

  528. Jemima Bond*

    Also, anyone else here ever worked in law enforcement, prisons or similar? A moment of silence please as we contemplate the first time we carried out a strip search.

  529. FormerGT*

    I was working with my best friend, who is gay and was 17 at the time. He was also sleeping with our 30+ year old MANAGER. The manager was not public about his sexuality. He knew I knew, and part of my job involved him escorting me to do nightly deposits, so we were alone in a secured room 5 nights a week…. The discomfort was so palpable. And it put me in such a weird position because aside from being bad business, it was illegal since my friend was a minor. But I wasn’t going to cost my friend his job by saying anything (aside from repeatedly telling him he could do better). Bonus? We worked at the “Happiest Place on Earth”. Not exactly a PG situation for good ol’ Disney haha.

  530. That Lady*

    I teach high school, so a lot of days are cringeworthy–usually things I observe, but also sometimes I want to melt into a wall after I say something. The absolute worst, though, was the student who, for no reason I’ve ever been able to figure out, gave me a Sieg Heil salute while I was passing out testing booklets for a mandated state exam. Because we were “on a clock” so to speak and I didn’t have time to really dig into what happened or pull her outside, I just sort of stood there flabbergasted while the student giggled and everyone else in the room was gobsmacked. It was my first year teaching, and I didn’t know what to do. I wished the floor would open up and take me or that I could have teleported off of the planet.

  531. drpuma*

    My old office provided a public service and was on the ground floor of our building. One day a woman walked in off the street on her cell phone, in the middle of a terrible break-up, which she proceeded to finish in the office. Except she tried to “hide” behind the plant in the corner by the door. This plant was closer to a sad little Dr. Seuss tree – it was a skinny, five-foot-tall green-and-white-striped stalk, with only two leaves coming out of the very top. The plant couldn’t hide a piece of paper, let alone a sobbing woman. She left without saying anything once her call ended. We never saw her again.

  532. Horatio*

    Oh boy…once, during an interview, the hiring manager started to tell me that the business had moved buildings due to an unfeasible rent increase, which is understandable, but then immediately proceeded to go on a very long rant about the old landlord’s “mental health issues” and all sorts of other things that were wildly inappropriate to tell a job candidate (or anyone). It was well before I had graduated college, so I sat there in horrified awkward silence for at least 45 minutes while she went on and on. I wish I could say I didn’t take the job, but, well, I was really desperate. I worked there for about a year and a half and yep, it was about as bad as you’d think given the initial interview. She used to call me at wildly inappropriate times demanding I do a (non-urgent) task RIGHT NOW – and wouldn’t stop calling until I woke up (since it was usually early morning) and did it.

    I was also hourly and there was some serious shadiness in that she classified everyone in that office as a “contractor” except herself (despite us very clearly being considered “employees” by the IRS guide) so she didn’t have to pay taxes, but that’s a story for another time.

  533. Fifty shades of Nope*

    At my last job, there was a group of women who got together during the workday (not even at lunch time) to read the Fifty Shades of Grey books. They did this in the conference room and would discuss certain parts in VIVID EXPLICIT DETAIL while other people were talking to their mentally ill clients on the phone. I don’t know if that’s more awkward or horrifying.

  534. Clumsy Ninja*

    I was new at a veterinary clinic, and we had two techs who held down part-time jobs elsewhere, in addition to working for that clinic. One day, one of them was talking about her other job, and how she had to go to this training session, and they were talking about how the key was to figure out the client’s problem so that you could then help them solve it. And we’d had a particularly exhausting time with clients that day, so I snapped, “I can tell you what your client’s problem is! They’re stupid!”

    Dead silence, then the tech starts laughing, then everyone else slowly joins in. Then, when she stops laughing, she says, “Clumsy Ninja, do you know what my other job is?”

    “Yeah, don’t you work for another clinic, like [other tech] does?”

    “No. I work with mentally challenged individuals.”

    Sink through the floor….I apologized profusely. I honestly thought someone had said that they both worked for other clinics, and I genuinely never would have said that (or thought it!) had I known the truth. To make matters even worse from my perspective, her daughter had Downs syndrome and autism. I felt terrible. She actually thought the whole thing was hysterical, but I was mortified. I’m just so glad that she asked if I knew what her job was, because I’d have felt even worse if I’d found out down the line and then realized what everyone must have thought.

  535. rageo*

    In my first job out of college, I worked at a scientific institution and had the opportunity to go to a lot of seminars by visiting speakers. In one especially boring talk I fell asleep and, many minutes later, snorted myself awake INCREDIBLY loudly. Everyone sitting around me started snickering or staring. My coworker told me after that from the front of the room, it sounded like someone was yelling “Huh?!?” — the speaker apparently stopped, looked taken aback and repeated the last thing he’d just said. I didn’t go to any seminars for quite a while after that.

  536. John*

    I was a few months into my first “real” job and had to go and see my boss’ boss to get him to review and sign some paperwork for a project we were working. I walked into his office and gave him the papers and a short explanation on what we were doing and what we wanted him to sign. I then proceeded to stand behind him and look/make comments over his shoulder as he started to go through the documents. He stopped and motioned to the chairs in front of his desk. I was embarrassed and awkwardly laughed and said oh yes, of course I shouldn’t be hovering over your shoulder, why don’t I just take a seat.

  537. Leah*

    I once accidentally showed my boss photos of my positive pregnancy test (that I had taken the week before). I was working part-time but had just unexpectedly been offered a promotion to full-time with a significant pay bump. So surprise, I find out I’m pregnant with my first. Not knowing if the two lines would fade on the test, I take a picture with my DSLR camera to show my spouse when he gets home.

    A few days later, as part of my job I needed to take photos of an event that was going on with my personal camera. (You can see where this is going, right?) I took lots of awesome photos. Totally forgot about the pregnancy test photos. After the event I stopped by my boss’ desk and told her all about the fantastic photos we got.

    She asks to see them and I pull out the SD card and plug it into the laptop so we can look through them together, and we do, until we reach the photo of the pregnancy test. She says (in shock – she is very professional and never would have asked otherwise), “Is that a pregnancy test!?” and I, also in utter shock as I flip to another photo, stammer a no, and somehow awkwardly leave the room and avoid her for the last 30 minutes or so of my shift.

    The next day (after realizing there was NO way she didn’t know what it was and also that she can’t legally ask me so it will be way worse to pretend it didn’t happen), I go in and confess that I’m 6 weeks pregnant and yeah, she totally knew. Thankfully she was cool with it and we agree to keep it to ourselves for at least a few months before I tell everyone else. Even now, 7 years later and knowing the outcome, it’s still mortifying to recall the moment as we both stared in shock at a photo of a stick I peed on with a positive pregnancy result. She was actually the first person to find out besides my spouse (and still one of the best people I’ve ever had the privilege of working for).

  539. Laura Mathias*

    My first year out of college I got a seasonal position at a mall candy store. I’ve always been super jittery and nervous in new situations, and my first day was no exception. One of my first customers was a briskly efficient man who I became irrationally convinced was a secret shopper. That of course upped my anxiety and my desire to impress him.

    However, because it was my first day, I hadn’t quite mastered fitting all the candy into their boxes (honestly I never mastered that). Possible Secret Shopper was very helpful/condescending, frustratedly giving me tips on how to fit each candy in.

    Obviously this increased my conviction he was a secret shopper. So of course I defaulted to my usual method when trying to brownnose: banter. The problem is when stressed, I’m about as eloquent as a turnip.

    So without thinking, and with a growing line behind Mr. Efficient, I actually heard myself say, “I like a man who knows how to fit it in.”

    ?????

    I swear, I wasn’t trying for an innuendo. I sincerely meant candy. But there it is. First day on the job.

    I wish I could say what happened next, but my brain floated away and the next few minutes are lost to me. Thankfully I think he and the other customers just ignored the comment, and I was never called out on it.

    But man. Mortifying.

  540. horrifiedgossip*

    Oh goodness. At an old position I had a desk in a rather open floorplan space. The only actual office was my boss’s, and it was visible from all the desks. One day the office was deserted, the boss’s light off and door left cracked open. I was sitting at my desk and chatting with my intern (by “chatting” I mean ferociously complaining about my boss). After several minutes of this I had to step into my boss’s empty office to grab something. Only, you guessed it, the office wasn’t empty. My boss wasn’t in there, thank goodness. Instead it was my boss’s friend & an employee from a different department within the same building. He actually ended up getting my boss’s job the following year. I like to think overhearing my complaints gave him the confidence to apply for the position. And no, I never found out why he was sitting alone in my boss’s dark office. I was too horrified to ask.

  541. Tazimodo*

    My most awkward work moment was when I stepped out of the ladies’ room to see my grandboss in the hall, whom I greeted very cheerily. He said a quick hello and looked away before leaving hastily. Which was when I looked down and saw that I had tucked my skirt into my tights all along the butt. So smooth.

  542. Summer Camp Exposed*

    One summer in college, I was working as a camp counselor. I saw some other counselors had cut the sleeves off their shirts. I thought this was a great idea and spent an hour doing the same to all of my shirts. I blissfully wore these sleeveless shirts for at least a couple weeks. These shirts were ones I had collected over the years attending that camp, so they all had the camp logo, and they ranged in size from skin-tight to over-sized and baggy.

    Then, I got called in to the manager’s office. She had a hard time getting started with the conversation. “Well, you see,” she finally said, “There’s this problem where, ah, people can see into your shirts through the arm holes. I just want you to know there’s nothing wrong with going braless, but, ah, in this case . . .” It turned out I was showing off not just side boob, but entire boob, via the combination of cutting off the sleeves of the over-sized shirts and not wearing bras. In front of children. For at least two weeks.

    I burst into horrified tears and swore I’d fix the problem immediately. I didn’t even have any bras with me, so there was only one solution. That night, I took out my sewing kit and sewed up the arm holes of every shirt so that they were just large enough for my arms and nothing more. And since that summer, I’ve never gone braless at work again.

  543. Kristine*

    I had a medical issue hit the red at the same time as a temp job. One day I had the choice of being unable to continue and leave after only half a day (less really)–or use my break to take a nap. I was off in a corner by myself, and I had no idea where a break room might be (if there even was one). I wanted to be out of the way, not bother anyone, so I figured I’d just take a nap under my desk. I did this for a couple days during my breaks, and it helped. Then my supervisor pulled me aside and told me it was bothering other people (“disturbing and creepy” are the words she used).

    Coming from years of it being common for people to nap anywhere that’s out of the way, anytime they can or need to (high school and college), I had no idea that this would be unacceptable behavior. My only frame of reference was ‘just be out of the way’. Still have trouble figuring out why napping on a couch in a public shared space (break room) is less awkward than somewhere where you’d have to bend over or kneel even to see me.

  544. anon please*

    I had a boss who was completely focused on his work. Long hours, seemingly no personal life. A couple years after I left that job, he passed away, and I went to the funeral. There were photos of him laughing, photos of him goofing around with friends and family. I was so happy to see that he had actually enjoyed his life, since I had never gotten that impression when I knew him. Somehow, the joy I was feeling when I saw those photos before the service manifested as SOBS during the service. I tried to stop, but couldn’t, and eventually had to just walk out.

  546. leukothea*

    I have quite a few, but this is the one that still makes me cringe.

    One summer in between years of college, I stayed on campus and worked in the dorms to host various summer camps and conferences that came through. One group was alumni from 40 or 50 years before — so many sweet little old people!

    We sorted them all into double rooms, men in one wing and women in the other. Upon check-in, we’d tell them their room number.

    One sweet little old woman, named Leslie, wearing a powder-blue suit and with a few strands of wispy white hair barely covering her scalp, came back to the desk and haltingly said that she was in the wrong wing. I looked at the room chart and confirmed that she was in the women’s wing. She kept telling me that she was in the wrong wing, and I kept looking at her name (Leslie) and confirming that she was in the women’s wing, as required. We both ended the conversation puzzled and adrift. I really didn’t understand why she kept saying she was in the wrong wing, and she obviously didn’t understand why I wasn’t helping her.

    HOURS later, it finally hit me — Leslie was a man. It was more common for “Leslie” to be a man’s name a few decades back, and the powder-blue suit jacket and wispy white hair didn’t read as “male” enough — to my very young and clueless mind — for me to understand that I was not actually talking to a sweet little old lady in a suit. I had been talking to him for 10 minutes at least and still thought he was a woman and was rooming in the correct wing.

  547. Chameleon*

    Okay, I know this is late, but…

    I teach Anatomy & Physiology. I am a terrible artist. This quarter particularly, I have gone to draw things on the whiteboard, everything from hearts to nerve networks to kidney tubules…and they have turned out looking like male genitalia. I swear I am not doing it on purpose and I never notice until I’ve already drawn it, and sometimes not until my students point it out.
    ;_; forever

  548. Irukandji*

    As is standard procedure, one of our high-level bosses sent out an All-Staff email notifying about the death of a colleague.

    It turned out the colleague was just fine (but on leave), and a person of the same name had died. That was a hasty (but far too late) email-recall, and horrified apologetic follow-up email. (Psychological assistance was offered to anyone who needed it.)

  549. Alternate for today*

    Too late to the party, but I have one: We were in a meeting with some colleagues participating remotely. We were looking at a presentation so you didn’t have an immediate overview who was logged in to the meeting. Anyway, we went over what had to be done next, who would have time to do it etc. Three colleagues, of whom 2 were in the meeting physically, were sharing a subsection of the workload. One started to complain about the third absent colleague. Some other colleagues in the meeting were joining in, talking about how colleague number 3 was incompetent and wouldn’t know how to do his work if not instructed on every single step. Laughs were had.
    At this point, someone asked, if colleague number 3 – the one everyone was talking about – was by any chance logged into the call. In fact, he had dialed into the meeting as his number was displayed when the organizer checked. He did not answer when the organizer asked if he was with us, but I died at this moment and continue to die on the inside every time I think about this. To this day we don’t know if he heard the conversation, but chances are definitely over 50%.

    (And I can honestly say I did not participate in the teasing and would have interrupted my colleagues if I had been the organizer/team lead because this is no way to handle performance issues.)

  550. Still mortified years later*

    I worked remotely for a large company and was setting up an urgent conference call with my boss and one of his teapot designers in a different state. Rang designer’s secretary and asked if she was available that day as urgent. Was told no she was at a conference for the day – I said it’s urgent could she make time once the conference is finished. Long silence on other end of line – so much so I thought we might have been cut off. Then secretary says – I don’t think she is going to be in any shape to take a conference call after having chemo. Arrrgggh – I don’t know if it was the phone line or my brain filling in words it expected to hear but I never heard the word chemo. I felt so awful – I apologized profusely – I must have said “OMG I thought you said she was at a conference” about half a dozen times. Secretary finally realized I wasn’t an evil witch – just hard of hearing that day.

  551. Mananana*

    I work for the US Army as a civilian. Soon after I started, I was attending training at a different Army post. The training was held in a WWII-era building, that did NOT have separate bathrooms for men/women. Instead, there was a sign on the door with a little swinging arrow that you were to use to indicate whether the facilities were occupied by a man or a woman. A 6 o’clock positioned arrow meant it was empty.

    And it was in the 6 o’clock position when I entered. And was greeted, penis-in-hand, by one of my Soldier/coworkers. Because apparently, my entering the room, startled him. Greatly. He turned around quickly (and before he had completed his intended act) and we just stood there for approximately 857 million minutes, before I backed out of the room. Did I mention we hadn’t actually met before? And that he was the one who was going to introduce me to the Company?

  552. KB*

    A potentially very awkward moment averted, but it still makes me laugh!

    I used to work at an art museum. One day a coworker who worked in the education department passed by my desk, and I noticed his hands and arms were covered in bright blue paint. I assumed he had been working on an art project with some students, but said something along the lines of “Wow, what have you been up to?” jokingly while gesturing to his arms.

    I remember this moment as if it happened in slow-mo. A large grin appeared on his face, followed by a confused, then almost panicked expression. I realized exactly what he was thinking, and then had to stop myself from saying it out loud myself. We just sort of stared sheepishly at each other for what seemed like a very long time.

    He finally asked, “Have you seen Arrested Development?” to which I burst out laughing, partly from relief that he would have gotten the reference as well.

    (If anyone is unfamiliar with the TV show, there’s a running joke where a character paints himself blue in the hopes of performing with the Blue Man Group and naively states, “I just ‘blue’ myself.”)

  553. Katrina*

    For this one, I have to identify myself- My name is Katrina, and I was born, raised, and still live in New Orleans. I was 16 years old when Hurricane Katrina hit. I evacuated and lived in a different state for a couple of months before returning home, and I was/am very stubborn about going by my given name out of spite.

    A few years ago I worked in a busy front desk position where I interacted with both locals and tourists. I was required to wear my name badge, and thus had heard every comment/joke about a Katrina in New Orleans you could imagine. One particular visitor quietly said, “Is your name REALLY Katrina?” I said yes while looking down to count her change. When I looked up, I realized she had a very distraught expression. I was surprised and meant to say something like “Why are you upset?” but all I stammered out was “Why?”

    “Oh my god, you don’t KNOW!” she exclaimed dramatically as tears filled her eyes. She then told me all about the natural disaster that had hit my own home/community/current workplace. I was so stunned, I never interrupted her, and let this poor woman cry over me for what seemed like ages as a line of people waited in line to buy tickets.

  554. NotTeachingAnymore*

    Early in my teaching career, wearing a new sweater dress, casually leaning against the big old wooden desk at the front of the classroom while leading a discussion, I started walking forward only to realize my dress had snagged on a splinter on the desk and was unraveling as I walked.

    And I think it was that same year that, again standing at the front of the room, this time next to a big wooden desk, I started to ease myself casually down into the chair that was always there beside the desk, and . . . kept going down, and down, and there wasn’t any chair. I ended up on the floor.

  555. Iris Eyes*

    So the owner/manager of a small business I worked with made the tactical error or bringing in his girlfriend to do some work for him, they were planning to share a business space (half for his, half for hers). Two of her teen/adult children also came to work for him. They got engaged, but then broke up. At one point we had to unconventionally enter the new property (him and I) because the locks had been changed. Long story short, she shows up, they argue, cops are called. And I’m just there awkwardly in the back ground, wishing I could just get home.

    There was also the guy who came in with his junk out of his pants. I’m not sure he was aware, but that was probably my most awkward customer service situation. I really hope mall security addressed that because I definitely wasn’t going to.

  556. Menley*

    My first job out of college was in the consulting world, and while I did well at several of the projects, on one project, I didn’t meet expectations. The partner on the client took me to lunch to discuss whether or not I would continue on the project. As the waiter approached to take our lunch orders, he handed me a list that had been put together by the other senior management on the team… the list was all of the reasons that they didn’t like me and didn’t want me back on the team (which included the hilarious list-ender “She asked if she could order food for dinner when the rest of the team was perfectly fine eating the trail mix from the hotel lobby”). Since the list was two pages long, I immediately burst into tears. I had never been so intensely disliked.

    The partner in question was a man in his 50s; I was 23. The waiter took one look at me sobbing at the lunch table across from an older man and immediately jumped to the incorrect conclusion that I was his mistress or something. When I stepped off to the restroom to pull myself together, he followed me down the hall and asked if I needed help and that he could cover for me if I needed to escape out the back door! I sincerely wanted to take him up on that but had to go back and endure the worst lunch of my life, at the end of which the partner berated me for wasting his money by ordering a meal I didn’t end up eating out of anxiety.

    1. stitchinthyme*

      Those management people were horrible. If you didn’t fit in, they should have been kinder about it. They could have given you constructive feedback if there was anything you needed to work on, but seriously, disliking you because you got hungry?? They’re petty assholes.

  557. stitchinthyme*

    I know the contest is long since over (I was away last week), but I had to share.

    I was scheduled for an interview that started at 3pm. I’d forgotten to charge my phone, and it was nearly dead, so I left it at home. And then I got lost on the way to the interview, so even though I thought I’d left plenty of time for mistakes, I showed up about 15 minutes late…and hadn’t been able to call to let them know because my phone was at home.

    But, I got there, and was naturally flustered and also sweaty (it was summer). The company owner offered to reschedule, but I said no, I was fine, so we did the interview, including talking to some of the other employees. The company owner was a talker, though, and between that and the interview’s late start, I was still there at 7pm.

    Around that time, the phone rang, and since it was a very small company and after hours, the company owner picked it up. Looking bemused, he said, “It’s for you.” Turned out that my husband had gotten worried because I was so much later than expected; he saw my phone at home so he knew he couldn’t contact me, so he’d found the company info on my computer screen and called to see if I’d left yet. In his defense, he didn’t know that the owner would be the one to answer, and he honestly thought I might have gotten into a car accident or something.

    Anyway, I was absolutely mortified, and after assuring him that I was alive and fine, I apologized profusely to the owner. He laughed about it later — I did get the job and was there nearly five years.

  558. stitchinthyme*

    There was also the time when a manager I knew only slightly (so not my manager) came over to my desk and asked to talk to me for a minute. I brushed her off — I was in the middle of fixing a production problem and needed to deal with it urgently. When I was done I went to find her…and she told me that my manager had just been laid off and she was my new boss. She never let me live down the fact that I basically told her to go away when she was coming to tell me she was now my boss. (She was totally cool and laughed about it. I said she should be glad my first priority was fixing an urgent problem!)

  559. mosaiclife*

    I was working a temp job as a receptionist, and it was the first day at a new job. I arrived to find a receptionist already there. Huh, odd, but okay. I introduced myself, told her I was there from the temp company to be the receptionist, she was confused, knew nothing about it. She tried to reach the boss, couldn’t. Eventually it occurred to the both of us that I WAS THERE FOR HER JOB. Apparently the boss wasn’t pleased with the current temp receptionist and FORGOT TO LET HER GO before telling a different temp agency to send a new receptionist. So I was replacing her. Super awkward, waiting there together in silence. A few hours later, the boss strolls in as if nothing was amiss. Good times.

  560. Heina*

    I once mocked the [Insert Famous White Male Atheist’s Name Here] Award for being “an award that famous atheists, invented to give to other famous atheists for being famous atheists, named after an atheist famous for being a famous atheist”.

    Unbeknownst to me, I was seated at the same table as the (actually rather nice) person who originally came up with the award. She was gracious about it but I still feel mean.

  561. NotCutOutForThisJob*

    Not one, but THREE embarrassing moments at the same job (that I’m still in). Leaving the office for the day in a dress with a somewhat flowy skirt, I trip and fall, and…you guessed it! Skirt flew up and I flashed two male coworkers. I think it may have actually embarrassed them even more than it embarrassed me.

    Second, I was speaking to one of our VPs, and intended to say something about “hand delivery” or “personal service” when I dropped off a document, but ended up saying that I was giving him “hand service” instead. He kindly refrained from comment.

    And finally, after getting angry with an outside caller for calling me “sweetie” in a VERY sexist and condescending tone when he disagreed with my decision, I took a short walk to calm myself. Grandboss saw me and asked if I was ok, so I explained what had happened. The CEO (who is very warm and extremely respectful) overheard, and to get a laugh out of me, jokingly called me “sugar bear” or something equally ridiculous. As he’s always very respectful and kind, it had the desired effect of making me laugh and calming me down, but that comment was overheard by others on the executive hallway, and I am still occasionally known as “cupcake” or “sweetie”. Only in a good natured way, never in meetings or in anything but a friendly, joking manner. I also get to call them “honey” or “sweetheart”, but it’s still a tiny bit awkward remembering the origin.

  562. KB*

    When I was a teenager, my dad owned a small business, and over the summers I would help out every once in a while- just filing, cleaning up, menial stuff. One morning my dad gave me some cash and asked me to pick up coffees for his coworkers from the grocery store down the street, which had a coffee kiosk inside. I was carrying the coffees in a drink holder through the store when a gorgeous boy walked by me. I tried to *subtly* turn back to check him out, but somehow angled the drink holder so all four HOT coffees spilled on my chest. I remember thinking to myself, “Do not yell the f-word in a public place, do not yell the f-word in a public place.” What came out was the sh-word… followed promptly by the f-word. Right by the grocery’s busy check-out lanes. I was too embarrassed to go back to the kiosk to replace the coffee, and I probably didn’t even have enough money on me. So I decided to deliver each individual cup (well, half-cup) of coffee to each coworker with a smile as big as the obvious coffee stain on my shirt. Nobody said anything, but I’m sure they put two and two together. At least they were paid for by my dad.

  563. Kristin*

    I hope it’s not too late to answer this – I think that book must have been written for me.

    My most (recent) embarrassing work situation happened a few weeks ago.

    I’m a substitute teacher, and I teach at a different high school every day. This means I never know what the bathroom situation will be. Gender neutral or not? Hidden two floors away inside an unmarked teacher’s lounge? Accessible only by a key I wasn’t given? The upside is that when I do something truly awkward, I never have to see the witnesses again.

    On this occasion, I was working in the library, where in the morning there had been a staff meeting, and a teacher had caught my eye. I didn’t recognize him, and I would definitely have remembered him because he was very attractive. I wondered if I might bump into him later.

    I sure did.

    I was using a bathroom on the second floor that was key-entry only (I had a key that day!), when in he walked. (I missed the second lock that would have flipped the “Occupied” sign.) I was naked from the waist down, hunched over the toilet seat (which directly faced the door) and texting. He was horrified. We both yelled apologies at each other in a mortified stupor. But in his haste to flee and unsee, the buckle of his key lanyard got caught in the door. I watched it move up and down on my side as he tried to free it, eventually coming to a halt. There was no way he was re-opening that door.

    “Hold on! Hold on, I’ve got it!” I yelled, as I tried to quickly pull my pants back up with one hand as I reached towards the door handle with the other.
    I opened the door, and the keys fell to the floor, abandoned.

    I bent over to pick them up at the same time as Attractive, Unwitting Bathroom Invader leaned over from out of sight of the door, facing AWAY from me so hard that he couldn’t even see where his keys were, felt his way to them and swept them up. I had to quickly back up into the bathroom to avoid a collision, and he fairly ran away. Frantic apologies were exchanged once more as all this took place.

    I haven’t seen him since.

    This might be why I’m single…

  564. Constant Reader*

    Adam Kotsko’s “Awkwardness” (2010) addresses the same topic, but more from an academic sociology perspective than that of The Cringe Channel.

  565. Oh My.*

    A few years back I was working at a remote construction site, and to access it you had to drive up a logging road. You were required to call out your location at specific points over the radio to avoid accidents with big trucks. One day I happened to be in the front seat of a truck and had the chance to use the radio to call out our locations on the way up to site. Yay. So much fun.

    Once I was at my desk one of my coworkers said they had heard me over the radio that morning, and in response I said something along the lines of “Guess I’m a call girl now!”

    It took a moment for what I had said to really sink in. I was teased about that for the rest of the job.

  566. Jane the ChairBreaker*

    A couple of years ago, I went to a seminar at a local lawyer’s office. I knew him through a political campaign and he had a seminar on copyright protection. They had set up it in one of their large conference room. Very nice…artistic furniture.

    My first indication was that there was going to be something wrong was a creak from the chair. Next thing that I know, I am on the floor in the midst of chair fragments. Fortunately I was not hurt, but it was terminal for the chair. Through the lawyer’s staff apologies (subtext: don’t sue us), all I could think of was…”I’m fat”.

    The only saving grace was that another chair broke in the same seminar.

    Whenever I go to another seminar at that office, I always get their early and snag the sturdy bench.

  567. SEOBossGirl28*

    Oh this book sounds so interesting! Interesting enough to convert me from a long-time reader to first-time commenter.

    We have a water delivery guy who is suuuuper awkward. Super nice, but just doesn’t always pick up on social cues. I think he has a crush on me, because he always, without fail, comes up to me every time he delivers water to discuss all things about our water (I’m the only woman in the office, so a bit of sexism may play into this). Without fail, he always asks how much we need, tells me how much we go through, asks how many refills I’d like him to leave, where to put it, tells me when he’ll be back, asks if I have his card to call him if we need more, etc. I’d understand if he had these questions while he was new and getting used to our account, but it’s been a good year now and my instructions literally never change. I thank him for coming and ask him to just replace the empties in the same closet we always keep them. Our last water delivery driver never even talked to us – this guy always makes a 15-20 min production out of delivering WATER.

    Today, we just appointed a new guy to take care of our snacks – including water delivery. This guy tried to take control of the interaction, but the delivery guy just would not leave my side (I’m at the executive level, so it’s a bit below my pay grade to coordinate this, hence the new, entry-level guy). Water delivery guy kept asking for instructions, new guy would tell him, but he wouldn’t listen to him – he kept asking ME what to do.

    Hopefully he’ll get the hint soon that I am not in charge of water deliveries. We’ll see. He only comes twice a month, so it’s not a HUGE imposition on me to handle it, but it’s pretty funny.

  568. Drew*

    I (unknowingly, of course) gave my first presentation in front of the big bosses with my zipper unzipped.

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