your 10 most awkward work moments

by Alison Green on September 10, 2013

I recently asked readers to tell us about their most awkward moments at work. Here are 10 of the funniest “whoops” moments you shared.

1. Misdirected love

“I told my boss I loved him at the end of a phone call. I was multi-tasking while we talked and distractedly ended the call with ‘All right, I love you, see you later!’ like I usually do with my family. I caught myself and was very confused and started rambling with such eloquent statements as ‘Oh my god! I didn’t mean that. I absolutely don’t love you….no, I mean, I like working for you but I know you’re married and I’m married, and I’m not flirting so please don’t report me to HR for harassment…’ At some point during my back-pedaling, he just hung up.

2. Hello, sailor

“I was working for a defense contractor and wanted to invite all the members of my team to a New Year’s Eve party, so I sent out an Evite using our Outlook distribution list. Or, I thought I did, until I started getting replies like ‘Am stationed in Italy but will try to make it.’ I’d accidentally used a Navy client list whose name was one letter different from my team’s. The invite went to about 7,000 sailors.”

3. Slapped my boss in the face

“I once slapped my former boss in the face. I’m a woman, he’s a man just a couple of years older than me. We had a good relationship, and we were talking and joking around. He said something sarcastic, and I raised my hand to mock-slap him playfully. (Note to younger self, that was really stupid.) He turned his head suddenly, into my hand, and it turned into a full on slap. He looked totally shocked and I was horrified.”

4. Construction zone

“I was supervising a design update to the office suite across the hall from where my office was located. It required some light construction – drywall, painting, carpet, stuff like that. The contractor randomly asked me to come over to resolve a quick issue. As we walked around, he mentioned that the new cabinets and counters had just been installed yesterday. Without even thinking, I walked right into the kitchenette to see them. Which was unfortunate because that room was full of flooring guys who were laying the mud for the new floor onto the concrete.

In my stiletto heels, I slid on the mud halfway across the room INTO the new cabinet area, executed a weird twirl that caused my knee-length skirt to fly up, and fell through the doorway onto a roll of unwrapped carpet. I shriek-mumbled an apology and limped quickly back to my desk across the hall. I didn’t realize til later that I’d left a trail of muddy high heel prints all the way out the door and into my office.”

5. Pants disaster

“One day I was walking into work, heading to my cube and out of no where, my pants fell down. Like around my ankles. I’d like to think this was because I had lost some weight, but I honestly don’t really know. Luckily it was about 7 in the morning on a Friday when most people worked from home. I was able to quickly duck in to an empty office to fix the situation.”

6. That’s not the doorknob

“Not once, but twice, while standing in a doorway talking to someone, I reached behind me to turn the doorknob while still facing the person I was conversing with. Both times, the ‘knob’ I grabbed wasn’t connected to a door. And both times it was a very flamboyant (but straight – think Robin Williams) guy named Andy. One more time and I would have had to propose marriage to him.

He knew it wasn’t intentional, and he was not upset by it. However, he wasn’t too happy that his being groped became a story that was told over and over again by those who witnessed it. He did finally ask someone in HR to speak to them to ask them to let it die a quiet death.”

7. The dangers of the mute button

“One time I was on a conference call for training. There was a code to punch on the phone keys that would mute and unmute the caller’s phone and I lost track of whether I had muted or unmuted. I then told a coworker, thinking that the phone was muted, that the training was so incredibly boring, I had better things to do, and I just wanted to blow my brains out every time I heard X (the trainer) speak. Well…it wasn’t on mute. Another caller spoke up and said, ‘Whoever just said that, we can hear you. You might want to learn how to mute your phone.’ Thankfully there was no way to know it was me, but I was mortified nonetheless. Now I make sure I keep the mute/unmute code posted at my desk.”

8. What’s under here?

“Our company had just moved into a brand new building. In an attempt to get everyone’s work space functional as quickly as possible, the computer techs came through and connected phones and computers, leaving the cables and wires in a mess under each desk. (This was just a big room with all our desks next to each other.)

I kept getting my feet caught in the cables while sitting at my desk and finally decided to just straighten them out myself. I pulled my chair out, got down on my hands and knees, crawled under my desk and proceeded to push back the cables when the president of the company came through, showing off the new digs to a couple of his buddies. Hmm, I thought, this is a little awkward, but maybe if I just sit still here under my desk they’ll pass on by and that will be that. They stopped right at my desk and as they stood and chatted, the president pushed my chair in under my desk. The resistance he encountered was, of course, ME, because I was crouched where the chair was supposed to go. Their conversation stopped, they stared at me, I crawled out from under my desk, stood up and mumbled something about computer cables and quickly excused myself. I might also add I was wearing a dress and high heels.”

9. Did we have kids together?

I sent an email to my ex-husband calmly, but in a very verbose way, explaining to him his responsibilities and how we had children together so his obligation to get the child support to me on time isn’t optional as their needs cannot wait, etc. Nothing nasty, but think more broken and weary. Actually, I meant to send to my ex, but rather sent it to a co-worker with a similar name. Yeah.

His response was awesome though: ‘I don’t think this was meant for me, but the 90′s were a crazy time for everyone so who knows. Will you take a check?’

10. Parental confusion

“I once called my boss ‘Dad.’ You know how school children sometimes accidentally call their teacher mom/dad? Well, I’m a young-30s woman who called her boss Dad. To his face. I think it was something like ‘Dad, what time is the conference call this afternoon?’”

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{ 46 comments }

{ 46 comments… read them below }

  2. Lily in NYC*

    These are so funny! I’m bummed that I missed the original post when I was on vacation or I would have submitted the time I accidentally mooned Maya Angelou at a board meeting. She was so mean. I also once emailed a regular update to my entire office and signed off “Love, Lily” without thinking – I got so many ridiculous responses to that.

    1. Liz in a library*

      You…mooned Maya Angelou?! What a story that must be!

      I’ve heard from a colleague who worked an event that she spoke at that she wasn’t terribly pleasant there either.

      1. Lily in NYC*

        I was wearing a semi-short dress and a thong and was crouching down fiddling with the a/v equipment when I slowly tipped over and fell – while my dress hiked up to my waist. I was so mortified. I tried to laugh it off but she gave me the most imperious glare I have ever seen and sniffed at me with scorn. Wayne Newton was there too but at least he laughed. We had a weird mix of celebrities on our board. Ms. Angelou was a nasty piece of work – she made everyone miserable.

      2. Anonymous*

        I worked on a student programming board in college and she had the same reputation in those circles as well. From what I understand, she refused to come if she had to work with students.

            1. Chinook*

              I would never judge a person’s personality based on how they treat someone like Oprah. Of course she is treated well – she has a lot of power and prestige. But, it wouldn’t surprise me in the least if some of Oprah’s guestss, on the other hand, treated her staff horribly (unless it is well known that Oprah stands up for her staff, but you get what I mean).

  3. LisaLyn*

    I loved that thread, although I read it mostly silently screaming in horror with my hands clasped over my mouth. I feel embarrassment acutely, for myself and others. ;)

  4. Ellie H.*

    These are great – a few I didn’t see in the original thread but I definitely think these are the greatest hits. I had a mortifying work moment the other week that I was just too embarrassed to share (and still am).

    1. Jessa*

      Everyone has one of these, whether they tell them or not, it’s fun to know that others share in the moments.

  6. Marigold*

    LOL. Even with pants falling down as an option, I still think calling my boss “dad” would be the worse for me. Well, that, or groping Andy.

    1. tcookson*

      Groping Andy the *second* time would have to be the worse . . . because how do you explain that you did THAT again??!!

  7. sharon g*

    I had a coworker say “Bye! I love you!” to me. He was leaving for the day, and said it as he was walking out the door. Luckily, we both have a sense of humor, and both busted out laughing.

  8. cwes1492*

    I just heard a story about one of my co-workers, who was walking vigorously towards a conference room. She rounded a corner, and her swinging arm nailed the head of the office in his manly parts. Apparently he doubled over and moaned so loud that the whole office turned around to see what happened! This happened before I joined the company, but it’s become legendary. Talk about an awkward moment!

        1. cwes1492*

          From what I hear, there was a reenactment at our company offsite that year that had him in stitches, so hopefully he’s amused. He’s one of those very smart, high-powered executive types, so it’s kind of nice to have a bit of a humanizing story about him! And the colleague that accidentally hit him is still with the firm and has been promoted a few times, so clearly he hasn’t held a grudge!

  9. Dang*

    HA! I have a strange paranoia about saying “love you” by accident or calling a superior mom or dad. So funny that those two are both in there!

    1. Secret for this one*

      This is bad, because behind her back, several of my coworkers call our boss “Momma.” As in, “Did you send that to Momma?” I’m terrified I’ll call her that for real, so I try not to refer to her that way.

      1. Cait*

        At my last job, a manager started referring to a new hire as “Snooki” behind her back. This went on for a week or so until he caught someone else using the nickname and went off on that person about how we all needed to stop calling her that because eventually someone was going to slip up and say it to her face. I’ve always wondered if he hadn’t already made that gaffe himself.

    2. Chrissi*

      I have a male coworker that works in another office and we often talk on the phone regarding technical questions, which then segues into a short chat about personal stuff from time to time. It seems like I’m talking to my brother in a way. I always concentrate VERY HARD to not say, “ok, love you, bye” at the end. I’ve come close a few times, and I would be mortified.

  10. EA*

    I had a pair of professors once, husband and wife, they were co-teaching a course, and on the first day, their introduction went something like this “You can call us both Professor D, you can call us by our first names, or, since we have teenagers, we will probably respond to ‘Mom’ and ‘Dad’ as well”

    1. Evan*

      That reminds me of my high school math teacher, whose husband was also a math teacher at the same school. Neither of them had a doctorate, though – or at least, everyone always addressed them as “Mr. G” and “Mrs. G.”

      Actually, they handled the situation really well; the only time it came up that Mr. G. was employed by the same school was a couple times when Mrs. G. was suggesting we might be interested in electives he taught, and once when I got an extension to turn in my homework after-hours to Mr. G. since he was already staying late that evening.

    1. QualityControlFreak*

      Hah. I am impeccably professional in answering the phone at work. It goes the other direction for me: I sometimes answer my home phone with a business greeting.

      1. Chinook*

        When I have had a stressful week at work and then go to visit my parents, I have been known to answer my Mom’s store phone with the greeting from my weekday job. It has happenned so frequently that I now pause to verify my surroundings before speaking.

  14. embarrassed*

    I was about 8 months pregnant and meeting with my boss to discuss the plan for training the temp we had hired to take over my work while I was out on leave. Suddenly I felt something warm trickle down my leg. I stood up to excuse myself… and my water broke. So I am standing there in a pregnancy dress and there is this huge puddle on the floor of my boss’ office! Then my (single, male, with no kids) boss starts to panic and asks if he should call 911. I ended up calling my husband to come an pick me up, the whole time, sitting there with my boss, and he just had this look of horror on his face like he thought I was doing to die. Now I am on baby # 4 and my coworkers STILL have not let me live it down.

  15. JenTheNiceHRGirl*

    Years ago I was in an executive meeting taking minutes. Apparently my boss was bored and she was picking at her fake nails… well one of them popped off and hit the president right in the forehead. LOL

  16. Anonagain*

    Yikes. I’m just sitting through an interminably boring phone meeting, and flipped on a Sudoku game to keep myself occupied (and awake). Of course that would be the moment when my Director pops his head around the corner of my cube to ask me a question – awkward!

  17. TheAssistant*

    Even though I read all 500 comments on the original thread, this moment escaped me until just now. But perhaps it will be cathartic to share.

    I online date, and I was texting a guy whom I’d never met in an attempt to coordinate a date. I was also the assistant to a very busy executive, and I had to keep my personal phone (our non-profit didn’t issue company phones) on my desk, not on silent, in case she texted me in a meeting and needed something. I received a text and I opened the message without paying attention, thinking it might be my boss. It was the guy I hadn’t met, and he sent me…a picture of his penis. I let out a tiny scream and locked my phone immediately.

    A few hours later, I’m scurrying with my boss to a meeting. She asks me a question about our consultant I didn’t know how to answer, and I volunteer to text him. She says yes, and is looking at my phone as I unlock it and pull up my messages. There, in all its glory, is the penis. I panic and lock the phone, then unlock. Again. The penis. At this point, I’m fumbling with the phone, trying to rid myself of the image, while we’re walking at a fast clip down a hallway. I stammered out an excuse that I’d join her momentarily and ducked into an empty office to once and for all delete the photo and text the consultant. I don’t know if she saw, but really, how could you not?

    The incident was never mentioned.

    1. tcookson*

      So this isn’t at all work-related, but I once had some random person send me a picture of a woman’s you-know-what with a football pointing toward it.

      I called the person who sent it to me, and this guy answered the phone. I said, “You just sent me a nasty picture!”

      He started stammering and stuttering and trying to explain. I said, ” I don’t care why you sent it to me, but you’d better take my number out of your phone and don’t you ever send me a nasty picture again as long as you live!!!”

      And he just said, “Yes, ma’am. Sorry, ma’am . . . ” and hung up.

      I was mad at the time, but it’s pretty funny looking back . . .

  18. Katy*

    Sent an instant message to a coworker about some of the folks at our Help Desk not being the “sharpest crayons in the box” when someone from the Help Desk was actually working on her PC. Let’s just hope he doesn’t remember my name was on that incoming message!

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