I ran into my new boss in the apartment of my one-night stand

by Alison Green on June 10, 2019

A reader writes:

I recently engaged in some, um, consensual adult activity under the mutual understanding that it would be a temporary relationship at another person’s apartment. No work productivity was harmed in the making of this hookup.

After a pleasant night, I walked out of a room to discover that, not only did the man I spent the night with have a roommate, that roommate had a pleasant night of their own WITH MY NEW BOSS.

I’m in my mid-20s and my boss is in his mid-30s. The roommate he was seeing is closer to his age (early 30s) while the person I was seeing is closer to mine (late 20s). Neither of us are married and we live in a large city, so it’s not like either of us learned something that would be salacious gossip.

As part of my job, I have to get up very early every morning to meet a deadline. As if the experience wasn’t awkward enough, my boss (who presumably was up early to take a look at my work once I was done) joked that he could make me coffee and find out the wifi password for the apartment at 6 am as I packed up my laptop to head to a nearby coffee shop to get the work done.

I declined. This was yesterday.

So I literally never acknowledge this, right? What do I do if he ever brings it up? My first instinct is to crawl into a deep dark hole and die.

But he’s doing a marvelous job of pretending nothing happened so far, so I’m inclined just to follow his lead?

Help.

Ohhhh.

I have to admit, I laughed. I’m sorry.

I actually think your boss is handling this kind of beautifully — cracked a joke in the moment (when something had to be said — can you imagine if instead he’d stared at you in panic?) and then promptly proceeded to ignore it.

Trust me, he felt the awkwardness too. But he’s handling it well!

Similar to the letter-writer last week who matched with his interviewer on a hookup app right before their interview, the best thing to do here is to wipe it from your mind.

If he does bring it up, you can simply say, “That was awkward and my plan is to pretend it never happened.” Subtext: Never speak of this again!

But ideally that won’t happen and you will now both engage in the polite fiction that neither of you spotted the other. Ideally you will even each silently admire the other for your discretion and tact.

Also, hurrah for this being a one-night thing. This would be much more problematic (and suitable for a sitcom) if you were each dating these roommates.

Read an update to this letter here.

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{ 203 comments }

{ 203 comments… read them below }

    1. Princess Consuela Banana Hammock*

      That was my first and second reaction! I like how the manager handled it, and I cosign on the “pretend it never happened” approach :)

      I suspect I’d find it incredibly awkward if I were in OP’s shoes, but I have to say… this is going to be an amazing story once there’s a bit more distance (it definitely made me laugh).

      1. Bee*

        This is simultaneously so, so uncomfortable and so, so funny. Ignore it as best you can, OP, and look forward to the time when you can tell this story to uproarious laughter.

        1. serenity*

          No work productivity was harmed in the making of this hookup.

          I think the way OP is framing this is pretty hilarious. Distance (and time) will only make it more so!

          2. SunnyD*

            I chortled at that line.

            Sooooooo awkward, OP, but also so delightfully human. Keep on acting with discreet class, and it’ll all be good.

  2. fposte*

    I also laughed, and I think it’s awkward in the moment but really no big deal. Follow the manager’s lead.

    And ultimately it’s not like he assumed you were never having sex, and it’s not like you assumed he was never having sex. You both just got a little closer to the reality than you’d have chosen. It’s kind of like a bathroom stall door swinging open while you’re on the toilet and the boss is walking by. It’s a “Wouldn’t have planned that,” but it doesn’t reveal anything compromising or novel.

    1. No Green No Haze*

      It’s kind of like a bathroom stall door swinging open while you’re on the toilet and the boss is walking by. It’s a “Wouldn’t have planned that,” but it doesn’t reveal anything compromising or novel.

      ^ This all the way. I would absolutely be on Team Crawl In A Hole And Die, but at the same time, this is being handled beautifully by both of you, as far as I can tell. Boss addressed the awkward at the right time with a graceful joke, you declined to stretch the experience out longer, both of you can sail forward knowing that the door of ever mentioning it again is firmly closed and locked from both sides.

      But keep that door locked. Once you get over feeling awkward about it and it starts to feel funny, its status as an amusing anecdote needs to be absolutely firewalled. Thanks for telling us, mind you! tell your best (non-work!) buddy, or your mom if you guys are that comfortable. Nobody at work, ever, nobody in adjacent business circles, ever, and certainly not Boss. This is a boundary you just can’t meddle with.

      1. Jen S. 2.0*

        I guffawed out loud at “No work productivity was harmed in the making of this hookup.”

        Yep, chuckle as best you can in the moment, lock it in the vault, and let Boss be impressed and bemused by your cool discretion. You’re allowed to have a fling, and you’re allowed to Not Speak Of It at work.

  3. Drew*

    For whatever it’s worth, OP, I think you handled the situation beautifully. “No, we’re not going to have a work conference in the kitchen shared by our mutual funtimes partners, see you at work, I’m going to get extra shots in my latte this morning.”

    Also, kudos on not making a “Huh, small world” remark where it might be misconstrued.

    1. Hey Karma, Over here.*

      Also, kudos on not making a “Huh, small world” remark where it might be misconstrued.
      I see what you did there. :)

    3. Snark*

      Can you imagine being the funtime friend? Walk outs sleepily, stop, stare. “Do you….know each other?”

      “Yep, he’s my boss. Synergies, amirite? Got a printer?”

        4. SunnyD*

          Right, but just real quick while I have you… Those TPS reports, they need a cover page.

        5. Ophelia*

          “We’re piloting a new performance review system, could each of you please fill out these questionnaires for the 360?”

  4. BRR*

    I’m with you that my first instinct would be to crawl into a hole and die. Thankfully your boss is handling this perfectly. Hopefully this is something you can laugh about after some time has passed because I think laughing at it or being embarrassed are your only two options.

  5. DC Cliche*

    It’s like the first episode of Grey’s Anatomy, with a twist! Best of luck to ya’ll.

  6. CmdrShepard4ever*

    I am curious Alison what your advice would be if this had happened after OP had gone on a few dates and really saw potential for a long term relationship with the person, and the OP’s boss also happened to be dating the roomate?

    1. Partially Bigoted Zealots*

      Write a treatment and pitch it to networks for direct-t0-series sitcom deal.

        2. CmdrShepard4ever*

          I think setting the show/movie where OP and boss work in HR department and calling the series “Friends and Benefits.” I think going along the rom-com route, to add a twist ending OP and Boss realize that they are more compatible with each others partner. Each of them then secretly tries to break up each others relationship and start dating the other roommate.

          1. Dr. Doll*

            Friends AND Benefits has me shaking with Austenien laughter! I LOVE THAT TITLE and I think someone should immediately make that show.

          2. MoopySwarpet*

            The details are just vague enough to not be able to tell for sure if all 4 participants were male, but if they weren’t, this would be an even bigger plot twist . . .

          3. BeenThere OG*

            I think you might save HBO with this series, run now and pitch this! I need something new to watch.

      4. Oxford Comma*

        There was a Britcom years ago about a married couple (I believe it was called Executive Stress) They were both looking for jobs and unbeknownst to the other landed jobs at the same company, which had a strict no couples policy. Both had to pretend to be unattached to keep their jobs.

        Not quite the same thing, but this reminds me of it.

        In any case, OP, I think your boss handled it well and I agree about taking his cue.

    2. Phony Genius*

      We could have been dangerously close to “My boss stole my girlfriend” territory. (I am sadistically waiting for this one to be a story here.)

    4. Becky*

      Anyone watch iZombie? I’m only at the end of season 2 but main character (Liv) has a roommate (Peyton) who has a semi-relationship with main character’s boss (Ravi).

      1. SunnyD*

        I have SUCH a crush on Ravi. Gah of course Peyton goes for him!

        /also have a crush on Peyton, so, kismet

      2. Bowserkitty*

        I always forget Ravi is technically Liv’s boss. They have a great comradery that I view as simple colleagues and close friends.

    5. SarahTheEntwife*

      At that point I would think you’d need to have a quick “so…this is moderately awkward” conversation with your boss just to establish boundaries.

  7. Jam Today*

    This is AMAAAAAAAAZING and has all the hallmarks of a scene in a saucy Hollywood sex comedy. I’m running through the imaginary casting in my head (any preference on who you would like to play you, OP?) as well as the rest of the script. I love this. I’m so happy about this letter.

      4. OlympiasEpiriot*

        Or Clark Gable.

        Yup, day late and and dollar short to this one, but yesterday was a madhouse, I kept all the plates spinning and today I had 15 minutes to recharge before heading back into the fray.

        Definitely a Cary Grant/Clark Gable/Carole Lombard/Jean Harlow/Frederick March/William Powell/Jean Arthur vibe.

        Pick two and mix-and-match as your fantasies require. ;-)

  8. L.S. Cooper*

    I think my first instinct would have been the same as yours. Definitely finding a dark hole to crawl into. Or just quitting the job. Or just laying face down on the floor, mortified, for the rest of my life.
    But your boss seems pretty reasonable, and I bet that, once the initial embarrassment fades, this will be a hilarious story for non-work friends.

  9. Fiddlesticks*

    Well, at least neither of you walked out of your hookup’s room naked….right?!?

    You and your boss did exactly the right thing in the moment of revelation. Now you’re continuing to do the right thing by not dwelling on it or discussing it further. And in a few years this is going to be one hilarious memory!

    And I admit it, I might have giggled slightly too. Sorry OP, and I hope you have a wonderful rest of your week. :)

    1. Traffic_Spiral*

      Yup. Provided that neither of you was naked, and neither one is married or has some other reason why you shouldn’t be sleeping around, it’s a pretty non-problem. Adults hook up. It’d be like if you saw him at a bar you go to: say hi and then go your own ways.

      1. NewHerePleaseBeNice*

        Um, I don’t think there’s any need to suggest the OP is ‘sleeping around’ on the basis of one one-night stand!

        1. Traffic_Spiral*

          Well, ONSs are pretty much ‘sleeping around’ by definition? I mean, there’s nothing wrong with it, provided everyone’s consenting, using protection, and not cheating on anyone else, but they aren’t exactly being celibate or restricting themselves to matrimonial congress?

          1. NewHerePleaseBeNice*

            It may be different in the US (I’m in the UK) but ‘sleeping around’ suggests promiscuity / lots of partners and is quite a morally judgmental (and even offensive) phrase to use, particularly used against women.

            1. SarahTheEntwife*

              In the US I think it varies. There’s a huge negative connotation if someone is supposed to be in an exclusive relationship, but it’s more neutral used for someone who’s single.

  10. Phony Genius*

    Alison, you’re right. This sitcom just writes itself. I wonder if any TV/movie screenwriters scan this site for material.

    OP: Keep us updated on everything that happens. We need more scripts for a 13-episode series order. (Just kidding, I think.)

    2. DC*

      I have…. actually written this pitch in past years. It is just as funny as you think (well, I think so anyway.)

    3. Ask a Manager* Post author

      There’s actually now a film and TV agent attached to the book and website! It almost certainly won’t go anywhere but it’s fun nonetheless.

      1. Phony Genius*

        I’ll be the first to say that I really think this could be made into a cable TV series. Actors would portray the situations (in a somewhat exaggerated manner), and Alison would voice-over advice of how to handle it. Then the actors would portray that advice (with the option to also portray the wrong advice and consequences). There could be 3-4 situations per episode.

        2. Washi*

          I actually want it to be kind of a Call the Midwife format where Alison and her cats are the stars of the show but there are vignettes of the letter writer’s lives each episode.

          1. smoke tree*

            I was thinking it could be like that BBC Beatrix Potter series (anyone else remember that?) where each episode opens with Alison having a cup of tea with the cats and opening her inbox to the story of the day.

        4. SunnyD*

          I want a Mystery Science Theatre 3000 format, with Alison and a robot watching shows with dysfunctional work dynamics, throwing popcorn, cracking jokes and giving sage advice.

          The Office
          Crazy Ex Girlfriend
          The IT Crowd
          Scrubs
          Parks & Rec
          30 Rock
          Bones
          Mysteries of Laura
          Dexter (too dark?)

      2. Detective Amy Santiago*

        Did you pitch my reality show idea where we toss the worst offenders in a house together? :D

        1. Rusty Shackelford*

          Who got voted out last night – Ghosted My Girlfriend and She’s My New Boss, or Refused To Give My Best Employee The Day Off For Her Graduation?

      4. OlympiasEpiriot*

        That’s great! (And fun. I think a series like this could work really well.) But, would the letter writers be credited as co-authors?

  11. animaniactoo*

    OP, I feel for you. On the plus side, it looks pretty clear that he’s not hypocritical or unprofessional himself, and not inclined to hold this against you somehow. Which is pretty awesome as far as “mining the good from the bad” goes.

    May the awkward pass quickly!

    (sorry, yeah, I laughed too. I hope you’re also laughing somewhere in all of this.)

  12. Bend & Snap*

    If it helps…I walked into a meeting last week to train some executives, and one of them was a one-night stand from a couple of years ago. We had to introduce ourselves and it was awk AF.

    I wanted to dieeeeeeeeeeeeeeeeeeeeee

    1. Ros*

      I’ve had that happen.

      Erm. Twice. *shrugs* My early 20s were fun, but really, you’d think this would happen less in a town of several million people.

      Much sympathy. Awkward AF.

      1. Elemeno P.*

        My early 20’s were also fun, but being in the same company as I was then has taught me that a Very Large Company (in different cities!) is not nearly large enough sometimes, even when you were (and continue to be) in very different departments.

        Thankfully, it’s an industry where Fun Early 20s is pretty common and people stay for a long time, so everyone from entry level to senior management has to maintain a polite fiction with someone, and there’s no judgement for it.

      1. Bend & Snap*

        Ooh, I don’t! At least I went into it dressed for the day and from a position of some authority. LW got a nasty shock the morning after.

    3. Close Bracket*

      A ONS of mine works somewhere at my company of several thousand. I’m not sure I could pick him out of a line up at this point, and I am sure he could not pick me out of a line up bc my appearance has changed in the last few years. I know he is here, and I am prepared to graciously act as though we have never met if we do run into each other. He, however, does not know I am here, so I am also prepared to laugh my ass off internally if he recognizes me.

    4. AthenaC*

      I’m actually connected with a couple one-night-stands on LinkedIn. Similar industry (or same company), and they sent the request, so … why not?

      2. Blue Horizon*

        “I noticed you were connected to X on LinkedIn. X has applied for a role with us and we’re doing a reference check on them right now. Are they a good performer?”

        1. Curmudgeon in Califormia*

          OMG, I had to squelch my laughter in my open plan office on that one. Thankfully I wasn’t drinking anything, or I would have needed a new keyboard.

    5. sheworkshardforthemoney*

      Years ago I met a friend for a ONS at a major downtown hotel, he was in town for a conference. I left early in the morning, not early enough because when the elevator opened at the main level, my boss, his boss, and several colleagues were waiting for the elevator. They going to a breakfast meeting in the hotel terrace restaurant. I had known that but the hotel name had slipped my mind. I pretended that I didn’t see them and no one ever mentioned it.

      2. Anonymous for this one*

        I worked for an ob/gyn department as a marketing manager in the institution where I receive my health care. After about three weeks, I realized that about 7 of the 22 physicians I worked with had — in the course of my annual visits over the years — seen all my girl parts at one time or another.

    7. embertine*

      I’ve started a new job at a small company to find out one of the contracts managers was a.. two night stand? from a few years back. Only awkwardness was that I had found out he had just got engaged at the time when he told me he was single, and he knew that I knew.

  13. The Original K.*

    I laughed too, and I am also on Team Pretend This Never Happened. (Hee hee hee.)

  14. Naomi*

    Usually the sitcom-hijinks letters are indicative of a terribly dysfunctional workplace. It’s kind of nice to have one where everyone handles the awkward professionally, and we can laugh instead of cringing in horror.

  15. Justin*

    Oh man thank you for this story. Just, thank you.

    Reminds me of running into my grandboss at our (mutual) college reunion years back. We were unsober. Nothing occurred of course but it was… well it was funny.

    1. LurkNoMore*

      I remember walking by the founder and CEO of my giant corporation in an alley in Kyoto – he was throwing up and the manager of my division was trying to keep him from tipping over. Just kept on walking….but if it was in the days of camera phones, I would have been tempted!

  17. MuseumChick*

    Ooooooh no, OP, I’m sorry! This is awkward enough to be an episode on a sitcom! Yes, continue to pretend that it never happened it is the “incident” that shall not be named.

  18. Seeking Second Childhood*

    I was so very relieved that your boss was there for a fourth human. Not surprising your companion as his regular own!.

    2. Carrie*

      Butbutbut there aren’t enough syllables, it doesn’t scan! It needs like four more beats to scan!

      1. AthenaC*

        Well that’s easy enough to fix –

        “Every morning I run into my new boss in the apartment of my one-night stand.”

        You’re welcome. :D

        1. Matilda Jefferies*

          Dammit! Now I’m going to be stuck with that earworm forever, tyvm!

          Also, it’s brilliant. :)

    3. Seeking Second Childhood*

      My mind skipped like a rock over the water and I have a Christine Lavin earworm: “Never Call Your Sweetheart By His Name.”

      1. detaill--orieted*

        And if you’re afraid it might happen again . . . well, heck, “If you want space, move to Utah”.

    4. KayEss*

      And the advice is even, “Shut the door [metaphorically, on the incident], baby, don’t say a word.”

  22. CatCat*

    These are some of the richest threads of life’s rich tapestry. Awks all around. Y’all are handling it well. And at least the boss wasn’t the roommate.

    1. Katherine*

      I was afraid that was going to happen, but luckily the boss was just visiting, too!

  23. Wendy Darling*

    Congratulations LW, you are now winning every “most awkward encouter” bar convo for life!

    I hope even if you’re not laughing now you are laughing in a few months when the awkwardness has had time to pass out of your system. It sounds like you both handled it as well as it could be handled and I have high hopes that your boss will get onboard with a “let’s pretend that never happened” strategy.

  24. Princess prissypants*

    Only thing that would make this better is if the roommates were Not Ugly Naked Woman and Crazy Trash Sorting Guy.

  25. whomever*

    My sister currently works with a (long ago) one night stand of mine, in a complete coincidence. She doesn’t know. One Night Stand rules are everyone pretends it never happens.

  27. The Man, Becky Lynch*

    Oh man…I thought that the boss was going to be the roommate. *snorts*

    Just wait awhile, this will be the funny story you tell at dinner parties with friends about awkward situations.

    1. Daughter of Ada and Grace*

      Oh, good, it wasn’t just me!

      And it’s definitely going to be a great story with some time and distance (and possibly a different job for either you or your boss or both).

    1. The Man, Becky Lynch*

      This can happen at so many ages though =X I know a lot of older people with roommates still and could see it happening!

      This is where my demisexuality is so delightfully wonderful >:]

        1. VelociraptorAttack*

          I wouldn’t be so sure. I don’t know your age but it’s a fact that STD rates among the elderly are increasing.

        2. The Man, Becky Lynch*

          Oh dear! You need to visit some assisted living homes and make some friends, the stories are fantastically heartwarming to say the least!

        3. SunnyD*

          I know plenty of freaky senior citizens – and the nursing home STI rates tell me the demure ones are having fun too.

      2. Can't use my regular name for this one.*

        No, it really isn’t but pre internet you were most likely to have casual hookups with someone just outside your regular circle (friend of a friend) so a bit more unlikely to have this scenario. Or random bar-hookup but that would most likely be someone in your immediate neighbourhood and again (due to income demographics where I live at least) unlikely to be in the same neighbourhood as your boss unwittingly.

        Also, when I was young there would have been a cover story. “oh hi [boss], isn’t this funny! I got caught out last night after the last train and ran into my friend’s cousin who was so kind to let me stay the night”. Polite fiction that no sex occurred makes it one more step removed away from awkward. Still awkward but a little less?

  29. Damn it, Hardison!*

    Oh, this reminds me of the time when I ran into my manager at 5:00am in the graduate dorm bathroom (he was an employee of the graduate school and apparently seeing the adult student living next to me). We shared a horrified reaction, averted our eyes and scurried off in opposite directions. We never spoke of it, but 22 years later I still remember that when I run into him in professional circles (it’s amusing now but at the time…)

  30. Jennifer*

    Cackling right now! Sorry!

    This is a sitcom. Somebody, please make this today. This is even more awkward than Grey’s Anatomy because her boss with getting busy with a different person in the next bedroom. ROFL!

    Okay, sorry.

    This will never be spoken of again. If he brings it up, change the subject without acknowledgment.

  31. Skeeder Jones*

    This might be one of my favorite posts ever! I can’t imagine, I mean, I don’t even like seeing the face of Mr/Ms One-Night-Stand the next morning. Congratulations on handling it as well as could be expected. It sounds like your new boss wants to pretend it never happened as well. I wonder if their experience was also a one night stand, the comment about getting the wifi password and starting work makes it seem like this was not a one night stand for them.

    1. Mr. Shark*

      I wonder if their experience was also a one night stand, the comment about getting the wifi password and starting work makes it seem like this was not a one night stand for them.

      Yes, I wonder about that. It would’ve been hilarious for them to sit at the breakfast table and work for a few hours before heading into the office.

      1. Traffic_Spiral*

        Yeah, be like: “well, since we’re here, we might as well hash out what we want to do with the Jones file.”

  32. Noah*

    I wouldn’t assume Boss was embarrassed, too. A lot of people would not be. But it doesn’t matter, because everyone is handling it fine.

  34. Holy Carp*

    Back many years ago when I was deployed with my military unit in a foreign country, my then-current squeeze and I (both from that same unit) were checking into a local hotel for some naked time, and we ran into three other soldiers (two men, one woman) from our unit checking out of the hotel together. We all stopped abruptly, then a couple of us laughed, and all we carried on. It was never spoken of, to my knowledge.

  35. Luke*

    ” and you will now both engage in the polite fiction that neither of you spotted the other. ”

    As the old joke goes:

    Unitarians don’t recognize the trinity
    Protestants don’t recognize the authority of Rome
    And Southern Baptists don’t recognize each other at the liquor store

  36. iglwif*

    Oh my goodness, LW!!

    I would also want to crawl into a hole and never come out … but Alison’s right, your boss is handling this really well and it sounds like you could 100% just Never Speak of This Again and neither would he. Which honestly is the best outcome I can imagine XD

  37. Mike B.*

    I choose to believe that this was also written by the guy who matched with his interviewer. He’s had a good spring.

  39. SecondChoice*

    I mean … it’s a one-night stand for you (OP), but how do you know it is a one-night stand for your boss?

  40. Perilous*

    Reminds me of the time I ran into my boss at the topless beach. We had a short chat during which he maintained steady eye contact. All was well.

    2. Blue Horizon*

      Yikes. I think I could pull that off in boss’s position, but good luck expecting me to remember anything we talked about.

  41. OP*

    Everyone has such good witty retorts! I’m seriously kicking myself for not thinking of any of them in the moment.

    I am laughing about it already, although in a slightly mortified, hysterical kind of way. Hopefully in a few months (years…decades) it will more on the funny-side and less on the sinking-pit-in-my-stomach-side.

    Not much in the way of an update except I immediately deleted Tinder. Nothing has been said and I’m actually very much enjoying working for him! I did let a few friends (who work in different, unrelated industries) take me out for drinks this weekend to hear the BEST WORST STORY EVER. I got free wine, they got a great laugh and all seems to be well? We’ll see!

    Also I’ve never actually seen Grey’s Anatomy, but you bet I’m about to.

    2. pegster*

      I know sometimes we can’t control these things, but OP, please allow yourself to believe you have absolutely no reason for slight mortification, sinking-pit-in-your-stomach, or deleting Tinder over this. People hook up and it’s totally OK. And running into people/roommates/hookups or roommates are a by-product of this. Hold your head high, pretend it didn’t happen, and carry on!

    3. Karen from Finance*

      Please don’t think you need to stop having this kind of fun just because you had this one embarassing experience, though. I mean, what are the chances of this situation happening again?

      … And actually, wouldn’t it be kind of hilarious if it did and you just kept bumping into each other? Now THAT’s movie material right there, lol.

      No, but seriously, I hope the awkwardness wears off and you consider reinstalling Tinder if you find you miss it.

      1. animaniactoo*

        Okay, it would be TOTALLY hilarious if it happened again at another apartment with different partners involved.

        But OP, I agree with everyone else… it’s perfectly fine to keep Tinder and keep having fun.

    4. Blue Horizon*

      I would have ordered you something from the top shelf for this one and considered myself amply rewarded.

    5. Fortitude Jones*

      Not much in the way of an update except I immediately deleted Tinder.

      So wait – are you the OP from the other day, or is Tinder just getting everybody in trouble these days? Lol.

    6. Hrovitnir*

      Haha, OP, I’m sure the mortification will fade! I can definitely imagine the horror but from the safety of my computer screen it’s the funniest thing I’ve read in a while. What are the chances??

      I’m glad everyone in this story is behaving sensibly, for once. I also want to support you un-deleting Tinder when you’re ready, because this really was a freak occurrence.

    7. Traffic_Spiral*

      Don’t think of it as embarrassing! Think of it as a way to get facetime with the boss.

  43. Sharrbe*

    Oh my God, after the embarrassment has worn off and some years go by, THIS WILL BE ONE OF THE BEST STORIES to tell at parties, etc. THE BEST!

  44. nnn*

    The thing is, OP, there’s no cause for embarrassment because a) no one was doing anything wrong, and b) you were both doing exactly the same thing, so you’re “even”.

    It’s like if you were both using the same public washroom at the same time and both let out a horrendous fart that was amplified by the toilet bowl. It sort of…meets the technical criteria for embarrassing, but really you were both engaged in a normal activity of life in an appropriate venue, and just happened to be there at the time time.

  45. MissDisplaced*

    Ha! That’s like OMG Awkward!
    What’re the chances?

    I mean, aside from it being really weird, neither one of you did anything wrong or out of line here.
    Best pretend it never happened and if you date that person again, go to your apartment.

  46. KingdomScrolls*

    I’ve got to admit, I cackled at this one too. Count yourself lucky, OP, that your boss seems chill about the whole situation. I suspect that neither of you will mention it at work, as befits polite society. If your boss does bring it up for some weird reason, just laugh it off with something like “Ha ha, how weird was that?! Anyway, about these quarterly figures…”

    At the end of the day, both you and your boss are at perfect liberty to enjoy yourselves with whomever you like, and neither of you should feel guilty about that. I hope you feel free to keep having fun :)

  48. Andy*

    I gotta say, my favourite AAMs are the ones where Alison starts her reply with “Ohhhh.” She outdid herself here with the followup sentence.

  49. LGC*

    As if the experience wasn’t awkward enough, my boss (who presumably was up early to take a look at my work once I was done) joked that he could make me coffee and find out the wifi password for the apartment at 6 am as I packed up my laptop to head to a nearby coffee shop to get the work done.

    *record scratch*

    You brought your work laptop to a one-night stand?! SIS. As the kids say, I’m screaming.

    On one hand, I admire your dedication and work ethic (and I’m sure your boss was also impressed), but also this is the part of the letter that I can’t get over. This is legitimately the most AAM thing I have seen on this site, and I’ve read a ton of letters here from the back catalog.

    1. Close Bracket*

      Yeah, I noticed that detail, too. I’d be in so. much. trouble if I did that, the ONS would be the tiniest part of that entire story. Clearly things are different for the OP.

      1. LGC*

        I didn’t even think of the IT implications (which I’m guessing aren’t that high since they logged in from a coffee shop)! It’s more like…OP can live their life however they choose, but also I want them to live their best life and to hook up freely without having to worry about work tasks. (Or running into their boss after a hookup, but unfortunately that was not meant to be for our dear OP.)

        1. Close Bracket*

          Eh, for some people living their best life includes taking a work computer to hook ups.

          1. embertine*

            I’m a quantity surveyor and I have met people with an unhealthy fascination with spreadsheets. No kinkshaming here, if you want to tantalise your hookups with a nice pivot table, you do you.

    2. OP*

      Haha! Uhh, work hard play hard? Girl’s gotta do what she’s gotta do.

      It’s my personal laptop, which my company pays me a monthly stipend to use in lieu the awful company-issued laptops. I might be a bit snobby about my technology. There’s nothing sensitive on there and no work VPN.

      1. Close Bracket*

        Watch the American version of The Bridge. She takes her ONS back to her place, but when they are done, she totally fires up the computer and gets busy (deliberate wording there).

      2. 'Tis me*

        Eh, boss knows that you’re not going to let living your life interfere with getting the essential early morning task done, but you do make sure to maintain a healthy work-life balance. These are good data points for them to have – if you do ever need to call in sick and are unable to do the task, they won’t wonder if you’re sick or hung over…

    3. NoLongerYoungButLotsWiser*

      Our laptops are password protected, but there is holy fire to pay if you have it stolen from your car, etc. Unless I have it locked at home – if I am stopping anywhere on my way home from work, or planning to go to work from wherever I’m at …. I take it in with me and keep it in sight. Foot on the laptop bag in the restaurant (no back of chair), no leaving it in the car – this is the SF Bay area, car break-ins are rampant.
      Even if the person can’t hack into it, the paperwork to file to explain what happened, makes it just “not worth” locking it in your trunk and running any risk. Hasn’t happened to me, but it did to a coworker (from trunk of his car, locked, in the carport of his house). It was a nightmare. Easier to just tote the thing with me. There’s HIPPA, corporate compliance, and more… sigh.

      1. CmdrShepard4ever*

        But then you make it easier for spies of a foreign government/corporation to send someone to get to know you as a romantic partner/ONS so they have access and can hack into your laptop/computer.

      2. wittyrepartee*

        I work with HIV/AIDS data. They don’t give us laptops. Makes everyone’s life easier (except when you’re moderately sick and wish you could work from home).

  50. Don't Trust the B in Apartment 23*

    If I may quote a criminally underrated TV show, “some day, you’re going to look back at this and laugh. I’m there already, and it’s hilarious.”

    1. Winry Rockbell*

      What show is this from? I googled it to look up the quote and this page was the only result, but with a line like that the show has to be funny!

      1. Don't Trust the B in Apartment 23*

        The clue is in my screen name. ;)
        Rather enjoyable sitcom, with Krysten Ritter playing the titular character, and James Van Der Beek playing an exaggerated version of himself. Only lasted two seasons. :(

        1. Funbud*

          God, I loved “Don’t Trust the B in Apartment 23”. It was criminal that they didn’t give it a second season.

          Watching Krysten Ritter’s character was one of the very few times I’ve ever said “OMG that’s me!” while watching a TV show.

  52. Jack V*

    Oh gosh, that’s hilarious.

    But also, it’s really nothing wrong. It’s not like, “if you’d been a bit more discreet, no-one would have known you had a personal life outside work”, you literally did NOTHING you could have done better.

    And in a way, having both of you in the same position is better. It’s awkward, but you both handled that. It’s probably better not to mention it at work unless you’re close enough you can tease each other. But it’s also a moment of humanising each other, and you both handled it well, and also you don’t have to worry that you’re being judged because you’re both in the same place.

    I mean, at least (I assume) you were both clothed. It could have been more awkward! :)

  53. londonedit*

    I read the subject line of this one and was initially confused…I was thinking hang on, is there a word missing here? They ran into their boss in their one-night stand’s apartment building? That would have been embarrassing, but hey, it’s a coincidence, the boss lives in the same building as the ONS buddy.

    Then I realised nope, the heading was right, it was IN THE APARTMENT. Cringe! Have to say though, I think you’re both handling the awkwardness brilliantly! And you’ll be dining out on that story for ever more.

  54. just trying to help*

    Great advice about letting it go. However, it now makes you two Eskimo brothers, once removed, kinda. It’s that little knowledge that lets you both make eye contact, knowing what the other did, and have a tiny bit of respect for each other. Walk tall!

  55. That One Person*

    I appreciate the boss at least trying to lighten the mood with a joke, well I opt to take it as a joke at least. Man though talk about some funny coincidences and I’m pretty much with various other peeps: just let it become one of those interesting stories you can reminisce and laugh about down the road.

  57. Candid Candidate*

    Someone please write the hell out of this modern romance novel and make it on the bestseller list and thank AAM in the acknowledgements.

  58. Astonished*

    I cannot believe that in 2019 people still think all disabilities are visible. I have congestive heart failure and diabetes. I am on a reasonable accommodation with my employer because of these conditions. My doctors certified me for my placard. People need to mind their own damn business. I don’t have to disclose my private medical information to anybody not of my choosing.

  59. Astonished*

    Oh, and I look like everybody else on the outside. But can’t walk too far and may go hypoglycemic.

  61. Elizabeth West*

    I’m sorry, OP; really I am, but I AM LAUGHING MY ASS OFF. This is prime sitcom material right there. *in Ian Malcolm voice* Life, uh, imitates art.

    This too shall pass.

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