Embarrassing moments with your boss… anyone else have a good story?

posted 2 years ago in Career
Post # 2
3773 posts
Honey bee
  • Wedding: October 2013

My boss and I are pretty good friends, so our lines of professionalism can be pretty blurry. (We spent a good portion of our day plotting to send a bag of gummy penises to a mutual friend, etc)

We were both prepping for a bodybuilding show at the same time last year. He asked me to send him some clients photographs so he could work on an ad for Botox. I accidentally sent him one of my progress pictures I had taken for myself… Full bare leg, in my underwear, side of my butt all out. I immediately texted, “Also, please disregard my butt thanks.” His response, “Hey it could have been worse!” I’m just thanking my lucky stars I didn’t accidentally send him a picture intended for my husband!

Post # 3
281 posts
Helper bee
  • Wedding: November 2019

I don’t know if this counts as uncomfortable but it was embarrassing and humiliating! I have fibroids (in the process of treatment) and before I started the medication, my period was soooo bad. I had a meeting with my boss so I changed right before going in his office and thought I’d be ok. Well mr man was particularly chatty that day and 40 mins later when I stood up, well it went everywhere!  What a day to wear a skirt. I should have stayed home but this meeting was important and I thought I would be ok. Ugh. Thank goodness he was good about it and offered me his jacket to be able to get to my car. He’s a great boss. I ended up in the hospital that night. I’m much better on this medication but he still looks at me with pity. Fml. :(. 

Post # 4
4272 posts
Honey bee
  • Wedding: August 2015

I had started a new job in 2013 and my boss at first scared me.  He was REALLY intense and I desperately wanted to do my job well.  Around the holiday season, 4 months after he hired me, I ended up drinking by myself — well, with my cat — and I started DRUNK TEXTING him.  I sent him a multitude of cat pictures and just jabbered on about random stuff.  He is actually a pretty level-headed guy and was mildly amused.  The next day I was mortified and I sent him another text to apologize for sending so many the night before…and he said not to worry about it and laughed it off.  Ironically that ended up sparking our friendship.

A few months after that he essentially gave me a promotion and we actually became very good friends because we were working closely with each other.  We don’t work together anymore, but remain very good friends.  We called each other “work wife” and “work husband” because we were spending more time together than with our significant others and we had more inside jokes than I can even count.  (PLATONICALLY might I add…for those who think someone with a penis can’t be friends with someone with a vagina, I beg to differ and don’t get your panties in a twist please.)

When we were working together he would find ways to embarrass/bother me, like he would dance awfully by my office door, which had a window, and he liked to see how long he could dance without me noticing.  He was basically the annoying big brother, and we had a TON of fun together.  I miss those days since he now lives 5 hours away, but am glad that we still keep in touch.  We actually just had a 2-hour phone call on Monday.  🙂  He knows my husband and my husband knows him and my husband understands our weird, wacky friendship.

Post # 5
4235 posts
Honey bee
  • Wedding: September 2015 - Hotel Ballroom

I am 34 weeks pregnant. My boss was standing next to me and I involuntarily let out a little fart. He glanced at me and I blamed it on my tummy rumbling. Fortunatly there was no smell and it DID sound kind of like that ‘dying whale’ noise ones tummy could make. He bought it (or at least ACTED like he bought it), then made awkward small talk with me for a few minutes and went away.

It could have been worse, but still……

Post # 6
933 posts
Busy bee
  • Wedding: October 2017

I had just started my second job out of college, and right after I was hired, I got invited to a work party in honor of the hiring manager’s promotion. A good friend of mine worked for the company too, so I was drunk-whispering to him about a new below-the-belt piercing I got earlier that day. The hiring manager overheard me, decided it was juicy gossip, so he ran over and whispered to the area manager. I walked up to them and smacked the hiring manager across the face. He reacted by bursting out laughing and buying me another tequila shot. I remember later that he told me to feel his bicep (he was an MMA fighter), and then I stole a really uptight manager’s hat. I worked there for over two years and still put those guys down as references. They’ve given glowing reviews to my new employers! Although they’ve told me in private that my new employers aren’t going to know what hit them…pun maybe intended? 

Post # 7
736 posts
Busy bee

My whole department was on a weekend away, team building type thing. The cottage we stayed in had several bathrooms, one of which had no lock. There was a chalk board on the door to write on whether it was occupied or not. 

I’m sure you can tell where this is going….


At one point in the weekend I was drying off after a shower and my boss walked in on me totally stark naked!

He’d cut his finger and in the panic to get it sorted, had forgotten that this was the unlockable bathroom and to check the chalk board! 

Totally embarrassing! However, he was much much MUCH more embarrassed than I!

Post # 8
115 posts
Blushing bee
  • Wedding: November 2017

OK this is totally my fault. I have a job as a PHRN – I’m a nurse with a Pre-Hospital license. It’s like a step over a critical care paramedic. I mostly do interfacility transfers but we answer 911s too. I was working nights and we would “post” at places to have different crews available at parts of the city. Anyway – I really really really had to pee and there was no where nearby that was open, it was like 3 a.m. and it was a slow night and OMG did I have to pee. So finally I thought – screw it, I’m going outside. My (male) partner pees outside in the trees sometimes, I am too. So as I did, our supervisor (not technically my boss but still) pulled up with his lights on directly illuminating me as I was pulling my pants up. I am sure he knew what I was doing, but he didn’t say anything. 

Our supervisors would check in with the crews to make sure if we needed anything. I didn’t. It was awkward. He left shortly after and neither of us mentioned it. lol. 

Post # 9
5125 posts
Bee Keeper

When I first started with my company, 11 years ago and at the age of 22 I made the mistake of keeping up with the boys at Christmas Party and did far too many shots of tequilla.  The CEO had his driver take me home and then the CEO carried me up 6 flights of stairs, got me in bed and THEN cleaned up my vomit!!  Talk about mortifying.  Luckily we all lived to tell the tale, I kept my job and now the CEO so kindly reminds me each year at the Christmas Party that its “our anniversary”. LOL

I never made that mistake again.

Post # 10
1471 posts
Bumble bee
  • Wedding: September 2015

gialovesshoes41 :  Omg! So I have a similar story. 

One time I was also on my period and having a meeting with my boss about a big case.  Was sitting on one of the sofa armchairs in his office and the meeting ran loooooooong.  

When I finally got done and got back to my office, I noticed with horror that I had a bloodstain on the seat of my pants. LUCKILY my boss had left his office after the meeting to go get coffee. So I grabbed some random papers and, in order to go into his office while he’s not there, I pretended that I needed to leave them on his desk for him to review.  Again, luck was with me–When I checked the armchair I was sitting on, there was no stain on the cushion.

So that turned out as good as can be, except now and then I wonder if my boss, or any of my coworkers as I was walking down the hallway between his office and mine, had noticed the stain on the back of my pants and just never said anything.  

Post # 11
6005 posts
Bee Keeper

This was years ago but I still remember it. I was going for an interview at a chain supermarket shortly before Easter and there was a chicken in a cage clucking and a display of Easter creme eggs. The manager, who was to be the one interviewing me, started walking over, but instead of using my best interview manners, I laid into him because shame on them, that cage is so small there’s barely enough room for the poor chicken to turn around in, using a live animal as a prop without even a food dish or water drip-bottle…..when he finished laughing his ass off at me, he explained that the chicken wasn’t real (damned thing looked real until you got closer). Lol even though my interview began with telling off my new boss, he hired me anyway- and had a great sense of humour because from that point on the fake chicken had food and water dishes 🙂

Post # 12
210 posts
Helper bee

I used to work in an art gallery, and as such we had monthly evening gallery openings with a lot of unlimited free alcohol. Our bathrooms were gender neutral with stalls (there were technically 2 restrooms but the doors were not labeled and nobody cared anyway). I go into one and push the stall door open during one of our events, and standing there – dick in one hand, beer in the other – is my drunk boss who forgot to lock the stall door!

We never spoke of it afterwards.

Post # 13
1192 posts
Bumble bee
  • Wedding: March 2017

I have a couple of stories! 🙂

1) My old manager a few years ago had an alarm set on her phone every day for her birth control pill. She was always in meetings when it went off, though. Since I sat right next to her, her phone would be buzzing and buzzing and I wouldn’t know what to do. Eventually, I started dismissing it and telling her when she got back to her desk. The first time I told her, she was standing up in the middle of cube-land and said “gosh, my vibrater is so annoying! I’m sorry!” OMG I died! She didn’t realize how it sounded until she saw the mortified look on my face! But we were fairly close in age and it actually became an inside joke between us from then on.

2) In my current role, our region is managed by one man. He’s not my direct boss, but responsible for our entire office, as well as a couple of others. He’s been focused on collaboration amongst the teams and hosted a happy hour. Afterwards, I went up to him (having never formally met him before – he was new at the time) and thanked him for hosting and what a great event it was.  He pretended to know me and said how great it was to see me again. I do not know WHAT got into me because I’m normally very shy around leadership/upper management, but I totally called him out and asked him what my name was. He turned red and stuttered a little bit. surprised  I introduced myself formally and ultimately, it was funny, but at the time I was shocked and a bit embarassed to have been so bold with someone so high up. Later that year, we spent 15 months working on a huge project together where we got to know each other really well. He gave me the full run down when he proposed to his now wife. When I got engaged, he wanted the full story of our proposal. I’ve gone out drinking with him and other leaders in the office where he invited us all over to his house to drink with him and his wife. LOL! He’s a super cool guy and still tells people that story and how he would never forget my name because of that. haha!

Post # 14
751 posts
Busy bee
  • Wedding: November 2015

I started working for my current boss in 2012. He’s only about…10 years or so older than me? I didn’t know it at the time and I had no idea what his name was or what he looked like. So I fly to Tennessee to the main office for a week of training, and I meet my supervisor at the time. I assumed (incorrectly) that she was the big boss, as I didn’t even know the other guy existed. 

As we’re walking through the building and she’s showing me around, this young guy walks up and he’s like oh are you the new rep? I said yes. He said, “I hear you’re from Alabama! ROLLLLL TIDE!” And I rolled my eyes and said, “My lord you can’t even leave the state without hearing that nonsense! I hope you have more interesting things to talk about next time I see you!” I said it jokingly but my supervisor just stood there like…omg this girl just got herself fired. She then introduces him to me as the owner and CEO of the company as I stand there mortified.

She eventually got fired, and I got promoted and now run his entire southeastern division. We’ve developed a very sarcastic, fun work friendship that is supported by dry wit, memes, and pop culture references. He is the BEST boss and he’s told me on multiple occasions that he knew I’d stick around because I wasn’t afraid or intimidated by him. He was right! 

Post # 15
9539 posts
Buzzing Beekeeper

Last I volunteered to help set up for a Super Bowl party. I was using a sizzor lift and I tried to to move out of a tricky corner but accidentally backed up instead hitting a foam board stand causing a big hole. In front of my boss. And casino executives. And a bunch of temp workers. They aren’t certified to drive a lift so I couldn’t get help.  So embarrassing. This morning my director is going around telling people my nickname is “Crash”. Great. Thanks. 

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