I got one: Recently had a job at a broadcasting station. After coming from lunch with the colleagues one of them (happened to be female) took 3 fruits from the front desk. A few moments later in the elevator accompanied by a few more male colleagues. Turns out she was holding a plum on either side of the banana's stem in one hand.
a while back my ex boss declared (in reference to fund raising) "Richard has the larger package so he will need caroline to handle it for him, Pete's is only a little smaller but he has more experience in handling these things so he can take care of himself" The boss concerned has no sense of humour so by this point we were all dying trying not to laugh
There was a time in which a fat, shirtless man walked into the place I work, and shoved two food items in his pockets. I'm sure he thought he was being sneaky, but it was pretty obvious what he was trying to do. I alerted the boss to call him out if he tried to leave without paying, and, sure enough, that's what happened.
My boss and his wife (who also worked with me) took a bit of a break in their relationship during which time she and I did things together. He found out and it was really awkward up until he stopped working there.
We handed out our new HR handbook with a memo attached saying “inter office reproduction is highly encouraged”
Microsoft's Outlook program stores all of its data (emails, contacts, everything) in a single file on the server with the extension .pst. I was our company's IT manager and I accidentally (and irrevocably) deleted the .pst file belonging to the company CFO (to whom I reported). A most awkward conversation.
there was also the time when Beavers had recently been reestablished on the river otter that our staggeringly attractive female biodiversity officer said in a heads of department meeting "So have you guys seen any beaver recently ?" then totally oblivious to the fact that we were all biting our lips added "If not we should go out one night so I can show you some"
A co-worker of mine accused me of disrespecting her and refused to do her job until I apologized, then she had a mental break down 5 minutes later when she saw an old friend for the first in awhile, and then while she was having her break down she prayed to some angels to protect her because she felt like she was being attacked by evil or something, and we were the only two people at work so it was pretty awkward/nerve racking.
A guy at a place I worked for years ago got promoted to a supervisor position. His whole attitude changed to one too patronizing for my taste, and his behavior could best be described as sitting back with his feet up expecting grapes to be fed into his mouth. I hate conflict but I didn't appreciate what was going on, so I did the cowardly thing and went to *his* supervisor and discussed the matter with him. And it was forever awkward between me and the other guy until I left.
When I was working fast food in high school, our very attractive (and only a year older) shift manager brought in breakfast from a competitor (McDonald's), then announced "Shoot, I didn't get the sausage, does anybody want to eat my muffin?" (regular, not sausage McMuffin). And then there was that time I was working in a customer service call center. A person with a deep, gravelly voice called in asking to know the balance of their account, and I said "Of course, sir, can I have your account number?" "I'm a ma'am."
I don't know about awkward, but there was a woman in our office who had kind of an unusual personality. One day, completely coincidentally, all the women in the office came in dressed in black, which the woman in question took as commentary on the fact that her daughter was having an abortion that day (no one knew). She went on a screaming, spitting tirade that the company president called "the most terrifying ten minutes of my life". They took her out strapped to a gurney, and we never saw her again.
One time I had a complete 'guy' moment at work, but it ended well. I worked with a female and she was really cool. One day we were standing and discussing work stuff. I randomly looked a t her and said "Congratulations". She gave me an odd look and ask why I was congratulating her. "Your pregnancy", I replied. As I said it I thought of my dad- the guy that said this to complete strangers. She gave an awkward smile and told me she wasn't pregnant, and we continued like nothing had happened. A week later she came up to me and asked how I knew. I was confused and asked what she was talking about. She replied that she found out that morning that she was pregnant. I lied. I told her she had been glowing and her hair was lustrous. She was happy.
One of the owners of the company got in the lift with me in the morning. I am, let's say, not a morning person. He asked me what I do at the company. I couldn't for the life of me remember my job title, so I blurted out, "Write... I... write. Bids." He nodded slowly and went off to his desk.
The department I used to work for at my 55k+ employee company voted to re-name our team Finance & Actuarial Planning (FAP). Apparently, out of 18 people I was the only one who knew what that meant.
"How to make the need of biodiversity well understood among society of Drooling Masculinity..." I start to see a pattern...
The "eat my muffin" girl was a twin, and her sister was also a shift manager. Could never remember which one I was on the bad side of and which the good side.
Oh how I could tell of my social ineptitude (and the somewhat gloriously funny, if in hindsight, moments) if this thread was just about awkward moments in general. But, in the thread of keeping to the theme: My last job, which I have recently quit, was working as a front desk mostly redirectingpeople to others whom could help them. Anyway, one of my colleagues was an lady in her 50s or early 60s. I didn't know her last name nor did I particularly care about her first name. Until one day her daughter came in to work to pick up her mother (the lady and my work colleague) whose car had broken down. I realised/remembered then that it was someone I had gone to highschool with... In highschool we were in the same group of friends and often got teamed up together. then we had a rather spectular falling out (highschool 'romance' (or lack thereof) and all that shenanigans). So, naturally there was not other customers to attend to and it was a absolutetly dead. So there we stood, the only two people in the lobby staring at each other wondering who would speak first and what would be said whilst her mother went to get her things. Then, came the awkward part of her mother asking how we knew each other the next day when she came in for work. She was annoyingly quizzical about it.
On my first day of a new job my male manager asked me if I had any plans for Valentine's day. In another job, a customer insisted I had shortchanged her, so the manager came out and removed the till and counted it through, whilst I stood there like a spare part. It was fine. She thought she'd given me a £20, when she'd only given me a £10.
