50 Awkward Questions That Made People Laugh Uncomfortably

“How would you feed yourself if you lost your job?”

I ended up being laid off as well as my whole division.

It was technically after hours, but we were all out drinking after working our lame retail job at an unnamed sporting goods store. As the night rolled along, my manager eventually asked me if I would kiss her. I knew she had a boyfriend and I didn’t find her the least bit attractive. I turned her down politely and reminded her that she had a boyfriend who, "probably wouldn’t like that." We all carried on like nothing ever happened - or so I thought. A couple weeks later, I get called up to the big bosses’ office and am told that I was being let go for failing to "meet their expectations." I had been late on only a handful of occasions and never called out, so it was quite a surprise. Then it made sense, my manager had been embarrassed by my rejection and probably put my a*s under a microscope in an effort to get me fired.

Ended up working out though, I went back to school and finished my degree and am very happy now not working in retail.

“Does your husband mind that you make so much more money than him?”.

I was asked - repeatedly - about my sexlife from a co-worker (amongst other things) at work. Went to my boss and she shrugged it off as “you should be flattered…”.

A coworker asked me if I liked having my a*****e licked.

Why do you celebrate Christmas when you are an atheist? Random question from an admin when I mentioned that I was not religious.

Oh, you were in Iraq... did you k*ll anyone?

I had to explain to my boss, a fully tenured professor, what a furry was after she showed our research group a pic of her cousin who goes to "conferences" in costume.

I use to work in one of the national chain pet stores way back in my very early twenties. Most of the staff of was about the same age as me. Anyways I hear over the intercom that a customer has a question over the phone for reptiles. 

I pick up the phone and they asked if we had any one eyed snakes. I said we do not, but they said to really check. I said no we don’t try another store. Then they say what about the one in your pants. And that’s when it hit me. My manager was cracking up. It was funny but unprofessional. .

I was working a construction job in a residential area of West Hollywood and a guy(neighbor) came out of home apartment and asked if I was gay, I politely said no, and he asked if I had ever tried it. Again I politely said no, he smiled and said if you ever want to try, I live over there and pointed to his door.

I was in the military, serving as an engineer, and there was a tour of high ranking officers coming through the building. We were told to brief them on the programs we were working on, but it was supposed to be fairly informal and for only maybe 2-3 minutes (they had a lot of ground to cover so they couldn't stay long). When they got to us, I did my brief, everyone was happy, until the lowest ranking in the group (an O-5) looked right at me and asked if I was on a operational experience tour (something that usually doesn't happen for a low ranking Leiutenant like me).
I told her no, and in front of the whole room asked "then why are you here?".
Ma'am, this is the department of engineering... I am an engineer... as are my squad mates...
I didn't know how to answer her question without being an a*s, so my supervisor stepped in before I put my foot in my mouth. My oddest experience by far.

A girl and her mother asked me to join an orgy they were organizing. I was working at Spencer gifts at the time, so I'm stretching the definition of 'professional setting' a bit.

When applying for certain clearances you will be asked in great detail about your p**n habits. They try and get you to admit to viewing something illegal or that can be used as blackmail. There’s a classic line of questioning that basically concludes with “how do you know she was over 18? Did you check her ID before you watched the video?” It’s designed to get you flustered and panicked.

Did you learn that in the “streets”.

In an open office my HR director asked me if I'd like to "enter her back passage."
She was referring to the fire escape staircase next to her office, instead of walking up the main stairs.
She thought it was hysterical.

You need to lie to our biggest customer, the number one software company in the world, and tell them that the team is twice as big as it really is, and those other developers - good ones - are hard at work in another state. And if the company loses this contract, it's the only one currently paying, and a hundred people lose their job.

And then I sat down with our customer as a 24 year old developer, not manager, just a code monkey. And the program manager took me aside in a disused office, closed the door, sat me down, and asked flat out how many developers were really on the project.

So yeah, answering that question, with a hundred jobs - including my own - all alone, a thousand miles from home, strung out from weeks of hundred plus hour work weeks, that's my vote for hardest.

Do you self pleasure? After I revealed I was asexual.

Can I give you a foot massage? The deputy director of the company told me at an office meeting and my colleagues heard it.

A married woman who works for the same company I work for suggested we should go have a beer and talk about what might “come up” I was so shocked, didn’t say a word.

I’m a happily married man who will celebrate 33 years with my wife this year, so needless to say, I was floored. Thankfully, we were on the phone instead of in person. I didn’t tell anyone, but I also have the date and time that occurred.

I also made a mental note to call it out if she does it again. It was very inappropriate, I was embarrassed and she shouldn’t have said that.

I applied to a tech company where the application asked who my Waifu was. And the question was required. That was pretty deeply uncomfortable.