40 People Share The Most Awkward Question That Made Them Uncomfortable At Work

Navigating a professional environment can sometimes be tricky, especially when it comes to maintaining appropriate boundaries. One person’s curiosity about awkward questions asked at work sparked a fascinating online discussion. When someone posted, “What is the most awkward question you’ve been asked in a professional setting?” the responses flooded in, revealing a wide range of uncomfortable and cringe-worthy experiences.

#1 During my interview. I am female. Interviewer was female. “Are you a breeder or non-breeder? Cuz we just hired a non-breeder and I like to keep the department balanced”.

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#2 “Can I see your underwear?” Said by a licensed mental health professional in her office.

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#3 In previous role managing hospital unit, was asked the following:

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Did this employee ask the other employee something about their “bun hole”?

Why yes, Employee A did ask Employee B something about their bun hole.

I had to give a verbatim description to a chief nursing officer that an ER tech put his finger in a female nurses hair bun, and then employee said that “he couldn’t NOT put his finger in that tiny little hole”

It was a low point in people leadership.

#4 My husband and I used to work in the same department at a hospital. My old charge nurse over headed for me to come to the front office then proceeded to ask me how well endowed my husband is. Mind you, she asked me that in front of my husband and about 7 other employees.

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

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#6 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. .

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#7 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.

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#8 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.

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#9 “Does your wife ever bring other women into the bedroom?” Needless to say, it wasn’t a healthy professional environment and I don’t work there anymore.

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#10 “Have you ever been with an older woman?” Asked by a ~40 year old of 16 or 17 year old me. Went over my head that she was hitting on me. She told me I reminded her of her son shortly thereafter, which seriously creeped me out when I reflected on this conversation years later.

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#11 “Do you know any gay candidates we can hire and fast?”.

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#12 “Have you been r*ped or something?” -a girl i was in college with in the medical field and didn’t want her giving me a breast exam.

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#13 I had a business owner ask me if I was a Christian as the first question of the phone interview. Had I been recording and a horrible human being I would have blackmailed him for the job.

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#14 Oh, you were in Iraq… did you k*ll anyone?

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#15 Did you learn that in the “streets”.

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#16 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.

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#17 Less than five minutes into a job interview they aggressively started asking if I was gay or not.

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#18 Ive lost count how many times random ppl have asked me about my breast implants.

(I dont have breast implants).

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#19 “Why does this chat log just consist of the two of you saying balls to each other for the past two weeks?” I don’t work there anymore. .

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#20 “What would you do if you got to heaven and found out that God is a woman? ” –The new HR Manager as I was just trying to fix her printer. She wasn’t around that place very long.

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#21 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.

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

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#23 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.

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

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#25 “You and your wife aren’t planning on having kids soon are you? Because the goals we have here … I’m not really sure that would work.”

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I was younger then, I now know how illegal that question is lol.

Was offered a job but turned it down. The place later went on to have many scandals and controversies and is regarded as a complete sh_t place to work.

#26 “We want to send you to help with our booth at the Indy 500. Is that something you’d be able to do?…You’ll need to wear a bikini.” I was the director of market research for a nationwide tire trade publication.

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#27 Do you plan to start a relationship with any coworkers and would you use a secret of your boss to blackmail them.

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#28 “I bet you’re one of those quiet guys that f***s like an animal.” On an email on our company server which could be looked at any time, and I’d be surprised if certain words don’t get flagged for HR. Technically a statement but the question was implied. Think she was still married at the time to a guy like 16 years older than her and her at least half that older than me and then later remarried a woman, so while she’s still a friend, I think it’s fair to say I like things less complicated so I politely declined.

(Obligatory manly bravado)…of course she *was* right.

Yeah, I can’t pull off manly bravado.

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

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#30 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.

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#31 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.

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

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#33 Old guy 30 years ago: “Do you think the owner is gay? “

Me: “No. Why, are you looking for a date? ”

Old guy: “What? No! “.

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#34 “Was it planned or an accident?”
About my pregnancy. I’m in my 30’s and married. I don’t know why people think this is an appropriate question.

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#35 Movie sets in the 90’s and early 2000’s were completely different. Everybody said and did whatever popped into their head. Ones I remember: “anybody wanna f**k after we’re done?” “dude, is that actress playing the daughter legal?” “can you write a sex scene for me and that blonde girl?” “does anybody have any c*ke?” “you wanna feel my new b**bs?”.

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#36 “How would you feed yourself if you lost your job?” I ended up being laid off as well as my whole division.

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#37 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…”.

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#38 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.

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#39bDo you self pleasure? After I revealed I was asexual.

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#40 “I’m sure my son has no problems listening to you, huh? ?”
By a dad at a parent teacher conference with his wife right there. I was fresh out of college teaching high school.

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