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50 Awkward Questions That Made People Laugh Uncomfortably
CuriositiesMAY 17, 2024

50 Awkward Questions That Made People Laugh Uncomfortably

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Being in a professional environment requires a certain kind of conduct. You can't be too familiar with people and talk to them like they're your besties. You can't ask too many personal questions, like how much they earn, who they voted for in the recent elections, or what they did with their wife last night.
Religion, politics, and intimate relationships should automatically be topics people should never breach at work, whether in a job interview or just a casual conversation at lunch. Yet some people still do it. So when a person asked, "What is the most awkward question you've been asked in a professional setting?" people had all sorts of stories.

#1

50 Awkward Questions That Made People Laugh Uncomfortably
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".
103points

#2

50 Awkward Questions That Made People Laugh Uncomfortably
"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.
97points

#3

50 Awkward Questions That Made People Laugh Uncomfortably
Less than five minutes into a job interview they aggressively started asking if I was gay or not.
94points

#4

50 Awkward Questions That Made People Laugh Uncomfortably
"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."
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.
93points

#5

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! ".
Report
90points

#6

50 Awkward Questions That Made People Laugh Uncomfortably
“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.
88points

#7

50 Awkward Questions That Made People Laugh Uncomfortably
“Can I see your underwear?” Said by a licensed mental health professional in her office.
86points

#8

Ive lost count how many times random ppl have asked me about my breast implants.
(I dont have breast implants).
84points

#9

“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.
84points

#10

50 Awkward Questions That Made People Laugh Uncomfortably
“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.
82points

#11

50 Awkward Questions That Made People Laugh Uncomfortably
In previous role managing hospital unit, was asked the following:
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.
76points

#12

50 Awkward Questions That Made People Laugh Uncomfortably
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?".
71points

#13

50 Awkward Questions That Made People Laugh Uncomfortably
"Do you know any gay candidates we can hire and fast?".
70points

#14

50 Awkward Questions That Made People Laugh Uncomfortably
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.
69points

#15

50 Awkward Questions That Made People Laugh Uncomfortably
Do you plan to start a relationship with any coworkers and would you use a secret of your boss to blackmail them.
66points

#16

50 Awkward Questions That Made People Laugh Uncomfortably
"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. .
66points

#17

"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.
63points

#18

“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.
62points

#19

50 Awkward Questions That Made People Laugh Uncomfortably
"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.
61points

#20

50 Awkward Questions That Made People Laugh Uncomfortably
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.
56points
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