25+ Unbelievably awkward questions employees have been asked at work: 'During an interview I was conducting, a candidate asked if [my wife] was single'

Author image for Isabella Penn
Isabella Penn
May 17, 2024 7:00 AM EDT

When you're at work, there are some topics you don't discuss in a professional setting. Sure, you can gossip all you want to your work bestie, but if you're in a meeting or any other situation with a large group of coworkers, you should probably play it safe and keep the controversial topics to yourself. We all know this, but sometimes there are those certain coworkers who have absolutely no problem asking the most absurd questions, putting you in an awkward situation as you try to compose yourself and remain professional. If there's one thing that this thread below proves, it is that those coworkers never last long at their jobs. Below, 25+ employees chimed in with the weirdest questions they've ever been asked, and these workers did not hold back. From extremely personal questions and controversial topics to harmless questions that are actually super insulting without context, you'll find all that and more below.

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  • 01
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  • 02
    18 18 r/AskReddit ⚫ 1 day ago OnlyMyProfit • What is the most awkward question you've been asked in a professional setting?
    via u/OnlyMyProfit
  • 03
    nahc1234 • 1d ago "Does your husband mind that you make so much more money than him?"
    via u/nahc1234
  • 04
    Digging UpTheCorpses • 2d ago "How would you feed yourself if you lost your job?" I ended up being laid off as well as my whole division.
    via u/DiggingUpTheCorpses
  • 05
    Avamedic 2d ago • In previous role managing hospital unit, was asked the following: Did this employee ask the other employee something about their "bun hole"?
    via u/Avamedic
  • 06
    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
    via u/Avamedic
  • 07
    Sliver-Knight9219 • 2d ago Do you plan to start a relationship with any coworkers and would you use a secret of your boss to blackmail them.
    via u/Sliver-Knight9219
  • 08
    Zolome1977 • 2d ago 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.
    via u/Zolome1977
  • 09
    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.
    via u/Zolome1977
  • 10
    montoya0142 • 2d ago "Do you know any gay candidates we can hire and fast?"
    via u/montoya0142
  • 11
    SeaBearsFoam • 2d ago Edited 1d ago "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.
    via u/SeaBearsFoam
  • 12
    myguyohyea • 2d ago Edited 22h ago "I heard that the lady in white dress is married. I wonder who the lucky guy is"-business colleague about my wife. Most awkward moment of my life Edit: No I'm not threatened by him nor will I ever be. It was awkward because | thought he knew she was my wife and was just joking but he was serious. Then I remembered he has actually never met my wife because I didn't invite him to my wedding. I invited everyone else just not him. He only knew her by name and has n
    via u/myguyohyea
  • 13
    filteredaccess • 2d ago 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.
    via u/filteredaccess
  • 14
    gwig9 • 2d ago Why do you celebrate Christmas when you are an atheist? Random question from an admin when I mentioned that I was not religious.
    via u/gwig9
  • 15
    waffle299 1d ago • 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.
    via u/waffle299
  • 16
    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.
    via u/waffle299
  • 17
    Shark_bait5 • 1d ago "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.
    via u/Shark_bait5
  • 18
    missanthropy09 • 1d ago My subordinate, a young girl a few years out of high school, was working at the front desk and checked in a young mother, carrying her child. This woman was young, maybe a year younger than my employee. And after that, patient was called back to the clinic, she asked me if I believed in abortion. Being a fairly new manager and caught off guard, I said something like I think every woman has the right to choose what happens to her body. And then she asked me my religious be
    via u/missanthropy09
  • 19
    atot806 • 1d ago When I started my business, my wife helped part time with the administrative stuff. During an interview I was conducting, a candidate asked whether she was single when I asked if they had any questions regarding the company.
    via u/atot806
  • 20
    Cheap_Explorer7030 • 2d ago 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"
    via u/Cheap_Explorer7030
  • 21
    LimaOskarLima • 1d ago 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 operatio
    via u/LimaOskarLima
  • 22
    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 , so my supervisor stepped in before I put my foot in my mouth. My oddest experience by far.
    via u/LimaOskarLima
  • 23
    linuxphoney • 1d ago "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.
    via u/linuxphoney
  • 24
    mark503 . 1d ago For me it was me being too friendly with my employees. I was doing some work by a cardboard baler. Some employees were hanging around crushing boxes. They're carrying on and I walk up and join the conversation. They're talking about families and stuff. I thought this was a good opportunity to get to know one of them better. I don't know why but I said "Hey Kasandra, how many kids do you have?" She gave me a dead eye look and just crushed me. She blurted out with the most serious
    via u/mark503
  • 25
    Keep in mind she was a very strong looking woman. It was obvious when she said it. I just replied "this is why I don't talk to you all. I'm never asking y'all personal questions again." They all started laughing at me. They all knew she was gay. I didn't want to make assumptions in sexualities. I wound up doing exactly that.
    via u/mark503
  • 26
    m_smith95 • 1d ago 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.
    via u/m_smith95

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workplace-stories employee job awkward moments Professional At Work work Awkward employer dumb questions workplace interview funny weird employment
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