50 Awkward Questions That Made People Laugh Uncomfortably

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.

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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".

Cheap_Explorer7030 , Christina Morillo / Pexels Report

Final score:

103points

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Ray Carrillo 6 months ago

illegal question

149points

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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.

linuxphoney , cottonbro studio / Pexels Report

Final score:

97points

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Sue Denham 6 months ago

Uh, no, we can't afford a cleaner.

84points

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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.

AmoremCaroFactumEst , Kampus Production / Pexels Report

Final score:

94points

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Stimpy 6 months ago

Follow-up question was : "do you know any gay people we can hire, and fast?"

59points

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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.

gavinashun , Edmond Dantès / Pexels Report

Final score:

93points

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Michael Largey 6 months ago

"Don't worry. No interference with work. We plan to conceive the child at home and have it delivered at the hospital."

46points

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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! ".

xubax Report

Final score:

90points

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Marcos Valencia 6 months ago

Well, that's a classic question-answer set. I've been there so many times that I automatically answer that.

39points

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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.

dumbf**k , SHVETS production / Pexels Report

Final score:

88points

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ZuriLovesYou 6 months ago

🚨 PEDO ALERT! PEDO ALERT! PEDO ALERT! 🚨

13points

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

Happy-Flan2112 , cottonbro studio / Pexels Report

Final score:

86points

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Bouche and Audi and Shyla, Oh My! 6 months ago

Sure. It's in the dryer. In fact, you can see all of the laundry. You can even put it away.

84points

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

(I dont have breast implants).

MrsBossyPantss Report

Final score:

84points

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Nina 6 months ago

What the actual flying fudge?

27points

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“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.

withextrasprinkles Report

Final score:

84points

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Marcos Valencia 6 months ago (edited)

"Did you purposedly commit pregnancy with the involvement of your spouse?"

50points

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#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.

Shark_bait5 , Fred Ortlip / Flickr Report

Final score:

82points

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Marcos Valencia 6 months ago (edited)

"Boss, I can wear the bikini if she feels uncomfortable with this."

43points

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#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.

Avamedic , Pexels Report

Final score:

76points

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jeffrey champion 6 months ago

I thought this was going somewhere else

105points

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#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?".

Wonderful_Whereas402 , Lê Minh / Pexels Report

Final score:

71points

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Sunshine Lady 6 months ago

And now we have scandals from that time rise up

45points

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#13

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

montoya0142 , LinkedIn Sales Solutions / Unsplash Report

Final score:

70points

POST

Marcellus II 6 months ago

Just strongly hint you're gay. It's not like they can fire you for not being gay when they find out, without losing a lawsuit.

36points

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#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.

m_smith95 , Li Lin / Unsplash Report

Final score:

69points

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Paul C. 6 months ago

I just know my dear wife would have to say, Oh he's hung like a Hamster! 🐹🤷‍♂️

34points

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#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.

Sliver-Knight9219 , Mimi Thian / Unsplash Report

Final score:

66points

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Bouche and Audi and Shyla, Oh My! 6 months ago

Interesting office.

43points

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#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. .

wallyroos , Anna Shvets / Pexels Report

Final score:

66points

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DetriMentaL 6 months ago

Goodness gracious, great balls of fire

29points

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#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.

Amanda_Lee1 Report

Final score:

63points

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Lauren K 6 months ago

Yeah, in nursing school we were supposed to give each other breast exams. I politely declined that one. I don't like to be touched in general, and certainly not on my breasts by someone I barely know.

7points

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#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.

vercertorix Report

Final score:

62points

POST

Marcellus II 6 months ago

She was right, just didn't specify the animal. [obligatory tortoise face.]

66points

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#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.

SeaBearsFoam , SHVETS production / Pexels Report

Final score:

61points

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Paul C. 6 months ago

I've seen the film, it's Alanis Morrissette, isn't it?

59points

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#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.

filteredaccess , Filip Rankovic Grobgaard / Unsplash Report

Final score:

56points

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Ronna Black 6 months ago

Well, I’m not Walking in Memphis.

22points

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#21

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.

DiggingUpTheCorpses , LinkedIn Sales Solutions / Unsplash Report

Final score:

54points

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Nathaniel He/Him Cis-Het 6 months ago

I would feast on the corpses of my ex employers.

77points

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#22

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.

calls_u_a_sea_word Report

Final score:

54points

POST

catastrophegirl 6 months ago

this is when you openly respond "is this because i wouldn't kiss my boss when she hit on me?" because at that point you either get to keep your job or you get a much bigger severance package. and it's a completely appropriate response because you were never the one in the wrong.

46points

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#23

50 Awkward Questions That Made People Laugh Uncomfortably “Does your husband mind that you make so much more money than him?”.

nahc1234 , Aleksandra Sapozhnikova / Unsplash Report

Final score:

52points

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Nathaniel He/Him Cis-Het 6 months ago

What has this to do with anything? What does it matter? Why are some men so threatened by this?

41points

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#24

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…”.

anon Report

Final score:

51points

POST

arthbach 6 months ago

Sexual harassment, pure and simple. Over here, that would have been dealt with by giving a formal warning. After 3 written warnings the person would be dismissed.

38points

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#25

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

SweetCosmicPope Report

Final score:

49points

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I AM A LOLLY SNEK (she/her) 6 months ago

they were fired right? right?

20points

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#26

50 Awkward Questions That Made People Laugh Uncomfortably Why do you celebrate Christmas when you are an atheist? Random question from an admin when I mentioned that I was not religious.

gwig9 , Jason Goodman / Unsplash Report

Final score:

47points

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Trillian 6 months ago

Presents and food. I will celebrate any holiday for that.

86points

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#27

50 Awkward Questions That Made People Laugh Uncomfortably Oh, you were in Iraq... did you k*ll anyone?

Dismal-You5645 , HIVAN ARVIZU @soyhivan / Unsplash Report

Final score:

46points

POST

Marcos Valencia 6 months ago

"If I tell you, I have to kill you. Let's talk about wages and leave days".

41points

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#28

50 Awkward Questions That Made People Laugh Uncomfortably 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.

Sleepy_scientistPhD , Polina Zimmerman / Pexels Report

Final score:

46points

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Marcos Valencia 6 months ago

And so?

28points

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#29

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. .

Zolome1977 Report

Final score:

44points

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jeffrey champion 6 months ago

We do, but they're not for sale.

22points

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#30

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.

highstone67 Report

Final score:

43points

POST

troufaki13 6 months ago

Is this what young people call flirting nowadays?

18points

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#31

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.

LimaOskarLima Report

Final score:

42points

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jeffrey champion 6 months ago

Stupid questions get stupid answers

27points

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#32

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.

DoomsdayTaco Report

Final score:

40points

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Michael Largey 6 months ago

"And her mother" ???????????????????????????????????????????????????????

14points

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#33

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.

bondsman333 Report

Final score:

38points

POST

Marcellus II 6 months ago

For secret service type jobs, they don't believe you've never committed any crime/offence; they don't mind admitting smoking weed 10y before --- they strongly mind denying it when there's evidence you did. Because hiding secrets makes you blackmailable.

39points

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#34

Did you learn that in the “streets”.

mastersheeef Report

Final score:

38points

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Trillian 6 months ago

Yes. More specifically, in *streetnamewherethecollegeis*

24points

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#35

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.

woolgathering_futz Report

Final score:

37points

POST

Trillian 6 months ago

"Isn't that just for emergencies?"

28points

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#36

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.

waffle299 Report

Final score:

36points

POST

HTakeover 6 months ago

Ooof, incredibly tough spot. Followup from OP when asked what they said: "The truth. All of it, the good and bad. We're engineers, we solve problems. He wanted us to succeed, and I could show him how. And together, we convinced his boss. My bosses weren't happy with my strategy, but couldn't deny results. I got a bonus (1/3 my overtime - six months of 100+ hour work weeks). Our customer? They awarded me the patent on what we built."

23points

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#37

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

Rachel1578 Report

Final score:

36points

POST

"Disembodied voice" 6 months ago

Being asexual makes other people think they can just act questions like that.

20points

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#38

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

Natalies_Harmony1 Report

Final score:

35points

POST

Michael Largey 6 months ago (edited)

How about I just take that foot and kick you in the groin instead?

11points

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#39

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.

imacmadman22 Report

Final score:

34points

POST

Michael Largey 6 months ago

Come on - "What might come up" could be almost anything. She could have been selling Amway, for all the OP knows.

6points

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#40

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

Johaggis Report

Final score:

34points

POST

Diana Lucas 6 months ago

I had to look that up. Did they think everyone has one of these?

19points

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#41

“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.

Agile_Deer_7606 Report

Final score:

34points

POST

Michael Largey 6 months ago

In a class taught by a women, I heard from a group of guys sitting behind me "I don't care if she has big tits - I don't like her!" A man of principle, in his way.

18points

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#42

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 beliefs, and that’s when I shut it down.

missanthropy09 Report

Final score:

32points

POST

Trillian 6 months ago

You don't have to believe in abortions. They exist. And if you are against abortions, just don't have one.

70points

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#43

The manager at my first job asked to borrow my car to go pick up some weed. He offered some as compensation. It was some pretty s****y weed tbh.

Fulk0 Report

Final score:

31points

POST

Pandemonium 6 months ago

Life is too short to settle for s****y weed

24points

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#44

My first boss in my field, “why do you want kids if you can’t even take care of yourselves?”

Luckily I was on the phone and didn’t hear that or I would have been arrested.

ldunord Report

Final score:

26points

POST

Marcos Valencia 6 months ago

There could be some context in this case, tbh.

16points

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#45

Was being seen for a rash on the hands- probably poison sumac- but after looking she wants me to spread my fingers, but says,” let me see between you legs”

Freudian slip? Who know but embarrassing for us both, especially as it was not a private setting with several people hearing this.

Thomas-can Report

Final score:

25points

POST

Michael Largey 6 months ago

Since we use our hands when going to the bathroom, the request would not be unreasonable.

4points

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#46

"What do you do in your free time, and how do you let that impact your job performance?"

Not my current job, but during a past interview, someone asked this. It's one of those poorly-worded questions made up by some corporate HR nut. WTF kind of answers do they expect?

profdart Report

Final score:

25points

POST

Stinky 6 months ago

Oh, I'm a pagan Furry who collects navel fluff and airsick bags, likes to race beetles, carve soap and undertake extreme ironing while mooing......nothing out of the ordinary......

39points

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#47

“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 I 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 never seen her.

myguyohyea Report

Final score:

24points

POST

Soy 6 months ago

I think I know why you didn't invite him.

21points

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#48

I once had to explain my polyamorous relationship in a job interview for a senior dev position. It was probably my fault that it came up, but going into detail was the right move and I got the job.

malsomnus Report

Final score:

24points

POST

Stimpy 6 months ago

Weird interview question, but if the topic was brought up by yourself, maybe they took it as an opportunity to check if you are easy to make insecure or if you remain sovereign even in uncomfortable situations...

10points

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#49

What church do you go to?

discostew919 Report

Final score:

21points

POST

Marcos Valencia 6 months ago

"La Ermita", Jerez de los Caballeros, Badajoz, Spain. Jerez-de-l...463462.jpg

12points

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#50

"Are these yours?" Male colleague holding up a super haggard black thong. We have a weird job, sometimes we do laundry at work. He and I both did laundry that day. Not mine, and we are throwing this embarrassing thing away like it never happened. We're not going person by person to find the owner of this ratty thing.

JustGenericName Report

Final score:

20points

POST

Al Fun 6 months ago

Sure awkward, but it doesn’t sound inappropriate. The colleague just wants to return some found laundry.

17points

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What do you think ?

This was a mistake. I'm gonna go find some articles about dogs.

Michelle 6 months ago

#44. Went to a dispensary after my move to California. Never encountered such gourmet weed. They asked what kind I wanted. [In my head: The kind that gets you high, of course] So they had me smelling ‘different’ strains, asking me how it smelled. Wellllll…they all smelled like weed. My boss’ boss asked me about my weekend and I said I had learned about some of the gourmet weed in CA. He proceeded to give me the rundown of the best sativas and indicas, and the cheapest places to get them. Now THAT was a weird, but useful conversation.

Alex 6 months ago

It's strange. Working in the arts (theatre) I've heard SO much worse than most of these. But I guess that's just expected witrh the setting...

Mike F 6 months ago

Working in a factory I've heard worse, lol. I had a warehouse job way back when and would be signaled by a buzzer when I was needed on the manufacturing floor. I answered the signal one morning and before I went back to the warehouse, I made the mistake of asking "anything else I can do for you ladies before I go back?" These old girls were the same age as my mother, some of the things they said to me that day embarrass me 45+ years later, lol.

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50 Awkward Questions That Made People Laugh Uncomfortably

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