People Break Down The Most Uncomfortable Questions Someone Can Ask
Photo by Hermes Rivera on Unsplash

People really need to think first.

Some questions, no matter how innocent, are not appropriate.

But the people with the questions never seem to care, so the gravity of the question is always on the person questioned.

Most people shake it off and just deal with the unease.

But maybe it's time to chat about what makes a good conversation.

So many times I know my face has said...

"Did you really just ask that?"

Redditor chickenoodlesoupp wanted to hear about some of the times we've been asked something that left us a bit uneasy.

So they asked:

"What’s the most uncomfortable question you can ask someone?"

I've been asked so many stupid things I can't even begin to remember.


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"Do you have a sister by chance?"


"This is made worse if the asking person is male and the receiving person is female and both are single."


Hold Me

"Where’s my hug?"


"Lol this gives me some flashbacks. After work on a Friday I was saying goodbye to ones of my friends and a gave her a hug. Here comes Brett 'Hey, where's my hug?' So I give him the biggest bear hug, the kind that traps their arms at their sides, and picked him up off the ground."

"There's your hug Brett. My friend said he didn't ask much after that, but you bet your b*lls I'd tell Brett 'Hey Brett, I got your hug right here buddy' with outstretched arms. He would give me an uncomfortable look like ew gross. Yeah Brett, that's how you are making everyone feel."



"Hey, can we have a talk about your search history?"


"For my generation that is 'Can we have a talk about what I found under your bed?'"

"I'm an adult now tho so I leave porn mags on the coffee table. Nothing funnier than watching a guest look through the magazines in your living room while you serve coffee only to find a Hustlers in the middle of the pile and not know what to say as you sit and stare at them."


Don't Ask

"Why don't you have any children? I was a chronic miscarryier. My son is a super duper miracle."


"Came here to say the same thing. I have one child, during the labor they both were very close to dying. The doc said if she gets pregnant again she will lose the child and possible die in the process."

"I ended up getting a vasectomy very shortly after. We’re incredibly grateful and happy with our little family; but without fail, we always get the same question: 'So when you getting a little brother or sister?' I don’t mind as much when people ask me or my wife, but ask my son? Why?"



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“How come I wasn’t invited?”


"I was once invited to a party... at the end of which the hostess asked me 'How do you keep finding out about these?'"

"That freaking stung. Never talked to them again."


Well, that is just a step above cruel.


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"Have you seen our toothbrush?"



"'Why are you so quiet?'"


"This makes my blood boil. I’m a fairly quiet person in social settings and have received this question a few times. It makes you AND the people around you feel awkward. Like... let people be quiet if they want to be. Not everyone is a social butterfly!"



"Why does everyone hate you so much?"


"I hate this one so much. I lived in a small town so everybody knew everybody. High school was rough, I didn't know how to stick up for myself and soon became the scape goat for bullies and rumors."

"Once our Sr. Year people matured a little and started being nicer to me. I made a lot of friends suddenly and all of them would ask 'Why does everybody hate you, you're not like they say.' It was awkward because most of those people were the ones contributing to the rumors/bullying."



"If you come in the back office with me right now, just you and me, are you gonna be cool about it, or be a snitch? Asked by my old boss at a grocery store, he just was offering me shots of fireball because it was almost closing time on New Years Eve, but that phrasing."


"White male privilege here, but that wouldn't make me uncomfortable at all. Like, I'm game, if we get back there and it is something super sketch, I'll just dip out."


Let's Chat

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"Hey we need to talk. This is the worst, especially over text."


"My boss texted me the other day, 'Call me.' My blood turned to ice. Of course it ended up being some inconsequential thing he had a question about."


Sometimes silence is best.

Do you have similar things to add? Let us know in the comments below.