Skip to content
Search AI Powered

Latest Stories

People Break Down The Most Uncomfortable Questions Someone Can Ask

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.

Siblings

Parks And Recreation Nbc GIF by HULUGiphy

"Do you have a sister by chance?"

umpalumpamonkey

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

BlandJars

Hold Me

"Where’s my hug?"

Lalalalanay

"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."

myusernamebarelyfits

Findings

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

SumoSamurottorSSPBCC

"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."

P00PY-PANTS

Don't Ask

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

kcooper1214

"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?"

Danfu777

Ouch

Will Smith Reaction GIF by Red Table TalkGiphy

“How come I wasn’t invited?”

Real_sg4bomb

"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."

REDDIT

Well, that is just a step above cruel.

Our?

Teeth Getting Up GIF by Paddington BearGiphy

"Have you seen our toothbrush?"

MrBurns1619

Speak!

"'Why are you so quiet?'"

spamcritic

"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!"

justaregularderp

Loathing

"Why does everyone hate you so much?"

REDDIT

"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."

PlanBaccount0987

Shots

"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."

pdxblazer

"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."

TeleKenetek

Let's Chat

Scrolling Michelle Obama GIF by ObamaGiphy

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

SubnautGames

"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."

coffeeordeath85

Sometimes silence is best.

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

More from Trending/best-of-reddit

Screenshot of @dhsgov's Instagram page; Kristi Noem
@dhsgov/Instagram; Kent Nishimura/Getty Images

Band Posts Epic Cease And Desist Letter After DHS Uses Song In Deportation Propaganda Video

The indie rock group Black Rebel Motorcycle Club called out the Department of Homeland Security (DHS) in a cease and desist letter, saying it is "obvious" the agency does not respect copyright law let alone constitutional rights and protections after using the band's song "God's Gonna Cut You Down" in a "propaganda video."

DHS used a Johnny Cash cover of "God's Gonna Cut You Down" as a backdrop for a cinematic video that depicts a U.S. Customs and Border Protection agent reciting Bible verses while other agents conduct immigration raids under cover of darkness.

Keep ReadingShow less
Meghan Reinertsen
@meghanreinertsen/TikTok

TikToker's Food Poisoning Chaos

After enough time had passed, TikToker Meghan Reinertsen felt comfortable sharing a food poisoning incident on a United Airlines flight while.

She also offered a long-overdue apology to those affected by the canceled flight thanks to a “disturbance deep, deep within my bowels.”

Keep ReadingShow less
Leah Remini and Maddie
@leahremini/Instagram

Leah Remini Posts Touching Tribute To Fan She Met Through Make-A-Wish Who Recently Passed

You never know when or where you're going to meet a person who will make a special impact on your life.

For Leah Remini, it was when she received a call from the Make-A-Wish Foundation, introducing her to a young girl named Maddie, who was a huge King of Queens fan and whose wish was to meet Leah Remini and her husband on the show, Kevin James.

Keep ReadingShow less
Rosie O'Donnell; Donald Trump
Olivia Wong/Getty Images; Samuel Corum/Getty Images

Rosie O'Donnell Fires Back At Trump With Epic Rant After He Threatens To Strip Her U.S. Citizenship

Actor and comedian Rosie O'Donnell condemned President Donald Trump after he announced in a post on Truth Social that he is considering stripping her U.S. citizenship, labeling her a "Threat to Humanity."

O’Donnell, who was born in the U.S., moved to Ireland shortly before Trump’s inauguration. In an April interview with CNN, she said it was his reelection that ultimately prompted the move, citing the risks Project 2025 poses to her and her nonbinary child—especially after decades of being in Trump's crosshairs.

Keep ReadingShow less
A grocery aisle shelf of Cinnamon Toast Crunch
OLIVIER DOULIERY / Contributor/Getty Images

Bacon-Flavored Cinnamon Toast Crunch Just Landed In Stores—And The Internet Is Not OK

Every now and then, a food brand will try something different in an effort to rejuvenate its products and hopefully attract new customers.

Sometimes these pay off handsomely, such as Peanut M&Ms, which are arguably more popular than the original.

Keep ReadingShow less