Skip to content
Search AI Powered

Latest Stories

The Most Uncomfortable Questions People Have Ever Been Asked

Reddit user Dr_Cloying asked: 'What's the most uncomfortable question you've ever been asked?'

Everyone jokes about not liking small talk and how ridiculous it is to talk about the weather, sports, and the traffic all the time.

But compared to the most uncomfortable questions someone might ask, those dull topics might be the way to go.


Redditor Dr_Cloying asked:

"What's the most uncomfortable question you've ever been asked?"

Almost Arrested

"Have you been dancing with my wife?"

"From an angry cop as his wife and I exited a country bar where we had danced for hours."

"Note: I met her there and she told me she was single."

- PantsDownDontShoot

Truthful Kids

"A small child crawled under the stall I was using and immediately asked me why I didn’t have hair down there."

- mahhhhhh

Lose-Lose Question

"'Am I fat?' from a random middle-aged woman I’ve never met before while I was at work."

"She completely caught me off guard."

- xanhadd

Jokes on Demand

"Can you tell me a joke?"

"My friend passed away in his early 20s and I was at his wake when his mom said she remembers hearing that I'm funny (I'm not) and asked me that question."

- Ok-Resolution-9625

Spectrum Radar

"My brother was asked by a girl on a first date if he had Autism."

"As it turns out, he did, but it was undiagnosed up to that point."

- PrometheusHasFallen

Adoption Costs

"'How much did you cost?' I’m adopted."

- RambleJar

"My sweet 10-year-old boy just came back from summer camp. He told me one of the boys in his cabin was a foster child and didn't have a family."

"He asked, 'Can we buy him?'"

"I gently explained that the correct term was 'adopt,' lol (laughing out loud)."

- yourmomprobably

The Most Important Question

"Some weeks ago, my mum asked me, 'Are you happy?'"

"That question hit me deeper than anything else."

- BuDDah77

Disability Awareness

"'What did you do to yourself?'"

"I was a kid with leg braces and a physical disability I was born with."

"I always replied with, 'I was born…'"

- Famous-Tumbleweed-98

Child Loss

"At the start of the pandemic, my hospital asked all pregnant staff to go home and shield. I was very early in the pregnancy and had had two previous miscarriages that no one at work knew about."

"Everyone found out why I was shielding, because what other reason did a doctor have to not work during the pandemic?"

"I ultimately had another miscarriage and came back a few months later."

"A male colleague I was friendly with said, 'It's so good to see you back, what did you have?' (Assuming I had the baby.)"

"I said, 'A miscarriage.'"

"(He literally stopped in his tracks, apologized a ton, and was extra gentle around me for a few weeks. I've got an amazing two-year-old now and am due with my second any day. )"

- DrBasia

Apparel Reveal

"Because of the size of my chest, people automatically think it's acceptable to ask what bra size I am/how big are they."

- SaraSmashley

Inappropriate Dates

"I got asked for my number by an overbearing sales canvas guy in town. He was way older than me and I was only 16. Ugh."

- c0mpromised

Invasive Questions

"I'm a disabled veteran and when some people learn that they say, 'Really, what's your disability?' which I find to be an invasive and highly personal question."

- Backsight-Foreskin

Digging Up the Past

"Because I have military tattoos and Dog tags and a tattoo of a rifle driven into the ground on my arm, it is clear I served overseas."

"I get asked by strangers all the time, 'Did you ever kill anyone, did you have any friends die, did any friends die in your arms, did you see anyone die, what is the worst thing you saw?'"

"I get that people are curious but holy f**k, who asks questions like that."

- Irondaddy_29

Dating Scene

"On the third night that my wife was in the hospital for blood clots, a nurse asked me, 'If she passes away, how long before you start dating again?'"

"WHAT?!"

"I told her that, 'Should she die, YOU are the first person I'll have investigated.'"

"I never saw that RN again the rest of my wife's stay in the hospital."

- GeneOTheGreen

In Need of a Filter

"I have a stepdaughter. She’s fair-skinned and has red hair. A clerk at a store asked me two days ago where she got her light skin, saying I’m much darker."

"That might not have been the MOST uncomfortable question I’ve been asked, but it’s a recent example of an uncomfortable question."

- Dovleti

These were undeniably unreasonable questions for someone to ask another person, especially if that is a person they do not know well.

As boring as it might be, sometimes it's best to stick with talking about the weather.

More from Trending/best-of-reddit

JD Vance; Jen Psaki
Johannes Simon/Getty Images; Kevin Dietsch/Getty Images

Vance Gets Brutal Reminder After Accusing Jen Psaki Of 'Attacking' People For Praying Following School Shooting

Vice President JD Vance was criticized after he lashed out at MSNBC host Jen Psaki for saying that "prayer is not freaking enough" to end school shootings after a shooter killed two children and wounded 17 others during the first week of classes at Annunciation Catholic School in Minneapolis.

Psaki spoke out on X shortly after the shooting occured, to stress that "thoughts and prayers" don't actually address or prevent mass shootings and gun violence overall:

Keep ReadingShow less
Screenshots from @andydouglas.trumpboy's TikTok video; President Donald Trump
@andydouglas.trumpboy/TikTok; Andrew Harnik/Getty Images

Video Of Little Boy Sobbing After Finding Out Trump Is A Real Person Goes Viral—And We Totally Get It

Whether it was Santa Claus, the Tooth Fairy, or some other important facet of childhood, most of us found out when we were kids that something we loved did not exist, and it was absolutely devastating and world-changing.

But imagine there being something that you deeply disliked or feared, only for you to find out that it actually exists on the same plane and in the same timeline as you.

Keep ReadingShow less
Screenshots from @originalsugarphly's TikTok video
@originalsugarphly/TikTok

Woman Stunned After Best Friend Of 23 Years Ends Friendship Over Her 'Mom Shorts'

We will all have friends who come into our lives for a reason, for a season, or for a lifetime. There are those situational friendships, like from work or school, that dissolve when we exit that space, and there are friendships that might form from knowing the same people.

Then there are those tried-and-true friendships that we think will truly stand the test of time—but even those sometimes fracture under pressure. And sometimes for the most ridiculous reasons.

Keep ReadingShow less
Screenshots from @nurse_xtina129's TikTok
@nurse_xtina129/TikTok

Woman Sparks Debate By Putting Out Small Fire At Dunkin' Donuts After Workers Ignored It

Imagine hitting that afternoon slump and seeking out your favorite caffeinated beverage: a highlight in an otherwise dumpster fire kind of day. But then you arrive at your coffeehouse of choice—and there's literally a fire.

TikToker Cristina Conklin was waiting in line for a beverage at Dunkin' Donuts in Warwick, New York, when she became either a villain or a hero, depending on who was watching her TikTok video.

Keep ReadingShow less
Former Republican congressman and Fox News host Trey Gowdy
Roy Rochlin/Getty Images

MAGA Fumes Over Fox Gun Control Talk

The nation is reeling after yesterday’s mass shooting at Annunciation Church in Minneapolis, where a gunman opened fire during a Catholic school Mass, killing two children and injuring more than a dozen others. The tragedy has not only shaken the community but also reignited the national debate over guns in America—this time sparked by an unlikely voice.

Former Republican congressman and Fox News host of Sunday Night in America, Trey Gowdy—long seen as a staunch defender of gun rights and a past recipient of National Rifle Association contributions—surprised many of his own allies when he called for a national reckoning on firearms access.

Keep ReadingShow less