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

Mehmet Oz
Celal Gunes/Anadolu via Getty Images

Dr. Oz Raises Eyebrows Over His Bizarre Defense Of New Guidelines For Alcohol Consumption

Dr. Mehmet Oz, President Donald Trump's administrator for the Centers for Medicare and Medicaid Services (CMS), raised eyebrows over his bizarre and surprisingly permissive defense of new guidelines for alcohol consumption, saying "it does allow people an excuse to bond and socialize, and there’s probably nothing healthier than having a good time with friends in a safe way."

Oz spoke as the Trump administration on Wednesday released updated dietary guidelines for Americans, emphasizing whole and minimally processed foods, reduced consumption of refined carbohydrates, and what officials described as a “war” on added sugars.

Keep ReadingShow less
Bowen Yang
Bruce Glikas/FilmMagic/Getty Images

Bowen Yang Gets Candid About Why He Decided To Leave 'SNL' After His Sudden Exit

Bowen Yang, who's well-known for his work on Saturday Night Live and his role in Wicked and Wicked: For Good, stepped off of the SNL stage for the last time, mid-season, after being a writer and performer for the past eight seasons.

During his final skit, Yang starred opposite Ariana Grande, with the couple playing a married couple. Grande was waiting for Bowen to come from after his final shift before retiring from working at an airport.

Keep ReadingShow less
Kyle Rittenhouse
Sean Krajacic-Pool/Getty Images

Kyle Rittenhouse Blasted Over Sociopathic Post Following ICE Shooting In Minneapolis

Kenosha shooter Kyle Rittenhouse sparked outrage after he offered to travel to Minnesota following ICE's fatal shooting of Renee Nicole Good, a mother of three, in Minneapolis on Wednesday.

Department of Homeland Security (DHS) spokesperson Tricia McLaughlin claimed Good “weaponized her vehicle, attempting to run over our law enforcement officers in an attempt to kill them.” But Minneapolis Mayor Jacob Frey pushed back against this narrative considering witnesses described seeing Good in the vehicle trying to flee officers when she was shot.

Keep ReadingShow less
LEGO's 'SMART Brick'
Patrick T. Fallon/AFP/Getty Images

Lego Just Unveiled Their New Tech-Heavy 'Smart Brick'—But Not Everyone Is Excited About It

LEGO has long been known for its fostering of creativity, independent play, and imaginative designs, both in their LEGO sets and free-form bricks.

Parents have long hailed LEGO as a viable option for fostering creativity and critical thinking, even when faced with the frustrations of children not cleaning up all of the pieces and the pains of potentially stepping on them.

Keep ReadingShow less
Alexis Ohanian and Serena Williams
Bryan Bedder/Athlos/Getty Images

Serena Williams' Husband Just Stepped In To Defend Her From Accusations That She's Lightening Her Skin

When the Williams family burst onto the scene in the tennis world as juniors, an inordinate amount of discourse focused on Venus and Serena's appearance. The Williams sisters weren't the first Black people—men or women—to play tennis at an international level, but they quickly achieved heights that set them on the path to legendary status.

The heightened attention brought with it a lot of racist and colorist comments about their hair, their skin, and their bodies—especially Serena's more muscular and curvy body.

Keep ReadingShow less