People Divulge The Most Awkward Question They've Ever Been Asked
Ayo Ogunseinde/Unsplash

I once had a man at a party very assertively tell me exactly what he wanted to do to me before my facial expression (I'm guessing absolute disgust) made him pause and awkwardly ask:

"Wait... how old are you?"

I was twelve. Turned out he was one of my dad's friends.

It was ... icky.


Reddit user KairoLlyr asked:

"What is the most awkward question you've ever been asked?"

I'm not alone in having people ask some seriously awkward stuff. Neither are you.

No Chance To Answer.

"When I was about 13, my mom and I were watching a parrot demonstration in front of a Rainforest Cafe. Another woman watching turned to me and said, 'May I?'."

"Immediately, with no further explanation, she took a strand of my long hair and held it out to the bird, who bit it. I was just standing there with my hair in a bird's mouth. We didn't know what to do. One of the weirder things that's happened to me."

- its_garden_time_nerd

"Id love to suddenly find myself standing there, a part of me inexplicably in a birds mouth."

- EquivalentExpensive4

"Wow. Just. Wow."

- angusderp

So Did You?

Loop Spinning GIF by WWEGiphy

" 'You look strong, can we wrestle?' - a man in the grocery store"

- yokononope

“Only if there’s a prize”

- TheChanMan2003

"Did he mean right then and there, or out in the parking lot?"

- Annihilated_Matter

"Who won?"

- bluehorde1781

Great Ice Breaker

"At the grocery store picking out some lunch meat (not from the deli, just some plain ole Oscar Meyer) when a man sidles up uncomfortably close to me and after a moment says, 'So….what do you think about the ham?'."

- beezholio

"Idk I think he was pretty smooth"

- Green_noob

"Ok, there are some creepy ones here. There are some funny ones too. This one... this is definitely the straight up weirdest one."

- PuzzleheadedAd822

Good Luck

Jim Carrey Flirting GIFGiphy

" 'Hey man, mind if I squeeze in to try for her number?."

"Dude wanting to hit on my wife whilst sitting together at the bar."

- spit2ee

"You could have said 'You can try but I hear she's married."

"Just hope she says I'm married to this guy over here. You have a smug smile on your face, more smug than Jeremy clarkson."

" 'Told ya buddy, I hear she's married'."

- More-Masterpiece-561

"Haha had something similar happen to me with my girlfriend. I told him good luck and watched him crash and burn as she turned around grabbed my waist and said she was taken. God love her."

- SolarAU

Because Breathing.

"I have no sense of smell, and multiple people have seriously asked me why I have a nose."

- Probablyprofanity

"My wife is anosmic, and has had legit had "so if you were in a room full of poisonous gas, you wouldn't die?" because apparently it's the smell that kills you in that scenario."

- SoylentDave

"That’s when you shoot back with a retort about their brain. I’ll let you get creative, you got this 👍"

- TheChanMan2003

"Same. I have no sense of smell. People nowadays just ask if I have co-vid."

- 4449trainlover

Damn It Grandma!

Arrested Development Flirt GIFGiphy

"Do you want to marry someone pretty like your sister?"

"~My grandmother, while all of us were in one room together"

- fatguy747

"My grandmother once decided to tell me my teenage cousin’s bra size and how proud she was. An aunt had to rescue me from that conversation."

- chief_sitass

That's the most awkward one. You can't even say yes so your answer won't make sense"

- The_SenateP

" 'I'd rather date someone with personality, unlike my sister'."

- Samukuai

​Lack Of Melanin 

"How come you're not black?""

"A 5 year old asked me this while I was teaching preschool. He was black. My assistant teacher and his one-on-one were also black. They both started laughing while my brain reset itself trying to think of a good answer and also trying not to laugh."

- Bells87

"I taught in south Memphis for a while and i was the only white person in the building. I had multiple kids ask me “when did you turn white?” and when i got pregnant, when my baby would turn black like she’s supposed to. For the vast majority of them i was the first white person they’d ever encountered."

- hakuna__frittata

First Language...

english snl GIFGiphy

" 'How was it learning a new language?'... We actually speak English in New Zealand"

- North-Cow1701

"I believe it's called the Common Speech in Middle Earth."

- raalic

"My friend once introduced me to his new girlfriend that he met on a trip while in Asia. After talking a bit, I complimented her on how good her English was. She still had an accent and all but it was pretty perfect. She just responded 'it’s my first language, we speak English in Singapore'."

"My friends just gave it a chuckle and moved on but I don’t think I ever fully processed the embarrassment."

- fuzzypeaches42069

Best Way To Answer

"I have wide shoulders and large breasts and a guy sitting next to me on a flight, after he had a couple drinks, asked, 'Home grown or silicone?' I told him I carried extra sanitary napkins in my bra in case I got my period."

- Nobody_Wins_13

"I want you to be my best friend! ROTFL! The best way to answer a shocking question is to give an equally shocking answer. If that did not turn him off, nothing would. You should have added you have periods heavy enough to float an adult diaper!"

- doehlberg

"I like that comeback"

- Rin720

"Mutual embarrassment is the only solution, but I pity you that you were stuck on a flight with that guy and didn't get to leave after that zinger. It would have been the cherry on top. Now I just imagine two awkward people sitting in silence for the rest of the flight."

- walkinghomeat3am

"It does feel like you're a captive there but he did ignore me after that."

- Nobody_Wins_13

A Bit Personal

canadian what GIF by CBCGiphy

"My husband is 6’11 and I was meeting one of his coworkers for the very first time."

"I told the coworker is was nice to meet him and the very first question that came out of his mouth was, ‘How endowed is your husband? Is he really big?’ "

"If that wasn’t enough he tried to get me to tell him by measuring the length of his thigh and moving his hands together or apart for comparison."

- Knightofthevegtable

"That dude was totally into your man girl! I would have said, However you've imagined it, thats exactly how it is. And I will fight you. LoL"

- Jetter37

"Lol, my boyfriend is 6’5 and I got this from a coworker too!"

“ 'So.. is it proportional? He looks like it’d be proportionate'."

- nowglobeSnot

Admittedly, none of my awkward moments have ended up with any part of me inside a strange birds mouth (familiar bird mouths only) - but I'm betting some of you out there have some awkward doozies.

Serve em up in the comments!

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