What is the most awkward question someone has ever asked you?

Question

Cormac995 · Accepted Answer

I have a friend online who is Chinese but moved here, and she has a friend in China that was single. I didn't know this when she asked the question though and I knew she was engaged. (Married now) Out of the blue she asks. "Hey, are you single?" with absoululty 0 context. I fucking froze in terror worried that she was hitting on me not to mention I was dumbstruck because that never happened before but I basically replied. "Dating never really worked out for me and so I stopped trying."

I cannot tell you how relieved I was when she mentioned she had a single friend and wasn't trying to start an affair. I later found out she offered to try and get another one of our friends to try and date her friend and he had the same panic attack I did when she asked if he was single! XD

I made sure to make myself presentable and brush my hair etc so she could send her friend a pic of what I looked like. Never heard a word about it from my friend since but I'm not stupid so I know her friend wasn't interested once she saw me. If she was my friend obviously would have told me within a week.

I knew it was going to happen, but it still hurt realizing I'm not even good enough for someone trying to flee their country. That hit my ego pretty hard for a few weeks. Still does when I think about it actually.

hahahmm · Accepted Answer

Was at a family reunion and in front of a bunch of people my weird aunt just casually says to me: so you work so much, how do you find time to have sex with your girlfriend?

Now keep in mind that I don't even talk about that with relatives I *AM* on good terms with and this aunt I hadn't even had a conversation with since I was 8 years old or something.

Everybody around me looked like 👀. I just switched topics and pretended I didn't hear her.

Plufem · Accepted Answer

Some questions here are awkward, but hey one's awkwardness may be normal to others, so I answer to all that I can!

I guess the most awkward question was when a boy asked me if I have milk in my tits and that too when people were around!

MzAsh · Accepted Answer

I had a perm in 7th grade, very 90s Melissa Gilbert like. My friends brother asked me “why are you black?” 🤔 I was like I’m white af bro, just have a perm

ohsheeT · Answer

Actually it was a question on here and I thought it was so freaking funny actually there's two questions on here the first
Do gay guys get turned on when they look at their own penis I don't know why but I laughed my ass off

The second one was a girl and she wrote can anybody tell me how I make a question it was something like that but it was funnier than funny because she just did it

Well I don't know they're not as funny as they were with my first heard them LOL

glennos89 · Answer

I had a blind first date with a girl and we arranged to meet eachother at my house to hang out and get to know eachother.

I offered her something to drink and after I gave it to her the first thing she asked me was

She: "what's your opinion about nudists?"

Me: "Uhm I don't know, I guess they should do what they feel comfortable to do. I don't judge them

She: "Do you mind if I take all my clothes off?"

Me: "Awkward silence"

This girl didn't even wait for my answer and she was taking off all of her clothes. Weirdest fucking experience ever

jamesgoldman · Answer

I won't use names excluding my own

When I was in the restaurant and we'd all had a few drinks and were heading out to someone else's place nearby when the head chef knowing I was relatively newly single pipes up with

James, would you rather fuck J or B? in front of B's dad and J herself

I answered J because clearly head chef wasn't going to take no for an answer and rejection beats a busted nose

As it turned out events that night transpired to me dating B for the next 4 months

Anonymous · Answer

I was in college, and my guy friend took me out to lunch. We barely sat down at the table and he asked me, "so, have you had sex yet?" We did not have this type of relationship where we talked about his or my sexual habits, nor did I have the habit of discussing what I do in the bedroom with others....so awkward, yes. This was also a very public eatery with children around. I was not amused by this, nor was he joking. Our friendship ended not to long after this for so many reasons, but he just had no tact or respect for privacy. It wasn't just with me either, a lot of friends ditched him for his behavior towards them.

HungTexan · Answer

My usual massage therapist (female) asked “OMG, are you getting an erection?” while massaging my thighs with only a small towel covering my genitalia. I was relaxed and almost dozing off, so I wasn’t sure! In shock, I pulled the towel off to look! Fortunately I wasn’t getting hard? Still it was awkward, but we laughed about it later.

Zack-Bann · Answer

I was 14 years old and had never had a girlfriend (not that I was supposed to at 14)
But my younger brother who was 12 was seen hanging out with a girl from our town.

So my aunt who lived abroad and came to visit during the summer started asking me if I was secretly gay and telling me how it’s alright to be gay in our day and age.

Basically: for her. If a 14 year old isn’t already having pussy for breakfast lunch and dinner then he must be gay

Anonymous · Answer

My parents asked me if I was going to keep my nipples. I was getting a surgery that could potentially remove them, so it wasn't an out-of-the-blue question, but it was still very awkward coming from them. I gave a very basic answer and tried to end that conversation as soon as possible.

gowildcats007 · Answer

I had a guy talk to me at a basketball game. He was 21 and I think I was 12. After about 10 minutes of talking and watching the game, he asked me to wait for him so we could get married when I was 18 and then said will you marry me.

Valdemort · Answer

"Your parents were very busy in the bedroom then, weren't they?" Very odd, having adults ask you this, when you're a kid, because you come from a large family 😀

12karen · Answer

"Why don't you wanna be my mom?" Then he proceeded to kiss me but I move so it landed on my left cheek. We were 6, making a queue in class to show the teacher our homeworks.

Anonymous · Answer

Urologist once asked me: "Can you achieve erection, how often are you sexually active"? And I'm still a virgin :/

Joshydavid25 · Answer

Some girl that was into me and me her asked me if I knew that her and someone else was together... It was pretty damn awkward..

ihateTaylorSwift · Answer

a long time ago  This weird perv on the phone asked me  what else are you doing 😏 And I said "hanging up..."

molonski2 · Answer

Did you know that Harper had been fcking Sue?

Wiredone · Answer

I don't remember being asked any awkward questions in the past

exitseven · Answer

I had a girl on the first date ask me if I was looking to fall in love.

Anonymous · Answer

I was a swimmer and we shaved as much body hair as possible to reduce drag. And I asked a fellow swimmer if he'd shave my coin purse.👀

LiamJHayden · Answer

I had a stranger on the beach ask if she could live in one of my spare bedrooms.

Nikki1989 · Answer

Awkward questions come my way almost every day on here. Hard to pick just one. This site is full of oddballs.

blackeagle007 · Answer

I couldn’t make this up “do you wanna be my friend?” 😆

debtfree_oneyear · Answer

IRL I have been hit on several times by other guys. I'm not gay.

dougeats · Answer

She asked... Are you willing to wear a pink dress for me

Flower7 · Answer

“How old are you?”

electromagnetic · Answer

“Are you black or Korean?”

NicholasRedone · Answer

Where do you see yourself in X amount of years -

Connie88 · Answer

How’s the weather up there? Being 6’0”.

What is the most awkward question someone has ever asked you?

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