What was the weirdest question a date has asked you and how did you respond?

Question

abc3643 · Accepted Answer

This is a good question, but my answer is going to be a bit odd.

This is the not-so-weirdest question that she DIDN'T ask me, but asked others.

30 years ago, I was in love with a beautiful blonde whom I very much wanted to marry. She dumped me in January 1992 and I've been devastated ever since.

About 2 months later, we were talking and she had mentioned that she'd ask previous boyfriends "What would you do if I got pregnant?"

I was surprised and asked her "How come you never asked me that?"

She said, "Because I always knew what the answer was."

You see:
1. She was a virgin and didn't want to do it until she got married.
2. I was madly in love with her and agreed to that - I wanted to marry her anyway and I could wait. We went to a nerd STEM college anyway, so not many opportunities for sex for guys who far outnumbered women. She knew I was always in love with her.
3. She knew that I was good with kids and would have supported her no matter what. She almost certainly knew that I would have married her simply out of love and not because I had to.

OlderAndWiser · Accepted Answer

I was trying to reconnect with a girl I had dated when she lived closeby but had later moved much farther away. I had not seen her in a few years and the feelings had subsided but I thought maybe they could be reignited. I visited her for a weekend and the visit was okay but not superlative. Apparently, her perception of what was happening was a bit different.

I called her a few days after I returned home. There wasn't any discussion of love or affection or do you want to keep seeing each other and let's things develop. Quite abruptly, she asked me, "so, when you move down here, will you buy a house for us to live in?"

I was so stunned that I didn't know how to reply. A few days later, I sent her a Dear John letter

silvermoon84 · Accepted Answer

My eyes have this weird trait where they look brown but also have a hazel hue. I was out on a coffee date with this guy I met on okcupid. He clearly noticed it and when he did he put his face right up to mine and asked me “are your eyes hazel or brown?” I was creeped out but stayed a while longer to be polite. He did himself in not even ten minutes later when he grabbed a strand of my hair and smelled it. I told him after that I wasn’t that interested and left.
I ALWAYS pay my own way on dates for this reason, so that if I don’t have any further interest in the guy I don’t have to feel like shit about him paying

spuitkaas · Accepted Answer

If I wanted to see his semen under a microscope. He told me he just bought a microscope so I was like 'oh that's cool!' and he asked me what I wanted to see underneath, so I said that I had no idea and then he asked if I wanted to see his semen under a microscope. He was a weird dude.

jennifer_bloom · Answer

One guy asked me if I would get angry if he chose to drink his coffee out of a straw.

coachTanthony · Answer

What would you say if I was married? LOL

livin_hi_808 · Answer

I met a girl from a dating app. It was really casual at first. Went through the basics and then after we went to drink with some of my homies at a pool hall. One of my boys started checking her out and he asked me she was my chick and I told him straight up that I just met her online and she's fair game basically. They talked a bit then came over to my table holding hands. I was like oh wow that was quick. So like I said it was casual at first until she out of nowhere ask me if I was busy the following night. I was thinking.. "WTF, why would she ask me that now?"
I told her I was just gonna chill at home to detox and recuperate from all the beer and blow my body was infused with. Well, just as my words escaped my mouth she asked me flat out...
WILL YOU WATCH MY KIDS FOR ME so me and what's his name can go out together?
She told me she had no money and if I'd them for her for free. 🤣🤣🤣

ChrisMaster69 · Answer

Would you sleep with my sister?

apparently her previous guy had been doing both of them, without either knowing.

I do not know if my answer of No was the right answer or not lol.

I think you needed both sisters to get a decent IQ level.

lovely girl but unless it was fashion related or Vampire Diaries (or some other series), then she was not interested and knew nothing about it.

Also I had to make all the decisions, I had a week of it and felt the urge to scream.

Even though her sister was not a twin, she was exactly the same.

I could very well see why the previous boyfriend was able to have both.

Makeushiver · Answer

Sorry this doesn't answer you question but there used to be a show named Family Feud, Richard Dawson was MC. The format was set up to have two sides each a fellow family member. Dawson would ask a question like "what beverage is consumed the most in your household". Each family member would answer w/o any other family knowing what the answers will be. On one show that never made it to network TV he asked, "what is the weirdest place you've ever 'done it' . Now each family member needs to answer what they wrote down and all the family members Dad, Mom, two siblings had answers like back seat, hotel lobby, whatever until it gets to the last family member, a teenage girl said, 'In da butt" . I think it's on Youtube

PaynefulPleasures · Answer

I haven't dated in so long. The last date that stuck out to me for off the wall questioning besides the way he dressed, was just before I met my late husband. This weido asked if I shaved, what dimensions were my who ha, do I least wash myself daily things kept getting worse. So I excused myself never to return, total creep factor 🤪

Ernie883 · Answer

Asked to drink my blood saying was only way she could truly experience me inside her. We were alone in a warehouse outside boulder I was living in myself with two floors a dock and my Harley Davidson!! Had much fun with that shit at night with nobody for miles! Had huge party's!# wanted a real donkey show I remember but had trouble finding donkey! What a let down! Got a girl. No donkey! WTF. Told ya I had amazing life and got stories for hours that all are true. But you won't believe any could be. It's still being made people. So come see the truth yourself before I die or cripple myself beyond repair finally. Admittedly am even dumber than average male. So luck is why I still get chances at excellence at my old age of 44. Luck and being so lucky my whole life is why I am not a vegetable as I should be today. Don't deserve actually deserve opposite. Is no justice motherfucker so ha ha! Suck it! Seacrest out!! Fuck that's funny someplace.

humanearth · Answer

So many years ago. A girl asked me “How come I dont care about making money?“ I said its not important to me.  She left in less then 5 minutes after asking that question.

BLMUSER · Answer

I met a woman for a lunch date and she told me all of her problems. She said she is seeing a Psychologist and trying to sort out her issues. She told me everything and I listened. I didn't say one word on that date. After about 90 minutes, she stood up, and asked me what my problem was? I told her I didn't know. Then she walked away. The sad thing is I called her for a second date, even though I thought she was craz, y because she was pretty. It never happened.

Bricealan · Answer

I suppose you could call it a first date. It was the first and LAST time I fucked a friend's wife. We were in bed, naked, and she had seen my penis, erect, and she asked if I was circumcised ! I could not believe it, she had been fucked by a few men besides her husband and I could not believe she did not recognize a circumcised penis from an uncircumcised one. I THINK her husband many have not been circumcised.

ArrowheadSW · Answer

Hummm... I can't recall any particular question that I didn't like. I do recall someone being a bit too business-like in her questions and that was a bit annoying.

AndrewMG · Answer

So I'm going to answer this purely 2020/2021 Covid style! lol, So I've been asked out for a date by a work colleague who we've only communicated on Microsoft teams for the last 18 months, she asked whether we could meet up in a beer garden once restrictions are lifted. Now nothing weird with the question but the fact that it's taken so much time to arrange a date despite technically working in the same office (pre working from home), makes it a weird question to me.

Leavesbound · Answer

She asked me if I'd like to come along and meet her ex husband's mother who she was friends with, with her ex husband in the room at the time. Talk about awkward.

Jazquee · Answer

"How many times have you fucked on a first date?" To which i replied..."not enough times for you to feel confident!"

libsaretards · Answer

Had a date ask me if I was gay because I showed no attraction to her. I told her it was because she was a shitty person and the more she talked the more evil she sounded.

Abi1710 · Answer

are you up to being filmed doing a lesbian 3some and maybe a 4some That was the weirdest and that was 3 months ago

TommyMountainFigure · Answer

I was asked.  Have I ever been with a prostitute? And I responded with, "No, Why have you ever been one?"

DJB72 · Answer

A girl asked me if I'd mind if she shaved my balls on our first date. We dated for quite a while...

sheikalana · Answer

Him - "How are you in bed?"  Me - "That's none of your business."

Morgooo · Answer

It wasn’t a date per se, but an old ex met me at his sister’s wedding. When I told him I had done some charity work for an Indian Rez, his first question was if I’d done peyote while I was there. I just said no.

Bluemax · Answer

One woman asked me if I wanted to join her in the ladies' room.

JackSmy · Answer

"Tell me how you got this scar?" as she was holding my hands, and noticed one.

Anonymous · Answer

He asked me if I got poo stuck in my hair when I wipe my ass, because it's so long. Disgusting right? I didn't have a response I was dumb founded at his ignorance

FilmGuy93 · Answer

I once had a girl keep asking me about whether or not my wife knew we were on a date. I'm not married.

Joshua0213 · Answer

She asked how much money I had and then I just told her I wasn't interested cause usually that just means they're in it for the money

blondfrog · Answer

She asked me if I was into witchcraft and she confessed to me that she practiced it. This was a first date by the way. After that never did online dating ever again.

Turtleneck22 · Answer

I had a girl ask how big I was. That was really strange and make for a awkward time. I laughed it off and just told her maybe some day she will find out.

Riddler1412 · Answer

That would be " would you beat up my ex boyfriend, if I give you " something in return" ( we all know what )?"

2ndTryatThis · Answer

She asked, “would you ever fuck a girl while her little sister watched? And would it make you harder?” I responded, “are you asking and good lord how old is your younger sister?”

TodsShadow · Answer

Should I bring my gun or my co worker? I said bring your gun. Still brought her co worker and got pissy when I refused to pay for her co workers food. Worst 1st date ever

MCheetah · Answer

A girl once straight-up asked me how big was my dick. I was confused. I told her "it would disappoint you." She insisted I tell her anyway. I did. I probably shouldn't have.

MasseurDeMojo · Answer

I have to have a first date. Most people I have met, have just talked casual. Or in some cases, they were ready to get it on, as soon as I started talking to them. Talk about complicated.

loveslongnails · Answer

I really can't recall, and that's probably a good thing.

SpaceGalaxy · Answer

Weirdest question i was asked by a date was : You are not a GAG member, are you? (as in Girlsaskguys GAG)  My response: No, what the heck is that?

princeofromance · Answer

I'm not spending too much of your money, am I? I responded by saying no, It is the man's responsibility to pay for his date.

exitseven · Answer

She was somebody I knew in high school. Four or five years after we graduated we went out a few times. She asked me why I never asked her out in high school because she really wanted me to.

Anonymous · Answer

Your tits are huge do you suck your own nipples when you masturbate? Same guy later told me his friends told him I was cool and he asked if we should fuck now or wait till after dinner.

Meghnanair · Answer

It was not a date, but the weirdest question asked by a boy was to let him watch me pee.

Marhaban-1 · Answer

They asked me what did I think of their ex boyfriend and talked about how great they were

krin_m · Answer

It has been such a long time since I dated, I don't really remember. Must not have been anything too weird if I don't remember! :-)

RickVienna · Answer

Good question. Hard to answer... okay let's try... question was "Would you show me how small you are?"... though on... later we went home and she found out

Lilbrown · Answer

I am too silly to ask a million questions. I usually allow her to talk. Being in sales, I have learned people will tell you everything without you uttering a word.

Bogoboj · Answer

How often do you fold the toilet paper when you whipe your ass! I said "twice"

scooogy · Answer

She asked if I wanted kids, on a first date with her ex's baby at hand.

justaguy173 · Answer

I was asked for permission to be jacked off into a specimen cup

Massageman · Answer

It was more of a rhetorical observation - "My- you are rambunctious tonight."

Wiredone · Answer

It's so long since I've been on a date. I don't remember what they asked

Anonymous · Answer

Wanna seem in a black dress, let me show you pic😂😂 Just why...

glowingsunsets2006 · Answer

I've never been on a date  * crickets *

DarkCarousel · Answer

What's your credit score?

Anonymous · Answer

I once asked this guy how many girls he’d fuxked like 9 messages after we started texting.

Jaylaaa2000 · Answer

Can you swim? I heard black people can't swim

Crazybeeguy · Answer

Never was asked weird questions.

ariadneR · Answer

Do you know how to make toast

KatherineJ · Answer

Honestly, he didn’t ask me anything weird.

Jessjoch · Answer

If I can fit my fist in my mouth.

Coolkat12345 · Answer

Lol I only dated my wife so I don’t know why some people date new people all the time. I mean why not just make smart choices and only date somebody your confident in that it will work?

Mark987 · Answer

Do you like giving oral? and I laughed

lsksni · Answer

"how often do you manscape?"

TonyMetal___86 · Answer

Never been in such a situation

What was the weirdest question a date has asked you and how did you respond?

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What was the weirdest question a date has asked you and how did you respond?

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