What was your weirdest dating experience?

Question

Anonymous · Accepted Answer

A girl and I were on a first date and we ordered our food and suddenly she answered her phone in a panic and just told the other person to hold on and that she would be right there. She kept telling him repeatedly to hold on. Right while we’re finishing up eating, she asked if I could spare some cash for an emergency for a family member. I felt so awkward like this was a weird request for a first date. She kept pestering me for this money, which I thought would only be like $30 but I was wrong. It was $1,000!!! She told me she needed the cash because a family member needed it for their safety. I had plenty of cash at the time and figured I would never see the money again because even if things worked out, it’s never good to send your girlfriend to collections. Anyway, I agreed to give her $1,000 in cash. I had to go to an ATM first. She then gave me an address on where we needed to get. The address looked familiar but we go there and it was downtown near where I live but then I see her run around the corner while I was waiting in the car. I thought someone needed cash for a medical emergency or something like that but I never expected her to come back around the corner not 30 minutes later (she did say it was going to take 15-20 minutes so I thought I’d be waiting for a while). I see her walking up the street with another guy. He gets in the backseat and my date gets in the front seat and now I was really curious what was going on. He wasn’t a really threatening looking dude. He was very skinny and kind of a nervous looking guy. I asked what she needed the money for and she introduced me to this guy whose name was Colton. I’ll never forget that name. Colton. Just a little twirpy dude. Anyway, the call was because Colton had gotten into a car that wasn’t his and he felt like going out and doing a little shoplifting. But Colton wasn’t just anyone to my date. He and my date had a 3 year old son together and she didn’t want to pay a babysitter to watch her son while we were out on our date. So she doesn’t have that kind of cash and assumed I did for whatever reason. So we bail out Colton’s sorry skinny ass from the county jail and we drop him off in some shady part of town in his natural habitat. I was so turned off that she would have anything to do with this dude much less make a baby with him that I never called her back. Her son was fine though. Idiot Colton left his son with a neighbor and she was much more responsible than him and actually took good care of him. I dropped her off at her house so the real babysitter could have a break since we kicked out stupid Colton so he could be with his own kind in the shitty part of town. So yeah I will never let someone borrow my cash from me like that. I did hear from her a couple weeks later. She did thank me and repaid me $40 and said she’d pay the rest back but I never heard from her again after that.

MCheetah · Accepted Answer

I once dated a woman who was the heiresses to a billion dollar pharmaceutical company. She was 30 at the time, I was 22, and her mother, the CEO, was 55. The woman and her family were British, so I didn't realize how much of a unhinged psychopath she was until much later on (@josyjosy and @karaspara know what I'm talking about; rich British women are nuts). She may not have literally been psycho, but she was something. I've known literal sociopaths before and most act like normal people. She was the kind of person that would talk about putting kittens in microwaves just for fun (couldn't ever tell what was a joke and what was based on a true story).

I won't recall all the details here, but she took me to a nightclub, where she proceeded to act like a big shot millionaire just to put on a front, even though she hated being rich and dreamed of being in a street gang. The funny part is, none of that bothered me. What bothered me was her fascination in me. One could argue she had never been with a black male before. Or, she just wanted to be "close to the ghetto" (since I lived only a mile or so from her company's US Headquarters in Philadelphia). Either way, she was just too intense for me. I'd be willing to try oxycontin. She was a hard cocaine type of gal.

muscularbumblebee · Accepted Answer

Was on a dating app swiping randomly (as you do) saw this cute intelligent looking guy, turns out to be a physciatrist by profession and I tend to date guys with different professions.. so anyway we meet after two weeks of barely messaging thinking it won't work out and during drinks and dinner everything seems to click and is going so well, (keep in mind this is during just after lockdown where eating outdoors is allowed in restaurants but some things are shut)

Now here is where things start going a little.. offf. He asks after the meal and drinks since everything is closed and he's nearby if I would like to come to his to have a drink then I could go. I told him I can't stay long jist one drink and he agreed so we went, and I don't know what happened but with the lights on I guess he must have appeared a little ddunker then he was at dinner but he had this crazy wide eyes look on his face. We make out. Cool. Always wanted to with a psychiatrist untill he proceeds to tell me about all the stories of how he followed his ex and was obsessed with her apparently. So neadless to say things didn't go further as I got pretty creeped out, he tried making more moves on me at which point I said I had to leave

Blocked him and never saw him again

Note: his profession seems quite genuine and everything else as he genuinely knew what he was talking about. He also clearly had the money from it

ButterflyHope · Accepted Answer

Went on a date with a guy off tinder…horrible mistake.
(I specifically said in my bio I don’t do hook ups & expressed this to this guy in messages) important for the story.
Everything was going good for the first 20 minutes…until he kept talking about his sexual fantasies, which was fine but then the entire date was him just talking about his previous hook ups, kind of bragging about how many girls he has slept with.
At the end of the date, I suggested he drop me off at my house, instead he drove to his place. I asked what he was doing & he said.
“What do you mean? Want to have some fun?” & then he pulls out a condom. I was disgusted. After telling him no, he kicked me out of his car as he shouted at me “don’t go on tinder if you don’t want to fuck!” & I had to walk home.
A week later he tried a “booty call” on me. He was blocked.

jennifer_bloom · Answer

I was in my early 20s and a guy told me he was 26 and wanted to meet me for a blind date and when I saw him - he looked like he was between 45 - 75 years old and I tried to talk to him about the book I was writing and he left after 10 minutes because he thought I "didn't respect him."

OlderAndWiser · Answer

I dated a lady who was the same age as my mom and took her home to meet my parents. I was 23 and she was 46. Plenty weird!

EpicTroller · Answer

I got an awful one soon after graduating uni. I splurged with my new income living in a small apartment. Bought myself jewelry, nicely tailored suits, a nice watch, nice car. Bling-bling. But then I attracted a girl at a party who seemed so into me presenting myself like that and then on the very first date, she wanted to go into a luxury store while we were strolling around. Then she picked out a Gucci purse for over $2,000 and I thought she was buying it for herself. Yet when they asked her to pay, she looked at me. Then I was like, "What?" Then she pointing to me and said I got it. Then I said, "WTF?" I refused not because I couldn't afford it but it's like she went hardcore gold-digger on me, and I thought she was interested in me for who I was and my job and things like that. So I aborted the mission and sort of ghosted her after that. That was the worst date ever. And since then, I've avoided wearing fancy watches, driving fancy cars, wearing the nicest suits. I just do t-shirt and jeans and sneakers while driving an economy car. And since then, I never had that problem.

Dayman343 · Answer

Met a girl at a club who seemed really into me. We chatted at length and I asked for her number which she readily gave me. I called her during the week to ask if she would like to meet for a drink. She said to come to her place and we could go on from there and we agreed 7 o'clock. On the night I arrived she answered the door but said she was running late so by the time we left the house it was around 8ish. I drove out of the town to a nice country pub I knew, ordered some drinks and sat down with her. From that point on things just were strange. Wanting to know more about her, I kept the conversation up but she became subdued and skittish. I asked her if she was OK and she replied that she was fine but it was clear things weren't. In the end it was me doing all the talking and she pretty much avoided looking at me or saying anything. I pressed her again if there was a problem and had I offended her in some way. She responded that I hadn't. I then asked if she wanted to go to which she nodded yes. So we got in the car and drove her home. Arriving at her door she got out of the car and I said goodbye. I sat there for a while absolutely perplexed. The next evening I was tempted to ring and check on her but decided to just leave it. Quite bizarre considering she seemed to be really into me.

ChrisMaster69 · Answer

This one…

I was single and my girl mates decided I needed to date,

so they set me up with a blind date, great not a problem ….

I was sitting in a nice pub chatting to one if my male mates and in walked 4 girls (3 girl mates and another girl I knew),

my mate, smiled at the other girl and went forward to give her a hug, only to be stopped by one of my girl mates, saying on the lines of ‘she’s taken go find your own girl’.

where upon he said ‘she’s my sister’

yeah my friends had managed to set me up with a blind date, but the blind date was my mates sister, they had not told her my name just stuff.

bloody embarrassing all around that was, then one girl piped up ‘so you planning on dating’

🤦‍♂️🤦‍♂️

Dazed0N0Confused · Answer

"Weird" is subjective, but...

I was meeting up with a guy for a round of bowling & when we were done he offered to drive me home. We got into his truck, we got situated, the car was moving and he pulls a gun out from his waistband & sets it between us. Doesn't put it away in the glove compartment nor the middle console. He hadn't told me he was carrying & i was already in a moving car... I'm here, but i was NOT comfortable! I thought i was going to get hurt. Neither of us got ahold of each other again.

I'm fine with guns, when i KNOW there's a gun!

Hentaibby · Answer

This one guy I met on tinder , well actually all my tinder dates where bad. But this one was the worst , this guy first of all showed up in an old mix match suit with holes in it and he looked like he hadn’t seen the sun in years. It was a night date to a movie , after we where in his car talking he kept saying I can’t believe you trust me not to kidnap you right now ( which was a creepy thing to say ) . He then started talking about his ex and how much he hated her and wished she would die. That’s when I realized i was with a total stranger who could murder me. I think he noticed how scared I looked cause he got all nervous saying he was just messing around. Luckily I drove myself to the movies and met him in the parking lot so my car was parked near by. I was like well this was nice we should hang out tomorrow I really have to go now and got out his car and sped walked to my car. Honestly a huge reality check to not meet up with strangers from the internet

Anonymous · Answer

I would have to say when I was dating a guy 5 years younger than me. He was 21 and I was 26 but I felt so much older compared to him, he was immature. We'd hang out with his friends and they would play video games and still talk like they were in high school- not just locker room talk but a lot of them still lived with parents. I wanted to be more serious and was looking to settle down, he was looking to play and have fun. When we slept together it was terrible and one sided. He knew nothing about pleasuring a woman. Nothing. He just wanted oral for himself. I dumped his a** the next day. Couldn't do it anymore.

hahahmm · Answer

When I was 20s I went on a blind date. She was wearing some kind of tracksuit. Not even a flattering one. Looked like a burrito stuffed in a wrapper. Together for maybe 5 minutes and she starts talking about how many kids she wants to have and getting married. Then started trying to nag the hell out of me for my choices and judge my job choices. I only went on 3 blind dates in my life and every one was a disaster.

DarkCarousel · Answer

Just generally online dating is awkward and weird.
I don’t have any specific date that was super weird.

When I was like 12, my friend had a boy she liked meet us at the mall. He brought a friend “for me” as like a blind date. He kept trying to hold my hand or put his arm around my waist while we were walking.
That was pretty weird.

exitseven · Answer

I met a girl when I was hanging out with some friends. She was the friend of a friend. We seemed to hit it off. She was a couple of years older than me but I thought she was pretty and nice. I ended up giving her a ride home and I walked her to her door. I was just about to aske her out when she invites me to a party on Friday that she and her roommates were having.
So I go over there on Friday really looking forward to hanging out with her.
She ends up ignoring me the whole night, spending most of the time talking on the phone with somebody and crying.
I ended up getting really drunk and just left without saying goodbye.

Luv2BRealExotic13 · Answer

There was a weird guy I went on like a date with. When we first actually met he wanted to constantly hold my hand even while crossing the street. I don't know I got a vibe I shouldn’t have agreed to the next date. He even bought a new pair of pants and shoes as a “date” experience. I’m sure he was a vampire. Pasty pale, who gets sunburn sitting in sunset? I witnessed it. His pictures were almost always blurry or just looked weird. He hated cilantro but the real dealbreaker he didn’t like washing his hands even after using the bathroom. He tried to low key hold me hostage over the weekend. Especially because I wouldn’t kiss him or cuddle him.

The foot fetish guy literally tried to put my foot on his d*ck. He was like kind of condoning domestic violence. Dude had issues.

Then there was the five hour date that left me at the club and the club got maced. It was crazy.

ArrowheadSW · Answer

Hummm... One that comes to mind... I met a lady at a wine event and then we exchanged a few emails. We agreed to meet up one evening, and she showed up all grumpy. She got a call on her cell phone from her best friend (who I also met the evening that I met her). So her best friend shows up. I was kind of glad because her friend was a bit more pleasant to talk to. Then after so long, they both took off. I emailed her afterwards asking if she wasn't feeling well, or whatever, and she emailed back but didn't address any of that. Definitely weird.

Bluemax · Answer

I double dated with a friend of mine. My then girlfriend was trying to set him up with a friend of hers. My friend wound up climbing into another friend's window (he lived across from a park where we were having fun at... at three in the morning). We were all eighteen. Dumb kids. Any rate, my friend said he wanted to show his date something he left at my other friend's house. He opened the window, silent crept in, and just as silently crept out. He didn't wake my friend or anyone in his family.

I thought for sure his date was going to be like, NOPE! But instead she just laughed and thought he was a lot of fun. So did my girlfriend. As I said, we were dumb kids.

dolemite89 · Answer

i took a girl out my senior year in high school. We had fun but i could just tell this wasn’t going to amount to anything. So we were driving back to here place and she randomly asked if we could stop at the store on the way home so she could get clamato juice. i was so confused like oh ok i guess you like drinking bloody mary’s and she was like no i just like clamato juice. i literally was so turned off by that i just dropped her off at her house and left 🤣 Like who in the actual fuck just drinks clamato juice straight? 😳🤢

Anonymous · Answer

I met someone in a chat, we talked for hours on the phone, his voice was too sexy. We agreed to meet and in the conversation we touched on the topic of kisses so we said that when we meet we would kiss to see if it was true that we were good kissers. We met and he was nothing my type at all. And I was just thinking that I didn't wanted him to remember about the kisses. We talked for more than 2 hours and although it was very nice, i was not physically attracted. We say goodbye and before I leave he held me by the waist and kissed me. I was holding my breath..🤢🤢 He didn't even understand why I blocked him everywhere!

JHNS98 · Answer

Each of the two dates I've been on do får would qualify here. I once dated this hot ADHD girl after she'd been with my class for a day.

We agreed to meet at this café where we basically sat quiet until she had to go back home for her sister's birthday.

The next year I met a friend from martial arts school at a youth party, I ended up getting her number after a session some weeks later, and we agreed to a date. We didn't really talk, we just walked around downtown.

Not really weird, just bad, really.

MzAsh · Answer

Short guy with a Napoleon complex. I never minded dating a shorter guy but he tried sooo hard to look cool.

Another guy flipped out when I had to cancel our date. He kept interrogating me about who I was going out with that night instead of him. It was only our 2nd date and he was already acting like a jealous psycho.

Anonymous · Answer

I’ve got a very embarrassing story. Guy met online invited me to go skating, which sounded so fun! But when I got to where we were meeting, he told me it was roller skating! Imagine how weird it is to roller skate in full snow gear. I’m talking thermal underwear, ski pants, turtleneck, hoodie, parka... yeesh, I don’t know how I survived

FilmGuy93 · Answer

I once dated a girl who concluded that I was only interested in using her for sex after I complimented her on an Instagram post where she was showing off. We were acquaintances for 4 years before I asked her on a date. She spent a month after the date trying to convince me that she wanted to date me, meanwhile getting sketchier and sketchier and ultimately blocking me, even after I tried to ask her what was wrong, and if in fact she wanted to date me.

karaspara · Answer

I haven't had any weird dates i'm probably the weird date 💁

Midnight_Kiss · Answer

I went on a date recently which turned out a little weird. We had agreed to go on a walking date an as there were more places to explore near where he lived I traveled to his village and all seemed well until almost strategically we bumped into immediate family members of his on practically every turn and "coincidentally" just has he started speaking of them. I felt like I was being paraded throught the village for viewings and was expecting to be rated at the end it.

Also had dinner type date once and all the guy did was rant about how women are b*tches who just leave you for their ex's (apparently that was how his last relationship ended) but the day go worse when I sent an SOS to my friend and when he arrived he just joined him because his bird had just left him so I was stuck with two of them whining about women.

Anonymous · Answer

First date, in a very busy, public mall, he grabbed my head and just started slobbering all over my face, like full out trying to tongue and everything. If I tried to pull away, he squeezed my head harder and followed me when I stepped back. Very disgusting, and as soon as he was done, I hightailed it out of there.

tatianamay · Answer

People have shared some of their really hilarious experiences, I just hope I get to experience something like this one day!

Anonymous · Answer

I was making out with a blind girl on the New York City High Line Park system I think she liked it so much she grabbed me in the middle of the street started making out with me again with people clapping and cars honking around me

cth96190 · Answer

It was a blind coffee date that had been arranged by an introduction agency.
It ended with her walking around the rim of a fountain in the city square, singing Broadway show tunes and talking with imaginary friends.
Bipolar AF. 🤣
Two policewomen stood with me to watch the spectacle, while they waited for an ambulance that had Thorazine and a net to arrive.

kyleelyn199723 · Answer

My weirdest date had to be a guy calling me his best friend meanwhile kissing me and stuff. Yup weird

Blindguyplaying · Answer

Two are tied for first. One was my first date moving to a new state and I got thrown threw a loop when she wanted to come up to my room on the first date, I turned her down and it was just jarring considering it was my first date as an adult. The other was when she decided to tell me she was married when I went over to her place for the first time.

Starwitch23 · Answer

The guy was staring at me like he's going to eat me up. He was weird and I completely forgot to smile. I have a resting bitch face when I don't smile. Guess, I was kind of weird date.

LeoElias · Answer

I remember she came off super pretentious like she was trying too hard to be confident. Confident to her was looking down at me and acting better than me from the get go. I remember she rolled her eyes at everything I said and checked the time on her phone ten minutes into the date.

TwoowT · Answer

The guy kept talking to his mummy on phone all the time.

Floppy2112 · Answer

Having a woman standing over me in bed yelling and slapping her stomach exclaiming that she was the best thing that ever happened to me. I disagreed, never saw her again. Thank God...

Anonymous · Answer

My ex took me to the Levi store and we played Legos he was a 22 year old man

Anonymous · Answer

Met a great guy and went home with him. Later I get up to get some water downstairs naked and run into his sons and their friends. All classmates, all guys I slept with before. He asks me if they can get a turn and I tell him his dad wore my ass out. Then I go upstairs and fuck him again and make sure they can hear me.

Andres77 · Answer

It wasn't really a date.
I was walking down the hallway in our dormitory and the payphone rang.
I answered it. The guy she was looking for had moved... the next night I spent in her apartment.
Not one of my proudest moments, certainly.

FakeName123 · Answer

A girl one time told me on a date that she really wants to experience near death while being banged. I noped the fuck out.

TallAnon · Answer

Girl was openly being racist against strangers, that's one hell of a nope for me.

Anonymous · Answer

Some guy who insisted on holding my hand even though it was our first date. His hands were so sweaty and disgusting and I wasn’t really (even remotely) comfortable doing that on the first date. He wasn’t attractive and I couldn’t wait to ghost him and I did.

EJlad · Answer

When I was doing online dating this one girl from this app kept calling me at 2-3 AM and screamed at me when I told her it was really late and I just wanted to sleep.

OutWestBandit · Answer

agreed to meet at club, she shows up with a fuckboy of hers like its nothing.

fred_durst · Answer

i drank too much coffee because lack of sleep , and ended up sharted and throw away my pants

Hxxmx · Answer

He was always calling me mum 😂😂

Iron_Man · Answer

Some girl looking for some type of drugs on a blind date

Anonymous · Answer

Some bitch told me after a date that she accepted a date with me out of pity. I told her "look in the mirror - you're not all that". I can't even remember her name now. LOL

MudRucker · Answer

I dated a buddies sister. Some how he heard details of my sexual activities.

Adam_West · Answer

I've only been on a date once so far. and there was nothing weird about it.

scooogy · Answer

Not sure, either the one who asked me for money or the one who had her ex's kid with her.

Slim57 · Answer

Went on 2 dates with a girl and she didn't talk both times whatsoever

rebeliouse · Answer

went round to hers and she opened her front door in a see through net body suit pulled me inside and deepthroated me just inside the door :D

Sambelfast198526 · Answer

I agreed to a meet up after 3 months of talking and she dumped me on the spot over my penis size.

Anonymous · Answer

When she gave me crabs...

micheal727jovanie · Answer

I was 11 and she was 15 my first date ever.

alexanderdelarge7 · Answer

There was a girl who wants to pie on me

Anonymous · Answer

She was a HE

orangecherry · Answer

A guy asked for my panties after the date

TheGreatAwan · Answer

I have never been on a date

NoLookingAtSoleil · Answer

I avoid weird

What was your weirdest dating experience?

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