First dates will often go one of two ways. They’ll either be a win-win or an epic fail you’ll remember for years to come. Don’t get us wrong. Dating can be an amazing experience. Unfortunately, dating can also turn sour, especially when you ask someone out who’s a major creep. You might have been looking for an adventurous hunk you could go for a coffee with, but for some reason, you ended up in a cringe-worthy date with a total weirdo. So, check out these Reddit users’ craziest and cringiest first date stories so you can hopefully avoid having a messed up first date like they did.
Her Date Had Alzheimer’s
MommaJess08’s first date was pretty normal. They went out for pizza and then played mini-golf and had a great time. It wasn’t exactly memorable, but when he asked her out on a second date, he had seemingly forgotten that they had gone out before.
Check out what happened in her own words:
“It was fairly normal we went out to a pizza place, and then went mini golfing. The weird part was afterwards when the guy straight up refused to acknowledge the date had happened. He messaged me the next day and asked if I wanted to go to a local amusement park, and I said sure, and he kept referring to that as our first date.
I asked him about it, and even told him we got pizza and went mini golfing, and he acted like he had no memory of that at all.”
She Was Dating a Gang Member
Xickennoogit will think twice about swiping right on Tinder again after her date took her on a ride down roads she had never heard of and then confessed to her that he was a former gang member who was on the run from his former posse. Check out her story. It’s insane:
“I met this guy on tinder. He was sweet enough so I agreed. I gave him an address about a street away so he doesn’t get to know my real address but somehow on my way over to the address, he spotted me.
No matter, he wasn’t weird about it. So he explained he had 3 things planned for today. I was like sure as long as I knew what they were. 1st thing was kbbq. 2nd was roller skating rink. 3rd was apparently a secret. So this made me kind of go ‘no no no’ but I held it in. I haven’t been on a date in a while and he seemed nice enough. 1 and 2 were fun. Then comes 3rd. He started driving through roads I’ve never been (which is weird given my profession was an auto parts driver. I knew my whole city like the back of my hand) So he gets to talk about his past life.. AS A GANG MEMBER. And I asked him “haha so funny. what gang?” because I through he was kidding. He said “the color of your shirt” but then he added that he no longer is affiliated with them. Ever since HE MOVED TO 5 DIFFERENT CITIES TO AVOID THEM. So that was a nope since I did love to travel and don’t want to randomly be kidnapped.”
She Was Dating a Drunk Cheater
Reddit user Leelu_ met a guy online who had two kids and rode a bike because cops took his license away after his sixth DUI. And not only did he barely let her talk during their date but she later learned he was a serial cheater who had no regrets.
“I went on a date with a guy I had met online. He wanted to meet for drinks, so I went to the pub and waited. He showed up 20 minutes late on his bicycle, proceeded to come into the bar and down two pints after giving me a point and a wink.
I overheard him tell the waitress to “put it on his tab” and then he came over to the table with another beer. He proceeded to tell me about his two boys (no mention of them in our previous conversation) and how his mom wanted to take them all to Disney World. He told her that would be too expensive, so he left his boys at home and he and his mom went to Disney World instead. Then he proceeded to tell me that he rode his bike everywhere because after his sixth DUI, “those dumbass cops” took his license away. He mocked me for drinking water, then in his next breath told me that he could really see falling in love with me. In 20 minutes, I got about ten words out, and most of them were me telling him I had to go. I later found out that he worked for a friend’s father, and that he was married.”
His Date Was Part of a Pyramid Scheme
Jex_head didn’t think he had anything to worry about when a childhood friend asked him to dinner. But then she brought a middle-aged man with her on the date and they both had a major ulterior motive.
“A childhood friend of mine asked me to go to dinner after we ran into each other at a party. I thought this would be great as she had gotten pretty cute since last time I’d seen her and it was all was going well when we were texting. I met her at the restaurant and to my surprise there was a middle aged business looking guy there as well.
As soon I sat down both of them tried to recruit me to a one of those pyramid marketing schemes. After I declined and went home I would get texts regularly over the next month asking me what went wrong and why I didn’t want to make all this easy money. I’m pretty sure I didn’t even get to order dinner as well.”
She Was Tricked Into a First Date
Sammie_SU went to the movies with a school crush. Then he invited her to his place to play games. But when they got there, his entire family was waiting for her and for some “mysterious reason” everyone thought she was his girlfriend.
Check out what happened on their first date:
“I went to the cinema with a school friend. At this point I didn’t even know it was meant to be a date. Afterwards he asked if I wanted to play some games at his place.
So I said yes. As soon as I walked into his front room I was met with about 8 of his family members. He had invited over most of his family to meet me. They all believed I was his girlfriend, and that we had just come back from a date together. I felt very uncomfortable, and couldn’t bring myself to tell them that we weren’t actually boyfriend/girlfriend.”
He Showed Her Off To His Mall Friends
SharMarali went on a date with a younger man who tricked her into going to a mall. But things got really weird when he kept introducing her to his friends who happened to be working at specific stores. But it didn’t end there:
“Went out with a dude who was a few years younger than me. At the time, I was late 20s and he was early 20s, so I didn’t think much of it. We went to dinner first.
After dinner, he wasn’t ready for the date to be over yet, so we went driving around. I was driving, but I got the feeling he was steering me someplace specific (hey let’s go left here, I don’t know what’s down this way!) Didn’t get a creepy vibe from him at all, and I was the one driving anyway, so I just went with it.
Eventually we ended up near a shopping mall. “Hey let’s go in, just for fun, I haven’t been to the mall in ages!” K, sure, why not. This is where this began to be the weirdest date of my life.
For the next 90 minutes or so, he kept acting like he was walking aimlessly, but then would make a beeline for specific stores. Each time I noticed this, he would just happen to have a friend working in that store right now, isn’t that so weird that we’d run into my friend here!
After the 3rd time it happened, I really began to feel like I was going on a tour to be introduced to all his friends in an effort to prove that he knew a girl. Finally, we left the mall, and he suggested we stop for ice cream to end the evening. There was a Cold Stone Creamery nearby and I suggested it.
No, he wanted to head back toward the restaurant where he’d left his car. Okay, reasonable enough. If you guessed that he wanted to go to a Dairy Queen where two of his buddies worked, you are way better at predicting things than I was.”
He Couldn’t Remember Her Name
Bubonis got a call from a girl who was a friend of his friend. She asked him out, but he didn’t know her name and couldn’t trick her into saying her name out loud on their date. But when he got home, he realized why he couldn’t remember her.
“Got a call from a friend of a friend who I thought I’d met once before, asking if I wanted to go out tomorrow (Saturday) night. Sure. Went out to her place about 40 mins away.
Realized upon arrival that I didn’t actually know her name. Had dinner, talked, made out a bit, talked about going out again, made out some more, called it a night at around 1am. Tried several ways to get her to reveal her name, to no avail. Dropped her off at her place, drove home, went to bed. Realized the following morning that she had never spoken my name either, not on the phone or in person. Further realized that I didn’t have her phone number. Called mutual friend to ask for her number. Mutual friend had no idea who I was talking about. Gave him address of girl. Said he didn’t know anyone from that town and the address wasn’t familiar. Never heard from her again.”
She Wanted Him To Shower
Cosmonaut4412 went on a date to a club with one girl who turned out to be crazy jealous when he started dancing with someone else. But after a weird confrontation, he got a weird invitation from the second girl to go to her house. Fortunately for him, this would end up being one epic night he could never forget:
“Invited me to a club, went to club, she was dancing with a bunch of different people after I had bought a couple of drinks. New gal comes up and asks if I want to dance, I said yes and we ended up having a good time. Fast forward and chick who invited me comes over and pours her drink on me for dancing with someone else.
Go to the bathroom to clean up and pretty embarrassed. Come out of the bathroom and girl I was actually dancing with asked if I wanted to shower off at her place. Turned out to be a pretty fun night.”
Falling In Love
Mypoorbrain knew that dating could lead to her falling in love. She just didn’t think that the word “falling” would literally come into play. Whoever said that love hurts must have had a first date like hers.
“I went on a Tinder date in January that ended poorly. At the end he tried to kiss me so I dodged, tripped over a curb, and broke my fibula while falling into traffic. The guy got down in the road with me, moved my hair behind me ear and said, ‘We could tell people that we fell in love.'”
He Was a Hit and Miss
Kittnbiscuits didn’t mind dating someone with a past, but when her date started drinking, he also started confessing about his past as a hitman. Yup, you read that right. And the more he drank the more she wanted to go into witness protection.
“A coworker who asked me out for a drink after work. He wasn’t really my usual type, but always seemed sweet so I figured I’d give it a shot. We hit a bar, and all seems well until he apparently has one too many.
He starts telling me stories about his past and how he was basically a knee-breaker/hit man for some crime organization out of Mexico. He gives me tons of details about methods and the going rates for XYZ. The stories get progressively worse and more graphic, but still I’m not really believing any of this. I think he’s trying to (very weirdly) impress me.
He’s quiet for a minute, stares off into space, and then leans over to me and his eyes just go dead cold. He tells me that if someone paid him $5,000, he would cut off one of my hands. But since we’re friends, he would do it quick and clean at the wrist, and put the hand on ice so I could possibly save it.
I start believing him then. I tell him I’m feeling sick and have to go home. I stayed ‘friendly’ with him at work until he eventually got fired for stealing from the bar – I was very concerned about the ramifications of no longer being on his good side. I still don’t know if I believe his stories about being a hired killer, but I do believe that he fantasized about it deeply enough to scare the sh*t out of me. I’ve never been happier to see someone disappear.”
He Loved Her Too Much
Amymariebe isn’t afraid of saying “I love you” to someone. It’s why she was going on a date in the first place. But she wasn’t expecting someone to say it to her on the first date, but when he did, things got really weird.
“I was going on my first date with someone I had met online. We had been talking a bit for about two weeks before we met. We went to dinner on our date, he wasn’t super talkative and it was mildly awkward.
Then when he was dropping me off, I gave him a hug good night and he takes this opportunity to whisper in my ear, ‘I love you.’ I didn’t know what to do, so I laughed awkwardly, assuming he was joking.”
He Broke Her Nose
Grindyoursoul went out on a date with a girl who was a bit of a klutz, but he was far from perfect too. He ended up hurting her and then he had to face the consequences of his actions when he met her dad.
“Went out with a girl in high school and did the usual, movie and a dinner. It had been going great up until dinner, when she stumbled over a curb. I went to catch her, and promptly whacked her in the face with my head.
This actually broke her nose, which lead to me panicking and trying to fix it. Of course that was a bad idea, and I think I made her nose bleed more to be honest. Thankfully she wasn’t upset at me (I spent a good half hour freaking out over it), but there was a very awkward and at one point terrifying conversation with her dad when I brought her home. He was a former marine who served in Vietnam and did the usual ‘scare the bejesus out of the daughter’s date’ by coming out sharpening his kabar knife when I picked her up, needless to say he really didn’t like or trust me after that. The girl and I dated for a year and we’re actually still pretty good friends. So I guess it worked out OK in the end.”
He Looked Like Her Brother
Dmelt253 discovered that the only thing worse than going on a date with someone who only loves you like a brother is a date who claims that you look exactly like her brother. But that didn’t stop her from dating him.
“I went on a date with a girl I met online. All throughout the date she kept looking over at me and then laughing, but not really in a mean way.
After a while I called her out on it and she basically said, sorry but you really look like my brother. Then she shows me a picture and low and behold, he looks more like my brother than hers. I still can’t figure out why she agreed to go on the date in the first place when she could tell this was the case from my profile pick.”
His Date Went All Britney On Him
Jsmys was making out with a girl with long hair and they were really into it. But after a smooch session, she went into the bathroom and came out a completely different person. Suddenly, he felt like he was dating Britney Spears.
“Once had a girl get up and go to the bathroom during a make-out sesh. Came back with her head shaved.”
He Joked About Killing Her
Madmax0909_ was dating a guy who just wouldn’t shut up. He also seemed to be a total momma’s boy who loved talking about himself way too much and joke around. But when he made a joke about killing her, she wasn’t laughing anymore.
“The guy talked and talked and talked all evening about himself, his parents’ divorce, his ex’s s*x preferences and his depressed best friend. And he joked about murdering me. And at the end he told me he lived at his mom’s but I can come by if I want to.”
Her Apartment Looked Like a Zoo
Catinreverse didn’t mind animals until the girl he went out on a first date with took him back to his apartment. Her apartment looked like a zoo and it didn’t take him long to realize her first love was animals.
“I went on a date with a girl who’s apartment looked like John Cusacks apartment in Being John Malkovich. Don’t get me wrong, I love animals. In fact, I work with animals, but when someone’s apartment has a kiddie pool with a turtle in it instead of a coffee in their living room it’s a little much.”
He Kept Looking at Her Silently
Literallyatree was locked in a one-sided conversation when she went on a coffee date with a guy who just stared at her. She tried and tried to get him to say something, but he was more of a gazer, not a talker.
“It was supposed to be a coffee date. I got there, on time, and he had already ordered and drank his coffee. I went up to get mine, he just stared at me from the table while I was ordering.
The date itself lasted about 2 hours and I honestly can’t remember a single thing we talked about, because he wasn’t contributing to the conversation at all. There was one point where I was just staring at him and I remember thinking “If he doesn’t bring up a topic of conversation in the next 30 seconds, I’m leaving.” Dude genuinely just stared at me. Maybe he was trying to communicate telepathically, I’m not sure. When I tried to leave, he insisted that I stay. Why???? We haven’t talked about anything and it’s been 2 hours! Weird guy. I did end up going on a second date with him, but it was just as awkward. Called it quits after that.”
She Wanted to Picnic at a Cemetery
Back2Bach didn’t mind a girl choosing where to go on a date, but one of his dates from college was so hung up on her deceased ex that she wanted to take him to the cemetery to have a picnic by his gravesite.
“The weirdest was when I was a college junior and dated a girl that was a classmate. She wanted to have a “picnic” in a cemetery at a gravesite where her ex was buried (he had been killed in a crash 2 years previously). I told her that I’d accompany her to visit his grave, but that picnicking and having a good time there somehow didn’t seem appropriate.”
She Liked to Play With Dead Mice
ComedyDude went on a date with a girl who had a thing for recreating historic battles using dead mice. Essentially, she told him she bought dead mice online, taxidermized them, and then dress them up like soldiers.
“Went on a date with a girl who revealed that her hobby was buying dead little mice, doing taxidermy on them and then dressing them up in tiny little metal battle armor and swords to stage historical battles…using dead mice…that she bought online. She showed me lots of pictures before the date ended.”
She Had a Thing for the Apocalypse
Reddit user Northerly went on a date but nowhere in her Tinder profile did it mention that she had a deep interest in the four horsemen of the apocalypse. So when he hung out with her, it kind of felt like the end of the world.
“I matched with a girl on Tinder – we hit it off in conversation right away and arranged a date at a tea place. We get there and the conversation seemed to be going alright until she asked me if I was fine with her doing some drawings. She proceeded to draw the four horsemen of the apocalypse, occasionally asking me what my thoughts were on them; aside from that the time was spent in silence.
The drawings were really, REALLY good – but I wasn’t into the date so I left.”
He Put His Foot in His Mouth
KarateKid1984 opened his mouth and inserted his foot after he told his date that there was nothing attractive about a bald girl, and then she dropped a bombshell shortly before literally kicking him to the curb:
“Met this girl online, started talking, arranged the date. It was around Halloween so all of her pictures had her in costumes and wigs, at what I’m assuming were Halloween parties? I was excited to get to see what she really looked like. Day of the date she happened to be picking up her new car and asked if she could pick me up.
Weird, but no biggie. So she picks me up and says “Mind if we grab coffee and drive around for an hour so I can get used to my car?”….weird again, but whatever.
So now we’re driving around for a good two hours and the conversation is wearing thin. I knew she had worked that day (we hadn’t really talked about it yet if you can believe it) and I said something like “So, how’s work been lately for you?” and she said “it’s slow this time of year. Sometimes I want to pull my hair out.” Like a f*cking idiot I decide to respond with “Well, don’t do that.
Nothing attractive about a bald girl” to which she replies “this is probably a good time to tell you. I have cancer. I’m actually wearing a wig right now”….and suddenly it all clicked. The pictures with all the wigs made sense.
I didn’t know what to do. You can’t put your foot any further down your throat than I did. I knew I had to say something, so I said “I feel really embarrassed about what I just said.
Maybe I should just go” (keeping in mind I’m in her car and have nowhere to go) to which she pulled the car over and had me get out. Literally 30-minutes from my house. I had to call my mom to come and get me….I was 32 years old at the time. So that sucked.”
He Dated the Blandest Human Ever
AALen went on a date with a girl that lacked any interests, and that included music, reading or watching TV. She also lacked any taste buds, which pretty much meant that the date was pretty much dunzo.
“I went on a date with a girl who does not ever listen to music by choice, who says all food tastes the same (kept emphasizing that “she eats to live and not lives to eat”), has never finished any book or TV series in her life, and was about the coldest (not angry, just cold) human being I’ve ever met. Conversation was as awkward as you can imagine. I’m no psychologist but I’m pretty sure she was my first (and hopefully last) schizoid personalty disorder date.”
He Got the Wrong Biology Lesson
PoorEdgarDerby wouldn’t have minded a biology lesson on his first date as long as it took place in the bedroom. Unfortunately, his date literally gave him a biology lesson and then got angry when he knew all the answers.
“We went back to her place. She thrusted a model of the cell in my hands and asked if I could name any of the parts. I got the membrane, nucleus, ribosomes, mitochondria, cytoplasm…at that point she ripped it out of my hands.
I guess I was supposed to not know them? Oh yeah we were both in our late 20s so that was also weird. More weird details after but not to do with our date.”
She Dated a LARPer Who Sucked at Dating
Geezenstack444 went on a date with a LARPer, (or a live action role player) who picked her up at work, insinuated she was stupid, and repeatedly asked her out on a second date for five years straight.
“I went on a date with a guy who was supposed to pick me up after work. He showed up before my shift started, stayed all day. He stole stuff from my work, or tried to.
I wasn’t aware of this until coworkers told me the next day. He brought me to the waffle house and blew his nose at the table repeatedly. He went to the bathroom a bunch as well. His car broke down when it was time to leave and our waitress, who he tipped in change, had to give him a jump. He also told me about his hobby of larping, which is live action role playing or dressing up like weird stuff for those who don’t know, and told me that the books I read were for stupid people. He asked me out for five years after this, and I blocked him on all media. I finally changed my email address and got rid of him.”
He Already Had Names For Her Kids
EmptyMoon22 was out on a date with a guy who was addicted to Dance Dance Revolution, but ignored her for most of their date. Then things got even worse when he started talking to her about names for their kids.
“The guy played Dance Dance Revolution for a good 45 minutes while I just stood there. I left and played a couple arcade games by myself, then came back and he was still playing. On the car ride home, he asked how many children I wanted and started suggesting names for “our kids”.
Then tried to make out with me when I got home. Nope goodbyeeeee”
His Date Was a Total No Show
5pe3d got stood up at the movies and ended up watching “IT 2” all alone. But after going on a dinner date with himself, he met a group of people from a robotics club and things finally started to look up for him.
“I went on a date with a girl who stood me up to the movies. I watched the movie (IT 2) then went to dinner at Marie Calendars by myself. There I met people from a robotics club from my college and wanted to participate.
My first meeting is this Friday. Best stood up, help me I’m lonely, outing/date so far. 10/10 would do again.”
He Acted Like a Creep and Then Vanished
JesusHoratioChrist went on a date with a guy but they had serious chemistry issues from the get go. To make matters worse, he ended up stealing their keys while he was in his apartment. Things got even creepier after he sent him a text apologizing for taking the keys, but the story has more twists and turns than a roller coaster (to say the least!) Grab some popcorn for this bizarre first date story:
“Oh god. I’ve been on a few, but the one that really takes the cake is the time that a guy stole my keys. I was young and dumb.
I started talking to this guy on a dating site. We agreed to meet up at a bar that was about a 5-minute walk from my house.
First of all, the guy is late. Like over 30 minutes late, which almost makes me back out but he keeps texting me updates that he’s almost there. I give him the benefit of the doubt since he is driving a long distance to get here.
Once he finally arrives (over an hour late) I immediately realize that I’m not as attracted to him as I thought I would be. Nothing I can put my finger on, there just isn’t any chemistry between us. From the vibe he gave off, it seemed like the feeling was mutual. We still got along pretty well though and he did drive all that way to see me, so I figured we could hang out for a bit before he went back home.
The bar we went to didn’t have anyone in there besides us and after an hour or so the bartender decides to close early. Since I live such a short distance away, I invite the guy over to my place to smoke a bowl and chit chat before he heads home. We stop at his truck to get something out of it before we walk to my place.
We get to my place and smoke a bowl, watch a few YouTube videos, have a fun conversation. Then, out of left field (because he had shown zero attraction to me all night and vice versa) he puts his arm around me and goes in for a kiss. I do an awkward shrug out from under his arm and say no thanks.
We both sit in silence for a moment until I change the subject and we resume watching a video. A few minutes later he tries it again. I do the shrug again to get away from him. This time, his response is to do this big, exaggerated cartoonish yawn-stretch and announce that he’s going to take a nap on my floor for a bit before he drives all the way back home. He then proceeds to lay down, close his eyes, and not respond when I talk to him.
If this happened now, there is no way I would do what I did then. Actually, if it was now, I wouldn’t have done most of the things that led up to this. Remember, young and dumb.
I turn out the lights and leave him in my room to go hang out with my roommate in the kitchen. A few minutes later I got a text from this guy that made my stomach drop. It said “Sorry I took your keys, I’m going to leave them in the center console of your car.” Now, I lived in a granny unit unattached from the main house that sat in the backyard. It was for this reason that I did not see him slip out of my room. I run back out and the lights are off and dude is gone. Sure enough, so are my keys.
I go out and check the center console. No keys. I call and text this guy over and over to no response.
I don’t know what he’s trying to pull but I know where his truck is parked so I run down to it. The truck is still there but he’s nowhere in sight. He still isn’t answering my calls. So, I start pacing around his truck, my logic being that he’s not going to get away with stealing my keys. At this point I’m completely freaked out thinking he lured me out of my house and he’s probably robbing me blind. I don’t dare leave the truck though, in case he tries to make a getaway. After about 45 minutes of pacing and calling him over and over, his phone starts going straight to voicemail and he still hasn’t appeared. Again, the truck is about a 5-minute walk from my place, so where he has been all this time is a mystery.
Eventually a police car drives by. They circle the block and pull in, curious why I’m pacing around an abandoned parking lot at midnight. I tell the cops the whole story: the weird date, the disappearance, the keys, the center console, everything.
The cops are just as weirded out as I am. I ask them if they wouldn’t mind going to check my center console again for the keys because I don’t want to leave the truck while he still has them. They oblige and come back a few minutes later to tell me that my keys are in fact in my car. I ask them if they wouldn’t mind giving me a ride home because I’m kinda terrified of this guy now. They kindly let me hop in the back seat. Once I got home and got my keys out of the car I gave them a statement and description and they said they’d be on the lookout for the dude. I go into my room and nothing is out of place, nothing is missing or disturbed. I drove by where his truck was parked the next morning and it was gone. He deleted his dating profile and blocked me on fb.
To this day there is so much I’d like to know about that night. Why did he take my keys in the first place? If he was planning on robbing me why did he tip me off that he took them? Why didn’t he steal anything if that was his intention? Most of all, where was he hiding all that time?
I’ll probably never find out. He did send me a creepy message on Facebook YEARS later with a half-assed apology and tried to explain that the reason he left was because he “misunderstood something I said,” but his excuse was weak and didn’t add up and he refused to answer when I asked why he took my keys and where he was hiding. Then he blocked me again.
Needless to say, I was incredibly foolish and also incredibly lucky that nothing worse happened. I used online dating here and there again afterward but was always much more careful about my interactions.”
First Date Turns into a Therapy Session
TheRealDannySugar went on a date with someone with mental problems and a thing for shark plushies. He wanted to be open minded but all she did was talk about her past traumas and then wanted to make out.
“Went on a Tinder date who made it clear she had mental health issues and PTSD from past trauma. We decided to meet for bubble tea. I get a seat and wait.
She walks in with a large stuffed shark. Cool. Plushies are fine. They can be a good therapeutic tool. She gets her beverage. We sit down to drink. Not even a hello was exchanged and we dive right into how she was assaulted and r*ped. I was in the health care field. I can listen. The thing is though… she was talking very loudly. Uncomfortable levels of loudness about tough issues. I could not redirect her or change the topic. Nothing. She wasn’t having any of that. So…. I panicked and said “want to go to your car and make out?” Her eyes light up and she loosens the grip on her stuffed shark. Ok. We get back to her car. We kiss very awkward. It was mostly teeth. And the shark was kind of between us.
I mentioned how I’m kink friendly to her previously. She hit me with a weird question in this awkward teethy kissing. “Can we do some r*pe play?” I kind of panicked again.
“Um you sure? I mean maybe? We can walk to a park?” I stammered We get out of the car. We walk towards a park. The entire time she is talking about her trauma. All that jazz. Just awkward. We get to a fairly private space. She softly says “maybe we shouldn’t do this?” Yeah? Sounds good to me. I ended up j*rking off while she watched me. I took an Uber home. I texted her that I had a good time. She ghosted me 100%.”
This Date Was a Total Bust
ThanksCancer_com was forced to tell her date about her sad cancer story after he asked her about her short hair. But she made it weird when she had him play a guessing game that ensured this first date was their last.
“Went on a first date where someone asked me why I cut my hair so short. I guess I could have lied or blown off the question, but I don’t like to start anything with falsehood, so I told him that I had chemo for breast cancer—that I’ll probably be completely fine now, and we absolutely didn’t have to talk about it. He asked me a few questions about the surgery (single mastectomy), and he said “I wanna know which one it is, but I can’t look at your boobs NOW!” I told him if he could guess which boob got the axe, I’d buy the drinks and appetizer.
He won, and I never saw him again. I’m positive I am the weirdest date THAT guy has ever been on.”
She Pulled a Knife On Him
Redditor _BeKindToAnimals_ had a weird encounter when his date confessed to being psychotic. But he didn’t actually need a lot of convincing after she pulled a knife on him in the middle of dinner. But hey! At least she apologized.
“Dated a woman who didn’t tell me she needed meds because she was psychotic. In the middle of dinner (at a restaurant) she got quiet and distracted. I asked if she was feeling okay.
Apparently one of the voices told her I was a horrible person and she pulled a steak knife on me. A customer was able to talk to her, and got her to put the knife down. The police were called, and she was arrested. I didn’t press charges, and about a week later, she sent me a letter with proof that she’s been in counseling for a long time, takes medication, and included a heart felt apology.”
He Wound Up With His Date’s Ex
Darmenda’s date got cut short when his date asked him to drive her back to her apartment to confront her drunken ex. In the end, she closed the door on both of them and he ended up spending quality time with her ex.
“My first dating app date. Starts off pretty good, we barely put in our dinner order and her phone starts blowing up. Her ex was drunk and causing a scene outside her apt.
Her ex kept calling, then her roommate started and then the landlord calls threatening to call the police. We get our food to go and I take her back to her apt. Long story short, both her and her ex are crying messes, she goes inside, leaves me outside with crying drunk ex who starts telling me all about how he messed their relationship. Dude is way too drunk to drive, I end up driving him to his apt, Uber back to my car, realize my date took all the food with her. The joys of dating!”
He Got Trolled on This First Date
MedusasSexyLegHair went on a date with a girl who had a major troll doll fixation. She even brought her collection on their date and introduced them to him one by one. But then she got mad when he showed no interest.
“I was interested in this girl, and she kind of tricked me into a double date where she was dating another guy and had fixed me up with her sister. Being a good sport, I went along with it and it was awkward but okayish. But then she set me up with her sister again and this time it was just the two of us.
We went to the park. She had filled the trunk of her car with troll dolls (I mean dozens and dozens of them) and spent the entire date introducing me to her trolls one by one. (I should mention we were in our 20s.) She was getting frustrated and angry because I didn’t seem all that interested in her dolls. So sitting there, hands full of troll dolls, she exasperatedly asks me “So are we going to have s*x? Do you even know how to have s*x?” “Umm, not with you I don’t.” I said, and got up and walked home. There’s only so much one can endure while being polite.”
He Wrestled With Her Emotions
Lesbian_moose felt like she was dating Hulk Hogan when her date started impersonating different WWE wrestlers. Then her coffee date got even weirder when he invited her to go to a WWE’s dream come true.
“I was talking to dude on tinder and decided to meet up with him for coffee one day. He only talked in impersonations of WWE wrestlers and then asked me to go to wrestle mania with him and his entire family later that night.”
She Was Making Him Feel Very Blue
AZScienceTeacher was stunned when his date brought a giant blue rabbit named Pebbles with her to the movies. By the end of the date, he tried to kiss her goodnight but she told him she had to kiss her special friend first or else.
“So I was 18, in the Air Force, and living in the dorms. My roommate set me up with his girlfriend’s cousin, and the four of us went to a movie. She brought a stuffed animal.
Not a tiny little thing some (young) women clip to their keychain. It was a gigantic blue rabbit at least as big as a toddler. She said she brought it because she sometimes gets scared in movies (we were seeing a comedy.) After the movie, we grabbed some ice cream and drove the cousins home. My date invited me to kiss her at the door, but told me I should also kiss Pebbles so he wouldn’t be jealous. Edit: Of course I kissed Pebbles. My date was actually out-of-my-league hot. But crazy.”
Scientology Tried Breaking Them Up
SuperNovaPangolin should have forked over for a decent restaurant instead of banking on a date with free food at the Church of Scientology. If they had, they wouldn’t have had to deal with the church trying to break them up.
“Went to the church of Scientology, roped in with promises of free food. We were on a date for Christmas. So, so odd.
Edit: they had us take the personality test and tried to break us up. They said we were completely incompatible, to the point of being toxic. We’ve been together 10 years lol.”
Curses Ended All Hope of Love
EpicSchwinn learned that when you go on a date with a girl, her parents need to stay home. Her mom and dad weren’t witches or wizards, but when curses started flying at the movies, their love story had an unhappy ending.
“When I was 15, a girl asked me to the movies. It was I Love You, Man. Her parents decided to attend too.
Then one of the characters cursed like 10 minutes into the movie and the parents told us we were leaving. They took me right home and that was that.”
It Was Over Before It Started
Redditor The_Blind_Ashland’s first date didn’t even have a chance to start. As soon as his date arrived, she came up with a lame excuse to bail and all he got to see was her backside as she high-tailed it back to her car.
“Was going to go to a bar with a girl I met on tinder. She showed up 15 minutes late, which wasn’t that big of a deal. Got out of her car, crossed the street, and then awkwardly shook my hand.
Told me she forgot her ID at home, apologized, and then left.”
She Was More Interested in His Roommate
Irrelevant_usernam3 thought the girl who messaged him on Tinder was interested in him. But shortly after their date ended, he discovered that he was not the object of her obsession. Her roommate was and things took a creepy turn.
“I went on a date with this girl from tinder. She “super liked” me and messaged first, so I was really happy to have someone interested. I asked if she’d like to go for a walk some time and she said she’d love to.
So we get to walking and like 5 minutes in, she asks if I have roommates. I said yes, I live with 5 people and tell her about a few of them. “Theres Max, Matt, Mark,…” “Wait, Mark Smith? I know him! What’s he been up to…”
So we start chatting about my roommate and she knows a lot about him. His family, the sports he plays, his girlfriend. Every time I try to move the conversation somewhere else, she brings it back to Mark.
She’s not even pretending to be into me anymore, she’s just fangirling out over my roommate. “I just love him, his hair is always so shiny and he smells so nice!”. She spends the full 2 hours talking about him and asking all sorts of questions. I didn’t really know what to do, so I just boredly keep answering.
When we get back to our cars, she shifts gears again. “Hey, so I had a really great time. Want to go back to your place to have some fun?”.
She’s really creeping me out at this point, so I tell her I have homework to do and maybe later. I get back and tell Mark about the date and he knows exactly who she is. He picks up his phone and immediately calls the police. They show up at the house find the girl outside in the back yard and arrest her for violating a restraining order or something. It turned out she was super unstable and had stalked my roommate since they went on one date almost a year prior. She recognized from photos she had of him and used me to find out where he lived.”
This Date Was Overcrowded
AtomicMojave went to a restaurant with a girl on a first date. But it wasn’t long before they realized that everyone in her relationship, including her ex, was either working or hanging close by.
“I went on a date with a girl to a bar and grill. The girl just got set free from a bad relationship. The bartender was her uncle, the server was her sister, and her fresh ex-boyfriend was there on a date with another guy.”
He Didn’t Choose Her
Mklintare met her date at a coffee shop. But after he took her home, she was shocked to discover that he was basically a man-child. To make things worse, she had some serious competition in the bedroom from Pokemon.
“I went on a date with a guy from tinder 2 years back. Met up at a coffee shop and things were going alriiight, not great. But he seemed nice just didn’t look like his photos.
Got to talking and said he didnt know his age? Who tf doesnt know their own age? I asked him how and he said his parents never told him. I somehow skimmed over that real fast because he invited me to his place and out of politeness I say yes.
We go to his room. And its pokemon EVERTHING. IM TALKING EVERYTHING.
-Posters -blankets -bedsheets -figurines -curtains You got the jist… everything. There’s zero chairs or elevated surfaces, his twin bed is on the floor and he is sitting on his knees and I sit from across the room. Suddenly hes knee crawling towards me and I sprung up on both feet and walked put the god damn door. Thank gosh I found the love of my life. I can proudly laugh about this but looking back one of the oddest creepiest things I have ever experienced.”