June 7, 2023 | Samuel Ira

People Share The Weirdest Date They've Ever Been On

Dating is supposed to be fun, but oftentimes, things can go south real fast. You always hope for the best, but the reality is, dating requires you to meet up with complete strangers. Even if you've looked up their social media beforehand, there's really no telling whether or not a date is going to be super chill or the total opposite. But that's part of the thrill, I guess—throwing yourself into the deep end and letting things unfold on their own. Frustrated daters from all over the world took to the internet to share the weirdest dates they've ever been on. From unusual behaviors to awkward moments, these stories will surely have you cringing.


Don't forget to check the comment section below the article for more interesting stories!

#1 Science Prerequisite

We went back to her place. She put 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... and 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.


#2 Get Out Of There

The guy picked me up and asked me where I wanted to go. I said, “Oh, just somewhere kind of nice; not too fancy, but a good place to have a conversation. Maybe a coffee shop? And maybe somewhere on the other side of town, I spend all day in this neighborhood.” He took me to a Hardee’s literally one block away. During the date, he talked almost exclusively about his fetishes.


#3 Distinct Tattoo

I have a very large tattoo on my arm. A guy on Tinder "super liked" me and then asked if I knew a girl who just so happened to be my best friend. I said yes and asked how he knew her. They had met on Tinder but she declined a second date. He recognized me from her Facebook page and decided to like me to try and get back with her. Didn't work.


#4 Cuddle Sesh

This girl from Tinder invited me over to cuddle. I got there and she cooked a lovely dinner, then we just kind of held each other and talked about our traumas for a while. I told her about stuff I never even really talked about with my closest friends. Then we moved to her bed and she fell asleep... fast... and we just sort of cuddled all night. We never even kissed. I woke up, we cuddled a little more, and then I went to work. It was an awesome, super intimate experience. Pretty weird though.


#5 The Voices

I 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'd been in counseling for a long time. She also included a heartfelt apology.


#6 Hard Read

My third date with a guy started off completely normal—we went to a pub for a few drinks, then when the place closed for the night, he invited me back to his apartment. When we got there, we had a few more drinks. At some point, I started feeling very sick and unable to move. The guy didn't have a bucket or bowl so he brought over the entire kitchen bin and placed it next to me. He then suggested we watch a movie. He put on American Psycho and I sat there for the next two hours paralyzed and paranoid, completely convinced he was going to do something bad. Also, he lived on a boat.


#7 The Horse Girl

I went on a four-hour date with a woman who rides horses for a living. The entire four hours, she told me everything I could possibly want to know about horses and then some. I learned so much about horses that I forgot most of the stuff she told me about herself. I mean, I guess the stereotype somewhat rings true: A horse girl's only personality trait is that she’s a horse girl. That's it.


#8 Unclear Motives

It's hard to say I was catfished because the actual girl was tfhere, but so was her boyfriend. She also brought along her friend who she thought I would be a better match with. What made it odder, is she had sent me intimate photos, complete with her face in them. I could see the chest tattoo on her in person, so there was no mistaking that it was her. I still don't understand what her intentions were with me.


#9 Excuses, Excuses

I 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. She got out of her car, crossed the street, and then awkwardly shook my hand. She told me she forgot her ID at home, apologized, and then left.


#10 Polish Word Police

I dated a man who corrected my Polish. Apparently, his grandmother was Polish and she told him how to pronounce some words. Mind you, I was brought up in Poland, went to school and college there, read a zillion books, saw a zillion Polish movies, etc. But this guy was very condescending about my pronunciation of the few words he learned from his grandma.


#11 Ball Pit Date

This chick suggested we go to this experimental art exhibit thing. It had a giant ball pit for adults (among other things). It was pretty interesting to have two 30-somethings in a ball pit for a date. Fun time. We had a blast but she ended up ghosting me like, a month later. Oh well, I choose to revel in the good.


#12 Ruined By The Ex

My first dating app date. It started off pretty good, but then her phone started blowing up. Her ex was tipsy and causing a scene outside her apartment. He kept calling her, and then her roommate, and then her landlord. We got our food to go and I took her back to her apartment. Long story short, both her and her ex ended up crying. She went inside and left me with her crying, tipsy ex who started telling me all about how he messed their relationship. The dude was way too tipsy to drive, so I ended up driving him to his apartment. The icing on the cake? My date took all the food with her. The joys of dating!


#13 Silver Lining

I went on a date with a girl who stood me up at the movies. I watched the movie alone, then went to dinner at Marie Calendars by myself. There, I met people from a robotics club at my college and wanted to participate. My first meeting is this Friday. It was the best result of a terrible date. 10/10 would do again.


#14 The Blue Rabbit

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 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 got scared watching 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.


#15 His Loss

I 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 chemotherapy for breast cancer. He asked me a few questions about the surgery (single mastectomy), and he said, “I want to know which one it is, but I can’t look at them right now!” I told him if he could guess which one got the ax, I’d buy him drinks and an appetizer. He won, and I never saw him again. I’m positive that I was the weirdest date that guy has ever been on.


#16 Just A Delivery Man

I matched with a Chinese exchange student on Tinder. She asked me to meet her at her apartment, so we could later link up with some of her friends at the waterfront. We were texting as I was on the way over, and that's when she said she didn't realize this was a date. Nonetheless, she asked me to pick up dinner for both of us on the way over.

I got to her apartment, and before I could even take my jacket off, she asked, "Do you have anything to say to me?" Presumably, because I'd spent 15 seconds in silence. I offered her the food she asked for, but she said she wasn't hungry. I tried to strike up a conversation, but she dead-ended every topic I brought up. She started texting and making phone calls. She was speaking Mandarin, but I was able to make it out.

She was telling her friends she was trying to get rid of me, but then in English, she told me something about how plans might change because her friend needs help. Throughout all this, I just sat by myself, eating my sandwich in silence. When I was finished, I asked if she just wanted me to leave. She said yes, then gave me $20 for dinner.


#17 Odd Vibe

I went on a date with a guy. He invited me over to his apartment. Little did I know that it was a basement apartment, so the air was awful (it was under reconstruction) and there was no daylight. It felt weird, so I send my location to a few of my friends just in case if he was some sort of dangerous criminal. It ended up going well. I mean, I'm still alive, so there's that.


#18 Girl A or Girl B?

I asked Girl A to come watch a horror movie with me in my dorm, and she ended up bringing Girl B along with her. I was like, whatever, I'm chill. Then, it became kind of obvious that Girl A didn't want to do anything with me, she just wanted me to talk to Girl B. Girl B was pretty cool and attractive, so I was okay with it. At some point, Girl A says, "Hey, you should go to this date night party with Girl B." I said okay, and by the end of the night, Girl B and I were making out. She stopped me in the middle of it said, "Oh no, this is so wrong... Girl A likes you!" It turned out, they both liked me, but Girl A was trying to play it cool. Well, it worked...


#19 Just There For The Food

We went to the church of Scientology, after having been roped in with promises of free food. We were on a date for Christmas. So, so odd. 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 for 10 years.


#20 What A Troll

I was interested in this girl, and she kind of tricked me into a double date. Being a good sport, I went along with it—it was awkward but manageable... until she set me up with her sister again and that 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.

She was getting frustrated and angry because I didn't seem all that interested in her dolls. Then, out of nowhere, she exasperatedly asked: "So, are we going to do it? Do you even know how to?" "Umm, not with you I don't," I told her. Then I got up and walked home. There's only so much one can endure while being polite.


#21 Nosy Family

On the first date I ever had, my whole family took the liberty to invite themselves. I guess by that point it wasn't even considered a date anymore. It was at the mall and I was 15 years old at the time. I suppose it was more awkward than weird, but still.


#22 Awkwardness After Applebees

We met at Applebees. She brought a friend with her which was odd because this was the first date, then she invited me to her place for more drinks. She lived in a single-wide trailer that was in the backyard of her parents' place, which was also a single-wide. She went to her room, shut the door, and left me there by myself. In the morning, I left and her dad was shirtless watching me leave. He was yelling at some dogs that I think had been trying to attack me.


#23 No Substance

I went on a date with a girl who did not listen to music by choice, who said all food tastes the same (she kept emphasizing that "she eats to live and not live to eat"), who has never finished any books or TV series in her life, and was about the coldest human being I've ever met. The 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-personality-disorder date.

photo-1529175283207-194a414b9ffa (1)Unsplash

#24 The LARP Enthusiast

I went on a date with a guy who was supposed to pick me up after work. He showed up before my shift started and 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.


#25 Smooth Move

On our first-ever date, we watched Ted 2. Halfway in, he showed me a picture of a dog sticking its tongue out with the text "Kiss?" above it. When I turned to him, he gave me a peck on the lips and went on as if nothing happened. We dated for about six months after that but... Dang.


#26 Helicoptered Date

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.


#27 DDR Freak

The guy played Dance Dance Revolution for a good 45 minutes while I just stood there. I left and played a couple of 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, he tried to make out with me when I got home. Nope.


#28 Animal Lover

I went on a date with a girl whose apartment looked like John Cusack's 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 in their living room, it’s a little much.


#29 Bugs Galore

It wasn't officially a date, sadly, but I went out to eat to a place by our houses with a girl I liked. We were sitting next to a wooden half wall type thing and roaches started to crawl up it. She was apparently afraid of bugs because she started whimpering and scooting away. For some reason I figured it would be a good idea to smack them with my bare hands to get rid of them and did so to one, only to find out that the half wall was flimsy and temporary, causing the front and backside to smack and rattle against each other and drawing attention. The waiter noticed this and had us stand up. He removed the booths' tops to reveal a whole hoard of those insects and he smacked each one individually with a newspaper. We stood there awkwardly and watched as he did this before he replaced the seats and had us sit down again. I actually didn't find it that odd at the time but did once I looked back at it. The restaurant did close down shortly after that.


#30 No Rainchecks

I had to cover for a coworker's class when I had a date planned. But instead of rain checking, she decided to come to the class with me, pretend to be a graduate student, and walk around giving kids bad advice. She has a 10/10 wit. Going out again tomorrow.


#31 Big Red Flag

I went on three dates with this girl. The first date, we talked about our experience in China. We had both lived there for a year, and we mostly talked about that. The second date, we talk about many different things, but some of her comments make me think that she's a little classist, but silly me ignored the red flags because... well, she's hot. The third date, we went to an annual event my city organizes where foreign embassies present their countries' culture. She went on a very offensive rant against everyone who had even the slightest tan. Nope.


#32 Dinner For Schmucks IRL?

I went on a date with a girl who revealed that her hobby was buying lifeless little mice, doing taxidermy on them and then dressing them up in tiny little metal battle armor and swords to stage historical battles... She showed me lots of pictures before the date ended. And no, I have never seen Dinner For Schmucks.


#33 Bulgarian Spy

I matched with this girl on Tinder. I was convinced I was being catfished. We started chatting and eventually decided to grab a meal together. Everything was going well until she got suspicious of a guy sitting near us reading a newspaper. Turns out, her ex’s family had links to the Bulgarian mafia and she thought this guy was a spy gathering info. She moved thousands of miles away from him and had a restraining order against him, but he still managed to get signals and messages to her. Needless to say, I felt like I was walking around with a target on my back. We never saw each other again.


#34 "Open" Relationship

I didn’t actually make it on this date, but... I had just gotten out of a five-year relationship and was using Tinder for the first time. I had been messaging a cute guy and he suggested we get drinks. I accepted the invitation. On the day of, he messaged me saying that he has an issue. He asked if it’d be a bother for me to pick him up. Apparently, his girlfriend was using their shared vehicle that night. He then went on to say that he was in an open relationship, but he didn’t like to tell people right away because it usually “weirds them out.” Also, he has a child under a year old. Yeah, that was a hard no from me.


#35 Cemetary Picnic

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 two 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.


#36 Obsessed With Happiness

On the first date with a woman, she tells me she's a happiness coach. She was very nice and sweet to everyone. Very upbeat. Then over dinner, she tells me if you see someone who isn't smiling then they aren't happy. "So many sad people in the world..." She wouldn't stop preaching happiness to me. I felt like I was in therapy.

Next, she said that all cops are bad. Even if a cop is a good person and is always doing the right thing they are still a bad cop simply because "all cops are part of the problem." Well, I know an LA cop who's the nicest most stand-up guy in the world. I started getting really concerned about this gal.

She asked me to bring a list of my top 10 deal breakers in a relationship. She said she's gone over these lists with lots of guys and no guy had ever told her she failed their list. But she failed the first three items in mine...


#37 In Love In A Week

I was friends with this guy and he wanted to hang out with me and a group of his friends. When I arrived, it was just him. He said that his friends couldn’t make it so I felt a little awkward but thought it would be cool to just chill and hang out. By the end of the evening, he claimed to be maybe in love with me and played me a song, saying that he’d never felt this way about anyone before. I had only known this guy for maybe a week? It was a tad overwhelming and I felt bad for rejecting this person, but I just wasn’t into him in that way.

#38 Formal Mini-Golfing

We were going mini-golfing and the dude picked me up wearing a full-on tux. It was so odd and everything about the date was uncomfortable.


#39 Bamboozled

After weeks of chatting online, we went on a first date. She took her sister and the sister's boyfriend with her. They wanted me to pay everything for them, and I said, "Sure." I was stood up and went home.


#40 Small Town Problems

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. I do not miss that about small towns. Back in high school, my boys and I were getting food in the next town over, and one of my buddies thought it would be funny to order a "fur-burger with a side of thighs." I got to the window and the older lady didn't think that was funny at all, but that made us laugh even harder. Then, very next night, I went to pick up my date for the Homecoming Dance and of course, it was the fast-food lady who answered the door...


#41 Serious Stalker

Another one: 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 sometime and she said she'd love to.

We got to walking and like five minutes in, she asked if I had roommates. I said yes, I live with five people. "There's Max, Matt, Mark,..." "Wait, Mark Smith? I know him! What's he been up to..."We started chatting about my roommate and she knew a lot about him... His family, the sports he plays, his girlfriend.  Every time I tried to move the conversation somewhere else, she brought it back to Mark. She was not even pretending to be into me anymore, she was just fangirling out over my roommate. "I just love him, his hair is always so shiny and he smells so nice!" She spent a full two hours talking about him and asking all sorts of questions. I didn't really know what to do, so I just kept answering.

When we got back to our cars, she shifted gears again. "Hey, so I had a really great time. Want to go back to your place to have some fun?" She was really creeping me out at this point, so I told her I had homework to do. I got back and told Mark about the date and he knew exactly who she was. He picked up his phone and immediately called the police. They showed up at the house and found the girl outside in the backyard. They then arrested 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.


#42 The Four Horsemen

I matched with a girl on Tinder—we hit it off in conversation right away and arranged a date at a tea place. We g0t 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. The drawings were really, REALLY good—but I wasn't into the date so I left.


#43 Same Meds, Same Wavelength

In college, I went on a date with a dude who got all excited that we were on the same psychiatric medication. Like, I'm pretty sure he thought it made us soulmates or something. It was...different.


#44 Talkative Nilly

The guy talked and talked and talked all evening about himself, his parents’ divorce, his ex’s preferences, and his depressed best friend. He also joked about ending me. And, in the end, he told me he lived at his mom’s but I could come by if I wanted to.


#45 Wrong Movie Choice

It was my freshman year of high school. I went to the first Silent Hill movie with a girl that was a senior. She didn’t like the movie, then my ride couldn’t pick me up, so my date had to drive me home. We awkwardly kissed a bit, and I think I traumatized her with my movie choice... We didn’t really talk again after that even though we had a few classes together.




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