Even at the best of times, dating is not for the faint of heart. From online mishaps to zero chemistry, there are so many things that can go wrong while searching for your better half—as these Reddit users found out the hard way. Here, they share the stories from their absolute weirdest dates.
1. Failing at Love
We went to the Church of Scientology, roped in with promises of free food. We were on a date for Christmas. So, so odd no matter which way you cut it. But it got worse: 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 for each other. We’ve been together 10 years.
2. Parental Advisory Warning
When I was 15, a girl asked me to go see I Love You, Man at the movies. Her parents decided to attend, too. Ok, that’s awkward enough, but hey, I kind of liked this girl. 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.
3. Identifying the Problem
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. 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 did not come back. Super believable.
4. Matchmaker, Matchmaker
It’s hard to say I was catfished because the actual girl was there, but little did I know, I was in for a rude surprise: so was her boyfriend—and her friend she thought I would be a better match with. What made it more odd is that she’d sent nudes, full-face nudes, not photoshopped. She had face-swapped them, but I could see the chest tattoo on her in person, no mistaking that.
5. Playing the Long Game
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 five minutes in, she asks if I have roommates. I said yes, I live with five people and tell her about a few of them.
“There’s 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 two hours talking about him and asking all sorts of questions. I didn’t really know what to do, so I just 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. That’s when his face turns white as a sheet. 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 backyard, 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 me from photos she had of him and used me to find out where he lived.
6. Love in a Northern Town
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. They really kept it in the family, I guess.
7. Patrick Dateman
This was a third date with a guy from Hinge. Started off completely normal—went to a pub for a few drinks. Pub closes. Guy invites me back to his. We get back to his and have a few more drinks, he then asks if I’d like to smoke. Hadn’t smoked for a few years, but thought “hey it’ll be fine.” End up feeling very sick and unable to move.
Guy doesn’t have a bucket or bowl so brings over the entire kitchen bin and places it next to me. He then suggests we watch a movie. Guy puts on American Psycho, and I sit there for the next two hours paralyzed and paranoid, completely convinced he’s going to murder me. Also, he lived on a boat, which didn’t help.
8. I Don’t Choose You
Oh my. I went on a date with a guy from Tinder two years back. Met up at a coffee shop and things were going alriight, not great. But he seemed nice, he just didn’t look like his photos. Got to talking and he said he didn’t know his own age? Who doesn’t 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 that’s when things get really weird. The whole room is Pokemon EVERYTHING. I’M TALKING EVERYTHING. Posters, blankets, bed sheets, figurines, curtains. You get the point…everything. There are also zero chairs or elevated surfaces.
His twin bed is on the floor. He is sitting on his knees, and I sit across the room. Suddenly, he’s knee-crawling towards me. I sprung up on both feet and walked out the door. Thank gosh I found the love of my life. I can proudly laugh about this, but looking back, it was one of the oddest and creepiest things I have ever experienced.
9. Well Actually
I dated a man who corrected my Polish, because 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 learnt from his grandma.
10. A Spot of Trouble
In high school (so the ages of the parties in this story are 16/17), I went with my friend to pick up a boy I liked so we could all go see Baz Luhrmann’s Romeo + Juliet. When I got to his house, his parents had me and the friend come inside so they could tell us that the movie was not appropriate for their son. They suggested that we see the live action 101 Dalmatians instead.
11. Mixed Messages
I matched with a Chinese exchange student on Tinder. She asked me to meet her at her apartment, then we’d go link up with some of her friends at the waterfront. We’re texting as I’m on the way over, and she says she didn’t realize this was a date. Nonetheless, she asks me to pick up dinner for both of us on the way over.
I get to her apartment, and before I can even take my jacket off, she says, “So, do you have anything to say to me?” Presumably because I’d spent 15 seconds in silence. I offer her the food she asked for, she said she wasn’t hungry. I try to strike up a conversation, but she dead ends every topic I bring up. She starts texting and making phone calls.
She was speaking Mandarin, presumably, but I was able to make out the name of the place we were supposed to meet her friends. She said 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. Girl straight up used me for food delivery.
12. Pebbles or No Bam-Bam
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. There was just one thing: 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 then invited me to kiss her at the door, but told me I should also kiss “Pebbles” the stuffed animal so he wouldn’t be jealous. Of course I kissed Pebbles. My date was actually out-of-my-league hot. But straight-up crazy.
13. Wing Woman Gone Wrong
I asked Girl A to come watch a horror movie in my dorm, and she ends up bringing Girl B along with her. I’m like, whatever, still chilling with girls and watching movies. Then it’s kind of obvious that Girl A doesn’t want to do anything and wants me to talk with Girl B instead. Her friend (Girl B) was pretty cool and attractive, so I was ok with it.
So then Girl A says hey, you should go to this date night party with Girl B. I’m like OK whatever, I’m down. End of night with Girl B, we start making out and I try making moves and she’s like, “Oh no, this is so wrong. Girl A likes you!” Turns out, they both liked me. And no, no threesome ending to this story or anything. Never got to do anything with either one…
14. Wrestling With My Feelings
I was talking to dude on a dating app and we decided to meet up for coffee one day. Our coffee did not go well. 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.
15. Trolling You
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. Ugh, I’m not into it already.
We went to the park. She had filled the entire trunk of her car with her freaking weird hobby: troll dolls (I mean dozens and dozens of them). She 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. Imagine that.
So sitting there, hands full of troll dolls, she exasperatedly asks me, “So are we going to have sex? Do you even know how to have sex?” “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.
16. Speed Dating
My first dating app date. Starts off pretty good, but we barely put in our dinner order and her phone starts blowing up. Her ex was drunk and causing a scene outside her apartment. 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 apartment.
Long story short, both she 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 up their relationship. Dude is way too drunk to drive, so I end up driving him to his apartment, Uber back to my car, realize my date took all the food with her. The joys of dating!
17. Love Hurts
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 counselling for a long time, takes medication, and included a heartfelt apology.
18. Guessing Game
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 the awful truth. I had chemo for breast cancer. I said 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.
19. Making It Work
I 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, and they can be a good therapeutic tool. She gets her beverage, and we sit down to drink.
Not even a hello was exchanged and we dive right into how she was assaulted. 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 awkwardly. It was mostly teeth. And the shark was kind of between us.
20. One Woman’s Trash…
I told a girl I was into granola environmental stuff. She replied “me too,” and we hit it off quickly. Anyway, she kept talking up how incredible her job was and that she taught a bunch of kids about environmental issues and how amazing this job was. Basically begging me to come check it out. So we picked a day and I took the day off from work.
It had been a while since we saw each other, so she decided it would be fun to send me real kinky texts about fun places we could sneak off to around her work, as it was her fantasy. I was down, and I was getting in the mood myself. I drive to her work, only to find out that she works at a trash burning power plant and recycling center, and on that day we’ll be giving a tour to a bunch of preschoolers.
Throughout the “date” basically every chance she could, she would try to get me turned on when no one was looking…even though there were about 20 kids and teachers right there! Meanwhile, we’re walking through piles of rotten trash, or looking at machinery that could kill you in an instant if you stepped over a boundary line. Anyway…The tour ended, she took me in her office and well, let’s just say it took three showers and a wave to a priest to feel clean after that.
21. Key Word: Creep
Oh god. I’ve been on a few, but this guy takes the cake. I met a guy from a dating site at a bar near my house. Even though it doesn’t seem like either of us is really into the other, he drove a while to get there so we get a drink and try to have an okay time. Because we were the only ones at the bar, the bartender decided to close early, so I, being very young and dumb, felt bad. I invited him to my house. BIG. MISTAKE.
We watch some YouTube videos and then, out of left field (because he had shown zero attraction to me all night) 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. A few minutes later, he tries again. Then he does this cartoonish yawn-stretch and announces that he’s going to take a nap on my floor for a bit before he drives all the way back home.
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 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.” 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.
In the end, I tell the cops the whole story and ask if they wouldn’t mind checking 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. To this day, there is so much I’d like to know about that night. He deleted his dating profile and blocked me on Facebook. So flipping weird.
22. Trailing Behind
We met at Applebee’s, and she brought a friend with her, which was odd because this was a 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 and shut the door, and I was left there by myself. In the morning, I left and her dad was shirtless watching me leave and yelling at some dogs that I think were trying to attack me.
23. Her Loss
I went on a date with a girl who stood me up at 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.
24. Grin and Bear It
This reminds me of a girl I saw briefly back in my late teens, I was 19 and she was 24. Mostly she came to my apartment or we fooled around at work, since we worked together. The first time I go to her place, as soon as I walk in, there’s just Care Bears everywhere, I means dozens of stuffed animals, posters, every single movie she owned, everything was Care Bears.
The first thing I asked was “Are you going to murder me?” Then she asked if I was hungry, but the only thing she had was left-over pizza from the place we worked. I figured it was a good time for me to leave at that point. I still sort of know her, too. She married a guy I know and eventually they got divorced. When we became buds, I learned that the creepy Care Bear obsession was just the beginning.
He complains to me about her all the time because she still breast feeds their four-year-old son, which is giving him digestive issues. A doctor even appealed on his behalf that she’s harming their children and should lose custody, but because of the state we live in, they still let her keep the kids. Also, he’s been re-married for a couple of years now, but she is still telling their kids that mommy and daddy are just fighting and he’s going to come crawling back to her any day now.
25. The Last Dance
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. But it got worse. 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 goodbyeeeee.
26. Playing Chicken
I was 15 and my sister was 17. The local farmer’s sons were interested in taking us on a double date. Oh, I so didn’t want to go. The younger son, my date, was a weird fellow who sort of jumped everywhere. As I love my sister very much and she really wanted to go, I went. Big mistake. We walked to their farm, and as we approached my date came bounding up the path, big jumps and strange air kicks all the way.
He jumps up and down and tells us where we are going…we’re all going to see their super duper excellent chicken farm way across town. Chicken farm? Yes, chicken farm.
So we get in their vehicle, and it was an ancient, ancient Jeep thing without doors and a ripped black tarp for the roof. So we drive across town, my sister and I scared to death by the older brother’s crazy donkey driving. They both jump out and the younger brother grabs my hand and says “come on!” We get to a massive, massive metal barn type thing, and like a magician, he waves his arm and rolls back the door and there it is.
Rows and rows and rows of chickens, stacked floor to ceiling. It was a battery farm, they took us to a battery farm. For a first double date. The noise was so awful, the smell too, but oh god, the chickens, the poor little chickens. I wanted to cry, and I think my sister sorta of did at one point. They both run in down this massive aisle stacked so high with unhappy clucking chickens, shouting for us to follow.
We don’t, since this is the most disturbing thing I had ever ever seen in my life. As we won’t go in, they start to bring chickens out for us to hold. My sister realizes this is all too much for us and asks to leave. They say they have one more “treat” for us, please don’t go! We foolishly agree and are taken to a farm supply store where they bought chicken feed and new buckets.
27. Ok, Now Role Play a Good Date
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 co-workers 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.
28. NOT the Kind of Biology I Was Looking for
We went back to her place. She thrust 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?
29. Blank Date
I went on a date with a girl who does not ever listen to music by choice, who says all food tastes the same (she 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. Ever. 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.
30. A Hairy Issue
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?”
She said “It’s slow this time of year. Sometimes I want to pull my hair out.” Like an idiot, I decide to respond with, “Well, don’t do that. Nothing attractive about a bald girl.” After she replied, everything started to make sense. She said, “This is probably a good time to tell you. I have cancer. I’m actually wearing a wig right now.” 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,” 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.
31. Bad Omens
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.
32. Mousy Girl
I 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.
33. Chivalry Is Dead
I dated this wacky woman several years ago. She was very big on chivalry, but I hadn’t realized it until our second date. I took her to a restaurant and she excused herself to go to the bathroom. I had my back turned to her, so I couldn’t see when she was returning. When she got back, she was upset that I didn’t stand up upon her return.
She then listed all of my missed opportunities to prove to her I was chivalrous (didn’t open her car door, didn’t bring her flowers, etc.). Then she sighed and said, “I’m not sure if you’re going to be a good role model for my son.”
34. Life’s a Picnic
The weirdest was when I was a college junior and dated a girl who was a classmate. She wanted to have a “picnic” in a cemetery for a truly dark reason. It was at the gravesite where her ex was buried, as 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.
35. Silence Isn’t Golden
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, and he just stared at me from the table while I was ordering. The date itself lasted about two 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 two 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.
36. Paging Ace Ventura
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 instead of a coffee table in their living room, it’s a little much.
37. I Only Love Myself and My Mama
The guy talked and talked and talked all evening about himself, his parents’ divorce, his ex’s bedroom preferences, and his depressed best friend. And he joked about murdering me. At the end, he told me he lived at his mom’s, but I can come by if I want to.
38. Not the Brainiest Choice
I dated a guy whose mother was a physician. I was in medical school at the time, and we were performing brain dissections. He wanted to meet me for lunch and peek in on our lab. It was a morning lab and when I got out, he was standing there. He got a giant waft of the preservative that the brain tissue is kept in as the doors opened.
He could also see the brains that were being refrigerated after the lab, sitting about 5 feet behind me. He passed out. The awkward part, though, was that he didn’t know what to say when he had 20 medical students standing around him. He was so embarrassed he walked said a quick goodbye, walked away. From the door I could see he jumped on the first bus that came to the stop outside of our lab. Good times.
39. Britney Moment
I once had a girl get up and go to the bathroom during a make-out session. When she came back, my jaw hit the floor. While in the bathroom, she had shaved her head. I will never know why.
40. Brotherly Love
I went on a date with a girl who 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 lo and behold, she’s absolutely right. 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 pic.
41. It’s-a-Me, Dustin
The guy faked an Italian accent the entire time. He was from Florida.
42. Moving Too Fast
I went on a date with a guy named Dan when I was in my late teens. Dan said, “I’d like you to meet my father, he’s going to love you.” So I got in the car and as we started heading out of town, I asked where we were going. Dan said, “you’ll see, we’re almost there.” 15 minutes later, we pull in to a cemetery, and he says come with me.
I was nervous as I followed him down a little hill and he kneeled down in front of a tombstone. He said, “Dad, meet shortcakie, she’s going to be my wife someday.” That was the first and last date Dan and I ever had.
43. Musical Urinals
We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn’t give it much thought.
I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn’t return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women’s room.
I peed in the stall next to her, and she recognized the boots I was wearing. She was totally freaked out. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.
44. A Special Guest Appearance From…
I had a mid-40s man with a young and attractive mid-20s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 minutes, a lady storms into the bar and immediately goes up to them.
She grabs the man by the shoulder and says, “You…You’re a [c-word]” and walks out. The man turned to his perceived date and says, “Yeah, she does that,” and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.