People Describe The Strangest Dates They’ve Ever Had
We have all had a bad date or two, and some of us maybe more. Awkward dates can actually be a good thing. They can help you become more comfortable going on dates and learn how to navigate them: practice makes progress. It can also help you realize what you don’t want in a partner and discover your big turn-offs.
After a horrible blind date, you won’t make the same mistakes again. Aside from learning from our own unpleasant experiences, we can learn from the not-so-great encounters of others as well. When we hear of strange mishaps and dating horror stories, we often think, “That will never happen to me!”
But the truth is, you just never know. Reddit explored that exact topic, covering oodles of the craziest date stories ever told.
Reading the Wrong Signs
I always saw this girl on the bus back from work and mustered the courage to talk to her. I got her number and MSN and asked her out that very weekend. She arrived at the restaurant, all dolled up, and things were going well. We started eating and chatting….
Then she drops the bombshell: “Oh, my boyfriend is working overseas.“ I couldn’t gracefully excuse myself, so I tagged along when she went window shopping. After a few hours of torture, I said goodbye, stopped contacting her, and never took the same bus from work again. Reddit User: theresjustme
Hi, I’m Hungry
I used Tinder and ended up on a date with this girl. Her pictures were massively touched up, and she told me she had eczema. When we met, I discovered two things. We had zero chemistry…I mean zero! Then she peeled eczema off her face. But over lunch, I noticed the third thing, which completely turned me off.
We were talking when I saw her peel off her eczema AND EAT THE DEAD SKIN. She saw that I saw and tried to play it off. I stuck with that date for another six hours, occasionally catching her doing that eczema eating thing out of the corner of my eye when she thought I wasn’t looking. Reddit User: mavyapsy
Didn’t Get Murdered or Whatever
I went out with a girl but didn’t really hit things off with her, the chemistry was off. After dinner, I decided to go, but she wanted to hang out. So I thought, let’s go to a bar. I mean, it’s a nice place to try and salvage the date. Plus, maybe some drinks would loosen things up?
I told her to order something for me while I went to the toilet. I came back to two towers on the table. She goes, “By the way, I don’t drink, but they’ve got a promotion now so you get the second tower 50% off.” Reddit User: Intentionallyabadger
Bad Dating Apps
I matched with a girl on a dating app, and we went out for coffee. She was a big k-pop fan (not an issue with me) but spent most of the time talking about her adventures on Twitter and the k-pop fandom on Twitter. Again, not really a big deal, a lot of those stories were quite amusing.
The problem was when we were texting. She spent so much time on Twitter, it’s like she forgot how to talk. Everything I said was met with a reaction gif. It was highly irritating. Reddit User: Zakmonster
Finding Love Overseas
I used OkCupid while living in Singapore and went out with a few locals. One I liked, we went out a few times, and I was planning on seeing him again. The day I was supposed to see him for our third date, I got really sick in the morning and couldn’t make it.
After telling him, he went crazy on me, claiming I was lying. When I assured him that was not the case, he spent the rest of the day trying to convince me to come to his place so he could “take care of me.” Creepy. Reddit User: Cycletothesun
Just Here for the Wine, Not the Scripture
I went out with a dude who was of a certain religion. I made it very clear that there would be no conversion of religions or anything if we wanted to proceed with our newly budding relationship, and he agreed. A few dates later, the topic was brought up again….
He basically insinuated that by the time it gets to the “marrying period,” he would’ve managed to “convince me” to convert. I got the heck out of there. Reddit User: CheeryIcicle
Age Is Just a Number, Right?
I met a guy on Tinder, and his bio said he was two years older than me. Turns out he was five years younger. Okay, no big deal. Was super quiet and awkward throughout the meal. I offered to split the bill, but he said that was rude since he’s the man and he should pay.
Okay, fine, sure, let him have his ego. Then he went to the cashier, came back, and asked me for a $20 because he only brought $50. It was his idea to go to the expensive sushi restaurant, by the way. I went home, and he texted me almost immediately….
The text said, “I wanted to show you my shy side first. I didn’t want to unleash my wild side. Ready for the next date?” Nope. Reddit User: eilletane
I went out with this girl after matching on Tinder. She wanted me to fetch her from her workplace even though we were just going to hang near where we lived (we live kind of close to each other). She suggested we go to karaoke, but then she didn’t want to sing….
She spent most of the time talking about her ex she just broke up with and didn’t offer to pay for (her share of) karaoke or dinner. A few weeks later, she texted asking if she could borrow money. I’ve never blocked anyone so fast. Reddit User: j_fat_snorlax
First Date from Hell
I was single going on seven months when I met a guy who reached out to me through my social media. We spoke to each other almost every day for two weeks before agreeing to meet up. It’s safe to say that I was pretty excited because hey, it’s been a while….
On the first date, the guy had my selfie as his lock and home screen. I was so taken aback that I didn’t know what to do. It’s safe to say it never worked out. Reddit User: littlesuperherogirl
I once went out with a guy that I had met on Tinder. We agreed to meet up, and the consensus was to go to this new restaurant. When we got our food, he held his fork like a 2-year-old who had just learned to use it to shovel food. And that’s exactly what he did.
I kept telling myself not to be shallow, but my eye was starting to twitch. Then he said his mum was trying to get him to marry his cousin. Direct cousin. Ok thanks, bye! Reddit User: droseng
Tinder Matches Be Crazy
I had one a few years back. Tinder was pretty popular, and I started using it. Matched this one girl, and we started chatting. After a week or so, we decided to meet up. I took her to the movies and dinner. She seemed really normal to be honest, but after sending her home, she texted me saying I’m her boyfriend now.
I replied that we never really said anything about a relationship, and we just went out on one date, and she started getting mad and blasting me with texts saying how I toyed with her feelings. Reddit User: frostyfit
I once dated a guy from Tinder; he couldn’t stop talking about himself and his basketball games. We went to play a video game, and while it was loading, he started to swipe on his phone. When I asked if something was up, he showed me some girl’s profile and said she was a catfish….
I wasn’t sure if he didn’t enjoy the date or was plain stupid. Afterward, he tried to get me to go for drinks, but I was annoyed. He tried texting me, but I moved on. Reddit User: doublechocolatecooky
Don’t Do Drugs, Mmmkay
I met a guy once; he was really chill, and we got along through text. I met this guy for the first time at a bar, and when he came in, I was already pretty buzzed. After we ordered a jug each, I began to ask him how his day was. He stared me down for a good half-minute and just said, “We don’t have to talk, you know.”
O-kaaay. We drank our drinks in absolute silence. After I asked for the bill (which he didn’t even offer to split, so I ended up paying for), he said, “So my place?” Um. Reddit User: existentialost
Love You Like a Brother
So I was talking to a guy from Tinder, and we hit it off. Neither of us wanted a relationship, so we were just friends talking about life, which was already so rare. I was bored, so I asked him out to watch a movie, and that was probably the worst thing I have ever done….
He was late, greeted me with a middle finger, and spent the entire two hours looking at his phone. He spoke like two words to me, and both of them were swear words. Then he texted that the date went well and we should chill again. Reddit User: arumlillies
Not Even a Salad
I met someone on Tinder a while back. We spoke for a little while and agreed to meet up for dinner. The girl showed up, looked beautiful, and then refused to order anything to eat. She asked me lots of questions and typed the answers on her phone as if to read them later on.
She also looked at the phone almost all the time. It was very awkward, with only me eating and answering questions like I was at an interview. Reddit User: Yeunkwong
Swiper No Swiping
I had a friend who went out with this Tinder dude. I was really happy for her since the guy seemed genuine and all. By the time they were on the date hours later, he had told her, “It’s easy to get matches on Tinder.” My friend was flabbergasted. Then the guy showed her his Tinder app and swiped right so fast on all the girls on his “decks.”
He didn’t even bother to look at their faces or bio at all. She felt humiliated. I don’t understand what the guy was doing. Reddit User: sallyg149
Thinking Too Far Ahead
It was a Tinder match, and we went out to a movie. Less than an hour in, he said, “If this all works out, your children will be mixed.” I gave him an awkward laugh. He didn’t laugh. And then proceeded to tell me about how he dated a single mother who went back to her ex. During the date, he posted a picture of himself wearing my glasses on Instagram. With a heart shape caption. In front of me.
After that, he wouldn’t take the hint. When I told him straight up that I wasn’t interested, he treated it like a breakup: long text messages and asking explanations. The guy was 27 years old. Reddit User: exotic_hadron
So Sweet (And Sour)
I met with a guy from a dating app and went for dinner at a chain restaurant. He was a gentleman and said he would foot the bill. But the dinner didn’t go well; we didn’t have anything in common. When the bill came, I could see that he hesitated to take out his wallet, so I gave the waiter my card.
The guy got upset, whipped out his wallet, and demanded I take back my card. On my way home, he regretted being a gentleman and texted to ask if I could transfer him my share of the bill. Reddit User: abcdppled
The Terrible 30s
I was around 30 when I met a woman online. She was older than me and was really nice; we got along well during our first meeting. The second time we met, she invited me back to her house, and I said okay. We ended up on her bed, and that’s where things went horribly wrong. I couldn’t get it up, even though she tried everything she could think of.
I’ll never forget the huge amount of shame I felt when I saw the look of disappointment on her face. We didn’t contact each other after that. Reddit User: PhantomWolf83
The Good Ol’ College Years
Back in university, I had a crush on a girl. During a school dance, I managed to ask her for a dance, and the event photographer took a photo of us. Through connections, I got the photo and developed it. I still pursued the girl, and once, I asked her out to study at a library. She said yes, and things were going well, and we were having fun talking and stuff.
Then I got the bright idea to show her the photo of us, which I had brought. And which I had kept in my wallet. Needless to say, she kindly rejected my next few invites. Reddit User: theresjustme
Her Dad Had the Password
Not exactly a first date, but an odd experience that prevented a first date from ever taking place. I matched with this girl and looked at her profile. It said, “FYI, this account is operated by my father. I do not have the password. You will have to meet with him one-on-one at least once before you get to meet me, with him present.
Do not message me if you’ve ever had relations outside of marriage, if you’ve ever looked at pornography, or if you’re divorced for any reason other than your wife abandoned you.” She was 27. Reddit User: AssistantManagerMan
Her Extensive Machete Collection
She talked about her extensive machete collection and how she’s threatened some of her exes with them just for fun. She also talked about how she got the massive scar on her arm for punching out a window. Her friend just sat awkwardly the whole night and got hammered. I felt bad for her since she didn’t like being the third wheel.
Here’s the fun part though: since I was bad about ignoring red flags at the time, I tried to organize a second date. Reddit User: rift_in_the_wrap
Dance Dance Revolution
I go out to dinner with a guy I had only met quickly once before. First, we go to dinner, which is ok, nothing special. It was a little awkward. At the end of dinner, he ask me if I like Dance Dance Revolution. He then proceeds to tell me he is really good at it and wants to show me.
So after dinner, he takes me to an arcade, where he spends the next thirty minutes playing/dancing to Dance Dance Revolution while I watch. He never asks if I want to play. Reddit User: Flowersinhercurls
Her New Antidepressants Were Causing Issues
She literally tried to commit suicide by jumping over a railing that was 4 stories up, then when I pulled her off the railing and moved her to a spot with no places to jump from, she told me that her new antidepressants were probably causing her to have issues.
I walked her to her car a bit later, and she said that she was going to a party. Then, all of a sudden, she kissed me rather passionately, jumped in her car, and peeled out. I never saw her again. Reddit User: [redacted]
That’s What the Prisoners Are For
Online dating. We met for coffee and walked on the beach. It immediately started to not go well. We disagreed about almost everything. He even mocked my religious beliefs. After walking a ways, he asked if I wanted to sit on the beach. I obliged. He set his coffee cup down, and it blew away but not far. I said, “Oh no, your cup blew away.” He looked, shrugged, and ignored it.
“I litter all the time. Yeah, like if I have a bag of McDonald’s trash, I’ll just throw it out the window. That’s what prisoners are for.” Reddit User: AbbyVanBuren
He Didn’t Expect the Owls
I met a girl online, and we agreed to meet up at her work on the day of our date. She worked at a local state park visitor center. So I drove up and was ready for our mini-golf date, but when I got there, she proceeded to take me into the back of their shop.
She ended up letting me help her feed the barn owls and red tail hawk that they were rehabilitating in captivity at the park office. Super cool, but I was not expecting that at all. Reddit User: Extrasherman
Women Who Read
I went out for coffee with a classmate. He showed up half an hour late wearing baggy sweatpants with suspicious stains all over them. I had been amusing myself by doing the crossword while waiting on this guy, and when he arrived, he sat down and pulled my crossword over to him.
He looked at it for a moment and then said, “Women who read are fine and all, but it isn’t very attractive to show off.” We did not have a second date. Reddit User: CowtheHankDog
Her Dad Was a Primitive Baptist Minister
I dated a girl in high school whose father was a Primitive Baptist minister. Anyway, I went to pick her up, and her dad answered the door wearing a wife beater and holding a gun. He invited me inside and proceeded to give me the “where are you going, what are your intentions” speech while cleaning his gun. Hung on the wall behind him were at least 100 other guns. Not kidding, you couldn’t see the wallpaper.
We left, went to a movie, and I got a BJ on the way home, so it didn’t work out if it was supposed to intimidate me. Reddit User: Soup_Kitchen
Went to a Starbucks with this girl and she ordered some sort of sugary drink. About halfway through, she got up and said she had to go to the bathroom. She came back after having very obviously vomited. She suffered through the rest of the date. End of the date, she leaned in, and I didn’t want to be rude.
I tried for a nice quick peck, but she went in hard core. It was kind of gross, but we did end up dating for a few months. Reddit User: Taygr
This guy invited me ice skating. I’d never been ice skating before and wasn’t very coordinated, but of course, I didn’t want to tell him that. We were skating for about 20 minutes, and I was feeling pretty proud of myself for doing so well. Then, BAM! I totally wiped out and pulled him down with me, which caused him to elbow me in the face as he landed on top of me.
My glasses broke, and I had a concussion and a black eye. I was too embarrassed for a second date. Reddit User: glitterphobia
The Fair Mix-Up
Went to the local fall fair with a group of friends, and after a little booze in the system, I end up making out with a girl I had been flirting with for a while. Walking to one of the rides, she pulls me aside, and we continue to make out. It wasn’t the same girl.
Just an acquaintance I barely knew that happened to be there. By the time I realized, I didn’t care. I never saw the first girl again, and now I’m dating the second girl. Reddit User: Sarfly
When I was a senior in high school, I agreed to go on a date with a nice guy because I felt kinda bad for him. We were going to the movies, and I had told him he could pick which one to see. It turned out he picked Rambo. Afterwards, we went to Target for some reason.
When we were leaving the store, he walked right into the glass doors because he thought they were automatic. Overall, it was probably the weirdest date I’ve ever been on. Reddit User: twest1
The Mad Roommate
I met a girl on an online dating site (this was back in ’99 or so). As it turns out, her roommate was a girl I had gone out with a few weeks earlier and banged, but nothing really happened after. Anyways, I guess something happened between them, I forget the details, but we went out and she insisted we go back to her place.
Her roommate was in another part of the apartment and was irate. Clothes were shed, loud noises were made, and I never saw either of them again. Reddit User: mayorjimmy
Awkward Hand Holding
I went to a movie with this dude, and the guy was determined to hold my hand. He actually took M&Ms out of my hand and forced his fingers between mine and wouldn’t let go for the last hour of the movie. We got food afterward, and he would not stop trapping my feet with his, and when we said our goodbyes, he gave me the longest, most awkward hug.
The whole drive home, I’d wished I “went to the bathroom” at the movie. I never saw him again. Reddit User: turangaleela1bdi
The Blind Date
My sister and her boyfriend at the time had tickets to a hockey game. So she invited me, and her boyfriend invited his best friend, and it ended up being like a blind date. Half way through the game, my sister and her boyfriend get in this huge argument, and me and this guy don’t know what to do. We didn’t know anything about each other but decided to ditch my sister and her boyfriend.
We ended up going to dinner and got a few drinks afterwards. We’ve been dating for 8 months now. Reddit User: Brittnay
There Was No Cat
I was set up with a friend of a friend. My date had to get ready after baseball practice. I hung out in his living room in the meantime. The place had a weird smell. Like an unseen animal lived there. The furniture also had a lot of stains. When he was ready to go, I asked if he had any pets. He said no.
Brought to mind the Family Guy quote, “It smells like there’s a cat, but I don’t think there’s a cat.” He didn’t get a second date. Reddit User: OtherKindofMermaid
Heidi Was Confused
My first date after an ugly divorce was with a cute girl named Heidi. She wanted to stop by a benefit that was being held for her friend who just lost her husband, and then we would go to dinner and whatnot. I didn’t see a problem with this, so I agreed. We walked into the bar where the benefit was being held and literally almost ran right into the guy my ex wife cheated on me with.
Heidi was confused as to what just happened, so I had to explain to her the situation in front of the other guy. Reddit User: cbrown80
We Weren’t Boyfriend/Girlfriend
I went to the movies 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 I couldn’t bring myself to tell them that we weren’t actually boyfriend/girlfriend. Reddit User: Sammie_SU
How Is Your Cat?
I was out to dinner with this girl. She starts looking at her phone and has this weird look on her face. I ask what’s wrong, and she says her cat has gone missing. She goes outside to make a phone call and comes back 5 minutes later saying we have to go. I drive her back to her dorm, and she runs inside with no goodbye.
Later that night, I check Facebook and see her on a date with another guy. I sent her a message asking how her cat is. Reddit User: ilivlife
It Was a Puppy Video
It was our first date, and we were in high school. We went to get some froyo at Tutti Frutti. He comes and picks me up and brings his mom along. He apparently can’t go on dates unless she comes with him. So we are sitting at our own table eating, and I leaned over to show him something on my phone.
His mom gets up and marches over to our table and grabs my phone, shouting, “What are you showing my son?!” It was a funny puppy video. Reddit User: Castianity37