Dating can be painful. Yes, sometimes if you get the right person and you hit it off, it can be a great time, even life-changing. But, a lot of the time dating is an exhausting ordeal. For those that have had the privilege of never having a bad date, congratulations, but for the majority of people, it is something that has happened at least once. But a horror story can be rare. So, here are some of the worst dating horror stories, as told by Reddit.
36. Missed Opportunity
I was on a first date with a girl and I also worked with. We’d been flirting for weeks and had wonderful chemistry. Our date was great and had a life of its own. She drove. At the end of the six-hour long date, we were sitting in her parked car in front of my house, continuing the captivating conversation. We had a work meeting the next morning, so when it came time for me to go, I started to exit the car and said “See you tomorrow.”
She sheepishly said, “I can’t wait that long.” Without thinking, I replied, “Well, you’re gonna have to” and slammed the car door. I didn’t realize what she meant, or how what I said came across, for some time, like the next day.
35. Post-Date Accusation
We had talked a bit online beforehand and gotten along and decided to meet up for a drink at a local dive bar. We get there and have absolutely zero chemistry and end up kind of standing there awkwardly nursing a single beer each that we never set down and making painful small talk. Eventually I make some excuse about work and leave. When I get home I get this text from him:
Don’t take this the wrong way but did you drug my drink?
34. Learning Not To Retch In People’s Face
In 8th Grade, this girl asked me out after we danced together at a dance. I was pudgy and horribly hormone-ridden, and she wasn’t hideous, so of course I said “yes” (mistake number one). We decided to see Houseguest, starring Sinbad (mistake number two). So she and her dad come to pick me up, and we go to get tickets, it was at this point in time that I noticed that this girl, we’ll call her Carly, seemed to have a bit of BO.
It wasn’t terribly obvious, more like a “sweaty shirt that hasn’t been washed in a day or two” sort of way, but when you got close, you could get a whiff of something. Still, 8th grade here, I wasn’t going to complain too much, so I bought Carly some popcorn and we sat down in the back of the theatre. I don’t know how many of you have seen Houseguest, but it’s horrible. Soul-crushingly, heart-achingly horrible. So horrible, in fact, that we can’t even make out, because the whole situation is just awkward.
Fast forward to the end of the movie, and it’s clear that Carly is angling for a kiss of some sort, so I lean over to kiss her, and I just see this clump of some kinda goop on her forehead (she had brushed her hair out of her face, and I guess it was grimy from the popcorn). That, coupled with the stress and awkwardness was enough to make me retch in front of her.
She snapped bolt-upright back into her seat and we spent the rest of the date in stone silence, including the drive home when her dad was asking us how the movie went. To this day the memory can ruin any steamy situation.
33. Did He Mention Blood?
Both of our first times. Blood. Everywhere. Throwing up. Blood. Everywhere. Blood. ಠ_ಠ
We had a mutual break up out of trauma, and we’ve never spoken a word since then even though we have the same friends.
32. Falling For The Friend
I had no car at 17 but thought I would be creative about taking a girl to a movie without involving my parents:
I invited this girl I had a crush on to come to the movies with me and two guy friends. We sat in the back seat together, and sat next to each other at the movies. For the most part, my friends left us alone and it seemed like we were on a quiet, awkward, conversation-less first date. I was pretty lame but tried my best to keep her interest in the few moments a movie-date provides.
But on the ride back to her house, my best friend happened to play some music she liked on the stereo and they started talking. She immediately opened up and the two of them hit it off instantly (while I was sitting next to her in the back seat, silently raging). She dated my best friend for a year after that. 🙁
31. Playing The Wrong Tune
Brought my date to my friend’s house. Friend pressures me into playing guitar.
I played “Needle and the Damage Done”; first thing that came to mind. Why? Dunno.
Turns out her brother had died of a drug overdose not long before. Awkward & chilly for the rest of life.
30. Learning About Her Diary
Let me sum it up for you: I was already trying to escape by the time she told me about her poop diary.
29. Hummer of A Date
Took a girl out on a first date in a rented car. I gallantly open the passenger door for her, she gets in and motions that she’ll close the door herself. I agree with this, so I circle around to my side just as a Hummer zooms by and SMACK! Takes the passenger door right off and doesn’t stop. Confirms everything I ever believed about Hummer drivers.
Girl is paralyzed with shock and horror, asks me to take her home. Rental place finds some reason that my insurance doesn’t cover this damage. Still paying for it. FML.
28. Talking Kids
He asked me on a date, I knew I didn’t want to date anyone but told him we could go to dinner as friends (as we had mutual friends and kind of knew each other), and he agreed. While we were at the restaurant he started talking about what our kids would look like—I’d change the subject and he’d change it right on back to what it was.
THEN, he told me about how while working at one of his previous jobs he stole $1,200+ and got away with it by telling his manager and the cops that he was robbed.
27. A Long List of Horrors
The following are all things I found out on the first (and only) date. Each individual one of these things was a massive red flag in and of themselves.
- He mentioned that he had done a B&E to somebody’s house to find stuff to sell to buy alcohol.
- He seems to be an alcoholic.
- He told me he robbed a liquor store.
- He says he has anger management issues.
- He is convinced that horror movies are accurate depictions of real events.
- He claims that “the moon is his guide.”
- I asked him what the that meant, and the explanation was messed up enough to merit being messed up thing #7.
- He stole somebody’s wallet after sleeping with them.
- The aforementioned individual in #8 was his drug dealer (this is an inference I made).
- He went to a mental institution when he was 15.
- He has a history of hardcore drug use (although that kinda is a given considering everything else).
- When a police car passed us on the road, he freaked out.
- There is probably a warrant out for his arrest.
- He threw somebody down a flight of stairs because they slapped him.
I wish I was making this up.
26. Guilt Trip With The Cops
So we’re still in high school, and we’d been hanging out forever, really liked each other. He’s a pretty decent nerdy guy, we play Starcraft together all the time, have a couple of classes together. He takes me to a Magic tournament. Cool! I register and I start playing. I advance, and he throws a hissy fit after I beat him… and refuses to drive me home.
The guy behind the counter guilts him into taking me home, and we’re about half-way through the awkward silence home when he gets pulled over by the cops for speeding. Instead of cooperating, he throws a fit and starts yelling. Officer asks him to step out of the car, and he eventually does. I’m in tears, so the nice officer calls my parents to come and get me from the side of the road, because he’s taking DateGuy to the station for belligerence and, as he said, “Totally ruining your night.”
I had to answer a ton of questions with the guy sitting in the back of the cop car, glaring daggers at me.
Worst date I’ve ever had, and I had to continue taking classes with him until the end of the year. We never spoke again.
25. Dad Jokes
She comes to pick me up (I couldn’t drive yet), she’s waiting with the car running in the driveway and calls me because she’s somewhat scared of my dad. I come out the front door, my dad follows me wondering where I’m going. He sees the girl and decides he’s going to “embarrass” me. He proceeds to tackle me onto the lawn and pretend like he’s kicking the crap out of me.
She drives off in panic. Thanks, dad.
24. Live Telling
Nightmare date occurring RIGHT NOW.
I rode 250 miles to see this redditor I’d been corresponding with for a couple months. She’s cute and we get along smashingly, but she had a boyfriend and I didn’t want to be in an awkward position so I refrained from visiting. She almost breaks up with him, but she wussed out. She assured me there’d be no problems(?), but sure enough, I pull into her seedy apartment complex and I see two people arguing.
My spidey sense tingle so I doubled back, parked, and called her. They are now arguing and I’m sitting at a convenience store…
23. First Date With Dreads
I was a 20-year-old working at an animal shelter. She was 29. She was a white girl with dreadlocks and didn’t shave her armpits, but she was pretty hot for her age. She was also quite direct and asked me on a date (my first date ever). For our first date, she took me to eat clam chowder somewhere, drove really fast in her Trans-Am, told stories about how she used to shoplift thousands of dollars from Nordstrom’s and outran the cops once in her car.
She was BLASTING “Punjabi MC” on the stereo when some black guys pulled up next to us and laughed. She said “ok man!! ok!” and switched it to Eminem and sped off. After that she wanted me to show me her paintings at her house. I gotta give her credit, she was productive. The entire house was cluttered with paintings. She showed me various paintings and told me the stories behind them.
One painting was of herself as a girl, stabbing her genitals with scissors. She said, “I thought he would stop touching me if I were less of a woman.” I was young, naive, and put up with it all, loving the fact that someone noticed me enough to take me on a date. She drove me home, stopped in front of my house and asked me if we were going to have a goodnight kiss. I said, “I Dunno, I’ve never done that before.”
She said, “Put your head back and close your eyes.” And she gave me a peck on the lips. That was my first date and kiss. I never saw her again because she had to take care of her cancer-stricken uncle who lived on a houseboat. Awkward date in retrospect.
22. Nope, Not Your Daughter
Long story short. Christmas party went well. Met a girl. Woke up in her apartment, in her bed, naked on top of the covers. Woke up because a man in the doorway was angrily asking me, “Is that my daughter?” He had come to pick her up for Christmas vacation and her roommates let him in. I answered, “No” by the way.
Seemed the only smart thing to do.
21. Best Friend Saves The Day
I went out with a guy and we ended up going shopping at the local mall. All the while, he is really sweet and hugging/holding me. After about two hours there, we run into someone who is apparently his current girlfriend, who happens to be with another guy. Miraculously I also ran into my best friend and was able to survive the incredible awkwardness that was that moment.
20. Bad Movie Choice
I was in high school. A girl I’d been talking to for a while texts me, saying her parents are out of town, and implies I should head over. I basically race over to her house, as excited as a horny porn-addicted 17-year-old could be. When I get there, I pull the “let’s watch a movie in your room” move. “What movie?” I look around, and see that she has Kids sitting on her dresser. I’d heard about it, but didn’t know what it was about.
I ask if she’s seen it. “No,” she says, “I borrowed it from a friend.” So we get comfortable, and start watching. A bit of making out, but as the movie goes on, we stop making out and start paying attention. By the end of it, she’s moved to the opposite side of the bed, and on the verge of tears. Even I’m feeling pretty disgusting, sort of like that feeling when you want to take a shower after doing something you regret.
The mood is totally killed, it’s like two in the morning, and she tells me she’s pretty tired. I drive home listening to “Coast to Coast,” kicking myself for choosing Kids of all possible movies. We see each other in school after that, but never ended up hooking up ever again. Probably the association of each other with that movie.
The moral: Larry Clark’s Kids is possibly the worst date movie of all time.
19. A Fork Of A Time
I had a friend who took this girl out to dinner for a first date. It was a disaster right from the start as this girl spent the entire date on her cell phone. Being the nice guy he is, he just decides whatever we’ll get this date done with and never call her again. At one point he gets up to goto the bathroom and on his way back, notices her sweater had fallen off the back of her chair.
He bends down (putting one hand on the table for support) to pick it up and feels a sharp pain run through his hand/arm. He looks up and she had stuck a fork into his hand and, while still on the cell phone, simply goes “oh it’s you” and continues her phone conversation. He found the waiter, paid for his half of the meal, and never looked back.
18. Bringing Race Into The Date
Two and a half years ago, I went to a concert at the Fillmore in San Francisco on a first date with this curvy blonde. We got dinner at a little Italian place, then we took a walk around Japantown while we were waiting for the doors to open. She starts spewing a wave of anti-Asian racism, including her desire to “kill off all the Chinese boys.” My best friend since fourth grade is Chinese.
After the concert, I stuck a twenty in her hand and told her it was cab and BART fare, so she could find her own way home.
17. G.I. Jane And Neediness
He wanted to watch a movie at his house. Turns out, he wanted to watch G.I. Jane. Turns out, it’s his favorite movie. Turns out, he gets so pumped when watching it he wears his army fatigues and spontaneously does pushups every five minutes.
Then we go for a walk and he insists on holding my hand and practically hanging on it for the entire walk.
Finally, I get to my house and send him home, relieved to finally be alone. Five minutes later, I hear something hit my window. Then again. He’s outside, throwing rocks at my window. He tells me he loves me, and gazes up at me with a grin. He had to see me again! I tell him, “Go home!” I think about how I’m going to break up with this extraordinarily needy dude.
It digs at me all night.
In the morning when I leave for work I find flowers under my windshield wiper, and a poem. First dates can be gruesome.
16. Surprise! Dating A Coworker Goes Bad
Last year, I started screwing around with a coworker of mine. BAD IDEA. We decided to go to a party as our first date-like thing. The party was at her house (she had like six roommates in this giant house). Now, I’m not really a big drinker, but these people (all of whom are well into their 20s) were just getting schwasted off of Barton’s Vodka. I’ve never seen a more childish abuse of alcohol.
Yada yada yada, everybody at this party (25 people or so?) started drinking at about ten, and were all passed out in piles of their own vomit all around the house, high-school style. The girl I’m with, after throwing up on her bed, drunkenly begs me to stay and take care of her. Because of my hatred of immature drunk people, I simply leave (kind of a jerk move, I know).
The next day my boss talked to me and said that I wouldn’t be working with her anymore because she threatened to fill out a sexual harassment case or something against me. Whoa!
Worst date ever.
15. Making A Mess On The Ice
I met a good looking girl and after talking for a bit, she told me that she liked ice skating. So, I took her ice skating and had a little dessert prepared for when we were done.
She was awful. She wore a skirt and a revealing shirt, with a very light jacket. Therefore, she was cold the entire time. What didn’t help that problem was that she kept face planting into the ice and getting covered by ice. After multiple falls and her beginning to bleed, I suggested we get off the ice and have some dessert. I grabbed the bag full of stuff and made our way toward the exit.
Right at the exit, she fell again and in my attempt to grab her and keep her up, she knocked the bag out of my hand, and then fell on it. She was then covered in ice, wine and chocolate.
It was not a good date. Needless to say, I didn’t get laid.
It was an amazing amalgam of ice, blood, wine, and chocolate.
14. Killing the Date
I was driving to the movies on a first date with a smoking hot girl and we saw a feral cat get destroyed in traffic. The poor thing got a paw run over first and it was doing this crazy leaping thing and people WERE NOT STOPPING and then a truck finished it. Game over, date finished, we went and sat on her couch for an hour and then I went home.
Poor little cat.
13. Hospital Waiting
I had a dud first date—we had nothing to talk about, and none of the social skills or inclination to make small talk.
We made it halfway through the second drink before both abandoning the idea.
I walk her back to her car—she collapses on the way.
I call an ambulance, and end up in the emergency waiting room wondering exactly what my obligations are to a girl I don’t know.
I stick it out for four hours until she’s discharged.
I ask her to call me when she gets home, to make sure she gets there ok—she doesn’t call.
12. It’s A Small World
Meet a girl at a nice dimly romantic bar that she picks.
We talk for an hour, everything is great.
Suddenly she starts crying saying that she can’t take it, she’s hung up on some guy. She proceeds to attempt to dump all this crap on me about some guy she’s been seeing but they took a break from each other and she thinks he’s been hanging out with this other girl.
I ask the guys name and almost crapped my pants because one of my friends had actually been dating him. I mention this to my date and she just loses her mind even more. Crying, getting pissed, and all the while I’m in shock.
I got up like five times lying that I had to piss just so I could go to the bathroom and be like WTF. Finally, I come back to the table and just say I gotta go. She calms down and apologizes and I bailed out. We stopped talking soon after.
11. Cat Conversation
It was a speed date. He talked about his dead cats, all of them from his past, for the entire five minutes or whatever. I’m not sure he knew my name.
10. Seeing Siblings
I was on a date with some girl in high school and I ran into her sister (I dated her like a year before) with her current boyfriend—my brother. Awkwaaaaard.
9. Turning To The Feet
Was set up on a blind date by a coworker. Things went reasonably well—ok conversation, he seemed to be genuinely nice. My co-worker and her boyfriend double dated with us for moral support. We went back to the co-worker’s house after dinner to watch a movie together. That’s when things got weird.
Co-worker and boyfriend left the room to give us some “alone time.” Immediately, my date tried to kiss me. It was one of those approaches with his tongue hanging out. I nicely rejected the kiss, saying it was too soon for that type of affection for me. So he shifted his attention to my feet. I was wearing open-toed shoes and he grabbed a foot in his hand and asked if he could rub my feet. I declined and he began to beg. Told me that he loved feet and would love to suck on my toes. I declined again, started to get a bit scared.
He made a last ditch effort by asking if he could just sniff them once. I gathered my things and left ASAP.
He followed me to my car and tried to beg me in a baby-talk voice to come back, me and my “widdle piggies” (toes). I kept expecting a camera crew to pop out from behind a tree proclaiming that I had indeed been “punk’d.” I was as nice as possible about everything, citing that I just needed some time to get comfortable with someone before becoming affectionate. I pulled out of the driveway in such a hurry that I squealed my tires a bit.
I had no intention of seeing him again since he had violated my personal space so much. I (probably wrongly) passive-aggressively ignored his phone calls and myspace messages. He couldn’t take a hint though, and called 20 times in one day. I finally manned up and told him that I wasn’t interested in pursuing a relationship. He immediately got nasty, called me a cock tease, and told me never to contact him again. Weirdest date ever.
8. Crappy Time
Took a chance on a questionable fart when she was in the bathroom. Crapped myself.
7. Parental Pick Up
He called 20 minutes before he was supposed to pick me up. Told me he’d be a couple hours late because he wanted to play basketball… the time he was supposed to get me rolled around… no show… twenty minutes later a car pulls up and his mom gets out… (keep in mind we’re freshmen in college).
He sent his parents to come get me. 20-minute drive to his house in the car. Alone with his parents. He proceeded to talk about the girl he was in love with for the rest of the date and ended it with an awkward hug stating that it wouldn’t work because we lived too far away.
6. Feeling Her Brains
I was to meet my girlfriend in a building near midnight for a date. When I got to the predesignated room in that building she directed my attention to a jar on the table. It had a human brain in it. She told me to don gloves and take the brain out of the jar. As I was holding the brain, it seemed very small. I asked, “Is this a child’s brain?” She said, “Yes.” I felt a shiver run down my spine as I held the weight of the child’s brain in my hands.
I started to imagine what this child was like before it died. What did its face look like? What kind of personality did it have? She interrupted what had become a rather chilling reflection by telling me I had to help her cut up the brain before midnight. We cut into the flesh of the brain that used to hold memories, feelings and dreams. Now it was cold and lifeless as my date became very attentive to every detail of structure that our knife revealed as we cut the brain apart.
When we finished, I put the pieces back into the jar and we left for the rest of our date.
She was a medical student and I often had to help her study in our dates. It was the only date I ever had in which I felt genuinely ghoulish for part of the date.
5. Twilight Times
I met a girl in a club whilst working as a nightlife photographer—you meet a lot of girls that way, it’s a good icebreaker. She was pretty, sweet and funny, and we kept bumping into each other throughout the night as I worked. Ended up finishing work and getting to chat to her a bit, things were great, and we ended up going back to her place for a bit of drunken rumpy pumpy.
When we got into her room it was like a normal student room, posters on the wall etc, typical girl stuff, y’know? Twilight poster, calendar of a boy band, some frilly stuff… all that. Quite cute. Anyway, we got down to business, and we were nearly naked when she whispers into my ear in the sexiest way possible, “Bite me like Edward.”
I had my clothes on and was out of the door faster than you could even imagine.
4. Bad Drunken Decision
I was out one night, and had beyond enough to drink. I went to a cafe next door to the bar, grabbed some food and hung out for a while. This guy walks in. He’s kind of cute, so we start talking and I invited him to share my sweet potato fries with me. One thing led to another, we went outside, made out for a while and then we took a taxi back to my place.
Everything seemed fine until I tried to drop him off the next morning. I asked him where he lived, and he kind of avoided the question, just giving me directions. To the local homeless shelter.
He was homeless. And he admitted he was homeless because he just got out of jail. For assaulting a woman.
I had given him my number before any of that came out, and he called constantly. After a day, I had to block all unknown numbers on my phone, because (being homeless and all) he called from a different number every time.
It was miserable, and it took nearly a month for the messages to stop (thank god for visual voicemail).
3. Dud Date
I went on a date one time when I was in elementary school with a girl I met through a girl in my class. We were going to see Grease, (the 20th anniversary release in 1998) and we had a lot of time to kill before the movie started. Being the adventurous young chap that I was, I decided to get some Milk Duds from the snack counter, as I had never eaten them before. I thought, “Milk chocolate? Caramel? I love both of them, so together, they should be amazing!”
I had a few of them, and they were pretty good. I waited for them to melt, then chomped down and ate them. After a few, however, I became impatient of waiting for them to soften up and started to just bite through them. It was a little challenging biting through solid caramel, but nothing terrible.
However, one Milk Dud was more difficult to chew than the rest. I popped this particular one to the back of my mouth, and the caramel core decided to latch itself onto one of my molars. I pulled and pulled to try to get it unstuck from my teeth, but the caramel was too much for my young teeth. In trying to open up my mouth, I ended up ripping the stuck molar from my mouth with the hard Milk Dud still attached.
The molar wasn’t even loose, it just got pulled out!
It’s strange enough going on dates when you’re that young. It’s stranger when it’s with a girl you met only once prior to the date. It’s strangest when you end up ripping out a not-loose tooth with a Milk Dud still attached, and then have to sit through Grease.
Note: I have not eaten a Milk Dud since.
2. He Did Say He Can’t Dance
Went dancing with a girl from work; first date with anyone, 25 years old—zero social skills, naturally. Wisely, I let her do all the talking, and we have a decent enough time. She doesn’t even seem to notice my awkwardness, and I start to loosen up and even show a bit of confidence. “Hey, this is sort of fun!” I say to myself.
I explain that I can’t dance, but she goads me into giving it a try—just one slow song. She’ll walk me through it, she says, no big deal. No one’s watching. My blood pressure shoots through the roof, but I’m still on a high, and hardly noticing my hands trembling and my pulse approaching a dangerous rate. We go over to the floor and she puts my hand on her waist and takes my other hand in hers.
Instantly, my breath leaves me and the room fills with pea soup fog. The arteries in my forearms and throat contract painfully and a crushing sensation overtakes me; fade to black. My memory cuts out at that point, but I’m told that I managed to crawl to the corner of the room after hitting the floor.
When I came to, I was completely numb and paralyzed from head to toe, gasping for breath, but getting almost none at all. The crushing feeling intensified and I lost consciousness several more times in the next hour or so as I lay in the corner. Eventually, I regained enough feeling in my legs to pull myself upright, stagger to a stool, and order an orange juice. My scalp and tongue were still numb, but I managed to drink it down and gather my thoughts enough to remember where I was, what day it was, and how I had gotten there.
In another hour I was aware enough to risk driving home, which I did as slowly and deliberately as I could with my still-dull reflexes and persisting numbness. I made it back to my room and slept until past noon the next day, still a bit numb and groggy even then.
My date, I found out later, had been profoundly embarrassed by my actions, and left immediately after I fell. She forgave me and never mentioned it to anyone, as far as I know.
1. Mistaken For A Cat Burglar
Suburban Chicago, age 16 or so, super-cold winter night on a date with the future homecoming queen, a sweetie who was game for anything legal for entertainment. I was feeling super broke driving in my parents’ ancient station-wagon with its not-great heater, and proposed that anything we did on our date, we do with money raised by redeeming bottles and cans we found around town. This was before homeless folk cornered that market.
We must not have raised much, because my next idiotic entertainment was “let’s follow a police car around, just for fun.” We found one and got behind it, not too close, but following. After a few blocks, the squad car took off like lightning, went around the block, and pursued us, lights flashing. It being cold in the car I had [winces] put on a knit cap/ski mask which had holes for my eyes, nose, mouth. I had never been stopped by a cop before, hadn’t had my license long, and thought it might be a courtesy [groans] to go see the officer in his warm car, so I promptly got out of my freezing wagon and approached the cruiser.
Out popped the cop, gun drawn, and I was spreadeagled against one of the cars. I did my best explaining to a not-amused cop, and got out alive; my date prolly wet her panties. Next night, at the “youth center” there was different village cop there and I asked him if he’d heard about a pullover the previous night blah blah blah and he said “Yeah; kid near got killed; shoulda never rushed a cop… and the cops last night were looking for a cat-burglar in that neighborhood.”