These Worst Date Stories Will Make You Feel Better About Your Non-Existent Love Life
Dating is like getting a massage. If it’s good, you will feel great afterwards: refreshed, optimistic, with a new lease on life. But if it’s bad, you’ll feel regretful, glum, and like you need to take a long shower.
If you’re someone who has been single for longer than you’ve ever stayed in a relationship then you’ve probably gone on A LOT of dates. This means that while some dates might have been OK — maybe even good?? — odds are that many of the dates have not eventuated into anything. Sometimes people just don’t hit it off, but we’re not here to talk about those kinds of bad dates. These are strictly about dates that are straight-up disasters, like the kind of bad date story that you tell all your future dates about.
It’s the great circle of life, or more accurately, the great cycle of dating in the modern age.
Over on r/AskReddit, users are sharing their bad date stories and I promise you, these will make you feel a whole lot better about your non-existent love life.
We picked out the wildest entries from Reddit users answering: “What’s the worst date you ever had?”
(Some entries have been edited for clarity.)
The date with a whole lot of baggage.
“I was set up by a friend’s girlfriend. Shown a picture and said sure. She was good looking and I liked the girl’s other friends that I had met. She couldn’t be too bad, right? I call her and set up the day and time for pickup at her house (we were both still living with our parents).
“I arrive to pick her up and there she is with her parents and brother sitting around the kitchen table just talking. I get a bad vibe from everyone but her when she introduces me. On the way to dinner, I mention the tension I felt from them all. She says it’s because she just broke up with her boyfriend a few weeks before — her family loved him and they were all upset with her dating someone else. OK, I can see that…maybe they’ll get over it and like me once they get to know me if we date for a while.
“Later on I ask about her brother. No brothers. OK, cousin? No boy cousins that she is close to. What about the guy with her parents when I picked her up? That was her ex. There to have dinner with her parents, they have had him over several times a week since the breakup trying to get them back together and had made sure he was there when I arrived.”
The date who brought her dad.
“Met a girl online, everything seemed OK and the conversations were good, so a few days later we decided to meet for coffee and go for dinner later. I show up to the cafe about 45 minutes early and order a coffee, intending to read for a bit. While I’m reading, I notice an older fellow staring and taking far too much interest in me before leaving. Odd, but okay. Continue to read until about 10-minutes until meet up, when I text the girl that I’m already at the cafe.
“Shortly after, the odd older fellow comes back in one entrance, and this sets off my Spidey sense so I’m making my way to the other entrance when my date catches my arm to say hi. I tell her we should step out for a minute, getting a bad vibe from this guy, she asks which one, so I describe him. It’s her goddamn dad, doing advanced recon for her dates at 24 years old.
“I was a bit sketched out at that, but thought maybe she had some bad dating history that possibly made sense. I meet her dad, he said they wanted to make sure I was who I said I was and to enjoy the date. He leaves and she says being an only child has its downsides. Makes enough sense, we get coffee and chat for a bit, walk in a nearby park and decide where to go for dinner. We get to my car and she asks if I could take her home to grab a jacket before dinner, no big deal.
“We arrive at her place (lives with parents) and I talk to her mom and dad while the date grabs a jacket. They seem nice, but overbearing parents. Date calls me back to her room to meet her cat, and the entire time I’m meeting her cat, the parents are hawking nearby, obviously eavesdropping and it’s obvious the date is dragging her feet for some reason. I said something about getting out to dinner before the rush and her parents who ‘happened’ to be walking by, ask where we were going before they start a dialogue on local restaurants, which pivots to ordering delivery/carryout and how we should just do dinner together at their place.
“I told them no offence, but I’d greatly prefer to dine in someplace relaxed and get to know their daughter. They seem really resistant to this, I’m agitated, and ask if this is how her dates normally go. They said ‘no, normally we don’t let her go out with men, but you passed the background check and your messages to her made you seem nice, like you’d have dinner with us.’
“I was flabbergasted, they ran a background check on me, read our exchanges online, as well as the advanced recon, and expected me to have dinner with two additional people I hardly knew when I was expecting a date. I told them that will absolutely not work for me and that they are being extremely over the top with their expectations and precautions. I left.
“Later received a torrent of text messages and calls to the general sentiment of ‘you were supposed to be better than this’. I don’t respond for a day before telling her/them this is not normal or healthy, I refuse to be any part of it and will be blocking their number and filing restraining orders if I find them lurking around.”
The date who had a boyfriend.
“Went to get drinks with a girl. Talk for about 20 minutes when she says ‘I have a boyfriend, but I’d still like to have sex with you. My boyfriend only lets me have sex with black guys though, so we’d have to film it and you’d have to edit it to make yourself black.’ I had to tell her I’m not that great of an editor.”
The date who got hammered.
“Got set up on a blind date once between mutual friends. She shows up to the restaurant already a little tipsy, orders multiple appetisers and only takes like one or two bites from each one. Then she proceeds to order three or four more drinks and is visibly drunk at this point.
“She gets up and says she’s going to the bathroom and staggers off. About 15-20 minutes go by, so I try to call her several times but no answer. Finally, I decide to pay the check and just leave. About two hours later, I’m sitting at home and I get a call from an unknown number. It’s the police department. She was picked up on a DUI on her way home after she ditched me and gave the cops my number to see if I could go bail her out!”
– @mox44ah
The date who told their whole life story
“She started talking about her life story from childhood to that day. Year by year, with every single traumatic story and emotion. That was our first ever date and she didn’t even let me speak for the duration. I was like ‘Oh OK, she is now talking about high school, six more years left, hold tight.'”
The date who was a fussy nightmare.
“I had a date send her drink back several times and eventually had our server bring out all of the ingredients in separate glasses so that she could mix it herself, the ‘right way’. What’s worse is we were both in the service industry at the time.”
The date that was gatecrashed by an ex.
“It’s a long one and a wild ride — buckle up! I was 22. I started a new job and met this super cute guy at work. He had a previous gf, who he broke up with about six months before we met. She would sometimes randomly come into the shop, and he would always tell her that she couldn’t be there, that they had been broken up for months, and she needed to leave him alone. Anyway, he and I started talking and flirted for several months. After about 3-ish months he finally asked me on a date (he’s very introverted and I am…not, so it took some time for him to feel comfortable enough to ask me out).
“We go out to dinner, and he’s just so sweet and cute and adorably awkward. I really liked him. After dinner he invited me back to his place to talk. I agreed, and we just chilled at his apartment talking and talking (no hanky panky!). I was sitting on one sofa and he was sitting on the other. All of the sudden, there was pounding on his door, he calmly gets up and locks it, and I hear a female yell ‘Did you just lock the door on me?!’ It was the ex.
“I’m sitting on the couch, and he’s calmly asking her to please leave through the door. All of a sudden the front window slides open, and she sticks her head in and starts screaming at him. At this point he’s still calmly asking her to leave, while I’m still sitting on the sofa, clutching my mace. She then CLIMBS IN THROUGH THE WINDOW and I see this HUGE woman (she was like 5’11 – 6′ tall…I’m 4’11” for reference) and I thought ‘Holy shit, I’m going on get my ass kicked!’ Then she sees me and says ‘Who the fuck is this bitch?!’ All the while he’s calmly trying to get her to leave.
“She went ballistic and started tearing down pictures in the living room, trashing them. Then she moved to the bedroom and I could hear her screaming, throwing things, breaking stuff — all the while my date was standing in the doorway of his room trying to get her to stop. He never raised his voice, and it seemed like this wasn’t the first time this happened. He went and got his neighbour, and said ‘I need help with S again’, so the neighbour came over, but she didn’t do anything except stand next to me in the front doorway in…shock?
“He calmly walks in the bedroom, and after a minute or so, he walks out of the bedroom with her in a bear hug, guiding her out of his house. Not shoving, not pushing, just as gently as possible (she was kicking and screaming) moving her out of his home. She then went and laid down in the courtyard, rolling around in the grass, crying and screaming, while the three of us (me, date, neighbour) just stood there for a minute.”
The date who put his finger in someone’s belly button.
“I went over to a boy’s apartment who I had [already] hung out with a few times to watch a movie. In the middle of the movie, he stuck his finger in my belly button. We weren’t even cuddling. Just randomly turns towards me and puts his finger in my belly button. I said to him ‘Get your finger out of my bully button?’, to which he responded by making a weird noise similar to an adult using baby talk and saying coo coo to a baby, and wiggled his finger still inside my belly button. I left immediately, never talked to him again, and my friends still refer to the situation as belly button boy.”
– @ab_1999
The date who was TMI.
“He was over an hour late, no text or call, and when he finally showed up, his excuse was ‘Sorry I’m late, my mom had to take a shit.'”
The date who tried too hard.
“A guy asked if I wanted to do Korean food and karaoke as our second date. Perfect! I love both. He picked the spots. He was 45 minutes late, but I put our names in and he arrived at the restaurant around when our table was called, so no biggie. He complained that he couldn’t eat much on the menu because he’s vegetarian, and that they didn’t serve alcohol. I mean, that sucks, but you picked the place! He kept lamenting that another place close by has vegetarian options and we should have gone there.
“When the food came, it became apparent that he did not know how to use chopsticks, but also was too proud to take a fork, so he visibly struggled to eat. The old couple next to us even tried to give him pointers because he was having such a hard time. I was feeling really awkward at this point — dinner felt like a disaster. I was looking forward to going to a karaoke bar and getting some drinks while laughing at drunk people singing. At least it would offer some distraction!
“We started talking about what songs we like to do for karaoke and I said something like ‘I like to pick songs that get the crowd excited and singing along’ and he goes ‘Oh! You like doing karaoke in front of a crowd? I could never do that.’ And then it dawned on me: he was planning to take me to private room karaoke. Just me and this virtual stranger taking turns serenading each other from a vinyl couch. I was MORTIFIED. I would rather sing in front of 10,000 people than just one.
“I’d like to say I noped out of that date then, but of course not. I followed him around to three different karaoke places as he tried to find one that would give up a private room for two people on a Saturday night (hint: they won’t, because that’s absurd). Finally, he gave up and asked if I wanted a drink at a bar. I should have said no, but I had some misguided faith it might get better? He told me about a cool bar he knew nearby. We walked over and it turned out to be the same place we went on our first date. I drank one drink and then told him I had to walk my dog and left.
“A few days later. he texted to tell me he was sorry, but also that he wanted to be clear that he wasn’t looking for a girlfriend, just someone to take to dinner and sleep with. I was like ‘Uh ok no thanks’ and that was the end. I mean, cool, but say that upfront and also you’re a terrible dinner date!”
The date who was far from romantic.
“Met a guy in OKC [Oklahoma City] when I was in between high school and college. We got chatting and agreed to meet for a date. Since we were both young and broke, he suggested a park in his area. He said he’d bring drinks, if I bring food. Sure! Packed some snacks and a blanket — thinking picnic.
Got to the address he gave me and it was his apartment complex. The ‘park’ was more like a grassy area for dogs and was a part of the complex. I had pretty low self-esteem from a recent breakup so I just said, what the hell let’s see where this goes… He met me at my car and we walked around for like 10 seconds when he mentions he left the beer up in his apt. Once in his apt, he immediately tried to shove his tongue down my throat. I made some excuse and luckily was able to leave. Still think about that sometimes and shiver.”
I’ve learnt my lesson: never date.