Dating can be exhilarating or exhausting, depending on how your experiences have been. If you’re currently in the honeymoon stage of a healthy relationship, you might feel optimistic and excited about the future of your love life. But if you’ve recently had your heart broken, dating might be the last thing on your mind.
Redditors have recently been recounting their worst dating experiences, so we’ve gathered some of their juiciest stories below. Enjoy reading through these tales that might make you happy to stay single, and be sure to upvote the terrible dates you’re glad you didn’t have to suffer through. And keep reading to find a conversation with Dating and Relationships Coach Rachel New!
#1
Guy brought a ring 💍 to the first date. Angrily stormed out when I obviously said no, and then he came back and started beating on the window next to me from the outside. The restaurant manager had to walk me to my car because the guy was flipping out in the parking lot. Horrifying.
Image source: MPD1987, Caleb Oquendo
#2
Finally went on a date with a friend I’ve have a crush on for years. Started very well, she even got me strawberries (inside joke) when I picked her up. Had dinner and drinks. Left the restaurant and waiting for a valet to bring the car. Kept checking and valet keeps saying they are busy and to give them more time. After about an hour the valet tells us they can’t find the car. We walk through 4 levels of parking structure to finally find the car, start heading back and I keep smelling something really bad. I’m not saying anything, she is not saying anything, we just keep smelling it. Back in the day, downtown LA had issues with navigations and service. I had 3 navigations to make sure I don’t get lost, still ended up getting lost. Each navigation was showing a different route and kept getting distracted by the horrible smell. After a while I can’t resist and tell her about the smell. She thought it was from me. Pull over and try to figure out what it is. It was the strawberries that were left in the car for hours in the LA heat. Finally throw them away and find our way home. I have no idea why she decided to go out with me again. Been married for almost 10 years after that weird event.
Image source: andooooi
#3
I went on a date with a guy who dropped the fact that he was a white supremacist on the date. I was in such a hurry to leave I slipped on spilled beer and hit my head.
Image source: growsonwalls, Jep Gambardella
#4
Met a chick by mistake, we set a date, we get to eat on a restaurant on the city center, 5 minutes later, her nephews appeared on the place, she asked me if we can buy them lunch, I said no, I didn’t have the budget for so many people…she gets upset and starts arguing as if it was mandatory. I went to the bathroom and left by a side door. The whole tab was on her.
Image source: mingocr83, Asad Photo Maldives
#5
Girl in college asked me to be her date at a banquet. She tells me she’ll meet me at the venue. Wearing a suit, I showed up to a pyramid scheme presentation. I noticed two other guys dressed sharply and they said the same girl said it was a date as well.
Image source: FlippyWraith, fauxels
#6
I took a girl to Lagoon Amusement Park in Utah. We spent the whole day together riding the rides and enjoying the park. Resting on a bench in the evening, she told me “I don’t even like you. I just wanted free Lagoon tickets.”.
Image source: Nannyphone7, Scott Catron
#7
I had an underwhelming after-dinner drink at a bar with a guy from Bumble. He walked me to the bus stop and on the way he kissed me. He started pulling my hair and I pulled away and was like, “hey, we haven’t talked about this. I don’t want you to pull my hair.” He apologised and we kept walking.
When we got to the bus stop he went in for another kiss and put his hand on my throat. I pulled away again and said forcefully, “stop. If I don’t want you to pull my hair, what makes you think I’d want you to choke me on the goddamn street?”
To which he replied, “no girl has ever complained before.”
Luckily a bus arrived a few minutes later. He actually asked me for another date and when I said absolutely not, he argued with me about whether most women would “really” feel unsafe being choked like that.
Image source: _fairywren
#8
His mom came along and even ordered for him, then questioned my choice (prime rib, this place was famous for their prime rib). She spent more of the date talking to me than he did, and she made it quite clear that there would be no second date.
Image source: anon, Diogo Miranda
#9
I went out with a cop on our first date. He had recently broken up with his girlfriend and wanted to move on.
Well, he took me to this really nice restaurant, one of the waitress came up to him while we were eating and asked my date “Wtf is this?”… looking at me.
I then find out she’s cousins with his ex girlfriend and he took me there for the cousin to see us together and for the cousin to tell his ex and make her jealous. Fucken idiot. Never went out with him again. He ended up marrying his ex.
Image source: paca1, René Ranisch
#10
Halfway through the date he goes, “I don’t think I experience emotion.” For the rest of the date I was convinced he might kill me.
Image source: discocowgirl5, Nguyễn Thanh Tùng
#11
He took me to Bob Evan’s..where I paid for my own meal and then he proceeded to beg me for road head bc his grandpa had died… I called my mom so damn fast.
Image source: wildlilmoonchild, Bill McChesney
#12
When I took the train up from Philly to NYC to see him—not a *short* trip for a date—the first thing he did upon seeing me was tell me that my dress looked trashy. Within ten minutes he had told me he was a proud narcissist.
He ditched me in the middle of the date to attend a meeting. I had to just d**k around in the middle of New York with nothing to do and nowhere to go for like an hour.
He took me in a drop ride at Coney Island. I am scared of heights. He laughed at me when I started crying.
For *some bizarre reason* he was shocked when I never called him back again after that date. The worst f*****g part was I got f*****g bronchitis from traveling and at the time I had a VERY BUSY summer job as a counselor for incoming freshmen at my university and it SUCKED!
F**k you Andrew, you weirdo.
Image source: wheniswhy
#13
She brought her mom and expected me to pay for both of them.
Image source: What_if_its_Lupus, Andrea Piacquadio
#14
Met through a dating app, we had decent conversation and she suggested we meet at a patio bar the next day. We met and it was fun. She asked if I wanted to meet “some of her friends” at a nearby place. It seemed weird for a first date but I agreed to meet here there.
As we walk in, I immediately realize there’s some kind of organized function happening, people are all standing and mingling, there’s food laid out, and there’s printed papers on each table that read “welcome Springfield Class of 1991”. I turn to her saying “hey I think there’s a reunion here” and she’s hugging someone. She says hi to a couple people then says, “and this is Steve!”. My name isn’t Steve, she forgot my name. It was bizarre. I ended up staying for 45 minutes and eating a quesadilla as Steve the reunion date, then told her I had an early morning. She texted me the next day but I felt this one time, ghosting was ok.
Image source: FishHikeMountainBike, Samantha Gades
#15
Worst first date: while we were waiting for our meal at the restaurant, the guy ransacked distant branches of his family tree to estimate his odds of having blue-eyed children with me.
Worst date that wasn’t the first: strolling the sidewalk at the beach, the guy verbally harassed passing women who weren’t thin enough for his liking. He didn’t comprehend my reaction from surprise to disbelief to anger because, in his words, “You’re not fat.”.
Image source: doublestitch, Michael Morse
#16
Went out with a pro (amateur?) wrestler. Had fun talking about a project he was doing. Then he spent 2 hours talking about his female cousin. He spoke very highly of her and her appearance. I left the date more interested in his cousin than him.
Image source: Pinkmongoose
#17
I went on a date with a man and he took me to a nice restaurant and as soon as we got there, left the table and was on the phone for almost 45 minutes. This was before Uber and he drove us, so I just ended up talking to the waiter and eating bread. He finally came back, ordered for us without asking me what I wanted and acted like nothing happened. Then when he dropped me off at my apartment, got extremely upset because I didn’t invite him up. He then called me and asked me out for a second date the next day. 😂.
Image source: BeneficialDemand567
#18
I once met a guy who not only told me about the time he ended up in emergency because of a tick bite to the nutsack, but he then proceeded to bring said tick out of his wallet in a ziplock bag. Wild move imo….
Image source: VitaminMorphine, Erik Karits
#19
Met him online, and it should have been a red flag that he only had one photo, a picture of him in his uniform when he was in the Army a couple of years prior. When I saw him in person, he was 100 pounds heavier and I didn’t recognize him. He was also wearing a camouflage kilt. Spent half the date talking about his recent ex girlfriend and how he loved her so much more than she ever loved him. The date was at a Mexican restaurant that had huge portions, and I couldn’t finish my meal because I was full. He told me “we don’t waste food around here” and went on a 5 minute rant about how there are starving people in the world and we should always clear our plates. I said “no problem, I can take the rest home” but he took the plate from me and ate the rest of my food. He tried holding my hand on the way out the door, and then asked me if I wanted to meet up with him the next morning to play Magic the Gathering. I respectfully declined.
Image source: Luna_Organa, Towfiqu barbhuiya
#20
She yelled at the waitress. I left as soon as I could.
Image source: DemomansGirlfriend
#21
Talked for a few weeks on tinder and seemed like a nice guy. False! We met for drinks but when I showed up he was already sitting down eating (I wasn’t late we were only meeting for a drink). He realized he “forgot” his credit card so I paid for his dinner and two bags of leftovers from BEFORE I GOT THERE. I never spoke to him again.
Another date I dodged bullet but it’s too good not to tell. I had been talking to a guy a couple weeks until we were able to meet up. I travel for work which I had talked about with him on multiple occasions. Our set date was a night I was traveling home from but my flight was delayed and I wouldn’t have been home until midnight on a weekday. I told him I’d have to make it another time but he flipped out and told me he’d rather not meet up with a flake and that there are plenty of other flights I could take to meet him. His anger was a huge red flag . The next day I met up with some gfs at a bar we had planned awhile back. I had told him the week before about my girls night plans and our favorite spot. I get there with my friends and a little while into us hanging out.. dude walks in with a date and beeline’s it for seating next to me and gives me a wink. I dodged a bullet never meeting this guy for our date.
Image source: whelpseeyoulaterr
#22
I used some savings for a nice dinner out bc I wanted to treat him…
When we get there .. not even 10 min settled in
He’s complaining that the place sucks,
He hasn’t been to the gym and shouldn’t be eating that much,
That the people working there are weird- looking,
That i should not have wasted time and money,
I cried in the car omw back.
Image source: brujabella
#23
We met at a bar one night when we both happened to not be drinking. I had a busy day the next day … idk his reason. He asked for my number like an adult and the next day after texting a bit he asked me to dinner the following night. Cute, sure.
I walked in, wearing a semi see through top with a camisole under it and he said something like, “I wish you weren’t wearing that shirt underneath.” Ooookay weirdo but maybe you’re nervous… he negged me several times and eventually asked me if my mom was hot. He proceeded to make several weird innuendos.
I excused myself to the bathroom and told the hostess not to tell the guy that I left. I skee-daddled to my car and drove to my friends’ house (all dude roommates, college town btw) and chilled there for 20 minutes until I was confident he didn’t follow me.
Image source: Radiant_Maize2315
#24
One time I went on a date where the guy played games the entire time on the little table top register thing some restaurants have.
Image source: sentpostcard, Pedro Vieira
#25
I asked a coworker out. She believed the man should take charge in everything in the relationship. She made me pick the restaurant, pick her up and drive her, order for her, carry the conversation, pay the bill, drive her home, the whole time acting disinterested in everything I said. I texted her I didn’t think we would work out and she sent back “I had a lot of fun what do you mean?”.
Image source: Pm_me_clown_pics3
#26
He picked me up in a convertible that had the price written on the window in marker and all kinds of papers on it. I lived in a student dorm; he came to my door and left the car with the music blasting so everyone saw us leave. We had ice cream and went to see a movie. He left me at the movie theater and disappeared for about 30 minutes. He came back, we watched a movie, and then went to leave. No car was outside. He said it wasn’t his and he had to return it. He took it for a test drive from a dealership. But he said he can take me back on the handlebars of his bike. We did that, with stops cause he was out of breath. Then he dropped me off a couple of blocks from the dorm “cause you don’t want your friends to see.” We had to see each other at work all summer but we just looked the other way. I was 19.
Image source: Designer-Weight7520, Gareth Williams
#27
He was more than three hours late, and was texting me telling me that he was 20 minutes away for two of those hours. As soon as he arrived he tried to tell me to leave the part of the venue/dive bar I’d already paid in to so we could go where he wanted, tried to start a fight with a friend I’d happened to run into, and called my aunt (who’d talked me into going out with him in the first place) a “cockblocking b***h”.
I just walked away from him after that last one, and we never spoke again.
–I waited so long because I liked the bands that were playing. I wouldn’t have stayed if I was sitting around doing nothing. He got there just before the last band finished, but I’d had about enough of him by then because he’d been telling me that he was on the train in the same place for two hours. We don’t live out in the middle of nowhere and he could have easily gotten a bus or tram the rest of the way in that time if there was a problem with the train. He never gave me a proper excuse but I didn’t really care at that point.
Image source: AccordingStretch1639
#28
The second day I went on with this girl, she basically spent the entire date aggressively complaining about her co-workers. She came off as the biggest b***h in the world. She didn’t come off great on the first day but it was the first date I had had in a while. But the second date that was all she talked about. No empathy, no compassion. Just “f**k these people”. Didn’t really ask me about anything. Just complained about her co-workers.
Image source: GreenFox1505, Tirachard Kumtanom
#29
She talked about her cat the whole time, didn’t ask a thing about me. I didn’t learn a thing about her other than she has a cat. I’m highly allergic to cats.
Image source: GrillDealing, NastyaSensei
#30
He was three hours late. Talked about his band the whole time. Then his car ran out of petrol and we had to wait for the rac to get us.
Image source: Worried_Cheesecake80
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