20 Times A Great Date Took An Unprecedented Turn The Wrong Way

Published 11 months ago

There are moments that get etched into our brains that we can relive again and again. A wonderful first date would likely be high on that list. But what about those great dates that took an unforeseen twist and ended up in unpredictable situations possibly because of the other person’s actions?

An interesting discussion took off when one Redditor asked people online to share their experiences of a date that was going well until one person managed to ruin it. As expected the stories are amusing and full of gaffes galore, but nevertheless, while some are just plain weird and uncomfortable, some still manage to end on the right note with love conquering all. 

More info: Reddit

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#1 He started telling me about how its normal for men to sleep with another woman when they are not sexually satisfied in a relationship without it being considered cheating. Yes, he did say it doesnt work the same way for unsatisfied women :)

Image source: emotionlessyeti, Dmitry Zvolskiy

#2 Literally went on a date last night and was going really well until dessert when he said “god, I can’t wait to put kids in you.”.
We hadn’t even talked about kids at that point.

Image source: Hannah1308, jonas mohamadi


I went on a date with a guy who owned a local trendy business. It kind of made him a bit of local celebrity. I am an introvert, I don’t like attention and prefer to pretend that I am invisible when out in public. We were on our second date at a restaurant, not super fancy but certainly a little romantic date type place. During our dinner, no less than 5 randoms stopped by our table to talk to him. They were all customers and he was trying to balance being an attentive date without totally alienating customers. It was super awkward. He was aware that I was an introvert and was apologetic about it. He suggested that we wrap up dinner, hit up a store to grab some drinks and dessert and go to the beach – a good way to be around less people. In the shop we stopped at, 2 more people came up to him to chat and then at the beach another person stopped and this one actually tried to sit down and join us. At this point, I decided this guy wasn’t for me. I really liked him as a person but I couldn’t deal with all the attention he attracted. Some how he convinced me to go on a third date which I am glad he did. It’s been 20 plus years that we’ve been together. He’s helped me come out of my shell a little and I’ve taught him the delights of being an introvert and taking some completely people-free weekends. He is my person and I love him more than anything.

Image source: monkey_monkey_monkey, Josh Willink


Oh my I have a story for this one, first date got dinner and everything was going amazing, so we decided to go for a walk on the trails, and this boy though it was a smart idea to climb a tree! Guess what happened next, he’s ten feet in the air and he’s climbing a dead tree after I told him it was a dumb idea. Next thing I know the branch breaks and there puke and blood everywhere. I ended up going to ER with him after calling 911 and even met his mom! He ended up with a concussion and five stitches in his head, but he’s okey now. Him and I are great friends now.

Image source: Lovelylace_03


This wasn’t a date going well and then being ruined, so much as he f****d it from the start and kept f*****g it all the way through.

I had been friends with a guy from school for a couple of years. We both clearly liked each other and things gradually progressed to flirtation.
When we were both 16, he finally asked me to go bowling with him because he knew through our previous friendship that I’d had this idea in my head that a bowling date was the perfect first date and he wanted to impress me. Problem was that we didn’t live near a bowling alley, neither of us had a car, I didn’t live near any public transport links, but he did have a bus stop near his house. We agreed I would walk to meet him at the bus stop and figure it out from there.

I start the mile long walk and within ten minutes, the heavens open. I texted him that I was going to keep walking because I was already soaked to my skin so what did it matter at this point, and I was so excited for our date. No reply. I finally get to the bus stop and he’s not there. I call him to ask what’s going on. He tells me he doesn’t want to walk to the bus stop in the rain so thinks we should give the bowling alley a miss… wtf? I had just walked A MILE in the rain to meet him and he had to walk like maybe 3 minutes from his house and he couldn’t be bothered…. like, r u okay?

He then proceeds to invite me to his house instead. I don’t know what possessed me, but I said okay. I guess I had just known this guy so long and had so been looking forward to this date that I just wanted to let the weirdness slide. But wait, I don’t actually know how to get to his house. Again, he doesn’t want to get wet, so naturally he doesn’t come and meet me. He just talks me through the most vague directions, while I continue to get soaked. For some reason, I perservere.

After another 25 minutes of aimless wandering in the rain, I finally arrive at his parents’ house, ring the doorbell… and a random man answers the door. I am freaking out that I’ve got the wrong house. Nope, it’s his uncle. Because, lo and behold, his entire extended family of about 25 people, who I have never met, are round for dinner, and this 16-year-old moron doesn’t think to wait at the door for me to avoid this exact scenario, or even mention this at any point or give me any opportunity to prepare myself. So here I am looking like I’ve been dunked in a swimming pool, mascara down my face, pink dip dye ends running down my top, and no date to be found.

Eventually he appears, leads me off into another room where he plants us on the sofa with no plan, just a plate of dry leftover poppadoms between us, and a parade of extended relatives popping in at regular intervals to size me up. We chat for a few hours between visitors, I call my mum to come get me, and he tries to kiss me at the door. My very first kiss ever, and he went in full tongues. Traumatising.

Anyway, it’s been 10 years and I married him 3 weeks ago. And yes, this did come up in the speeches.

Image source: clovek7, cottonbro studio

#6 “Dinosaurs never existed. Fossils are the devils way of testing our faith” – check please.

Image source: bearblastingg, Mike Bird


The date started normal and fine, I was visiting town and wanted to have some fun and found him on tinder. He was taking me to a bunch of different bars in the area that he liked.

Then randomly halfway through, while walking to another bar, he does a 180 and randomly starts giving me s**t and being snarky at me because “you women hate short guys like us.”

???? What????

He was short, yes. But I hadn’t said anything? I didn’t draw any attention to something that didn’t seem to matter. And I was ON the date! I chose to go out with him! We were having fun! It’s not like he’d tried anything and I turned him down, so I’m to this day baffled as to what made him snap. Was he expecting me to randomly throw myself at him at some point? Was I supposed to try to cut the date short and insist on f*****g right then and there or what??

I just stood there while he gave me, the woman who gave him a chance, s**t for all the s**t he felt other women gave him. And then I tearfully said “I thought we were having fun, but thanks for making me feel like s**t” and I *literally* ran away leaving him standing in the street and blocked him like the madman he was.

I feel bad for him, but not enough to accept abuse when I did nothing to deserve it. Ask me why I only dated tall, confident men after that.

Image source: Efficient_Board_689

#8 she got jealous because I was nice to the waitress.

Image source: TrailerParkPrepper, ELEVATE


I was out with a guy having a lovely time and he made a comment about a copper bangle bracelet I was wearing. I told him that it was really special to me, I got it during my semester abroad in South Africa from a local. It was a solid copper band but in the middle there was copper wire woven around. He asked to take a closer look so I took it off and handed it to him. He then snapped it in half thinking the copper wire was a spring. I was visibly upset and he said that it was a sign that I needed to move on from my trip and stop living in the past (?!!?). I never spoke to him again

Image source: kelseyboo1001, Castorly Stock


Went on a date with a girl and we were hanging out at my place when she saw a spider. I went “Hang on, please don’t squish it. I’ll just get a piece of paper and put it outside.”

From the kitchen I hear a thump and she stomped it, and then laughed when I got upset. Asked her to leave pretty soon after that and there was no second date.

If she had instinctively squished it, then I would be more understanding. But she did it after I specifically asked her not to and was so spiteful about it.

Image source: gentlybeepingheart, Pixabay


Our *first* date was amazing. I still reminisce about how incredible that night was and how incredible I thought my life was about to become.

But the afternoon before what was supposed to be our second date, I got a voicemail, “I know you went out with my fiancee last night. I’m not mad at you. I’m sure you didn’t know I existed. But I do, and I’d appreciate it if you stopped seeing her.”


Image source: CarpeNivem, Tim Samuel


I had some odd dates after I got divorced and was trying to meet new people.

So when meeting someone for the first time I would always invite them to do something kind of noncommittal like getting coffee so I could end things early and leave if they get weird. The girl shows up and has her two young children with her that I didn’t know about. That wasn’t a problem for me and she was super nice so we talked for about twenty minutes outside the coffee shop and I suggested we do something more kid friendly like getting ice cream and everyone loved the idea.

So we googled a nearby place and went there instead, kids were happy and we had some really good conversation for about an hour. I asked if she would be interested in dinner and she said yes but it would have to be several hours later and she might still have the kids, her sitter had bailed last minute. We met later that night and she had the kids again and we ate at a low end steak house, we got along great and the conversation was good! But she got sloppy drunk off the three drinks she ordered with dinner and then drove her kids home after (I did offer to pay for her to get a ride home) and that just killed any interest I had.

Image source: DasBarenJager, Josh Willink


It was a first date in a little restaurant. She was a bit late and had 2 shopping bags, even though we were going to the film after dinner, but ok, it was a Saturday afternoon, so, lots of shopping. The meal was nice, conversation was interesting, she looked cute.

And then the police arrived and arrested her because she was shoplifting and security cameras had caught her.

Image source: comicsnerd, Pixabay


“do you like to read?”

“Not really”

“What kind of music do you like”

“I don’t really listen to music”

“Do you like TV or movies”


There was no second date

Image source: thebeardedcats, Pixabay


Not me but a friend of mine. This was when we were around 22, 23 years old. She had a first date with a guy. They were meeting at a restaurant for dinner. She gets there and sees not only him but 2 other people at the table. Turns out he invited his parents to their date! So she, of course, excused herself to go to the bathroom and then just bounced. Talk about awkward. I have never laughed so hard as when she recounted her evening.

Image source: 3rdandfinalwife, Marina Abrosimova


After a nice dinner, we were waiting in line to go see a movie when he started making some super racist comments about a group of black teens ahead of us.

Image source: Hrekires


It was me. We were having a great time, we had a couple of cocktails and we were laughing constantly and flirting. I dont think I’ve ever hit it off so well with anyone. I’d not long come back from Afghanistan, she asked about the temperature out there. 2 minutes later I was crying my eyes out and all my s**t that I’d bottled up was coming out. She got all the details that she never asked for and it was awkward to the point where she couldn’t leave as I kept talking and crying, for 1.5 hours. 1 hour of hilarious drinks, 1.5 hours of crying and talking about dead children.

Image source: Banditofbingofame, cottonbro studio

#18 As soon as he found out I was Latina (apparently I didn’t look nor sound like whatever Latino stereotype he had in his head), said “Latina!? CALIENTE!!!!”, and quickly started making sexual remarks and talking about how he loves Latinas ‘cuz they’re so hot and spicy and sexual… Nope’d the f**k out immediately.

Image source: auramistress, CREATIVE HUSSAIN

#19 Ordered a pint of beer, it was really good. Got halfway through waiting for the date to show up. She sat down, chatted and said “this isn’t what I was expecting” then got up and left. Ruined my beer. My dating pictures were accurate, so not sure what happened.

Image source: Tiffanlyn, cottonbro studio

#20 He showed up remarkably, extravagantly, supernaturally high.

Image source: Astondisa, Anastasia Shuraeva

Shanilou Perera

Shanilou has always loved reading and learning about the world we live in. While she enjoys fictional books and stories just as much, since childhood she was especially fascinated by encyclopaedias and strangely enough, self-help books. As a kid, she spent most of her time consuming as much knowledge as she could get her hands on and could always be found at the library. Now, she still enjoys finding out about all the amazing things that surround us in our day-to-day lives and is blessed to be able to write about them to share with the whole world as a profession.

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date gone bad, dating anecdotes, dating chronicles, disaster dates, dramatic dates, unpredictable dates
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