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Strange First Date Stories, As Told By The People That Suffered Through Them

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Despite what romantic comedy meet cutes have led us to believe, first dates tend to always be plagued by awkwardness. Going out with a complete stranger can lead to some seriously strange situations. While some first dates are followed by many more, there are others that end right then and there.

Anyone who has dipped their toes in the dating pool will have at least one date that took a turn for the bizarre, which is why one Redditor asked the community to share stories of the weirdest first dates they’ve ever been on.

If you thought you’ve had some peculiar dating experiences, wait until you read these 25 unbearably cringeworthy first date stories.

1. Introductions: “An acquaintance from school asked me to go to the movies with him and to be honest, I didn’t even know it was intended to be a date. We had a pretty good time and he asked me if I wanted to go play some games at his house after 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 that we had just come back from a date. It was very uncomfortable but I did not have the heart to say that we weren’t a couple.” (Reddit user: Sammie_SU)

2. Litter Bug: “I met a guy from online for coffee and walked the beach. Immediately, things did not go well. We disagreed about pretty much everything and he even had the nerve to mock my religious beliefs. After our walk he asked if I wanted to sit on the beach. I couldn’t believe he wanted this nightmare to last longer, but I obliged awkwardly. He set his coffee cup down in the sand and it blew away but not very far. I said, ‘Oh no your cup.’ He looked at it, shrugged and said, ‘I litter all the time. Yeah, like if I have an empty McDonald’s bag, I’ll just throw it out the window. That’s what prisoners are for.’” (Reddit user: AbbyVanBuren)

3. Somber Setting: “I met a guy at the skate park when I was around 14 years old and he asked me if I wanted to go out with him the next day. I thought he was gorgeous so I happily obliged. He told me specifically that I should dress up so I was expecting something really special. He took me to his little sister’s funeral.” (Reddit user: [deleted])

4. Table Manners: “I went to a Japanese steakhouse with the most embarrassing date I’ve ever had. She started by heckling the chef and then threw pieces of food at the next table. I’m pretty sure she had drank a bit before our date and she clearly did not handle alcohol well. She managed to piss off the chef to the point that he doused her plate, set it on fire and then just walked away. Plate was completely engulfed in flames.” (Reddit user: [deleted])

5. The Reddest of Flags: “My lab partner in college asked me out and we met for dinner. He locked eyes with me over salad and told me I was ‘as beautiful as Hitler’s niece.’ I found that very strange but didn’t think too much about it. He then later described to me how he thought I would be ‘exquisite while pregnant’ and how he had searched so long for ‘a woman so compatible with his genes and heritage.’ He rolled up his sleeves to reveal a swastika tattoo and I was out.” (Reddit user: noshouts_nocalls)

6. Ulterior Motives: “A childhood friend of mine asked me to go to dinner after we had run into each other at a party. She had gotten very pretty since the last time I saw her and things were going well over text message. When I met her at the restaurant I was surprised to find out we’d be dining alongside a middle aged business man. Turns out our date was really them trying to recruit me to one of those pyramid marketing schemes.” (Reddit user: jex_head)

7. Shamelessly Nosy: “I went on a first date with this guy I met on Tinder and things were going pretty well. We grabbed something to eat first and then decided to go bowling on a whim. When I went up for my turn, I looked back and found my date looking through my phone. He didn’t even act like it was a weird thing either.” (Reddit user: doe_rahh)

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8. Questionable Buy: “I knew right off the bat that things weren’t going to work out with me and this girl but I rode out the date. We had a quick dinner at the Macaroni Grill and then she requested we stop by Petsmart. I followed her around the horse feed section for a good 45 minutes and then bought a big bag. I asked if she had a horse, she looked at me like I was crazy and just said ‘no.’” (Reddit user: aruc217)

9. Fork You: “Went on a date to a sushi bar with this guy I met online. He was really cute but I could tell he was a little demanding right off the bat. Without asking me, he ordered us both Ramen as a side and proceeded to order for me. I’m no chopstick connoisseur so I was struggling to get food into my mouth. I asked the waiter for a fork and my date screamed, ‘You do not use a fork! It is disrespectful! You are supposed to use chopsticks! If you can’t then don’t eat!’ I just got up and left.” (Reddit user: [deleted])

10. Missing: “Was on a dinner date with a girl when she kept looking at her phone in a concerned kind of way. When I asked her what was wrong, she said her cat was missing. We dipped out of the restaurant early and spent hours on the streets looking for her cat. Eventually her roommate called her saying she found it and it was inside the whole time. Weird first date but we’re still together.” (Reddit user: iguanainfluence)

11. Misleading Information: “My best friend finally landed a date with her dream boy. A few nights before, she called me asking me to join her for a double date because his cousin was in town. She relayed that his cousin was fun to be around and that I’d really like him. I got dressed up and met them at the restaurant. This guy’s cousin was 8 years old.” (Reddit user: parmafizz)

12. Giant Bear: “I went to go watch a movie over at a girl’s apartment and there was a giant stuffed bear that occupied half of the couch we were sitting on. This was like a grand prize carnival game sized stuffed bear. Eventually, I had to ask, ‘How’d you score the bear?’ She told me she didn’t know. I kept asking about it but still she just said she didn’t know. I told her it was okay if it was from an ex or even if she stole it, I was just super curious. She just responded, ‘Listen, I do not know how that bear ended up in my house. Are you going to be able to let this go?’ I made eye contact with the bear and said, ‘I don’t think I can.’” (Reddit user: bitterbillsfan)

13. Smoke Break: “I was on my way to the movies with a date and she asked, ‘Hey, do you mind if I smoke?’ I figured she was talking about a cigarette or even a joint would have been okay, but she just pulled out a crack pipe and started puffing away. Still saw the movie with her but that was certainly the last date.” (Reddit user: Badger_Silverado)

14. Murky Past: “I was on a Tinder date that went pretty well considering it ended with us making out in my car. However, we were parked in a residential neighborhood after dark and apparently looked suspicious because a cop came tapping on my window. He told us to move along but ran our IDs before letting us go. The cop ended up arresting my date and I never heard or saw from her again.” (Reddit user: ultimate_jack)

15. Location Is Everything: “I was on a date with a girl and we were just kind of driving around. She kept directing me where to go which I kind of liked because the pressure was off of me to make a plan. We finally got to her destination, got out of the car and told me, ‘This is where Ted Bundy supposedly hid the bodies of his victims.’ No second date.” (Reddit user: WaitingOnTheWind)

16. Say Cheese: “I went on a dinner date with a guy I met online. I knew he was in the tech field and I admired that because I’m also into that kind of stuff. However, I was not expecting him to wear Google Glasses for our entire date. He kept getting distracted by them and when I asked what he was doing, he said, ‘Taking pictures.’” (Reddit user: caprinae)

17. Magic: “A guy took me on a date but didn’t tell me what we were actually doing. Turns out, our date was going to his father’s magic show. We ended up staying in a hotel room his father rented us in the hotel that this magic show was being held at. Honestly, it was a pretty good date but still really weird.” (Reddit user: anthropomorphisis)

18. Miscommunication: “My name is Andrea, his name was Sam. We talked quite a bit over text message and decided to finally meet up. It was at that moment, in person, that we realized we were two dudes. Both of us thought we were talking to a girl.” (Reddit user: zerolinks2014)

19. Whale Dreams: “Was at a wedding when I hit it off with one of the bridesmaids. We went out to the beach and started making out when she abruptly stopped me and asked, ‘Wait, what’s your lifetime ambition?’ I said I didn’t really know and she said, ‘Mine is to touch a whale. Actually, it’s to touch the same whale twice.’ I kind of ignored it and she got super offended that I didn’t share the same passion and ditched me.” (Reddit user: NineFeetUnderground)

20. Crossword: “I went out for a coffee date with a classmate. He showed up half an hour late and decided to wear baggy sweatpants with suspicious stains all over them. I was keeping myself entertained by doing a crossword while waiting. When he arrived, he sat down and pulled my crossword over to him. He looked at it for a second and then said, ‘Women who read are fine and all, but it isn’t very attractive to show off.’ No second date.” (Reddit user: CowtheHankDog)

21. Late to the Show: “I asked this girl what she wanted to do for our first date and she was very adamant about wanting to go see Happy Feet. Decided to take her because penguins are pretty cool. Halfway through the movie, she leans over to me and whispers in complete seriousness, ‘Oh I get it, they’re dancing penguins.’ She wanted to see this movie so bad and didn’t know it was about dancing penguins? Also, it took her half the movie to realize that?” (Reddit user: end32urzm)

22. The Aftermath: “Had a date with a guy and it went pretty well there was nothing weird about it. However, when I got home I got an email with a link to a SurveyMonkey asking me to rate the date and select a date and time for the second one. That was pretty weird but I did fill it out anyway.” (Reddit user: lalahehehe)

23. Crash: “My first date ever ended before it even began. My date rear ended the guy in front of us on route to the movies. No one was hurt but she lost a headlight and her bumper was dragging. She just started crying uncontrollably while I awkwardly comforted her, despite not knowing her at all, until her mom showed up.” (Reddit user: JuRoJa)

24. Good Texter: “I was really excited about my date with this guy because our conversations through text message leading up to it went super well. However, the night was a disaster. He cheated at bar trivia, used Purell on the silverware, and got into an altercation with two different homeless men on the way home.” (Reddit user: quirkywitch)

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