If you missed the memo, we’re well into the spooky season, AKA the more fun way of saying it’s fall and Halloween is coming up. While we could give you this years’ trending couple’s costumes, or talk about cute fall date ideas, we decided to go a bit of a different route.
Fall also means cuffing season is upon us, and that can be stressful for our single squad. The pressure is real sometimes, and we want you to have the fun single experience you deserve. That means turning that pressure dial all the way down and being okay with authentic experiences that won’t always be winners.
Our friends over at @weshouldntdothisagain know this all too well, and gave us some good old-fashioned comic relief in the form of some spooky dating stories that will indeed probably leave you saying, “Oof, we shouldn’t do this again.” Whether you take them as a what not to do roadmap, validation on your own dating journey, or just as a bit of entertainment… we hope you sit back and enjoy.
1. Austin, TX
“I briefly dated a 32-year-old man whose only furniture in his luxury apartment was made of legos…”
2. Banc Café, NY
“Got positively hammered on a first date. Split the check, hooked up, the business. A few days later, I get a notification from my bank about a weird charge. We had accidentally swapped credit cards and had been spending each other’s money for 3 days. He went on a date the day after we hooked up…and I paid for it.”
3. West Village, NY
“A super cute guy invited me over to his west village apartment so he could cook me dinner. When I got there, he said he had to finish something for work. 45 minutes later I was still sitting on his couch so I said I’d get dinner started. He said, “Great! There’s a box of pasta and Trader Joe’s red sauce on the counter. For dessert, I got something really special… it was a BAG OF GUMMY BEARS.”
4. Eataly
“I went on a date with this guy from Plenty of Fish and on the date, he challenged me to a….thumb war”
5. No. 1 Chinese
“A guy once approached me while I was reading American Psycho and waiting for Chinese takeout. Although it would’ve been clear to any normal person that I wasn’t interested in a conversation, he sat down and told me he was impressed that I read. He said, “I’ve been reading a lot of RL Stine recently.” This GROWN MAN really tried to flex by telling me he reads Goosebumps.”
6. Hanover, NH
“I was seeing this outdoorsy guy and he was bragging to me about all the animal calls he knew how to make. I asked him if he could make an elephant sound and rolled his eyes and said “woodland creatures only.””
7. Gingerman, ON
“I went on a date with a man who asked me out for drinks. When I got there, it was a happy hour with his coworkers. I met his boss.”
8. Columbus Circle, NY
“I was on a first date with this guy. We were having a bite to eat on the sidewalk when a gigantic Saint Bernard walked by and he goes, “That’s the biggest dog I’ve ever seen. It definitely weighs more than me, and ~probably~ weighs more than you.” Really?”
9. Ithaca, NY
“A date once asked me to pay them back for a $30 concert ticket three months after we stopped hooking up. I paid them back in pennies.”
10. Richmond, VA
“I went out on a date with this guy to a bowling alley. We played one game and I won. He got so upset that I won, that he didn’t speak to me the entire drive home.”
11. Long Island, NY
“The last time I legitimately tried to date a man, he picked me up in his car for a surprise movie date. When I mentioned I didn’t have enough cash on me, he deadass drove me to my bank. I learned how to write a withdrawal slip that day.”
12. Greenwich, CT
“I was waiting to be picked up for a date. I got the “leaving now” text and after about 20 minutes I started to wonder where they were. I texted back asking how far away they were but got no response. After 30 plus minutes of waiting, I looked out my window and saw my date standing outside their car examining a piece of paper. Turns out, they broke their phone and had been texting me off their computer before they left and printed out directions on how to get to my house. A+ for effort, D- for execution.”
And last but definitely not least…
13. Chicago, IL
“So we met on Plenty of Fish. He was nice enough, we sent a few messages, and scheduled a date. I met him at a bar, and we had a couple of drinks. He told me all about his goal of creating a movie theater-type situation where folks go to watch VHS tapes. So basically, Blockbuster with a screening room. After talking about this plan ad nauseam he asks if I want to “see his VHS collection.” I take the bait and we go back to his place.
We throw on a movie I don’t even remember what and after not too long we are making out on the couch. We adjourn to his bedroom, he opens his iTunes and puts his library on random. The next thing I know one of his Rosetta Stone French lessons comes on. We laugh it off, he skips it, moving on. Three songs later MORE FRENCH LESSONS. Why he put his whole library on random is beyond me, but it really wasn’t working for me. I got out of there as fast as I could. French lessons are surprisingly not sexy. Needless to say, I did not contact him again.”
Now after what I hope was a good laugh, I want to be clear. By no means are these stories meant to discourage you from your own dating journey – that would be against everything we stand for, after all! They’re simply meant as a reminder that not every date is a good one, and that’s okay.
If you’re single, you’re meant to enjoy the ride – wherever that might take you! Don’t forget to see the humor in the journey along the way.
PS – for more hilarious dating stories, don’t forget to follow @weshouldntdothisagain on Instagram, and DM them your very own stories to see them featured.
