Magic Tricks, Serenades, and Pirate Escapades: Hilarious Dating Fails

6. The Mysterious Disappearance

I went on a date with a guy who loved magic tricks. He kept pulling coins from behind my ear and making silverware disappear. For his final trick, he said he would make himself disappear. He covered himself with a napkin and vanished. After 15 minutes of searching, I left. The next day, he texted saying he had hidden under the table the whole time. I didn’t respond.

Submitted by: Lucy from Nottingham

7. The Surprise Serenade

I went on a date with a girl who seemed sweet. During dinner, she mentioned she was a singer. I complimented her, and she suddenly stood up and started singing “My Heart Will Go On” by Celine Dion at the top of her lungs. The whole restaurant went silent, and everyone was staring. She finished with a dramatic flourish, and there was an awkward silence before a few people clapped politely. I was speechless, and she sat down like nothing had happened. It was one for the books.

Submitted by: Sam from Edinburgh

8. The Costume Party Confusion

A guy invited me to what he said was a costume party. I showed up in full pirate regalia, complete with an eyepatch and plastic sword. It turns out that it was a formal dinner party, and I was the only one in costume. Everyone else was in evening wear, and there I was, looking like I had just sailed in from the Caribbean. To his credit, he introduced me to everyone as his “pirate date,” and we laughed about it the whole night. He even made me a makeshift pirate hat out of napkins to match my outfit.

Submitted by: Chloe from Cardiff

9. The Overly Honest Date

I met this girl online, and we decided to have coffee. Within the first five minutes, she started telling me about all her ex-boyfriends and why each relationship failed. She even pulled out a notebook where she had listed their names and reasons for the breakups. She asked me to add my name to the list and write why our date might not work out. I wrote, “Too much information on the first date,” and she laughed so hard that coffee came out of her nose. We didn’t go out again, but it was a memorable coffee date.

Submitted by: Harry from Bristol

10. The Bowling Alley Mishap

I met a guy online, and we decided to go bowling for our first date. I’m usually pretty good, but I was nervous and accidentally bowled the ball straight into the next lane, causing a strike for the family next to us. They cheered while I turned bright red. My date couldn’t stop laughing and even high-fived me for the unintended strike. It was embarrassing but a great icebreaker.

Submitted by: Sarah from Manchester

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