Thought Catalog

Dates From HELL: 25 Women Share Their Cringeworthy Tales

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lookcatalog / Illustration by Daniella Urdinlaiz.
lookcatalog / Illustration by Daniella Urdinlaiz.

1. He cried a little bit when I beat him at chess.

“I met up with this guy from the internet at a bar with board games. He wanted to play chess, but I don’t play chess, so he offered to teach me. I learned from magazines that boys feel manly when they teach you things so I was like, sure, why not. Well, I’m a quick study, and I ended up winning the second game. He got so upset that he cried a little bit. We did not checkmate.”

–Madelyn


2. He left me alone in the dark while he jerked off in the woods.

“I met a guy a bar who told me he ‘owned his own business’ which turned out to mean he drove a bike taxi. We met to see The Breakfast Club in Central Park, and he said I should ride in his bike taxi to ‘save time.’ I told him, ‘The only way I’m riding in your bike taxi is if you’re carrying my dead body to the morgue,’ so I walked next to him as he rode slowly. After watching The Breakfast Club, he showed me a romantic, secluded section of woods in the park. We made out there for a short time, but it was dark and I started getting creeped out. When I told him I wanted to leave, he said, ‘Hold on, I need to take care of something.’ Then he left me alone, in the dark, sitting on a rock in the woods while he disappeared to go jerk off. He didn’t seem to think he’d done anything wrong. I gave him one-word answers as we walked back to the main drag of Central Park. He got zero more dates.”

—Ashley


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