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Who Is The Biggest Oddball You’ve Dated?

The other night, a friend invited me to an event where her new crush would be reading an excerpt from his book. He was a mustachioed beat poet with a three-piece-suit and a red crocodile pocket protector. No judgement on my end. I have dated some oddballs in my time. I may be queen of the oddballs. I found my mind wandering as he read his 12-page poem, trying to decide how The Poet stacked up against the theater tech guy I dated in high school. When I told Techie I just wanted to be friends, he chased me around his house pretending to be a vampire while threatening to overdose on acid. Oh … memories. After the jump, Frisky staffers and contributors share some of the wackiest dudes they’ve had the pleasure to know. Please share your oddball catalogue in the comments.

“The last guy I went on a date with wanted to put me in a dog cage. He was super kinky, so that was kinda OK, only … it wasn’t. I don’t want to be put in a dog cage as part of someone’s sexual fantasy.”

“Back in college I dated a guy who was a pot dealer who kept lots of pet fish in his dorm room. He also insisted on wearing two condoms every time we slept together. Probably a good thing.”

“An ex of mine wore pink women’s pajamas to bed. Enough said.”

“I slept with a guy whose profession was ‘Superhero.’ Also, I dated a fire-eater. Maybe I should just join the circus.”

“One guy was a 9/11 conspiracy theorist. He told me all about how Bush was behind the World Trade Center attacks over dinner on our second date.”

“One ex-boyfriend could ONLY ejaculate by rubbing his erection between by butt cheeks as I lay on my belly.”

“I dated a professional dancer who refused to wear deodorant or open a bank account. Ironically it wasn’t his B.O. that turned me off, it was the mangled wad of singles he pulled out of his highwater corduroys when he went to buy me a drink.”

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