• Relationships

“You Stuck My Flash Drive In Your … ” And More Crazy Dating Horror Stories

Craigslist is a dependable source for roommates, concert tickets, bromancing and, best of all, missed connections! Feast your eyes on how the tale of this date started out:

”You stuck my flash drive in your vagina. If you are reading this, you know who you are. I don’t think this is a fad sweeping the city, so this one’s for you.”

The poster goes on to describe the case of the missing flash drive in graphic details (which you can read in its entirety here), ending his tale with a plea.

“The number you gave me doesn’t work. I am confused. I’d like to see you again. I’d like to see my flash drive again.”

Wow! There really is someone out there for everyone. Reading about this ridonkulous date inspired us to take a stroll down memory lane, because we’ve had some seriously nutso ones ourselves. From getting the finger to a real crazy cat lady, here are the best of our worst nights:

”I was on first date with a guy, everything seemed to be going well. We were on my steps saying good night. He went to kiss me and at the same time reached his hand up my skirt and shoved a finger in the booty. No boob grope, no make-out warm-up, just, ‘surprise!’”

“I was really into this guy. Our first date was pure fire. I went back to his place. We were making out on his bed. I wasn’t even touching his peen and out of nowhere he came. Best part: it compromised the Mike Tyson poster over his bed.”

”My freshman year of college, I took this girl to the movies. Just from that minimal interaction I could tell I didn’t want to go out with her again. But then she asked if we could go back to my place. So, I figured, well, why not? Then, after she talked non-stop for an hour about her favorite hippie jam band, she told me she worked at a cat shelter and started purring like a cat while rubbing up against me. I asked her why she was doing that. She said she really liked cats and then would only respond to me as a cat, a sexy cat. She managed to find the one way a 19-year-old man will turn down sex. I had to ask her to leave.”

”The dude told me he was under federal investigation and that he believed women should change diapers. I don’t know which one was worse.”

”Date one, over dessert, and totally randomly in the middle of a very typical getting to know you conversation, the guy leaned in and whispered to me that he was completely shaved. Completely … not that I stuck around to confirm his claim.”

”I had a date with a fellow who entertained me during dinner with his 9/11 conspiracy theory.”

”A guy told me he was polyamorous one sip into our first drink. I appreciate the honesty, but he should have at least let me get a couple cocktails in before dropping the bomb.”

”I went out with a guy who took me to a really swanky restaurant. He then refused to order anything that wasn’t alcoholic, but insisted that he wanted to watch me eat. In fact, he tried to feed me, but I wasn’t down. As if that wasn’t awkward enough, when I was done, he cried about how he had just gone on a diet with his mom. Must have been a liquid one…”

”A guy told me about going to sex therapy with his ex because he couldn’t orgasm and then cornered me and asked me to tell him if I liked him or not. He couldn’t tell? Then he called me the second I got in the cab to tell me he wanted to go out with me again.”

”She was two hours late, but I waited because I had schlepped over an hour to meet her. We went to a bar that she picked out. She told me she doesn’t drink and doesn’t really like when girls she’s seeing do either. I awkwardly sipped a glass of wine and felt too self-conscious to get another. Then we just sat in this ugly bar for hours and hours. There were tons of awkward silences. At one point I went to the bathroom and she texted me that she thought I was really cute. I wasn’t feeling it, but to make things less awkward I kissed her. Big mistake. She got a little too attached after that and I ended up having to tell her I wasn’t interested.”

”The Look: striped pants, Fresh Prince color block shirt, Jew fro, mustache.

The DL: Bisexual, philosophy PhD student writing a manifesto on drugs and running some shady theatre company out of his home.

Bonus Round: He talked about using My Little Pony as a sex toy.”

Posted Under: , , ,
  • Zergnet: Simply Irresistible

  • HowAboutWe

  • Popular