63 Crazy-but-True Unlucky Dating Horror Stories

From guys who dine-and-ditch to ones who have an obsession with Hello Kitty (no, really!) -- these dates gone wrong will totally crack you up (64 Photos)

Robin Hilmantel & Lindsay Tigar on Mar 6, 2013 at 11:27AM

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Invoice Me

Joseph Clark/Photodisc/Getty

a Robin Hilmantel & Lindsay Tigar on Sep 28, 2012 at 4:43PM

After a dinner date that grew increasingly awkward as the night wore on, I reached for my wallet when the bill arrived. An empty gesture, yes, but I felt bad since I knew had no interest in seeing my date again. Pasta and a glass of wine, a whopping $20 total on my end, he wouldn't possibly… and yet as he reached for the bill he said, "Here's what we can do, we can agree to split the bill or I can pay this time and next time, you treat." I felt myself do a double-take.

Wait -- he's asking me out on a second date (that I don't want) on the condition that I pay next time? I must have nodded or mumbled as he paid. A couple of weeks later, after many texts and calls on his part, I sent an email via Match.com’s site, thinking it's more polite than ignoring him, saying "I didn't think we connected but good luck on the search" or something like that.

He immediately texted me: "Hi there. Thank you for your message and your candor. I concur with your sentiments. I do insist, however, as agreed that evening you would treat for the next date that you remunerate me for your portion of the bill that evening. Please advise how you would like to handle that. Thank you." No, I did not reply. No, I did not remunerate. Friends suggested ways I could do so, however….all in pennies, all in nickels, or in checks for one dollar each so he'd have to sign each one. Good grief.

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