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My worst date was back in college in France couple of years ago, during my freshman year. At that time, I was pretty bad with women: I had just one serious relationship before and nothing else, so my knowledge about women and "dating" was null!
There was this good-looking girl, same college year, let s call her "Elle". We had mutual friends and she was quite shy.. My friends told me that she had a crush on me, but even if I felt happy about it, I was uncomfortable with the situation. Anyway, I finally ended up having a date with Elle, scheduled by our friends (how charming). I was supposed to take her to dinner in a chill spanish restaurant. So I did! And it was horrible: the girl did not say more than 10 sentences during the whole meal, and I was pretty silent myself, I did not understand what happened. 80% of the dinner was silent, it was one of the most awkward moment in my life! We said goodbye to each other at the end and we left separately. I was really pissed at my friends!
The next day, at the campus, an older guy came over to me and started talking shit about me having this date with Elle. This guy was actually the brother! He heard about our little rendez-vous and started to threatened me to not come near her anymore. I think he did not really like my harsh answer, he started to push me and we ended up fighting. He accidentally felt on a chair and broke a rib. It became a big deal, he went to the hospital, and guess what... I got expelled from the university!
So I can honestly say that this date was the worst date ever because it cost me a lot!