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Oh I got some good ones but this is the funniest.
I was in college and was dating a girl whose family was loaded. Sick "f-u" type money. Anyway, we were really going along great for about three months and we were coming up on the Christmas break. She was going to her families' house in the Cayman Islands (Grand Cayman). I was basically getting drunk with my buddies. A week before her family leaves and over pizza she says, "Come with me, I want you to meet my parents."
I say OK. I tell my parents about it, they're not cool with it at first, but I talk them into it. I get my papers in order and meet them at the airport. We get there, I'm charming as hell, it's all going well.
Then, out of freaking no where, day three into my week long trip:
"I think we should cool off."
I spent the rest of my time in my room, stuck in her parents vacation house for three more days. The trip to the airport couldn't come soon enough.
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