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Welcome to Puerto Rico, where the locals are friendly, the beaches are beautiful and the nightlife is hot.
I am sure it feels off to try to go there with someone, but if it does, then the time is wrong or the person is wrong for you. Got any advice on how to get over this and just someone out. The trick is not "writing a note after gym class" about it. We ran into each other at a mutual friend's house: introductions, helloes, not much more than that. Uh, well, I guess it wasn't SO bad if she still wanted to go out with me.