how NOT to ask a girl out, take 2

In this entry, I mentioned one surefire way to not get a date with me. Here is an even better one. There was this one guy in college, CRF, whom I had a huge crush on. He was my total package- the awkward Jewish dorky mama's boy next door, except that he wasn't actually Jewish. (I was one of like 10 Jews in my school.) Of course, he had a girlfriend all through college. He was a great guy- really fun, easy to talk to, made me laugh, blah blah, and so we kept in touch after graduation. Like J, he is superflirty. (Why do I always seem to go for those guys, anyone want to analyze this for me?) After college, he decided to pack up and move all the way across the country. His girlfriend didn't like this and broke up with him. We remained in touch and would call/flirt/text a lot. Eventually we lost touch. A little while ago, he sent me an email asking how I was doing and saying he missed our chats and wanted to see what was up. He moved back to NY and was trying to reconnect with all of his friends. We started talking again and he's been all Debbie Downer all day today. About two months after he moved, his girlfriend found someone else and has been dating him since then (for about 3 years now). He never really got over her and it has caused him to screw up all chances at having a serious relationship with anyone else. He still thinks about her, etc. After telling me all this, he asks me if I want to go out with him. Right. While I appreciate the fact that he's 1) incredibly honest, and 2) my friend, I have zero desire to delve into THAT can of worms. I've had enough crazy this year.