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Sounds like Cynthetiq got it right.
I had a friend who did this. She was an 8 out of 10... yet only ever put out for really ugly/rude guys. She'd pine over guys she liked for years without showing any interest (and flat out denying it at all costs). It wasn't until after I moved away she came out and said she was in love with me and wished I would have made a move on her. The truth was I did a couple times when we first met, until I gave up and stayed just-friends because she'd reject me.
Honestly, my suggestion would be to use flirting styles which really doesn't put you "out there" as you're obviously afraid. A simple wink and smile during a conversation ranks high in the flirty-but-safe file. It's a great way to say "hey I dig you" without laying yourself fully on the line. It's also casual enough that you can play it off as being friendly if things don't go the right way.
Either way, think of it as rewarding bad behavior. You're effectively saying that the cute guy needs to gain 50lbs of fat before you'll sleep with him. Instead it should be something like, he needs to treat you kindly and show you a great time before. Either way, what you reward is what you'll end up with.
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"Smite the rocks with the rod of knowledge, and fountains of unstinted wealth will gush forth." - Ashbel Smith as he laid the first cornerstone of the University of Texas
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