Have you seen the movie "With Honors"
I am all for the scene where he walks up to his best female friend and she says "what are you doing" and he says "ending our friendship" and they get mad passionate
-sigh- alas, I say talk to him. He is giving you all the flirty signs, but has some emotional baggage and may feel it is a little hard to deal with a relationship now. That being said you may want to show him how much you will be there to support him and how happy he makes you.
Just my $.02
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Just another squirrel trying to find a nut
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