Convice yourself to just LET GO. Stop choking yourself with the maybe-could-should mentality. Stop thinking so abstract and start thinking in terms or do-or-do-not. Just go for it, and forget the million what-ifs.

She's giving you IOI's already, your job is halfway done.

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-The good can never be measured, but the great can never be controlled-

If you're looking for the truly ultimate resource geared specifically towards overcoming rejection issues with women read Without Embarrassment by Mike Pilinski you are not likely to find a better book focused specifically on overcoming rejection with women.

Yeah you really got to pull the trigger. Sometimes I find it helpful to game a few side girls just for the hell of it to make yourself "care" less about this girl. Its funny the less I started to care about this girl I was really into, the more comfortable/alpha I came across and the more she was into me. Sometimes you just gotta bust in there even if its to throw a DHV and go just to reconnect with her. "Run" into her and just say something like "Hey I have to go (do something important) but blah blah blah I'm going to grab some sushi with my roommate later (or whatever) but we'll have to chat again soon". Then you can run into her again and have a more in depth convo and maybe segway into a # or meeting.

The IOI's are there and you know it so just let go and go for it. You have nothing to lose, have fun, be fun, and no matter what look on the up side of things. Thats just my advice.

You're a man. You can control your emotions.

Take a look in the mirror. What do you see? A boy or a man?