A: Generally, its good to know what he likes and go from there. If he like baseball find out what his favorite team is and learn a thing or two about them. Then, he will not think of you as a total putz.
A: Dude I think you were a little to pushy and she might have weirded out. I am a shy dude all the same, but you must learn to control your need for contact with her. Be aloof.