I've always dated crazy, outgoing guys. Now a new guy has caught my eye but he is very shy. I don't know how to approach the situation because I'm... Show More
Most Helpful Opinion
He could be nervous. I'm shy - when I realize I start liking a girl then I get nervous and say the stupidest things. So I overcompensate by pretty much ignoring her and playing it cool even though I really want to talk to her.
Friend him on Facebook or whatever and find out what he's interested in and passionate about. If you don't do FB, try asking his friends or just pay attention to anything he says. That way you can start conversations with him where he doesn't feel out of his depth and he feels comfortable talking to you. If you see him on IM or whatever, don't be afraid to be the first one to start the conversation.
Oh, and be sure to smile a lot around him. Not like creepy/stalkerish, but in a way that you convey interest clearly to HIM rather than any other guys who might happen to be around.
Bottom line: do NOT wait for shy guys to make the first move. If you're interested in this guy, give him some kind of OBVIOUS signal. Shy guys don't want to come across creepy, so they tend not to pursue girls without some kind of green light.