[gacook]

You can't "teach" someone confidence; either you have it, or you don't. Usually, guys that don't have it are self-conscious about some perceived flaw. Get over your personal hang-ups and learn to love yourself, and the confidence will flow. Tell him not to go into a conversation with a chic with an end goal in mind; just go at it to enjoy talking to a pretty face in hopes she might have a decent personality, too. If anything happens to progress from that point, bonus! I've never really understood guys that can't talk to women. Maybe it's because I had a ton of sisters, I dunno.