need your experience on wing situation

[ninjamatt]

Me and this new wing I have are both 34. I met him through another buddy who's not running with us anymore. He's newly divorced of 12 years. His wife left him. He talks about her a lot and hopes they get back but the chances are slim. He's on dating sites he watches often. He's 6-2 blond skinny and real good looking and hangs sometimes with some semi-fat online girl he met but tells me he doesn't like her.

I've had him out 5 times maybe. It is obvious he's scared shitless to talk unless I get a conversation started. I do not know how good his conversation skills are with women but the 2 times I have sacrificed good 2 sets for him, they seem to be in to him. This past weekend, I put him in positions where he was sitting by pretty girls and I was telling him simple shit to say that has no chance for rejection but he was still scared. He told me next time he will.

In you guys experience will these types of guys ever start a convo with a girl? or do they just settle for some fat internet thing