I realize this is probably something I could google, but I'd like to hear some more personal advice and experiences from you guys. Maybe a link to a good article.

Basically, I just got out of a LTR, and my best friend has never had a girlfriend. I would definitely consider us each others wing man, but with that being said we are both clueless. I have no problem talking to women most of the time, however he has pretty bad approach anxiety. What can I do to sort of help him? I realize he mostly needs to just stop being a pussy and help his damn self, but when he finally does stop being a pussy, how can I push him along or just help him out?

Edit: Probably should've posted this on r/AskSeddit