Look how he reacted when you tried to have a 'talk' in the car on the way up to your parents. As you said he is avoident - he will hate a 'talk'. I would go down the line of having fun with him and it will naturally happen rather than forcing it.
JMO but if it were my best friend who was divulging all this personal info to my ex gf, even if it was in my 'best interests', I would be really pissed off. I would feel like people are conspiring against me. I'm just saying, can't you form your own GAL interests and include him in that rather than pump his friends for info?
