I asked a shy guy I know to go for a drink with me, so we could catch up. We used to hang out regularly in the fall, but he had just gotten out of a... Show More
Most Helpful Opinion
On both ways don't rush things out, besides you said that you're good friends so this means while having that drink you can discuss his personal relationships, that way you can get some of those answers you're seeking and only time will do the rest.
P.S.:get him drunk and you'll get some precised answers :P.