It really depends... I know I don't do well with knowing personal things. I get obsessed easily and that usually hurts. But I don't mind knowing some bits here and there. As long as I feel everything he tells me is for a reason, i.e. he doesn't tell me about his upcoming birthday party unless it has a direct connection to something in my life.

I could not deal with seeing him with his family or friends at all though. I know a bit about his family, and he probably has friends, but seeing them interact would hurt way too much to be useful in any way.