how can i get my friend to realize that he's better off without her?

are you two close? maybe you can ask him - if he's not happy then why does he stick to that situation? can't he like introduce you guys to his girl so that she can get to know his friends and somehow learn to trust them. as a friend you have to help him or make him see that this relationship is destructive.

This is what my daughter just went through only it was the guy that was controlling. I posted many discussion on their relationship and I think that it is finally over. I have no suggestions other than get someone who can talk to people to have your friend understand this relationship is no good. (My daughter's best friend help her)

As a woman i admit i am guilty of reacting the same way when my boyfriend was not "around all the time" and wanting to "be with his friends". It was wrong and yes it can make the guy feel uncomfortable and smothered. I have experienced guys doing the same to me and i don't like it so now i try to compromise! Maybe he could sit down and talk to her about why she doesn't like being around everyone and what it is she is afraid will happen if he goes to hang out with friends. USUALLY it is a jealousy issue. I know i would feel left out when my BF went out with his friends because it was like i was left out and since they were long time friends i just got suspicious that something was going on or that they were talking about me. It is wrong for her to say choose me or them. If she doesn't like the fact that he is human and had friends BEFORE she was his GF than maybe she should try to find someone less sociable to hang out with. Maybe all of you could get together and do something she might like one evening so she could feel more comfortable. Sometimes its just an issue with the friends and not the BF for us woman. We just need to get to know them and feel comfortable with them.