My boyfriend and I are both in our late 20s and have been together about two years. When we were in the "dating" phase of our relationship (not exclusive), I found out he was still seeing his ex and a friend of his exes. I broke it off (too much baggage for me), didn't speak to him for a while, and after he broke things off with both of these women, we started dating each other exclusively.
He has a friend who always talks about my boyfriend's exes when they hang out. My boyfriend told me that he has been trying to get him to stop, and he stops briefly, but then brings it up again. It's not so much that the friend talks badly about me, but that he says things like "You remember when you and Ex hung out doing this with me? Do you ever miss Ex2?" Then when my boyfriend tells him to stop because it's inappropriate, friend says things like "Are you sure you are really over her?". In addition, this friend somehow got the idea in his head that he would give my boyfriend's wedding speech (We aren't engaged, but have talked about when it should happen-not for awhile!) and has already written it!! My boyfriend said there was no way he would ever be in that position!!
Here's the thing, this friend and my boyfriend were friends in high school. but my boyfriend isn't the same person he once was back then. This friend is in his late 20's and has never experienced a lot of things people his age has (a relationship!). There's a guy on the Big Bang Theory that is like him, only not as bad (Sheldon?). My boyfriend is getting a phD, and works for the military.
My question is, how do I handle this friend? I can talk to him, but what I have to say won't be as nice as my boyfriend would say. I really think this friend acts the way he does because he's not very mature. I don't think he means harm, I think he's just high school. However, I told my boyfriend if it keeps up, if we ever GOT married, theres no way I would want him in our party if all he does is talk about my boyfriend's exes.