I don't know what to do about my boyfriend's female friend.
The background: My boyfriend and I dated for two years and broke up a few months ago due to communication issues. We're trying to see if we can work things out. This "friend" was chasing him before we broke up, knowing we were in a relationship and still trying to get his attention. After we broke up, they dated a little, but according to him it "wasn't real" and didn't go anywhere. When he decided to work things out with me, he told her what he was doing and that they were over, but she won't go away. She was not the reason for the breakup, but she definitely made things worse.
She's still around constantly, flirting and hanging off him, trying to get his attention. And he returns the attention to some degree; they talk constantly. Obviously I have an issue with this, he knows I have an issue with this, and he won't ask her to stop or go away because she's his "friend" ... but she's not. She was a mutual friend to both of us for months, but she would do attention-seeking things and it got to the point where our other friends didn't want to be around her anymore.
She decided she wanted my boyfriend and tried to date him/sleep with him, then tried to lie about not knowing we were dating when I confronted her. Those are not the actions of a friend. I'm pretty sure he's just enjoying the attention from her because he's lonely and depressed. He gets attention from me, but many of our friends are busy doing other things and don't talk or spend time with him. Some of them don't want to be around him because of her as well. Not really sure what to do.
This sounds like a deal-breaker to me. Your relationship is fragile right now, yet he's choosing to spend a significant amount of energy on a person who threatens what you have. He stopped hooking up with this woman, but based on what you told us, he didn't set any other boundaries. If that doesn't work for you, that's that.
I wish you'd told us a bit more about his loneliness. That sounds like one of the big issues here – that he's having trouble being a good partner because of how he feels about his life. Does he agree that he's missing his friends? What is he doing about that? It might help to talk to him about what you both can do to create community.
But really, if he is unwilling to change his friendship with this woman – and you can't deal with her presence – this relationship might not be worth a Take 2. The thing about communication is that it's often a two-part process. You have to talk about how you feel and what you want, and then you have to do something about it. He knows you're uncomfortable, but nothing has changed.
Think about why you wanted to try again and whether you're both working for the same thing.