The first two "clues" seem relatively harmless to me. He's been her friend for a long time, so would obviously pay more attention to her while in a group, and make attempts to see her one-on-one. But what I would be concerned about was the fact that he "didn't want to see you again". Why did he say this? I find it a little odd that he would not make an attempt to be cordial with his friend's boyfriend, even if you two did not get a long.
I would ask your girlfriend if there is anything you can do to help you and said friend get along better. You never know, the problem might be an easy fix. And even if the situation continues to be awkard, remain friendly to this guy. She has a right to spend time alone with him, and if you trust her you shouldn't attempt to deny her this. Even if she is a people-pleaser, she should have boundaries and will not let a guy make a move on her if she's in a relationship. If you give her (and him) the benifit of the doubt, you also look very good. And if he still won't try to get along, then he's the one looking like the idot. But if you ask her not to hang out with him, it will be the other way around. Try to get to know this guy, if you can. You might be surprised to find out that there is something about him you missed. If your girlfriend is friends with him, there must be something good about him.
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