Yeah, that's skeevy. He's probably attracted to you, and maybe bored in his relationship. Or he's just an inappropriate creep. A harmless joke here and there is one thing, but if he's asking details, that's just weird. He shouldn't be asking you about that kind of thing at all. Anything beyond who casual questions about your dating life is simply TMI.
Definitely say something to your friend. I'm surprised she's okay with it. Why doesn't she tell him to tone it down? Or the next time the boyfriend says something, punch him hard in leg and go, "Oops. I was aiming higher."
Definitely say something to your friend. I'm surprised she's okay with it. Why doesn't she tell him to tone it down? Or the next time the boyfriend says something, punch him hard in leg and go, "Oops. I was aiming higher."
This is definitely a sign that his relationship is going down...and that he's a freak. If you're the only one he does this to, he might be interested in you. If he does this with all of her friends, or just all girls, he's really just a creep.