Thanks so much. I guess I brushed it off since my girlfriend is a "bro" girl and has majority, if not only guy friends. The closest ones she does tend to playful flirt with. Kinda like the occasional "Ay what it do baby?" to them so I just learned to live with it. I figured I was just overthinking this situation with what she normally does with her close friends.

Thanks for the reply! I'll bring it up with her.

Hmm if I had to say it, I think she doesn't see it as flirting and inappropriate comments. I would say she's optimistic that he's a good guy and since he has a girlfriend himself, he won't push any boundaries that would jeopardize that relationship. She's definitely said straight forward that she has a boyfriend, but doesn't state his comments are inappropriate. She sees the hangout as friends finally hanging out after a while of basically being pen-pals.