This is what I would tell my boyfriend. No! and No! If she needs money (since she is YOUR friend) she should address this to you. Personally I think he disrespected you. I know my boyfriend looks, (a man for you) but I think when he brought up the fact about giving her money, that's a red flag IMO. Like you said if he wants to help people why couldn't he offer your sister help also? This is what I have told my boyfriend about looking, because men just need to look. I said that I know that you look. I don't care that you look, but when your around me, show me some respect, and look, but don't stare. If this doesn't work then this is what you do. You excuse yourself from where you are at. You go up and start socializing with other men. Then when he gets upset.(which he will) then say what honey, you can dish it out, but you can't take it. I guarantee that he will get the hint, and probably won't do it again. If you want to tell him about his behavior, than do so. I would just say what I need to say about him looking, but I also wouldn't argue about it either. Tell him once, and if he doesn't listen repay the favor.