I have a friend like that. Constantly gets into relationships with girls who treat him like crap, and it kills me! He seems to think manipulation = female, and selfishness = self-confidence = sexy. Drives me bananas!

I love my friend too. Of course you love your friends! How can you not?

Why can't you confront your friend about it? Yes, you might get some backlash. But a true friend is honest and really wants to help the other person. You can set it up however you want. Why not forward your message? It says it all right there. You're concerned, you want to help, you feel stuck because you don't want to come off as possessive, etc.

Have you tried asking what you can do to help? It could be your friend has been wondering why you aren't interested in helping him get through it.

I can see not wanting to cross a line, but I don't understand why talking about heartache is off limits? It's one of the best things about cross gender friendships, you can get the insight from the "other side" so to speak.