Masochistic Friendship

1. Deriving pleasure from the pain of a friendship that you wish was something more.

2. Protecting a friendship by not making a move despite having feelings for the other party involved.

3. Attempting to remain friends with a person that broke up with you, knowing full well it will destroy you.

The guy knew that continuing to talk too, and hang out with, her would mean he's in a masochistic friendship at best.

He has so many girls as friends that one or two are bound to be masochistic friendships.