I'd say you should have sex first. Then break up. Then make up for the ever lorded "make-up sex." Then turn over to him and say "but seriously... it's over." Dem's idea works better. ~~~~~~~~~ BUT CONSIDERING HE'S HOMELESS! Just bring him a styrofoam cup. Throw some change into it along with a note saying you've broken up with him.
Theres a high chance he won't do anything about it. Tell him to take his meds and grow a pair of balls. Tell him its not healthy for you to be in a relationship when he's being such a fem.
So you're back together with him out of pity? Good luck with that. If he was smart he'd realize that.