This happen to my friend and his girlfriend. They were dating and then she broke up with him because she felt too bad about herself, then she got back with him and then broke up with him. This happen three times. Then she tried to get back with him, but he just ignored her. If you really like this guy and want to date him first take care of yourself and then ask him if he wants to try again. But don't make him feel used and degraded. Other wise he will never want to try again.
I hope this helps. :)