What does it mean when a man cries over a breakup... does he really love that person?

It means he made a bad choice breaking up with his girlfriend or a family member or someone close to him died. But if your are talking about a relationship between you & him, then it means he shouldn't have done what he had done, & might want another chance. He doesn't know what he wants because he is a guy.You know guys can be. If he wants a second chace, give it to him if you really love him, or he did something unforgiveable or unforgetable, for get about it.