Most Helpful Guy
I'm probably going to get killed for this, but similar situation happened between my first real girlfriend, and I. I cried as I broke up with her because I loved her more than anything. She had been growing distant for some time as I was gearing up to go to college. I really didn't want to do it, but I knew that If I didn't it was going to be drawn out and eventually it was going to end a lot worse. In the end I wanted to stay with her, but I couldn't force her to want to be with me even though she hadn't outright said she didn't want to be with me anymore. I don't doubt it hurt her to, but in the end she got over it and found someone new before I did. So in summation I'd say he cried because it was difficult for him and because he really loved you.
Most Helpful Girl
You can love someone and still not want to be in a relationship with them for a wide variety of reasons.