I could not think of anything exactly like you are saying but..
sang doo, lets go to school - Guy does lots of things to try to get the girl back.. even goes back to school as a high school student while she is a teacher. He did not really break the girl's heart but they did separate for a pretty long time..
proposal daisakusen - He does not break the girl's heart.. but never lets her know how he feels. He goes back in time to try to fix things he did wrong in the past to try to stop her from marrying some other guy.