(Nice) Bad boys

This is the non-romanticized version of bad boy turned good. He was a bully whose actions had repercussions in the one he loved and he was full or regret and pain for doing so, causing many hardships in their relationship even when they confessed their mutual love the trauma (it was a real trauma this time, not only grand words) set them apart because you can't erase the past just like that. Good thing is that he grows and shows his repent, apologize but the important thing is he actually change

The seemingly aloof and cold guy but is actually pretty loving and caring.