Welcome back to Humor Nation. There have been only a few times when we truly saw the real Damon Salvatore, the humane side of him. Ever since the show started, we have seen him playing the tough guy act, saying he doesn’t care whether one lives or dies, he is cold and this evil manipulative villain, using his sarcasm as a defense mechanism. But beneath all that, he’s a terrified child who suffered abuse at the hands of his father, who was denied love from the woman he loved, who has always been the second choice. It affected him to the core, but he chose to hide it.
There are several moments when Damon displayed his true emotions. One was when Rose who had developed quite a friendship with Damon got bitten by the werewolf Jules, she was dying and was in extreme pain. Damon went inside her mind, calmed her down, shared a beautiful moment with her, and granted her mercy by killing her. The death of Rose shook him up, he tried denying himself feeling that way and ended up killing an innocent just so he can deal with the loss.
Damon has turned off his humanity quite a few times in order to stop himself from feeling too much. When he failed to rescue Enzo from the captivity while he himself was free. He switched off his humanity in order to survive and overcome the guilt. He abused and used Caroline in the beginning, but as the show progressed, he developed a good relationship with her. After the death of Stefan, they became close friends.
Elena and Bonnie are to be credited with the transformation of Damon. His relationship with Elena made him realize what true love is, how to accept himself, and open his heart to others. But it was Bonnie who made him practice all this. Apart from Elena, he didn’t care much about the others, but Bonnie became his best friend, and he went to great lengths to save her. He even chose her over Elena when waking up Elena meant killing Bonnie Bennett. Damon Salvatore married Elena in the end, even though it was not revealed, but it is mentioned that they had kids together.