A century after Damon and Stefan leave Mystic Falls, they both return and meet Elena Gilbert (also Nina Dobrev), a mortal who looks exactly like Katherine.

As an expression of his anger, pain, and hopelessness, he snaps Jeremy Gilbert's neck, not realizing he is wearing a ring that reverses the damage done by supernatural creatures or forces.

In one episode, Damon joins Rose to find out why the originals are after Elena; after some time and clever banter, the two have sex, stating that they could rid themselves of emotion.

However, when Rose, Damon's old friend, is mortally bitten by a werewolf, he gives her the memory of her life prior to becoming a vampire and helps her remember how good it felt to be able to walk and feel the sunlight, without it burning her.

Damon begins showing another side of himself in small acts that help build what once was an impossible friendship between Elena and himself after she clearly stated that he has lost her forever.

The rocky relationship between the two continues until the sexual tension hits the fan and in a moment of heated passion, Elena – for the first time in the three seasons – kisses Damon of her own accord.

In the next episode, she begins to believe that Stefan is lying to her and takes things into her own hands to kill the vampire hunter who is holding her brother, Matt, and April captive.

The sire-bond can only be broken when Damon leaves Elena and tells her to stop caring about him according to a witch in New Orleans named Nandi.

At the end of the episode Damon invokes the sire bond telling Elena to return to Mystic Falls while he trains Jeremy "O Come, All Ye Faithful".

However Kol shows up and has killed all the vampires, determined to stop them from finding the cure & waking Silas, and threatens Jeremy's life.

Damon spends the next episode locked up and bled dry by a jealous and snarky Stefan and engages in a conversation with Klaus about Caroline, Rebekah, and Elena.

After Katherine kills Jeremy in 'Down the Rabbit Hole' Damon stays behind determined to find the missing Bonnie, telling Stefan he cannot come home without her.

He admits that he had his emotions off and Lexi had come to help him on Stefan's behalf, however, he tricks her into believing he fell in love with her only to leave her trapped on the roof during the day as revenge.

He gets shot by Vaughn with a bullet laced with werewolf venom, and almost dies, but Klaus comes back to Mystic Falls and saves him.

As the season progresses, Elena falls for Damon all over again as they search for a way to free Bonnie and she becomes a large part of his support as his good friend Liz Forbes becomes more and more ill with cancer.

With his help, he, along with Damon, Elena, and Jeremy, are able to visit the Prison World and remind Bonnie that there is still magic residing in Qetsiyah's headstone in Nova Scotia.

Damon confronts Bonnie, who had taken the Ascendant, and tells her that Lily is threatening to destroy the cure if he does not return with the means to get her "family" back.

In the last episode of the 6th season titled "I'm Thinking Of You All The While" Damon rushes Elena to the hospital after vampire blood fails to heal and awaken her.

After consuming Lily's blood and killing himself, Kai's ability to siphon magic allowed him to become another Heretic (a vampire with witch-like power), but he was soon bitten by a transforming Tyler, who had re-triggered his werewolf curse.

Stefan and Damon move the coffin holding Elena to a crypt and have Bonnie seal the door magically to keep away those seeking the Cure.

Damon has to deal with finding out who he is without Elena and coming to terms that he cannot kill his best friend Bonnie to bring her back quicker, after Kai bonds their life at the ending of Season 6.

Caroline gets kidnapped when Damon and Bonnie murder one of Lillian's 'children', and finds out from Valerie, Stefan's first love, she is pregnant with Alaric and Jo's twin Gemini babies.

The murder spree then leads to the reincarnation of a siren named Sybil, who has the powers to seduce and erase specific memories in anyone's mind, thus making them committed and loyal to her.

In a flash-forward scene, a medical student Elena is seen writing on her diary outside the Salvatore crypt in the cemetery, while a crow flies over her head as she sees Damon.

In the final season of the show's spin-off series The Originals, a medical clinic in Mystic Falls has the name "Elena Salvatore M.D" embedded on the glass.

His classic car was shown being driven, specifically by Alaric's now-grown-up daughter Lizzie Saltzman and her vampire love interest, Sebastian.

However, in the episode "Original Sin", Tessa, who is revealed to be Qetsiyah, tells Damon that the doppelgangers are fated to fall in love and that he is only a bump in the road that makes their story interesting.

Julie Plec stated that "I think the only hope that he's holding on to is the idea of the two of them living in Tribeca in their brownstone and raising kids and having a life together as humans when this is all said and done.

When Damon returns home, he does everything he can to find a way to bring Bonnie back, including a long road trip to Oregon to seek the Gemini Coven and also compelling Alaric to steal the Ascendant from Jo.

In season 7, Damon initially detests Bonnie presence as she reminds him of Elena being missing from his life but later they both end up saving each other's lives a couple of times.