After 3 years, when Stefan wakes Damon up, Bonnie admits in a medical care centre that a person whom she loved and admired dearly, abondoned her and didn't even care to even contact her after being back and now she has decided to move on. When Bonnie tries to kill Damon, he apologizes for leaving her and admits that he admires her and loves her a lot (just like Elena did). He then calls Silas and tells him to come to get her.
Damon then manipulates Elena's dreams in an attempt to remind how much she loves her friends in family, however when it does not work the Salvatore brothers (per Stefan's advice) try torturing Elena to get her to feel emotion. Damon's drinking buddy. Back home, things are not as Damon expected them to be. Unfortunately Damon ticked off Jules, a werewolf, and she showed up on a full moon for revenge. 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. The scene is a nod to the cemetery scene in the show's pilot episode of season 1 when Damon can control fog and crows. Damon hands over the Salvatore Boarding House to Caroline, which she then turns into the Salvatore Boarding School for the Gifted, where Alaric's daughters are staying. When Bonnie returns from the prison world, she gifts Damon with the cure for vampirism, knowing that he wanted to give it to Elena.
Nora and Mary Louise Heretics spend the season dealing with their relationship problems and their own family, along with the death of two of their brothers. The rest of the group search the whole house to find Amara. However, it does not work on Stefan after he enters Damon's mind to make him conscious, but it does work on Damon. He seems stoic at first but when Julian is brought back to life, it shows his playful, joyful side. As Elena reunites with her family in the Gilbert house, Damon reunites with Stefan in the Salvatore Boarding House with the words, "Hello, brother." However, when Rose, Damon's old friend who turned Katerina, 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.
Amara is then awakened and revealed to be the mystic anchor.
Elena and Damon then begin to mend fences, and Elena gives him an affectionate hug to help comfort him after Rose's death. The decision to give up on the cure after Elena kills a waitress and threatens to kill people. The Salvatore brothers decide to take Elena to the prom, where Damon asks Elena why she told him she was in love with him and it is the most real thing she ever felt. After he spares Caroline's mother, Elena says how that was the person she was once friends with. Kai is irritated that his plan to torture Damon with an impossible choice had failed and, while he is distracted, Damon decapitates him from behind. When Elena focuses her hate on Katherine Damon tells Elena where Katherine is but tells her she should not try and kill her. She recalls a memory from season 4, where Damon declares that there would be nothing more miserable than becoming human again. After Stefan wakes Damon from his desiccation, Damon continues to be devoted to his future with Elena. Stefan then gets left with no choice in order to protect Caroline and their friends.
Damon, who is trying to stop Alaric, accepts what she says and she tells him that maybe if she had met Damon before she had met Stefan, her choice may have been different. Damon has had a challenging relationship with his younger brother After learning of Katherine's deceit, Damon starts to fall for Elena. He got under my skin and no matter what I do, I can't shake him." At Salvatore's mansion they bring a desiccated Silas, to trade Silas's life with Bonnie he must become mortal (witch).
At the end of the episode, Elena proclaims her love for him stating that of all the decisions she has made choosing him will prove to be the worse one. During the wedding, Kai shows up and stabs Jo before causing an explosion. Silas gives Damon a crash course on why he looks like Stefan and tells where was he the whole summer, shocked to know about this he starts to search Stefan with the help of Stefan. After a tumultuous, back and forth relationship, Damon and Elena get back together at the end of the season, and they choose to sacrifice themselves together to save Stefan and Alaric and their other friends on the Other Side. Deputy Digital Content Manager | Entertainment & Family Alaric is brought back to life by the Gilbert ring. Their relationship has even come to a point where Damon is visibly worried about Bonnie's well-being and was devastated when he found out about her death. Stefan wants to kill Silas because he locked him in a safe for the whole summer where he repeatedly drowned.
When Sybil erases Elena from Damon's consciousness only to insert herself into their memories, Damon fights back, instinctively drawn back to Elena. Afterward he is captured by Vaughn, another member of the Five, who tortures Damon and leads him around with a noose around his neck. 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. Elena takes care of him, and right before he is cured by the blood of Klaus, the original hybrid, she gives him a "goodbye" kiss, because she is sure he is going to die.