In the episode, "Memorial", it is clear that Damon still misses his friend as he talks to Alaric at his grave.

In an interview before the season finale, Julie Plec stated that "This year, she's had a very traumatic roller coaster of life experience and it's changed her irrevocably—and at the center of it all was the diehard belief that she loved Damon, that she loved him more than she'd ever loved anyone." “You’re talking about 70 men and women who, when they’re at their best, allow the actors to perform their best. At Salvatore's mansion they bring a desiccated Silas, to trade Silas's life with Bonnie he must become mortal (witch). In the following season, Elena realizes that her feelings for Damon cannot be denied any longer. Elena has compelled her memories of their time together and moved on. 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. 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. When she becomes a huntress, after her best friend Caroline and her boyfriend Enzo fail, Damon is the one to wake her up from her deep sleep. Bonnie brought back with her a strange video she had caught while leaving a second Prison World she had been moved to set on October 31, 1903. Damon is disturbed to learn when he gets to Lily that she has been trapped with other vampires and they allowed her to drink their portions of blood to stay alive.

She pretends to be happy, but she is secretly taking witch herbs to hallucinate Damon. 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 care to even contact her after being back and now she has decided to move on. Damon returns to the wedding to find Bonnie badly injured on the floor and Kai's reminder that letting Bonnie die will allow Elena to regain consciousness. While Damon is already holding onto Katherine while waiting for the hellfire to kill both of them, Stefan injects the cure to Damon. The decision to give up on the cure after Elena kills a waitress and threatens to kill people. Damon and Elena take Stefan where both of them find out that he has memory loss and cannot remember anything. She forgives him, telling him that she cares for him through grief-stricken tears.

They both reconcile. 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. He says that it is the only time that he becomes a good brother to Stefan, compelling him to leave and stay away from the tunnels. After saving Elena with Stefan in episode 8 of season 2, Damon shows up in Elena's room with the vervain necklace that was ripped from her neck earlier in the episode. Meredith Fell seems to be one who convinces him in 'When the group goes to the mysterious island to find the Cure, Damon continues to be suspicious of Professor Shane. At the start of season 1, Damon was a self-proclaimed loner,Damon's most prominent love, aside from Elena, was Rose. Despite the Salvatore brothers rarely (if ever) seeing eye-to-eye, “When you talk about performance on set, you’re actually talking about the performance of an entire crew, as well as the actors,” Somerhalder tells TVLine. Damon, who still has his humanity off, forces Stefan to join him. He writes to Alaric that before Elena, he did not know what it was like to be happy, fulfilled or complete and that he does not want to continue living without that feeling. Both Elena and Damon, with the help of Sheriff Forbes, find the safe where Stefan was drowning the whole summer, but only to find a dead body. However, when Bonnie almost died while saving Damon, he decides to leave Bonnie to ensure her safety and dessicate himself until Elena wakes up (or Bonnie dies) which leaves Bonnie heartbroken. 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. They discuss what human life together would be like. Elena interrupts the torture session and Damon storms out and Elena follows. Bonnie was one of the things that kept him going while Elena was away, and one of the positive influences he had.

Unfortunately Damon ticked off Jules, a werewolf, and she showed up on a full moon for revenge.

He then calls Stefan and the brothers attempt to track down Elena. Elena wakes up during Stefan's funeral, where Damon and Caroline are saying their goodbyes to Stefan. Caroline also receives a gift from Klaus, saying that he will always be waiting for her no matter how long it takes.

It is soon revealed that the vampire that Alaric is hunting is actually Damon. But with Elena's death, Alaric dies as well while Damon holds him. After the death of Liz, Caroline is unable to bear the pain of losing her mother and chooses to turn off her humanity just as Bonnie returns. It’s then the actors’ job to show up prepared and ready to explore [the material].”Somerhalder says he’s learned a lot over the years by closely observing his superiors, including executive producers Julie Plec and Kevin Williamson, and producer/director Pascal Verschooris.“Production managers and the crew are really the unsung heroes of our performances,” he says. His love for her prevails, and he breaks the siren's mind control, regaining his memories of 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.

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