With striking, intense light blue eyes contrasting wonderfully against dark eyelashes and eyebrows, a "bad boy" smile, he can be described as relatively athletic, tall, strong, sexy and seductive. He cured her from a congenital heart defect, which is why Megan had a picture of Grayson Gilbert in her phone. Elsewhere in the room, Elena pulls out a flask and Damon swoops in to take it from her. Damon tells him that her new priority is to give Enzo a spanking, to get him to flip his switch. As Stefan tries comforting and explaining to him that all of it was hell faux, he loses it completely and goes on an attacking spree over Stefan, Caroline, Matt & Bonnie, killing them all. Damon talks about how Enzo kept him sane in captivity, reminding him he was lucky to have any family at all.
He leaves her and rejoins Stefan, who worries that Damon won't be selfless enough to do the same with Elena. You've managed to use that sire bond pretty well so far, haven’t you?” Stefan said. She apologizes for keeping Enzo's death a secret and he says he doesn't care about her lies. Damon told her that the person he cared about wasn't Katherine, it was her. Ambrose tells him he doesn't care much for the taste of blood. Tyler tries to shoot Damon, but Damon puts him to sleep instead. Damon first introduces himself to Jules, the werewolf.While Damon is distracting her, Alaric pours wolfsbane into her drink. After snarking Alaric for hiding it in such a cliched place, Damon asks if Alaric is really telling him that he is missing a stake that could kill his line of vampires. Damon finishes his hole and Kai comes back with his things. With Elena influencing him throughout the second and third seasons, Damon becomes slightly kinder, if only for the fact that he no longer mindlessly kills and torments humans without good reason, and he controls himself to be strong for Elena's sake.
Flashback to them double-teaming a woman in the club, which is what Damon and Elena did now.
They band together against Jeremy is Damon's new roommate and Elena's younger adoptive brother/biological cousin. When Kol tries to kill Damon is in bed beside Rebekah. Peter Maxwell runs into Damon who has been waiting for him. Sybil asks her two loyal subject if they would mind if she were to take back her promise to spare Bonnie's life. Enzo mentions that Wes poisoned him and he has to return for the antidote.
But she still kept her distance due to Damon's constant immoral and impulsive behavior. She says she keeps it as a reminder not to trust the wrong people. Damon smiles and they start eating. he asked. Figured that'd be you.” Stefan forces a quick grin and they make their way upstairs. Damon accuses him of being on vervain but Pete denies it saying "I don't know what you're talking about." Everybody is dead inside. Then he bails out of the car through the open window. At the end of the episode, we finally see Damon and Bonnie. Stefan finds him sitting on a picnic table outside the high school. Stefan hides the fact that Enzo is dead and tells him that what happened with Enzo wasn't his fault. Stefan joins him and, right away, Damon bombards him about flirting with his girlfriend on the dance floor. After Jeremy leaves, he ends Mason's life by ripping his heart from his chest. Katherine keeps pushing him. Stefan pleads "Damon don't"! Stefan asks Damon if he remembers playing hide-and-go-seek when they were young. High quality, unique, printed one-at-a-time, and fast delivery.
They first go to visit Stefan's old apartment, where Damon shows Elena Stefan's list of killings. "Hello, me." He reveals that one of the scientist spared him. The Salvatores arrive with Aaron at Wes's classroom and find Enzo waiting for them. So he picks Elena's graduation picture and draws a cartoon picture of himself around her. He's even cruel to her, accusing her of trying to make him into something he's not. Luke tells them about Travler's leader Markos and how he is back from the other side. On May 10, 1994, Stefan and Zach hear screams and rush to the library to find bodies everywhere and Damon covered in blood, holding Gail hostage.
He also snaps and feeds from Caroline's father, and, after a very violent fight with Caroline, he is confronted by Elena. Then he sees Sybil again. He manages to free himself, snapping broken bones back into place. Damon hesitates and Klaus accuses him of trying to appease Elena by doing the right thing of not involving innocent civilians. Klaus thought he'd compelled Damon to stay in the cellar, but Damon had been drinking that bottled water Stefan gave him, which had vervain in it.
Damon after Dr. Fell told him that she had given Elena vampire blood.Much later, in a fight with Alaric after leaving town, Alaric dies. Damon calls the EMT and finds out that they are just meandering along on their way to the motel to meet Valerie. Enzo tells him he doesn't understand what the "boss lady" is up to; why she's pushing pause on her master plan. Damon saw her there on a road and mistook her for Katherine. Ambrose says he'd be willing to jump into the body of a transitioning vampire and he'd gladly give Stefan's body back. When Elena reaches the Salvatore house, she sees a Mistletoe hanging on the door and laughs at Damon's clever antics.
Damon tells him to get on it and hands him two sealed envelopes. Because they needed him to get Bonnie back.
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