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. Kai, who escaped the Prison World without Bonnie and merged with Luke, has absorbed some of Luke's qualities and is now moved by guilt to help free Bonnie. 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. After arriving at the island, Shane offered Damon sunscreen with Damon asking, "Is that suppose to be a joke?"Damon declined to tell Elena if he'd take the cure when it's found. On the island, the hiking began. Rebekah recapped what everyone brings to the table including Elena (nothing) and Damon ("nice behind"). When Shane skated the question of whether Bonnie should trust him, Damon pressed for answers. What Shane means is that after his son died in a car accident, his witch wife tried to resurrect him with Expression. It overwhelmed her, and she died. Bonnie was understandably pissed that Shane taught her the same magic that killed his wife. But his wife, Shane said, was undisciplined, and he's learned the warning signs so he can keep Expression from consuming Bonnie. That's why they can't kill him once he points to the cure: Bonnie needs to keep him alive so he can keep her alive.

In Lost Girls continues with Damon feeding on his new victims and burning their corpses, using one of their arms to wipe the blood from his mouth. Strangely enough, these actions were performed outside of a crypt with the word 'Salvatore' carved in it. Damon calls Stefan as he burns the dead, demanding to have his daylight ring returned, going so far as to threaten Elena's life. Death does not stop a witch from dispelling the amulets. Before the collapse of the Other Side, the spirit of Emily Bennett was able to influence the effects of Damon's ring at the Witch Burial Ground. Damon enlists Sage's help to get into Rebekah's mind and see what she is hiding. He ends up sleeping with Rebekah, and through Sage's special ability to get into people's minds, she discovers that White Oak tree from the Old World which potentially could kill the Originals is not totally burned down.In Original Sin, Damon and Elena along with Katherine go in search for Stefan when Elena and Katherine both have a same nightmare about him. While traveling Katherine taunts Elena and Damon about their relationship, annoying them both. After reaching Jo's bar, the place which appeared in their dream, Elena and Damon happily leave a sleeping Katherine in the car.

In the books, it seems that the power of lapis lazuli is transferrable, as Elena wears Katherine's ring without any problems. A Daylight Amulet, also referred to as a Daylight Ring, is a piece of jewelry with a lapis lazuli gemstone enchanted by witches, which help to protect vampires from the sunlight. This also allows vampires to walk freely in the day. Their werewolf counterparts are the Moonlight Amulets. Later, Bonnie comes home to the Salvatore house to find Damon making pancakes, chugging booze and dancing to Salt N' Pepa's "What a Man." She got a grimoire from her Grams' empty house and hopes she can reteach herself magic. The paper says May 10, 1994 again. They're both surprised when suddenly there's another solar eclipse. Sometime later, a sad Damon is seen reminiscing about a memory of Elena. During dinner, Bonnie tells him she misses everyone too. Damon notices Bonnie finally got the crossword clue that was stumping her (Yellow ledbetter). But she didn't. It's filled in, but neither of them did it. They both realize there are not alone after all.Damon joins Elena and Bonnie outside. Bonnie accuses him of wanting Elena to be like him, and he argues that she already is and needs to learn to revel in the feed; not hating herself and enjoying it will be the only way she, like him, can make feeding fun and not get carried away. Damon walks away, leaving Elena crying about what had happened. He accompanies her home and she apologizes for letting things get out of hand at the party, confessing that she hates that, deep down, she agrees with Damon's point of view. She starts to say she doesn't want to be that way, and Damon finishes her sentence to say she doesn't want to be like him. When Stefan opens the door, Damon leaves. He then hurries to Whitmore and finds Enzo with Stefan and Elena tied with vervain ropes. He reveals to them that on November 8, 1960, he got a message at the house that a woman wanted to interview him. He didn't know she was Enzo's Maggie. She wanted revenge from him for leaving Enzo behind in the fire but she didn't stood a chance against Damon. Damon had killed her and made it look like Stefan did it because of his grudge of Stefan not coming to get him the five years he was in Augustine captivity. Damon asks Enzo to resolve this among themselves and not to include others. Enzo confesses he can't hate Damon because then he has nothing left. He realizes there is another option and switches off his humanity.