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Damon confesses to her that Bonnie kept him alive while the two of them were stuck in 1994 and she was the one giving him hope, explaining that this is the reason he wants to save Bonnie, not only to make her fall in love with him again. Back in present time, Kai kills a cab driver and once he arrives in Mystic Falls finds Liv.
Emily leaves Bonnie's body and Damon, who is mad at Emily, attacks Bonnie. Stefan pulls him back and saves Bonnie by giving her his blood. Damon is devastated because his only shot to bring Katherine back is gone and he tells Stefan that Katherine never compelled him, that he knew everything from the beginning and he really loved her.
Damon saves Bonnie's life and they go to the Salvatore boarding house to say their goodbyes to Elena, deciding that they will allow Bonnie to live her life, and, when she dies, Elena will wake. Damon allows himself to enter Elena's subconscious to say his goodbye, dancing with her and telling her that he'll never be ready to live the next 60 ...
Kai reveals that he has been following Damon and Bonnie, right before he announces that he wants to kill Damon just as Damon takes a drink of bourbon laced with vervain. Bonnie saves Damon by regaining her magic, and she and Damon capture Kai, who later admits that he faked the attempted killing of Damon to motivate Bonnie to regain her magic.
Damon and Alaric arrive and Alaric goes through first. Damon asks where Elena is and Bonnie assures him she is safe. At the same time, Luke cannot let his sister die and chants a spell making her stop. Damon tries to pass through Bonnie after the spell has stopped but it no longer works, leaving him trapped in the Other Side.
Kai and Damon go to save Bonnie who remains trapped in the prison world and they eventually save her, bringing her back into the modern day. To repay Kai for trapping her in the Prison World Bonnie betrays Kai leaving him in a second prison world where he remains with the Heretics until the season finale.
Bonnie and Valerie are able to resurrect him both times, but the second time, Stefan gets trapped within a corpse while his own body is possessed by the spirit of Ambrose, a sadistic vampire and serial killer. Stefan's friends save him once again, but his relationship with Valerie is brought to a final end.
Damon goes for the crystal, and Emily uses her power to throw him up to the branch of a tree. Then Emily performs the ritual to destroy the crystal and thwarts Damon's plan. Emily releases Bonnie from her possession. Furious, Damon attacks Bonnie, but Stefan saves her by making her drink his blood.