Kai is dying because he merged with Luke instead of Jo. They're enjoying breakfast made by Lily. Luke and Liv are sick of everyone blaming them for everything. Liam apologizes to Elena for false accusations after Jo had altered Lady Whitmore's medical track. He starts a spell to kill Jo and then tries to kill Damon but Stefan arrives in time to fend him off with a magic knife Jo spelled in 1994 while at the same time, Elena saves Jo with her blood much to Liam's shock whom she compels afterwards. Unable to move on, Caroline is desperate to find a way to reverse the anti-magic spell the Travelers have put over Mystic Falls and grows frustrated when her calls to Stefan go unanswered.
Damon decides to let Elena go while dropping her off at her dorm. Meanwhile, Stefan takes Damon to his home where he stayed while Damon was trapped in prison world, to know whether he really wants to become human or not. In a surprising turn of events it is revealed that Kai is Jo's twin brother, Luke and Liv are both siblings to them and stem from the same family. Kai takes Bonnie to the same location and tells her his parents called him an abomination and tried all they could to keep their home hidden. Alaric proposes to her, telling her that he had already been planning to propose before the news, and she accepts.
Meanwhile, Elena and Damon are having a pleasant morning. It was also announced that Michael Trevino would also vacate the role of Tyler Lockwood after season 6. The aftermath is a well-looking person who seems to have defeated the tumor. As Jeremy leaves, it is revealed that he lied and instead of going to art school, he is going to go hunt vampires and Alaric is the only one who knows about it. Kai agrees to let Bonnie leave unharmed with his car if she has one last dinner with him. Matt reluctantly goes on a walk with Sarah to the tunnel, and Enzo purposely hits Matt with a car.
In flashbacks, Stefan explains how his rivalry with Damon began. Caroline, on the other hand has Stefan help her surprise her mother with a vacation while the sheriff is with Damon attempting to solve an old unsolved case: the Gilberts' accident. It tells the story of Elena, a young high school girl 17, who survives the death of his parents trusting in her diary and her two best friends. After spending the past four months coping with the loss of Damon in an unconventional and potentially dangerous way, Elena has returned to Whitmore College for the start of sophomore year. Now Stefan has to track down Caroline and get her to flip the switch, too. Stefan appears at Whitmore College, surprising Elena, who has just invited Liam to the party at the swimming hole. After Liz's funeral, Caroline returns home, but Elena follows her and confronts her after realizing that Caroline plans to turn off her humanity to stop her pain and prevent what Damon warned her about.
Meanwhile, in Savannah, Stefan attempts to show Elena what it is like to start over and create a new identity, while unsuspecting Matt finds himself in a disturbing situation when Tripp lets him in on a dark secret. Tyler is blindly hopeful, model student Caroline shocked to discover that Elena, finally returning to college too, is the mystery vampire who lurks around town bloodthirsty, in fact a side-effect of the herbal potion witch Luke gives her to communicate with dead Damon, who also feels she must make a clean break and seize life again. They trick Kai and send him out of border where Alaric puts a gun on his temple but Jo comes out and asks him not to kill him because she might be able to beat him in the merge, and that she needs a little time to get strong. Enzo turns on Matt telling him that he will let him live if he helps him take away all things that makes Stefan happy. While searching for answers, Damon meets Kai's father, Joshua, who casts another cloaking spell on him.
Liv and Luke's father arrives to celebrate their birthday. Kai refuses to give Damon information about his mother unless he helps Kai apologize to Bonnie in order to alleviate Kai's guilt. There was immediate speculation as to whether the series would continue without Dobrev, but the continuation was confirmed. Jo freaks out over her lost slippers and her wedding coordinator who was unavailable at the last minute. Meanwhile the sheriff is brought to the hospital where it is revealed that she has a tumor on her brain, and Stefan says to Caroline that she will die because vampire's blood cannot heal her.
The episode ends with the patient slowly dying in a brutal way, just while Liz is drinking Caroline's blood, with whom she now believes can be saved. Jo tells Alaric to be a father for 18 years and then he can run around killing vampires. Stefan has decided to live a normal life and started working as a mechanic after giving up on finding a way to get Bonnie and Damon back. She tells Bonnie and Elena that she will avoid killing anyone if they give her a year to live freely without her pain, and they initially agree. Four months after the final fight against the Wanderers brought down the Other Side, Mystic Falls remains magically protected against supernatural live beings. Damon finds Elena in front of the fireplace and she confronts him, telling him that she had asked him before to take the cure with him and he had refused, saying that to be human would be to have the most miserable life in existence. Caroline still believes Stefan has no humanity while they're locked inside a room and being tortured.
Kai casts a spell linking Elena and Bonnie's lives, rendering Elena unconscious while Bonnie is alive and tries to force Damon to choose Bonnie or Elena. It is explained that they were locked inside the prison world because they were perceived as too dangerous and worthless. After an awkward run-in with Jo at the hospital, Alaric steps in to help Jeremy get his life together and cope with the loss of Bonnie. In the barn which is prepared for the wedding, Elena is approached by Damon who said he had thought this through and he chose to be human not for her, but for them and he would grasp any chance to be with her and they kissed. Tyler says that he is too afraid to become a werewolf again. The patient is feeling alright again so Caroline and Stefan rush back to Mystic Falls.
Luke promises Liv he will come back and go and look for Kai. On April 6, 2015, Nina Dobrev announced her departure from the series at season's end on her page. Jeremy manages to open the door, and Bonnie survives. Stefan and Caroline are setting up Liz's room together and the two of them kiss on the porch. It was announced, right after the of , that 's character, , who left the show at the end of after being killed, will return as a regular for Season 6. Matt is still being blackmailed by Enzo, but he is starting to develop feelings for Sarah.
On the way Stefan goes to the art exhibition held by his niece, the true Sarah Nelson, but he is followed by Enzo. Back in the Mystic Falls, Stefan meets a girl claiming to be Sarah, the daughter of their uncle, but it is revealed that she is actually an impostor who goes by the name Monique. Caroline decides to go through with it anyway and breaks Elena's neck. First Aired: October 2, 2014 Season 6 begins with Elena returning to Whitmore College for the start of sophomore year. As human, Alaric's compulsion is gone and she gains her memories back. Caroline invites Liam and Enzo to a rave, and Elena, Bonnie, and Stefan come to confront Caroline. Elena says that she isn't going to let him take the cure until everyone has tried to talk him out of it, to ensure that to be human is what he wants and that he isn't doing it just to keep Elena.