After the loss of Elena and Jo, Damon, Bonnie & Alaric had been spending the summer in Europe while Stefan, Caroline & Matt make a deal with Lily & her Heretics when they failed to defeat them. Stefan & Caroline makes a deal with the heretics to keep the town’s people away from Mystic Falls, and they wouldn’t become Heretics' blood meal. Alaric consults psychics about his dead wife. They returned to an all new Mystic Fall and told of the deal that was made with Heretics. Damon & Bonnie make their own plan and kill a Heretic. When Lily learns about the death, she attains revenge by kidnapping Caroline with the help of Enzo. Valerie put a spell on Caroline, which keeps her away from other vampires. Damon & Stefan attempts to rescue Caroline from the house with the help of Bonnie making Matt's heart stop temporarily, as Matt was made the owner of the house. Damon is told by Enzo that the Heretics have Elena. Lily threatens Damon into admitting to the murder of the Heretic & tells him to keep away from Mystic falls. Meanwhile, Alaric tests the Phoenix stone on a corpse in the morgue. Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother, Lily. They found Oscar a heretic who defected from Lily's group. Damon asked for Oscar's help in siphoning magic from Bonnie, who has side effect after touching the Phoenix Stone, but Oscar refuses and knocks Alaric & Bonnie unconscious and brakes Damon's neck. However, they late captured Oscar to use a bargaining chip with Lily for Elena's coffin. Meanwhile, Caroline, still being held hostage by the heretics, learned that Valarie had a relationship with Stefan and that she was his first sexual partner. And Stefan learned that meet Valarie was scheme Lily had setup. Also, Alaric turns to Bonnie for her help after coming clean that he has the Phoenix Stone, which can bring the dead back to live. Lily sets Caroline free out of admiration for Stefan's honesty with her. Valarie is trying to keep her secrets kills Oscar leaving Damon to scramble for a plan B which later drew the attention of Mary Louise and Nora. To help Damon, Stefan and Caroline are forced to spend the night distracting the girls at Whitmore College’s Heaven & Hell ball. The Heretic couple threatens to kill a Whitmore student every hour if Damon did not comply with the deal and bring back Oscar. Damon, Bonnie & Alaric bring Oscar back to live with the Phoenix stone and Damon exchanges Elena's coffin for Oscar. The side effect of the Phoenix stone sends Oscar killing spree in Mystic Falls. Damon break Oscar's neck & Lily returns Elena to his care. Damon sorrowfully writes in a journal for Elena, and he sends her away in Tyler's car. Alaric and Bonnie's worlds turned upside down when Jo comes alive with the magic of Phoenix stone. Damon & Stefan team up with Valerie, who is searching for Julian's coffin to destroy it. Meanwhile, Rick is dealing with Jo adjusting to being alive again. Bonnie went to the Salvatore manor to ask Oscar about the Phoenix stone but got attacked by him. Enzo gets the Phoenix stone as Bonnie loses it when she tries to run away from Oscar and then stabs Oscar when he goes crazy. When the Salvatore brothers and Valerie reach their location, she explains that the Phoenix stone does not bring people alive, but it transferred vampire souls imprisoned in the stone into a body. Just as Valerie tries to burn Julian's corpse, Lily & the heretics arrive & rescue him. Valerie, tells Damon that it was Lily's plan to make Elena sleep as long as Bonnie is alive. Damon tried to murder Lily but was unsuccessful when they made the coffins explode which left Stefan, Damon & Valerie hurting. At the Salvatore house, Enzo is in possession of Phoenix stone and asks Lily to choose between him & Julian but to Enzo disappointed she choose Julian. Enzo gives her the stone, and she and the other heretics revive Julian. Bonnie sadly informs Rick about the stone and that Jo's body might not have his wife's soul. Bonnie is joined by Damon, who vows to get revenge on Lily, who destroys everything that makes him happy. Lily & the heretics throw a party at Salvatore manor which Stefan & Damon also attend. Bonnie arrives with Enzo & she tries to make Lily jealous for Enzo. Rick deals with Jo’s declining health and Valerie explains to Rick and Caroline that Jo was human, and the vampire soul is not compatible with her body which meant that she was as good as dead. Back in the manor, Julian & the Salvatore brothers get into an argument which brings them to fight until Lily intervenes & says she will never let her children suffer. Rick has to let go of Jo, but Valerie finds out the twins are still alive and then try using a locator spell which seems to points nowhere until Valerie realizes that the twins are inside Caroline's body. Lily, Damon, and Stefan carry out a plan to take down Julian after learning that he killed Valerie and her unborn grandchild, but first she must unlink herself from Julian with the help of heretics. Valerie discloses to the rest heretics about her miscarriage caused by the beating of Julian, and they were all on her side completely except Mary Louise. Caroline informs Stefan about her pregnancy which he did take well or as expected. After a talk with Lily, Stefan apologizes and says he will always love her. Enzo finds himself vervain & kidnapped by Matt and his new hunting friends. Damon and Stefan finally corner Julian but are interrupted by the heretics. Julian forces Lily to choose between killing Valerie, or Damon. Not realizing they are no longer linked, Lily decides to kill herself in order to protect her actual children. Nora breaks up with Mary Louise as the latter doubted Valerie's story and sided with Julian. The heretics and Stefan bid heartfelt goodbyes to Lily and Damon is still unforgiving telling Lily “You made your bed. Have a nice nap!” Lily is put to rest and Stefan and Damon's search for Julian based on Bonnie's locator spell and ended up in a town outside Mystic Fall. They end their search at a bar filled with dead men dress as Santa with Julian arriving later, and there is a tiff between the brothers and him which later worsens back home. Meanwhile, Nora becomes friendly with Bonnie during a toy drive. Alaric fears that Caroline is struggling with her pregnancy as her feeding urges keep her on the edge. Valerie teams up with Stefan to abduct Mary Louise in order to force Julian to come out in the open and fight. The fight between the Salvatore brothers and Julian finally leads to Damon being stabbed by the Phoenix stone dagger and getting trapped in his hell. The same happens to Stefan as a revengeful Nora stakes him too after siphoning out Bonnie's magic. It is shown that Damon is reliving his Civil War days while being trapped inside the Phoenix stone where he is gravely injured and scared.
Three years into the future, Stefan is seen in a storage unit opening a casket containing a desiccated Damon. After reviving Damon against his wishes, Stefan proceeds to tell him that his scar opened up which means that "she's back" when they are attacked by an old (yet unknown)foe. Caroline is seen working at a TV station in Dallas, Texas when her assistant informs her that she got a call from her fiancée that he's planning a trip back to Mystic Falls. When Caroline hears that, she says they cannot go back there. Later, when her assistant tells her that she got a call from Stefan, she responds angrily citing never to accept calls from him. She and her assistant are then shot with stakes by an unknown person. Tyler is seen driving around in New York City when he gets a call from a frantic Stefan, who tells him that his scar opened up and that he needs Tyler to get hold of Caroline to warn her as she's not taking his calls. Stefan is about to leave town and sets his beloved car on fire. Alaric is seen trying to fix a teddy bear revealing that he is the father of two daughters. When they become quiet, he goes to the front door and sees them looking at Damon, who threatens Alaric in order to be let in. Bonnie is living in a mental institution and during a group session, expresses guilt for what she has done in the past. When she goes back to her room, she finds Enzo, who tells her that she needs to come home. They then passionately kiss. Damon and Rick are in deep conversation about his twins when Caroline appears on television bloodied announcing there is a message for Stefan Salvatore. Damon is held captive by some woman whom he hallucinates as Lily; he asks for forgiveness as he bid her goodbye in the harshest possible way. At the end of the episode, the unknown woman says that Lily's been dead for years and that Damon will die soon as he has been poisoned with werewolf toxin. She kicks him in his face knocking him out. Stefan is picking up some stuff from Valerie's place in Chicago and borrows her car to travel to Dallas to rescue Damon. She wants to go with him, but he refuses to let her come along. Valerie says that if something should happen to him, she will rain hell down on anyone responsible, and they part with a kiss.