Instead of attending the homecoming festivities, Caroline is preoccupied after Stefan shows up unexpectedly and needs her help cleaning up a mess created by Enzo.
When Damon and Bonnie realize that uncovering a time in Damon’s past may provide clues to finding their way home, Damon is forced to relive one of the worst days of his life.
In an attempt to bring some fun back into their lives, Elena persuades Caroline to meet her at the swimming hole where she plans to introduce her to Liam.
Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life.
After spending the past four months coping with the loss of Damon in a potentially dangerous way, Elena has returned to Whitmore College for the start of sophomore year.
Trailer to tease next season
In the season finale, Damon's plan causes a huge explosion in Mystic Falls, and everyone is caught up in the confusion, leaving a trail of heroism, sacrifice, relief and despair.
When Stefan and Elena escape from Markos' (recurring guest star RAFFI BARSOUMIAN) control, only to find themselves stranded in a remote location, Stefan gets philosophical with Elena about her relationship with Damon. After their attempt to protect the doppelgangers goes badly, Liv (recurring guest star PENELOPE MITCHELL) and Luke (recurring guest star CHRIS BROCHU) come up with a dangerous new strategy. Damon recruits Matt and Jeremy to help him set a trap for Markos, who turns out to have a devastating surprise of his own. Bonnie finally admits to Caroline that she's been keeping the truth about the Other Side from everyone. Finally, while Bonnie searches desperately for a way to stop Markos, Caroline is witness to an unthinkable act of violence by one of the Travelers.
When Tyler turns up at the Salvatore house with the news that Markos' (recurring guest star RAFFI BARSOUMIAN) plan to break the witches' curse puts Stefan and Elena in imminent danger, Damon suggests they hide out in the remote cabin once owned by Caroline's father. Once there, it becomes obvious to Caroline that Stefan and Elena are keeping a secret, so Damon comes up with a parlor game designed to expose the truth. A ghostly presence at the cabin uses violence and fire to make itself known. Meanwhile, Matt takes charge of Tyler's plan to get information from one of the Travelers, and Bonnie continues to keep the truth about the Other Side from Jeremy, despite warnings from Grams (recurring guest star JASMINE GUY).
Through flashbacks to election night 1960, Enzo (MICHAEL MALARKEY) reveals to Elena, Stefan and Bonnie what happened to his long-lost love, Maggie (HEATHER HEMMENS – Hellcats).
Bonnie has a disturbing encounter with Grams (JASMINE GUY). When Damon finds Markos (RAFFI BARSOUMIAN), he is both relieved and troubled by what Markos has to tell him.
Bonnie has an unsettling encounter with Luke (CHRIS BROCHU), and learns more about his family history. The Travelers' leader, Markos (RAFFI BARSOUMIAN), arrives in Mystic Falls.
When Stefan tries to explain recent events to a very sick Elena, her first instinct is to call Damon. At the same time, Damon is trying to figure out how to make a disturbing confession to Elena. While going through Dr. Wes' files, Caroline discovers a frightening secret, and is surprised when Enzo (recurring guest star Michael Malarkey) appears, claiming to have the solution everyone is searching for. At Enzo's insistence, Caroline asks Stefan to meet her at a mysterious location where they are joined by a group of Travelers, including Sloan (recurring guest star Caitlin McHugh), who reveals new information on the importance of doppelgangers.
While Nadia (recurring guest star OLGA FONDA) remembers her centuries-long search for her mother, Stefan, Caroline and Matt come up with a desperate new plan to save Elena's life. For the second time, Bonnie and Jeremy must turn to Liv (recurring guest star PENELOPE MITCHELL) for help. Damon baits Tyler into a nasty confrontation, then takes off to seek revenge on Dr. Wes (recurring guest star RICK COSNETT). Caroline and Tyler come to a new understanding. Finally, Bonnie learns of a terrifying secret that will threaten the lives of all her friends.
As Damon's behavior escalates from destructive to deadly, Stefan begins to regret their last conversation and decides to track Damon down and intervene. For reasons of her own, Elena volunteers to come along. Dr. Wes (recurring guest star Rick Cosnett) enlists the Travelers to set a trap that will once again test Damon's friendship with Enzo (recurring guest star Michael Malarkey). After a heart-to-heart talk with Nadia (recurring guest star Olga Fonda), Matt enlists Caroline and Tyler's help to protect Elena, leading to a violent confrontation. Later, when Stefan tries to comfort a dejected Caroline, their conversation leads to a horrifying realization.
Hoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student named Liv (recurring guest star PENELOPE MITCHELL – Hemlock Grove), who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia (recurring guest star OLGA FONDA). After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo (recurring guest star MICHAEL MALARKEY). Dr. Wes (recurring guest star RICK COSNETT) struggles to continue his research project with help from a new benefactor named Sloan (recurring guest star CAITLIN McHUGH). Still bent on revenge, Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them, but their plan takes an unexpected and horrifying turn.
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