Heartbroken by an unexpected tragedy, Damon is focused on holding himself together, while pushing Bonnie harder than ever to find a way to stop the Other Side from disintegrating.
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.
When Enzo (recurring guest star MICHAEL MALARKEY) brings Damon a gruesome present and insists that they bond by committing an act of revenge, Damon makes an effort to do the honorable thing. After finding himself in awkward and confusing conversations with Nadia (recurring guest star OLGA FONDA), Matt impulsively decides to throw a party, where Caroline makes a stunning confession to Elena, then has to face the consequence of her actions with Stefan and Tyler. Aaron (recurring guest star SHAUN SIPOS) does his best to make amends for his family's past misdeeds and start a new life for himself. Finally, Elena suddenly finds herself in a life-threatening situation with only minutes to figure out how to save herself.
As she faces a new crisis, Katherine remembers the traumatic night in 1490 when she gave birth to the daughter who was immediately taken from her. Stefan lets Elena, Caroline and Bonnie know that Katherine's health has taken a turn for the worse, while Damon, Matt and Jeremy discuss some of Katherine's most notorious moments. Nadia (recurring guest star OLGA FONDA) comes up with a frightening plan to protect her mother, and Stefan and Elena are forced to help her. Meanwhile, Caroline is mortified when she realizes she forgot to fill Elena in on the latest shocking gossip, then indulges in a little scandalous behavior of her own. Finally, Elena and Katherine share an unexpected moment of connection.
Damon realizes Elena is in danger and enlists Stefan's help to find her. The brothers pay a visit to Aaron (recurring guest star SHAUN SIPOS), and Damon shocks Stefan by revealing his first-hand knowledge of Aaron's family. In an attempt to stop Damon, Dr. Wes (recurring guest star RICK COSNETT) unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes' confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine turns to Matt for help, until she realizes that Nadia (recurring guest star OLGA FONDA) may be the one who can solve her problem.
Elena turns to Aaron (Shaun Sipos) for help. Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades. Stefan continues to offer Katherine support.
At Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse (recurring guest star KENDRICK SAMPSON) suddenly needs Caroline's help. At Elena's request, Damon comes up with an effective method to get Wes (recurring guest star RICK COSNETT) to answer his questions. At the party, Elena finds that she and Aaron (recurring guest star SHAUN SIPOS) have a lot in common, and Caroline grows more concerned about Jesse. Meanwhile, Katherine does a favor for Matt and manages to get through to Stefan, who is still struggling to overcome the events of the summer. Finally, Bonnie does her best to cope with her new reality, and Damon makes a terrifying discovery about a secret society.
The power of doppelgangers . . . While Elena and Damon try to explain Amara's (played by series star NINA DOBREV) situation to Stefan, Dr. Wes Maxfield (recurring guest star RICK COSNETT) gives Katherine some deeply disturbing news. Nadia (recurring guest star OLGA FONDA) shows up at Caroline's dorm room searching for Katherine. After a surprising conversation with Amara, Jeremy and Bonnie share a glimmer of hope. Silas fails to keep a promise, causing Damon to turn to Tessa (recurring guest star JANINA GAVANKAR) for help with his new plan, and Stefan makes a heartbreaking confession to Damon and Elena.
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