In the season premiere, Damon is forced to navigate his new reality without the love of his life. Stefan takes an active role in protecting the town from Lily (Annie Wersching).
When an impulsive decision by Damon threatens to unravel a carefully negotiated deal between Stefan and Lily (recurring guest star Annie Kersching), he has no choice but to make amends with his mother before things spiral further out of control. However, Lily remains one step ahead and carries out a harsh plan that hits Damon where it hurts most. Elsewhere, after returning to Whitmore Collage, Alaric turns to Bonnie for help with a mysterious and potentially dangerous artifact he has obtained, while Matt is forced into making a risky life or death decision. Meanwhile, Caroline, who finds herself a pawn in Lily and the heretics' plan for retribution, uncovers a shocking detail about Stefan's past.
In the aftermath of a clever plan orchestrated by Lily (recurring guest star Annie Wersshing), Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother. Meanwhile, Caroline, who is being held hostage by the Heretics, learns some shocking information about Valerie's (recurring guest star Elizabeth Blackmore) past, while Stefan learns a few unexpected details about his own past from Lily. Finally, Alaric turns to Bonnie for her help after coming clean about a secret he's been keeping.
Just as Damon thinks he's gained the upper hand in his fight against Lily (recurring guest star Annie Wersching), an unexpected turn of events leaves him scrambling for a "plan b." Elsewhere, when the fallout of Damon's actions gains the unwanted attention of Mary Louise (recurring guest star Teressa Liane) and Nora (recurring guest star Scarlett Byrne), Stefan and Caroline are forced to spend the night distracting the girls at Whitmore College's Heaven & Hell ball. Finally, after suspecting that she's up to something, Enzo sets off on a mission to find out what Valerie (recurring guest star Elizabeth Blackmore) is hiding, while a plan set by Alaric and Bonnie leaves their worlds turned upside down.
After realizing the downward spiral he was on, Damon decides he's going to turn over a new leaf and that his actions moving forward will do right by Elena. Lily (recurring guest star Annie Wersching) prepares for the arrival of a special figure from her past, while Enzo stands by not sure what to expect. Elsewhere, at Caroline's urging, Stefan comes face-to-face with Valerie (Elizabeth Blackmore) and learns some upsetting details about her past, while Enzo and Bonnie find themselves at odds when they're forced to fend off a violent threat. Finally, when Bonnie learns some disturbing information involving the Phoenix stone, she is forced to confront Alaric.
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