Jaiden Kaine

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.

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.

After being reunited with her former love Julian (guest star Todd Lasance), Lily (recurring guest star Annie Wersching) hosts a dinner party to introduce him to Damon and Stefan and to declare peace between her family of Heretics and the residents of Mystic Falls. Damon and Stefan find themselves at an impasse when they realize they have differing views on how to handle Julian's arrival. At the party, Bonnie and Matt uncover a strange mystery involving some unsuspecting residents, while a devastating revelation causes Alaric to reach his breaking point.

As Julian (recurring guest star Todd Lasance) and Lily (recurring guest star Annie Wersching) throw a party to celebrate Mary Louise (recurring guest star Teressa Liane) and Nora's (recurring guest star Scarlett Byrne) anniversary, Stefan and Damon set in motion a risky plan to eliminate a new threat posed by Julian. Meanwhile, following a major revelation uncovered by Valerie (recurring guest star Elizabeth Blackmore), Caroline is forced to face her new reality, even as it threatens to destroy her relationship with Stefan. Finally, determined to do what's best for her family, Lily makes the most difficult decision of her life.