Todd Lasance

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.

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.

In order to get through to Lily (recurring guest star Annie Wersching) about Julian's (recurring guest star Todd Lasance) manipulating ways, Stefan and Damon confront their mother with painful memories from their childhood. However, when Lily reveals a dark secret she's been harboring for over 160 years, Stefan and Damon are left questioning everything they've ever known about their family. Determined to prove himself to Lily, Enzo comes face to face with Julian and challenges him to a duel, but an unexpected twist threatens to complicate things. Elsewhere, Matt finds himself in the middle of a deepening mystery involving the residents of Mystic Falls, and Caroline's world is turned upside down when Valerie (recurring guest star Elizabeth Blackmore) reveals some life-changing news to her.

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.