Just as Damon thinks he's gained the upper hand in his fight against Lily, 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 and Nora, 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 is hiding, while a plan set by Alaric and Bonnie leaves their worlds turned upside down.

After finding himself on the wrong end of Julian's plan to avenge Lily's death, Damon awakens to find himself trapped inside the Phoenix stone, tormented by a traumatic experience from his time in the Civil War and forced to face his darkest demon in order to get out. On the outside, Bonnie is in a race against the clock to get Damon out before the effects of the Phoenix stone take over and leave him changed forever.

When Damon's risky attempt to save Bonnie takes an unexpected turn, the consequences of his actions forces everyone to band together to help her pull through. Meanwhile, when a new threat leaves Caroline's life in jeopardy, Stefan makes a rash decision that ultimately forces them to face the fallout from their relationship. Elsewhere, Enzo tries to hold it together as he painfully watch Bonnie in the fight of her life, while Matt takes matters into his own hands to save one of his closest friends.

Tasked with finding a mysterious artifact, Damon’s latest mission takes him to Texas where a violent run-in with Peter Maxwell leads to a surprising revelation. Meanwhile, after gaining the upper hand in their fight to save Damon and Enzo, Stefan and Alaric team up and uncover the origins of the mysterious force they’re up against. Finally, Matt returns to the fray after his past and present collide in an unexpected way.

Stefan and Damon return to Mystic Falls at Sybil’s request as she is still in search of the historical artifact. Bonnie returns from Paris wearing a vile of Enzo’s blood making Caroline, wonder if she will become a vampire. Stefan, Damon, Caroline, Bonnie and Enzo all attend the Miss Mystic Falls pageant where Sybil continues to taunt Damon with memories of Elena.

Damon and Alaric come face to face with an old enemy after they obtain a weapon that may be able to destroy Cade. Stefan is held captive by a surprising acquaintance and is forced to confront a dark secret from his past. Meanwhile, Caroline and Matt try to keep Stefan’s violent history from destroying him. Cade focuses his attention on Bonnie and digs deep into her mind.