Damon tries to find the right way to make a disturbing confession to Elena. Caroline discovers a scary secret in Dr. Wes' files. Enzo claims to have a solution everyone is searching for. Sloan reveals new information on the importance of doppelgangers.

After a twisted plan left the life of his girlfriend Elena linked to that of his best friend Bonnie, Damon is forced to navigate his new reality without the love of his life. A newly empowered Bonnie has decided that she will be Damon's moral compass and keeps a close eye on him as he, in turn, cautiously keeps tabs on Alaric, following the loss of his fiancée Jo. Meanwhile, as he waits for Caroline to sort out her emotions, Stefan takes an active role in protecting the town from Lily and her family of Heretics, who have wasted no time wreaking havoc in Mystic Falls.

Elsewhere, Enzo struggles to find his place in Lily's new life, and is quickly forced to decide where his true loyalties lie. Finally, with the stakes higher than ever, Matt, who has recently completed his deputy training program, teams up with Stefan and Caroline to put a stop to the Heretics, but an unexpected turn of events leaves one of them in a dangerous position.

When his experience in the Phoenix stone leads him to do the unthinkable, Damon finds himself without a care in the world, spiraling out of control and under the influence of a dangerous and reckless Julian. Refusing to give up on his brother, Stefan attempts to reason with Damon only to uncover the devastating reason for his descent.

Elsewhere, Caroline begins having some dangerous side effects as a result of her supernatural pregnancy and is forced to turn to Valerie for help. Meanwhile, Bonnie, Nora and Mary Louise attempt to track down a ruthless vampire hunter named Rayna after they suspect that she has reemerged.

After learning that someone from Stefan’s past may be Damon and Enzo’s next target, Stefan, Bonnie and Caroline head to North Carolina. There, Bonnie takes drastic measures in an attempt to break Enzo free of whatever has a hold over him. At the Armory, Alaric and Georgie stumble upon a mysterious symbol that may be related to the supernatural force controlling Damon and Enzo. Finally, Caroline gets an unexpected surprise from Stefan.

Damon and Stefan must join forces against Cade in order to save Elena’s casket. Meanwhile, Caroline and Alaric deal with their daughters’ burgeoning magical powers.