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 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.