When his experience in the Phoenix stone leads him to do the unthinkable, Damon (Ian Somerhalder) finds himself without a care in the world, spiraling out of control and under the influence of a dangerous and reckless Julian (guest star Todd Lasance). Refusing to give up on his brother, Stefan (Paul Wesley) attempts to reason with Damon only to uncover the devastating reason for his descent. Elsewhere, Caroline (Candice King) begins having some dangerous side effects as a result of her supernatural pregnancy and is forced to turn to Valerie (guest star Elizabeth Blackmore) for help.
Meanwhile, Bonnie (Kat Graham), Nora (guest star Scarlett Byrne) and Mary Louise (guest star Teressa Liane) attempt to track down a ruthless vampire hunter named Rayna (guest star Leslie-Anne Huff) after they suspect that she has reemerged.
