Wrestling with whether or not to tell Elena about the cure, Damon brings up their future together and what life would be like if they weren’t vampires. Meanwhile, it’s all hands on deck when attempts to stop a humanity-free Caroline doesn’t go as planned. Elsewhere, when Bonnie discovers that Damon has betrayed her trust, she takes matters into her own hands, setting off a chain of events that leaves Damon dealing with the fallout. Lastly, after being forced to face his traumatic past, Enzo sets out for answers and is surprised when he learns the truth about the day he was turned into a vampire.
Holding on to Hell — Gin Wigmore
(0:00) Stefan takes Caroline to a B&B where he pretends his humanity is still off. (Flashback) Stefan, Damon and Elena discuss the plan to get Caroline to turn her humanity back on.
Cocoon — Catfish and the Bottlemen
(0:09) At the Mystic Grill, Matt calls Bonnie when Lily arrives early for their lunch date. Bonnie tells him to tell Lily that she is running late. Enzo arrives.
Ready — Kodaline
(0:15) Lily awkwardly orders food.
Madman — Peter Cornell
(0:18) In the bathroom, Matt changes his dressing and shirt.
This World — Lena Fayre
(0:34) Caroline looks through victim reports of the people she murdered and Stefan and Caroline talk.
Can't Take My Eyes Off You — Cary Brothers
(0:38) Lily breaks down in Enzo's arms. Damon tells Elena that he'll take the cure with her.