Age of Innocence

Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother. The trio searches for and meets the last heretic, Oscar, who used the pretext of a mission for Lily to defect from the group. Damon asks for Oscar's help in siphoning magic from Bonnie who is still getting horrible visions after touching the Phoenix Stone. Oscar refuses to help when he finds out about the stone, fleeing after knocking Alaric and Bonnie unconscious, and breaking Damon's neck. The trio captures Oscar and makes a deal with Lily in exchange for Elena's coffin. Meanwhile, Caroline, still being held hostage by the Heretics, learns some information about Valerie's past. Flashbacks to 1863 show Valerie meeting Stefan for the first time. Valerie was sent by Lily to check on her son, but she and Stefan fell in love and enjoyed a sensual evening together. When Valerie was forced to leave by her chaperone, Julian, she promised Stefan she would return. As Valerie tries to do just that, she is found out by Julian, who beats her so badly she loses Stefan's unborn child before dragging her to the ship. There, Valerie killed herself which turned her into the very first heretic as she had died with Lily's blood in her system. At the same time, Stefan learns a few unexpected details about his own past from Lily about how she first met Valerie. Also, Alaric turns to Bonnie for her help after admitting that he still has the Phoenix Stone, which can bring the dead back to life. Lily sets Caroline free out of admiration for Stefan's honesty with her. Valerie kills Oscar because he has found Julian, the murderer of her baby and the love of Lily's life.

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Flashforward: Three years later, Tyler is seen driving around in New York City when he gets a call from a frantic Stefan, who tells him that his scar opened up and that he needs Tyler to get hold of Caroline to warn her as she is not taking his calls. Stefan is about to leave town and sets his car on fire.

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