Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother. The trio search for and meet the last heretic, Oscar, who defected from Lily’s group. Damon asked for Oscar’s help in siphoning magic from Bonnie who was getting horrible visions after touching the Phoenix Stone, but Oscar refuses when he finds out about the stone, knocking Alaric & Bonnie unconscious and breaking Damon’s neck. The trio then capture Oscar and make a deal with Lily 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 and showing how they fell in love. In actual fact, Valerie was sent by Lily to watch out for her son but they fell in love. When Valerie planned to run away while pregnant, Julian beat her & brought her back 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 coming clean that he 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.

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