This is the year that Lily is leaving for Europe and we are introduced to Julian. She is telling the story to Stefan while Valerie tells Caroline her side. Lily describes Julian as a vampire gentleman friend and that she wanted to make sure her boys were safe before she left. So she sent Valerie to check on Stefan and Oscar to check on Damon. Both were just witches so they couldn’t compel Lily’s sons to do what they want. Oscar was able to talk Damon out of fighting with the south and Valerie was able to make Stefan fall in love with her. After the fair, Valerie takes Stefan’s virginity. Afterwards he takes her to his mother’s grave. He tells her he blames himself for her death. His father sent him to get flowers for an herbal tonic, but Stefan didn’t make it home before she was taken to the infirmary. Julian arrives to pull Valerie away. Valerie tells Stefan that she will find a way back to him.
Valerie says she sent Stefan a telegraph saying she would meet him. Stefan waited and waited, but she never showed. Valerie tells Caroline there was a change of plans, but we get to see what happened next. She told Stefan to meet her the day Lily was setting sail for Europe. Valerie didn’t want to go, but Julian knew if she didn’t go, Lily wouldn’t go. So he takes away her amulet of witch power and then beats her so hard that he killed the unborn Salvatore baby she was carrying.
Stefan didn’t know why Valerie never showed, but he tells Lily he’s not mad anymore. He goes to sit on the same bench where he waited for Valerie all those years ago and she shows up next to him. She tells him how Julian told Lily he found her robbed and beaten so Lily healed her with her blood. Valerie didn’t want to live any longer with Julian so she took medicine and drowned herself in a bathtub. Valerie became the first Heretic. But Stefan doesn’t hear any of this because Valerie has cloaked herself.
Caroline is freed by Lily and asks Stefan if he still has feelings for Valerie. He says things have changed.
Damon and his team are hunting down the sixth heretic, Oscar. Damon plans to trade Elena’s coffin for Oscar’s body. Bonnie hopes Oscar can siphon away the visions she’s having. But Oscar doesn’t need capturing. He is a party boy who knows who Damon is.
Damon offers not to tell Lily that Oscar is avoiding his mission as long as he siphons away Bonnie’s pain. He agrees and then asks where the Phoenix Stone is and then knocks them all out.
When they wake Alaric is missing his Phoenix Stone and Bonnie realizes he didn’t destroy it like he said. They track Oscar down and work together to knock him out. They retrieve the Phoenix Stone, but Bonnie warns Alaric that Jo’s spirit might not still be around. But Alaric takes Bonnie to the morgue where he shows her Jo’s body.
Damon calls Lily and tells her about Oscar. He says he understands she grieved her own family and moved on to another. And he has too he says as he glances at Alaric and Bonnie.
Valerie finds Oscar with a tracking spell. She knows Oscar’s mission was to find Julian, and she can’t let that happen, so she rips his heart out.
3 Year Later
Stefan calls Tyler and asks him to warn Caroline about this mysterious woman.