On the first day of their senior year, Elena, Caroline, Bonnie and Matt are still reeling from recent events, while Tyler seems to be enjoying everything a little too much. Damon is annoyed by a new houseguest, and everyone is surprised by the arrival of a new student in Alaric’s history class. Matt asks Bonnie for help when he realizes he made a serious mistake. Meanwhile, Stefan continues to carry out his latest assignment from Klaus.
Despite all that has happened, Caroline is determined to see that Elena, Bonnie, Matt and Tyler all enjoy a traditional Senior Prank Night before the school year begins at Mystic Falls High School. However, when uninvited guests shows up, it doesn’t take long for the evening to take a deadly turn. Damon convinces Jeremy that he can use his new connection to the other side to help find a way to defeat Klaus. Klaus deepens his hold on Stefan and uses him for increasingly violent and dangerous purposes involving Elena too. And finally, Tyler and Caroline's relationship will suddenly be in danger.
Still in Chicago, Klaus (Joseph Morgan) uses Gloria (guest star Charmin Lee), a witch he knew long ago, to help him track down missing information that will explain why his plan isn’t working. Gloria’s spells reveal intriguing glimpses of the truth, but she soon realizes she needs Stefan’s (Paul Wesley) knowledge to complete the puzzle. When Stefan suddenly finds himself in danger, help comes from a surprising ally. Back in Mystic Falls, a frustrating new enemy pushes Damon (Ian Somerhalder) over the brink and he lashes out in a way that will have lasting consequences. Caroline (Candice Accola) struggles with her own emotional issues, even as she tries to help Elena (Nina Dobrev) face her feelings. Jeremy (Steven R. McQueen) makes a brief but disturbing breakthrough with one of his ghostly visitors, leaving him more confused than ever. Finally, Bonnie (Kat Graham) has a strange encounter that will affect everyone. Matt Davis also stars. Wendey Stanzler directed the episode written by Brian Young
Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire who hasn’t really moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus’ whereabouts from an unexpected source (Katherine), he and Elena follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help. Stefan also learns that Klaus might be running from someone who may be hunting him.
Elena and Alaric secretly head to Tennessee to find a pack of werewolves, who they believe might lead them to Stefan. Matt and Jeremy team up to summon Vicki's spirit. Alaric tips Damon off to where he and Elena are. Klaus attempts to turn all the werewolves of Ray's pack in to hybrids. But the hybrids not only turn out rebellious but defective, with the newly turned Ray escaping Klaus and Stefan's guard and nearly killing Damon. Upon Carol Lockwood discovering that Caroline is a vampire, Caroline's father Bill is summoned to Mystic Falls.
Klaus and Stefan begin hunting for one of the oldest werewolf clans so that Klaus can turn them into vampires in order to continue the breed of hybrids. Stefan and Klaus find out that Damon has been tracking them down through the reported killings and animals attacks mentioned in newspapers and other sources. Stefan goes back and gives Damon a 'warning' to back off by killing Andie, Damon's semi-compelled girlfriend, after compelling her to fall off a high platform. Meanwhile, Elena's 18th birthday arrives and Caroline holds a party for her. During the party, Jeremy continues to see the ghosts of Anna and Vicki, but keeps it to himself. He eventually admits the hauntings to Matt, though Matt jokes and brushes the matter off. Alaric, who has settled as Elena and Jeremy's guardian after Jenna's death, decides to move out of their house, as he considers himself a bad role model for them. Elena finds out about Damon's plans to find Stefan, without notifying her and confronts him, though he is already upset by Andie's death and Stefan's change of attitude. Caroline becomes jealous of Tyler's date Sophie at Elena's birthday party and compells her to leave. Tyler then confronts her about their issues, they end up kissing eachother and leaving the party for Tyler's house. In the morning, Caroline attempts to leave the Lockwood household quietly but is caught by Mrs. Lockwood. As Caroline grabs her purse to leave, her skin suddenly burns as it turns out the purse had been spiked with vervain. This confirms Mrs. Lockwood's suspicions that Caroline is a vampire. Mrs. Lockwood then shoots Caroline several times with vervain darts, leaving her unconscious.
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