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Connor continues his search to uncover the secrets of Mystic Falls and tries to convince Jeremy to work with him. With Dr. Fell’s help, Damon and Klaus question Connor, but the confrontation takes a lethal turn. Trying to keep her new life as normal as possible, Elena is determined to continue her senior year at Mystic Falls High with support from Matt and Caroline. Rebekah’s arrival at school makes it difficult for Elena to control her anger, but she learns that confronting Rebekah can be extremely dangerous. Later, Rebekah realizes how alone she is, and reaches out to April. Stefan takes Elena on a thrilling motorcycle ride in an effort to show her that life can still be fun. Tyler gets a surprise visit from Hayley, a werewolf who helped him through the ordeal of breaking his sire-bond to Klaus. Concerned about Elena, as well as his own emotions, Stefan turns to a sympathetic Caroline for advice.
Liz and Jack find themselves battling to influence voters in the upcoming presidential election. Meanwhile, as Jenna goes to great lengths to please her new fan base, the writers seek out new ways to mess with her.
The gang celebrates Halloween at Stuart’s comic book store. Meanwhile, Leonard seduces Penny with science.
Even though he despises bankers, Holmes agrees to consult on a case involving the death of a Wall Street executive who appears to have overdosed on heroin. Meanwhile, with Holmes’ encouragement, Watson tries to re-enter the dating scene.
As Halloween approaches, the Hecks get quite the scare when Sue receives her learner’s permit, and it’s time for Frankie and Mike to teach her how to drive. But when a freaked-out Sue loses her nerve, she ends up running over Axl’s foot, which could put an end to his high school football career and his hopes for a scholarship. Meanwhile Axl looks forward to voting in his first election, and Brick undergoes an unexpected transformation when he eats too much Halloween candy.
When a famed music historian is murdered and left in a piano, it has an emotional effect on Sanders, who had a past with her.
When the drunk driver who hits a car and paralyzes a 16-year-old boy turns out to be the son of a dirty cop, Lieutenant Casey must decide whether or not to turn him in. Facing pressure and subsequent threats from the powerful and well-connected Detective Voight, Casey decides to tell the truth, inviting a stand-off. Additionally, Severide, who’s fighting off the advances of the Chief’s new assistant, learns he has a fractured vertebra in his neck that may never heal if he doesn’t get treated, but ignores the doctor’s advice so he can continue working.
