Shane Callahan

Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire (recurring guest star Claire Holt – Pretty Little Liars, H20: Just Add Water), 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, he and Elena follow their trail. Meanwhile, back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes (recurring guest star Marguerite MacIntyre) for help.

As she looks for Owen (Lex Medlin) following his wedding day heart attack, Jane (Brooke Elliott) fights to stop a drug company from discontinuing the drug trial that is keeping an eight-year-old cancer patient alive. Meanwhile, Kim (Kate Levering) represents a high school friend whose vengeful ex has posted nude photos of her on the Internet.

Ichabod and Abbie fight against those who want to re-awaken a powerful witch coven and Jenny learns a disturbing truth about Frank Irving.

Selina is annoyed by the press' reaction to her running mate's charm; Selina decides to attend a fundraiser without her team; Amy tries to adjust to her new life; Jonah gets ambushed.