A FLASHBACK TO NEW ORLEANS IN 1942 — When Stefan ({Paul Wesley) confronts Damon (Ian Somerhalder) with a suspicion about Elena (Nina Dobrev), Damon has no choice but to help Stefan investigate. Searching for answers, Damon and Stefan visit modern day New Orleans to see if they can find anyone who remembers the events of their last visit in 1942, including one of Damon’s former flames, Charlotte (guest star Madeline Zima). Elena, Caroline (Candice Accola) and Bonnie (Kat Graham) share a girls’ night while the Salvatore brothers are out of town, and emotions run high when Elena delivers some shocking news. At Hayley’s (guest star Phoebe Tonkin) urging, Tyler (Michael Trevino) confronts one of Klaus’ hybrids, Kimberly (guest star Alyssa Diaz), and the situation quickly escalates into violence. Finally, Damon is faced with a heartbreaking decision. Jesse Warn directed the episode written by Charlie Charbonneau & Jose Molina (#408).