When Stefan confronts Damon with a suspicion about Elena, 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. Elena, Caroline and Bonnie 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 urging, Tyler confronts one of Klaus' hybrids, Kimberly, and the situation quickly escalates into violence. Finally, Damon is faced with a heartbreaking decision.

Appearing unexpectedly at Mystic Falls High, Rebekah wastes no time trying to force Stefan, Elena and Caroline to answer her questions about the search for a cure, leading to a bombshell piece of information from Elena. When Bonnie's father, Rudy Owens, accepts the role of Interim Mayor, he makes it a priority to protect his daughter, who isn't at all comfortable with the role he suddenly wants to play in her life. Professor Shane continues to encourage Bonnie to believe in her powers, but he soon finds himself in danger when he reveals too much to the wrong person. Later, Caroline does her best to comfort Tyler after a violent confrontation. Meanwhile, at the lake house, Damon and Matt train Jeremy, trying to raise his game as a hunter, but Klaus is impatient with their progress and intervenes to speed up the process.