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.

Elena’s new outlook has everyone concerned, leading Stefan and Damon to agree that going back to the normal routine of high school would be the best thing for her. Caroline is pleasantly surprised when Elena decides to rejoin the cheerleading squad, but her pleasure turns to shock when Elena’s behavior proves dangerous. Not giving up on their search for the cure, Damon and Rebekah work together until his unwanted advice catches her off-guard. Klaus tries to use Hayley to get the information he’s after and makes an intriguing discovery in the process. Meanwhile, a bored Elena throws a wild party and gets into an ugly fight.

Elena and Katherine both dream that Stefan is in danger and convince Damon to help them find him. But their plans are thwarted by a mysterious woman who seems to know everything about Stefan's past and Damon's disturbing future.

As Alaric and Jo reluctantly participate in their bachelor and bachelorette parties, Damon and Elena discuss the ramifications from an impulsive offer that Damon makes. Unsure of what to do, Elena turns to Bonnie and Jo for advice, but is left conflicted when Bonnie raises some unanticipated concerns. When Enzo realizes Lily is on a dangerous downward spiral, he asks Stefan to help intervene before it’s too late. Lastly, fed up with the supernatural threats that plague their town, Matt takes his frustrations out on Tyler, while Alaric considers a life-changing piece of advice.