Elena Gilbert and her brother Jeremy come to terms with the death of their parents. Elena is popular amongst her peers and the perfect straight A student, but has difficulties hiding her grief from the world. Meanwhile, Jeremy treads on a dangerous path of using drugs to ease his pain. The arrival of new student Stefan Salvatore, however, makes Elena think about romantic possibilities.

Stefan has his own ideas about Elena’s new plan for the future. While Damon tries to get the truth out of Jules, he asks Elena to keep an eye on Rose, a situation that turns unexpectedly dangerous. Caroline and Matt try to be honest about their feelings for one another, and Tyler’s reaction to Caroline’s generosity comes as a surprise to her... Damon struggles to hide his true feelings when a life-and-death crisis hits him harder than he expected.

Stefan tells Elena about a dark time in his history and the surprising person whose influence changed everything. After getting the truth out of Luka, Jonas makes his feelings clear to Bonnie and Jeremy. Trying to catch Elijah off-guard, Damon arranges a dinner party for him with Jenna, Alaric and Andie, but last-minute information throws Damon’s plan into chaos.