Robin and Barney make their relationship official but Barney is finding it hard to adjust from being a bachelor to having a relationship. Robin worries whether Barney is capable of being in a relationship and Ted overhears and tells Barney. Will Barney try harder in his relationship?
After spending a passionate summer with Damon and ensuring that Jeremy is adjusting to his return from the dead, Elena moves into Whitmore College with Caroline; a student named Megan shows up in Bonnie's place at the dorm.
Damon asks Matt and Jeremy to keep Elena's doppelganger Katherine out of sight while Silas searches for her but the situation quickly spirals out of control, while Elena tries to get to the bottom of her new college roommate's death after receiving some information from fellow student Jesse.
Elena is intrigued by the story of sad and secretive fellow student Aaron and, at the Whitmore Historical Ball, Elena shares a dance with Dr Maxfield, who has a disturbing message for her. Meanwhile, Stefan's doppelganger Silas demands that Damon commit an unthinkable act, leading to a violent confrontation.
Damon and Elena try to explain her doppelganger Amara's situation to Stefan and Stefan makes a confession to Damon and Elena.