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?
It's Fashion Week in New York and Betty is hustling to ensure Mode's runway show goes off without a hitch. To Betty's dismay, Daniel offers Hilda a job helping out with the show.
After a passionate summer with Damon, Elena heads to college nearby with Caroline as her roommate. Meanwhile, Elena can't shake the feeling that something is wrong with Stefan, and Silas makes a terrifying appearance at the "End of Summer" party in the town square.
Without telling Elena that Stefan is missing, Damon turns to Sheriff Forbes for help finding his brother. Elena and Caroline try to find out who is covering up a campus murder, and a fellow student gives Elena some intriguing information about Professor Wes Maxfield.
Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student dabbling in witchcraft. Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them get revenge.