In 2002, Lainey causes a scene in a dorm at Columbia University. Taking pity on her as she is about to be kicked out by security, Jake claims her as his guest. He learns that Lainey was there in order to lose her virginity to her T.A., Matt, who Jake thinks is the most boring guy in the world. Lainey eventually realizes that Jake is also a virgin, and the two lose their virginity to each other.