Brandy Klark (Aubrey Plaza), from Boise, Idaho, is an overachieving but socially awkward teenager who graduates as the valedictorian of her high school in 1993. After the ceremony, Brandy's two best friends, Wendy (Sarah Steele) and Fiona (Alia Shawkat), take Brandy to a party, where she gets drunk for the first time. Brandy makes out with a muscular college boy she has a crush on named Rusty Waters (Scott Porter). Since the room is dark, he mistakes Brandy for someone else and when he realizes who she is, he rejects her. Brandy blames her lack of sexual experience and resolves to learn all about sex over the summer to prepare for college. She decides that her end-of-summer goal will be to have sex with Rusty to complete her "To Do List".