Brandy Klark (Aubrey Plaza), from Boise, Idaho, is an overachieving but socially awkward teenager who graduates as the valedictorian of her high school in the summer of 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. At the party, Brandy makes out with a 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”. Brandy gets a job at the local pool as a lifeguard so as to be closer to Rusty, along with her study-buddy Cameron Mitchell (Johnny Simmons). As the newbie, she is hazed by her slacker boss, Willy (Bill Hader), and her other co-workers by being given the most unpleasant jobs, including fishing a turd out of the pool. She assumes her co-workers are playing a prank on her, based on the Baby Ruth joke from the film Caddyshack, so she takes a bite of it only to find that it really is feces. Embarrassed, she pushes Willy into the pool as revenge and learns that he does not know how to swim, despite managing a swimming pool. She agrees to teach him how to swim in exchange for ending the hazing. Brandy gets advice from her sister, Amber (Rachel Bilson), and her mother (Connie Britton), as well as her two best friends, while her father (Clark Gregg), a judge and devout conservative, is uncomfortable with the talk of sex, especially since his wife is more sexually experienced than him. Using this information, she makes a “to do list” of sexual acts to learn and perform. As the summer progresses, Brandy has several sexual encounters with Cameron and other boys, all while trying to catch Rusty’s eye. Cameron begins to fall in love with her but is crushed after discovering her list and realizing he was just part of her “mission”. Meanwhile, Willy catches Brandy, Wendy, Fiona, and adult members of a male grunge band in the pool after hours. After a scolding, Brandy is sent home where she is confronted by Cameron over the list. Cameron leaves in a huff and Brandy starts to cry. An ex-boyfriend of Wendy’s comes over to comfort her and the two have a hookup. When Wendy and Fiona come over to watch the film Beaches with Brandy, they discover her list and see the list of boys with whom she had experimented. They get upset after finding out that Brandy hooked up with one of their ex-boyfriends and leave angrily. They declare that Brandy has failed to put “hoes before bros” and call her a slut. Brandy finally gets close to Rusty when they vandalize a rival pool, but they get caught because Brandy leaves her bra, with her name on it, at the pool. Willy is then forced to fire her. Brandy asks out Rusty, and he takes her to a popular make-out spot to have sex. However, the sex is brief, which disappoints Brandy. She sees her father and mother in the Dodge Caravan next to them having sex, causing her to freak out and demand that Rusty take her home immediately. Meanwhile, Willy goes to the Klark house to stop Brandy from having sex with Rusty, but is met at the door by Amber, who immediately seduces him. When Rusty and Brandy arrive home, a jealous Cameron is there to meet him with a sucker-punch, and they fight until Brandy breaks it up. She compliments them on their good qualities, apologizes sincerely to Cameron for using him, and offers her own view of sex. Afterward, she seeks out Wendy and Fiona to apologize to them. She sings “Wind Beneath My Wings” at Wendy’s door, and the two girls eventually join in, forgiving her. Brandy meets up with Willy at the pool, and he offers her his job if she comes back next summer as he has decided to quit and follow the Grateful Dead while Jerry Garcia is still alive. In the fall, Brandy and Cameron meet again at Georgetown University where they have both matriculated. Brandy apologizes to Cameron once more and they agree to try dating. They have various forms of sex in her dorm room and eventually, during anal sex, Brandy finally achieves orgasm, the last thing on her list, right as her father walks in on them.