Sutter Keely is a charming and popular 18-year-old who has spent his senior year of high school partying and drinking alcohol. When his girlfriend Cassidy Roy breaks up with him, Sutter goes home and writes a college application supplement, in which he says that his biggest hardship in life has been getting dumped by her. He goes out and gets drunk.
He is woken up on a front lawn by Aimee Finecky, a girl in his year whose name he does not know. Aimee is in the middle of her mother's paper route, and Sutter joins her to track down his car. The next day, he asks her to tutor him in geometry. He learns that she is smart, funny and into sci-fi and comics. Sutter goes home and deletes the supplement he wrote about his life's biggest hardship. He takes Aimee to a party the next day, and they go for a walk and drink. Aimee confesses she has never been drunk before, never had a boyfriend and does not think she can go to college because she has to take care of her mother. Sutter tells her she is not responsible for her mother before complimenting and kissing her.