One night while out driving with Aldys, Josie encounters Guy and his gang at a local hangout called "The Court" where promiscuity and underage drinking take place. Her managing editor Augustus "Gus" Strauss (John C. Reilly) loses patience with Josie after a rival paper scoops The Court story, and orders Josie to become friends with the popular kids. He arranges for her to wear a hidden camera, and soon the whole office becomes obsessed with her story.
Josie confides in her brother Rob (David Arquette) about her fears. Rob, who was their high school's most popular boy in his teens, urges her to let go of her old self and start anew. To help her, Rob enrolls as a student and becomes an instant hit. He then uses his influence to draw Josie into the cool crowd, much to the dismay of Aldys.