Cheri is an innocent fourteen-year-old raised in a small town in Nebraska. Her father lands a promotion, demoting her to a status of ‘nobody’ in a much larger and inhospitable city. One of the few people she connects with in her new school spills the beans that Cheri is still a virgin. Some of her cool schoolmates frown on that condition and exert pressure on her to ditch her inhibitions. Faced with the loneliness of the new environment coupled with relationship problems with her father, Cheri finds the temptation growing strong. When her father assigns an older babysitter, she is ready rebel. However, she finds that Jean Macalester is no ordinary sixty-year-old, especially to a girl with aspirations of resuming a love affair with music. Jean's womanly wisdom, background as a flute teacher, and love of God provide a counterweight to the peer pressure of Judy Green, the girl who goes on a personal crusade to convert Cheri to coolness. When Cheri and Duke Williams, Cheri's new crush, discover the church youth group planning a chastity pledge, they have to decide whether to join. In addition to dealing with guarding her own purity, Cheri tries to help friends in distress, win top chair in the flute section of the band, and set her dad up with her teacher from the chastity class .