Skipped Parts (2000)

Synopsis
In this comedy-drama, a teenage boy gets a crash course in the mysteries of love and sex. Lydia Callahan (Jennifer Jason Leigh) had her son Sam when she was only 14 years old. Now 14 himself, Sam (Bug Hall) finds himself in the small community of GroVont, WY, after his mother is run out of town by her own father (R. Lee Ermey). While Lydia is helped through her transition by Hank Elkrunner (Michael Greyeyes), Sam doesn't fit in at school and runs afoul of bully Dothan Talbot (Brad Renfro). But he soon makes friends with classmate Maurey Pierce (Mischa Barton), who makes an unusual proposal: since she doesn't want to seem inexperienced when she loses her virginity, perhaps Sam could help her practice the finer points of sex. While Sam is more than willing to help, this arrangement creates complications that his fantasies about his Dream Girl (Drew Barrymore) have not prepared him for. Skipped Parts is based on the novel of the same name by Tim Sandlin. ~ Mark Deming, All Movie Guide