Set in Nelsonville, Ohio in 1956, Eugene "Gene" Harbrough—a bold, extroverted nonconformist—moves from Chicago and ends up living next to the introverted, clumsy Jonathan Bellah. The two quickly form an unlikely friendship, and Gene decides to take Jonathan under his wing, teaching him how to attract women. Through patient coaching and a steady stream of impulsive escapades, Gene promises to show Jonathan the social dance of dating and the confidence he needs to shine.
Jonathan Bellah [Doug McKeon] is determined to win over Marilyn McCauley [Jami Gertz], a sexy, popular girl who seems out of reach to his shy, awkward self. Gene proclaims that he can guide him to victory within a month, turning Jonathan's longing into a plan and a series of practical steps to seize opportunities, read signals, and project self-assurance. Marilyn becomes more than a distant crush as Jonathan starts to grow more at ease in social settings, and the two begin to connect in a way that surprises even them.
Gene also has his own romantic pursuit, with Bunny Miller [Kelly Preston], who reciprocates his feelings. As he juggles his budding relationship with Bunny and the mentoring of Jonathan, he defends both of them from Kenny, a wealthy class bully whose jealousy and swagger threaten their progress. The tension between Gene’s impulsive, free-spirited nature and Kenny’s domineering attitude adds a sharp edge to the town’s social scene, culminating in moments that test Gene’s loyalty to his friend and his own ideals.
A confrontation at the drive-in leads to a dare that Kenny issues—center line chicken with their cars. Neither man backs down, and both cars end up damaged. Gene’s father—a widowed man with little patience for Gene’s wild escapades—punishes him harshly, striking a blow that reveals the complicated, sometimes strained relationship they share. This tension fuels Gene’s drive to prove himself, even as he wrestles with fairness and responsibility.
Jonathan offers unwavering friendship, and Gene, in turn, helps him build self-esteem. Marilyn agrees to go out with Jonathan, and they become deeply involved, discovering a connection that offers Jonathan a taste of the life he once believed was beyond his reach. Meanwhile, Gene’s relationship with Bunny continues to grow, with Gene dreaming aloud about a future of owning a horse stable—a symbol of independence and a life chosen on his own terms.
A late-evening diner scuffle incited by Kenny results in significant damage to the premises, and Gene’s father responds by kicking him out of the house. Gene disappears for weeks, only to reappear on prom night. He and Jonathan arrive at the prom without tuxedos, and Marilyn ends up going with her ex, the quarterback she dated the previous year, while Bunny attends with Kenny. The event becomes a turning point, a moment that pushes them toward choices about loyalty, love, and what they truly want from life.
Outside of town, Gene relocates to Kentucky, landing work in a stable and re-evaluating what he wants for his future. He decides to come back for Bunny, but now fears she might not come with him. Jonathan heads out to find her, and the two friends—along with Bunny—reconcile. They leave for Kentucky on Gene’s motorcycle, chasing a shared dream and a new chapter together.
Back in their hometown, Jonathan tells Bunny’s father that she’s gone, and he finally stands up to Kenny by totaling Kenny’s car. In a moment of courage and change, Jonathan also works up the nerve to ask out Rosalie, a classmate who recently had her braces removed, signaling a new and hopeful direction for his own life.
