Matt Larkin, Andrew McCarthy, is a University of Cincinnati senior whose life seems almost too good to be true: a comfortable upbringing, stellar grades, popular among peers, and a steady engagement to his girlfriend Alice. His world starts to tilt when his best friend Tipton, Ben Stiller, introduces him to Sproles, Doug Hutchison, a fellow student who has a brother working as an undercover cop. The three recount a recent night out in the country—crammed with seedy characters, beer, and music at a house owned by a woman named Jean, and they invite Matt to join them on the next visit. Matt, initially skeptical, begins to weigh the pull of this new nocturnal world against the upcoming vows he’s planning to take.
The pair drag Matt out to Jean’s house with the expectation of a wild party, only to discover the aftermath of the prior night’s events. Disappointed, Matt heads to the kitchen to grab a beer for Tipton and meets Jewel, Molly Ringwald, a neighbor who has come to Jean’s place to escape an abusive stepfather. Matt feels an immediate pull toward Jewel and returns to the countryside to spend more time with her. Their connection deepens quickly, and Matt ends up breaking off his engagement to Alice as the relationship blossoms into something more intimate and real.
As Jewel and Matt grow closer, Tipton comes with troubling news: Jewel is married, and she is sixteen years old. When confronted, Jewel denies the underage allegation but admits she is married to Green, a man she married to escape her stepfather. She explains that Green has proven abusive as well, and that the marriage was never consummated. Matt seeks an annulment for Jewel and asks Tipton for help from his cousin, but the situation escalates into a heated argument with Tipton. Afterward, Matt is kicked out of his parents’ house when his father discovers him and Jewel sneaking around in the middle of the night, forcing Matt to relocate to a run-down shack where the lovers would meet.
In a diner meeting, Tipton and Sproles press Matt to see Jewel as someone who has been manipulating him. The pressure pushes Matt back toward his family home, and he even leaves money behind for Jewel to use in pursuing an annulment. Later, after drinking with Tipton and a few friends, Matt brings them to the shack. Jewel interrupts their gathering and privately asks Matt to loan her his car so she can meet Green. When his friends urge him to leave, Matt refuses and waits for Jewel to return. When she doesn’t come back, Matt goes to Jean’s house, where she reveals Jewel has gone to her mother’s place.
Matt meets Jewel to uncover what happened the night before. She explains that she met Green at a bar and tried to get him to sign the annulment papers, but he refused. She recounts being exhibited and sexually assaulted in the back of Matt’s car, and adds that she saw Sproles at the scene. Sproles counters that he was merely a bystander, saying he was there with his brother, who would have arrested Green and his thugs if Jewel had been mistreated. Confused and frustrated, Matt decides to confront Green directly. He knocks on Green’s door, then lets himself in when no one answers. Green finds him in the living room, and a heated confrontation erupts—until Jewel walks in, throws the annulment papers at Green, and ends her relationship with Matt as she walks out.
A year later, Matt returns from graduate school for Christmas and unexpectedly runs into Jewel at an ice skating rink. He learns that she is now divorced from Green, back in high school, and has quit smoking. Jewel introduces Matt to Steven, a classmate she’s dating, signaling a new chapter in her life. Jewel bids Matt goodbye with a kiss on the cheek and a warm thanks, and he watches her depart with a bittersweet smile, recognizing how far they’ve both come and how their paths have diverged.
