Matt Leland, Chris O'Donnell, is a careful, responsible high school senior in Seattle who quietly shoulders a lot at home. He lives with his workaholic father, Clifford Leland [Kevin Dunn], and their 9-year-old twins, Adam Leland [TJ Lowther] and Joanna Leland [Amy Sakasitz]. With a telescope trained on the lake at night, he becomes fascinated by a girl who has just moved into the area—Casey Roberts [Drew Barrymore]—and soon learns she is a new student at his school who arrived from Chicago. Their first encounter is electric but tumultuous: Casey’s free-spirited demeanor clashes with Matt’s methodical streak, yet curiosity draws them together. They end up at a concert, sharing a moment of connection that signals the start of a whirlwind romance built on opposites attracting.
Casey is not just a spark of rebellion; she carries a volatile interior, swinging from intense passion to sudden fear and destructive impulses. She confides in Matt about her mood swings, and her insistence on feeling everything deeply becomes part of the attraction and the strain. When she is suspended after deliberately triggering the school’s fire alarm to grab Matt’s attention during his SATs, the tension with her parents grows. Her domineering father, Richard Roberts [Jude Ciccolella], and her mother, Margaret Roberts [Joan Allen], worry about her future and even consider sending her away to a boarding school. The emotional pressure of Casey’s condition intensifies as she overdoses on sleeping pills and is involuntarily admitted to a psychiatric ward, a turning point that makes Matt confront how far he will go to help someone who is slipping away.
Matt visits Casey in the hospital, driven by both affection and responsibility, despite his father’s objections about his studies and his younger siblings. He and Casey manage a risky escape during a later visit, slipping out with the help of a moment of quiet to plan a longer, bolder course. They drive toward Mexico in Matt’s SUV, seeking any chance to be together away from prying eyes. A reckless “trust game”—with Matt blindfolded and Casey directing him—ends in a wreck, but the real danger arrives when a salesman tries to press a dangerous advance on Casey. She defends herself by striking him with a lit cigarette, and the two escape, stealing the car to continue their journey.
As the trip toward the border continues, Casey’s behavior grows increasingly erratic and anxious, and Matt’s feelings deepen into a selfless commitment. He repeatedly puts her needs before his own, hoping to stabilize the situation and keep her safe. Yet the deeper he looks, the more he realizes that her illness may be beyond what he can fix. He eventually makes a difficult call to Casey’s worried parents, and Mrs. Roberts explains that Casey is manic-depressive and needs her medication. She pleads for Matt to bring Casey home so she can receive proper treatment, but Matt fears the consequences of returning her to a hospital environment. The misinterpretation of this moment—Casey hearing Matt’s call as a betrayal—adds another layer of heartbreak to their relationship.
The couple’s bond is tested in a remote desert as Casey’s crisis peaks. She steals the car’s keys and retreats, and Matt chases after her in a desperate bid to save her. In a tense desert confrontation, Casey threatens suicide and points a gun she took from the salesman’s glove compartment at Matt. He urges her to shoot, but she cannot bring herself to pull the trigger and collapses into his arms. The moment is both dangerous and tender, revealing the depth of their connection even as it strains to hold.
Ultimately, they return to Seattle, where Casey is readmitted to the psychiatric hospital, and Matt must resume the life he had paused—caring for his siblings and facing the gap left by Casey’s absence. Time passes, and a letter arrives from Casey, letting Matt know she has moved back to Chicago and is feeling markedly better. The message closes with warmth and a hint of what might still be possible between them:
> "I had a dream last night, you were in it. You waved to me, maybe to say goodbye, it doesn't matter. Whatever happens, I'm proud of what we went through. It helps me get through the day. That, and you in my heart," implying a future for their relationship.
