In Seattle, straight-laced Matt Leland (O'Donnell) falls in love with Casey Roberts (Barrymore), the new girl at their high school who's from Chicago. They begin a sexual relationship. His father disapproves of this and her parents try to stop them from continuing to see each other. She deliberately sets off the fire alarm at school, knowing that there is no fire there, and is subsequently suspended. She has an argument with her parents when they tell her they are sending her to a boarding school. She takes an overdose and her parents subsequently arrange to have her committed. Matt helps Casey escape from an acute psychiatric ward, and as they run away they both deal with her borderline personality disorder.
Casey is eccentric in nature. Her impulsiveness and extreme risk-taking attitude and behavior is attributed to her illness, in which she experiences severe highs and lows of emotion. Her frequent intense feelings, of passion towards Matt and of fear and destructiveness, dominate her persona. Throughout the relationship, Matt selflessly puts her needs before his. The severity of this increases as her mental state worsens.
Heading toward Mexico in his SUV, Casey becomes increasingly reckless and over-emotional. They crash and abandon the vehicle. They hitchhike, accepting a lift from a salesman (Liev Schreiber). He puts his hand on her crotch and Casey puts her lit cigarette on his face. He throws her out and a fight ensues between him and Matt. They steal his car and continue their journey. Casey becomes more distressed and Matt does his best to help her. He becomes scared, and after Casey threatens suicide, and also threatens to kill Matt with a gun she took from the glove compartment in the salesman's car, they return to Seattle and their families, where she is readmitted to the psychiatric hospital. Matt goes home and later receives a letter from Casey telling him she has moved back to Chicago and now feels significantly better. Casey says she has good memories of their time together.
|Chris O'Donnell||Matt Leland|
|Drew Barrymore||Casey Roberts|
|Joan Allen||Margaret Roberts|
|Sarah Haugland||High School Extra|
|Jude Ciccolella||Richard Roberts|
|Amy Sakasitz||Joanna Leland|
|Kevin Dunn||Clifford Leland|