Charlie Bellow, a polite, kind-hearted young man, hopes he will one day secure a managerial position with the Tiller King agricultural company, where his father works as a maintenance mechanic. When he starts business school in New York City, he hears news that his cousin has suddenly died. His friend suggests that they play a game in which they say whether they would sleep with any of the women they see while sitting in the park, which is where Charlie sees Jordan for the first time, but leaves to meet his grieving aunt who wants to set him up with someone. On the subway platform, Charlie sees Jordan drunkenly leaning over the guard rail and saves her from being hit by an oncoming train. Taking responsibility for the drunken, blacked-out girl, he sobers her up and begins a relationship with her over several weeks. While becoming fascinated with Jordan, he soon comes face-to-face with her volatile personality and learns more about her past through wild, drunken dates. Among other things, Jordan tells Charlie that her fiancé recently left her, tells a Tiller King representative she is pregnant with Charlie's child, sabotages Charlie's job interview with another Tiller King representative, and gives a piano recital where she asks him to bring her a single red rose and pushes him into the sea – and then saves him. Despite this, Charlie begins to fall in love with Jordan but clashes with her father, who believes Charlie is responsible for her erratic behavior. Because of this, Jordan begins to drift away from Charlie.