Dex (Logue) is an unlikely Lothario – an overweight, thirtysomething part-time kindergarten teacher – who has developed an effective method for seducing women. “The Tao of Steve”, Dex’s own personal pseudophilosophy on seduction, combines a Taoist outlook with the qualities embodied by TV characters such as Steve Austin (The Six Million Dollar Man) and Steve McGarrett (Hawaii Five-O) and, above all, by the actor Steve McQueen. He meets up with Syd, an old college conquest whom he can’t remember, but to whom he is instantly attracted. However, she never forgot him, and is hurt that he got over her so easily. Slowly, Dex subjects Syd to the “Tao of Steve”, but Syd is immune to Dex’s charms. Gradually, he develops genuine feelings for her.
During a camping trip with Syd, Dex suffers chest pains and has to be taken to the hospital. A doctor informs Dex that what he thought was a heart attack was merely heartburn, but cautions him that his lifestyle is endangering his health. Later, at school, the husband of one of his conquests punches him in the face in front of his students. Syd comes to Dex’s house to console him, and they end up sleeping together. The next day, however, she finds out about his “philosophy”, and leaves in disgust. Dex finally realizes that he needs to make changes in his life.
Sometime later, Syd is in New York City, working as a set designer. She leaves a message on Dex’s answering machine asking him to call her and talk about their relationship – only to see Dex himself standing before her, ready to give her a chance.