The Tao of Steve 2000

Dex is an unexpected Lothario—a thirty-something who teaches kindergarten part-time and is notably overweight. Despite these traits, he has discovered a unique and successful approach to attracting women. Dubbed “The Tao of Steve,” this philosophy melds Taoist principles with characteristics seen in iconic TV figures like Steve Austin from The Six Million Dollar Man, Steve McGarrett from Hawaii Five-O, and the legendary actor Steve McQueen.

In a twist of fate, Dex crosses paths with Syd, an old college flame whose name he struggles to recall, yet he feels an immediate attraction towards her. However, unlike Dex, Syd has never forgotten him and feels heartbroken over how swiftly he moved on from their past. Despite Dex’s attempts to woo her using the “Tao of Steve,” Syd remains immune to his usual charms and, in time, Dex finds himself genuinely falling for her.

On a camping expedition with Syd, Dex experiences severe chest pains, leading to an emergency hospital visit. The doctor reassures him that he has not suffered a heart attack, but rather heartburn, while warning him about the serious risks his lifestyle poses to his health. The situation takes a turn when, during a school day, an aggrieved husband of one of Dex’s past flings confronts and punches him in front of his students. Following this, Syd comes to his aid, and they share an intimate night together. Yet, come morning, Syd discovers Dex’s “philosophy” and, feeling betrayed, leaves him in disgust.

Realizing he must transform his life, Dex contemplates his choices. Time passes, and Syd has relocated to New York City to pursue work as a set designer. She reaches out to Dex, leaving a message on his machine, urging him to talk about their relationship. To her surprise, she finds Dex standing right in front of her, ready to seize the opportunity to rekindle what they once had.