The story begins with Dex (Donal Logue), our unlikely hero, who is currently living in Santa Fe who is at once endearing and exasperating.
He and his friends have twisted the philosophies of Lao-tzu (founder of Daoism), Heidegger and Groucho Marx into a foolproof theory of dating which have decided to call "The Tao of Steve". This philosophy provides rule by rule guidelines for how to transform ordinary Joes into charismatic Steve McQueens.
Back in college, Dex was the big man on campus. But now, ten years after his graduation, he is an overweight kindergarten teacher and must now endure the humbling experiences of the college reunion. Here, Dex is immune to the shocked stares of the young women who were once his conquests.
While trying to pick up the young bartender, he is struck by another woman - the gorgeous Syd (Greer Goodman), who now rides motorcycles and designs sets for the Santa Fe Opera Society's performances.
Through a series of circumstances, Syd and Dex are thrown together and he soon finds himself questioning his belief in all things Steve, even as he continues to be the ultimate Steve guru.
As Dex falls in love with her, Syd appears to be totally immune to his charms....and with good reason. When the truth comes out, Dex is finally forced to confront the realities of his life: not in terms of conquests and image, but on the most fundamental emotional level