The Tao of Steve (2000)

Dex and his friends have twisted the philosophies of Lao-tzu, Heidegger and Groucho Marx into a foolproof theory of dating, The Tao of Steve, which provides rule-by-rule guidelines for how to transform ordinary Joes into charismatic Steve McQueen's. Back in college, Dex was the big man on campus. But we meet Dex ten years after graduation as he endures one of life's great humbling experiences; the college reunion. Now an overweight kindergarten teacher, Dex is immune to the shocked stares of the young women who were once his conquests. While trying to pick up a student bartender, Dex is struck by another woman, the gorgeous Syd, who rides motorcycles and designs sets for the Santa Fe Opera. Through a series of circumstances, Syd and Dex are thrown together and he soon finds himself questioning his belief in all things Steve. As Dex falls in love with her, Sy appears immune to his charms and with good reason.