Back in college, Dex (DONAL LOGUE) was probably the smartest guy in school and he had a well-deserved reputation for luring many women into his bed with his unique, self-styled philosophy about romance. Now ten years later, Dex still manages to attract various women - including Beth (AYELET KAZNELSON), a married woman with whom he's having an affair - but he's become an overweight, underachieving kindergarten teacher who spends his free time smoking pot and spouting philosophy with his buddies.
Combining the thoughts and comments of various philosophers and comedians, Dex has fashioned and lived by a guideline for dating - what he calls "The Tao of Steve" - regarding how to transform everyday guys, such as naïve Dave (KIMO WILLS), into cool dudes -- best epitomized by actor Steve McQueen - who then have no problem getting women into bed.
While his married friends Rick (DAVID AARON BAKER) and Maggie (NINA JAROSLAW) often think he's full of it, they get to see his act in full force when he meets their friend Syd (GREER GOODMAN) at their college reunion. Although Dex doesn't remember her from school, the set designer clearly recalls him, but certainly doesn't allow herself to fall prey to his manipulative charm.
That, of course, completely perplexes him, and when the two end up sharing Rick and Maggie's truck for transportation to and from their respective jobs, he steps up his efforts to get her in bed by acting like he doesn't want to do just that. With her repeatedly ignoring his attempts, he slowly begins to realize that he's actually falling for her, a point that carries added poignancy considering his previous die-hard philosophy and a secret from their past that's eventually comes to light.