Generally, a lot of philosophy (which, by the way, is one of the most useless endeavours of man---look at what it has done for us in the last few thousand years) is an attempt at simplifying the complexity of our lives. The Tao of Steve is a film that simplifies Taoist philosophy by using to get lucky with girls, thereby generalising their collective complex behaviour in a few simple tenets. Perhaps the most interesting aspect about the film is that it mixes half-truths with half-lies by generalising broadly.
"We pursue that which retreats from us" is the basis for the Tao of Steve (so named after three cool "Steve"s --- Steve Austin, Steve McGarrett, and Steve McQueen). The plot revolves around the life of Dex (Donal Logue), a self-acknowledged slacker who compares his lifestyle to the ascetics of the East. He asks, rightfully enough, why what they do is considered a great sacrifice while what he does is considered slacking. Syd (Greer Goodman), the person Dex eventually falls for, points out that the discipline level is different. That, however, doesn't deter Dex who uses any philosophy to advance his laziness: Dex is so much of a slacker that he has come up with a tao for getting laid, involving three rules: (1) eliminate desire; (2) be excellent; and (3) retreat.
Considering that we're all biological organisms, some of Dex's generalisations are indeed true, although it applies to both male and females in general (one could argue that females use this tao very effectively, even across species). However, there's nothing here anyone who hasn't been in a few relationships hasn't figured out. Such a person could've easily told Dex what the outcome of his situation would be.
Soon, Dex finds out that the dishonesty he has to indulge in to get his way comes at a price as he meets someone he truly cares about. Personally I'm all for consensual relationships of any kind between people capable of consent, but I consider dishonesty to be self-destructive. Besides, it's not necessary: as an undergraduate, I had a friend who would simply go up to complete strangers and ask whether they wanted to have casual sex. Most of the time, he was refused but every once in a while he'd get lucky. In Dex's case, his dishonesty leads him to a life of discontentment.
In any event, as soon as Dex starts breaking his own rules (with a predictable outcome), the movie becomes cheesy and hackneyed. The dialogue has some interesting quotes, but again, there is no novelty here. Perhaps I've been hanging around (pseudo) intellectuals who quote from the Tao Te Ching (and other famous philosophies) and apply it to every situation, from programming (there is actually a brilliantly written Tao of Programming) to playing ultimate frisbee.
The biggest problem I had with this film has to do with the only reason I'd even vaguely recommend people check it out, and what separates it from most other films that have this same rehashed plot device (boy sleeps around; boy meets attractive girl and falls in love; boy changes lifestyle for attractive girl). Even though The Tao of Steve ambitiously mixes ancient Chinese and Buddhist philosophies, pop culture (Josie and the Pussycats; The Bugaloos), and opera (Don Giovanni), sometimes all in the same breath, the result is lacking in any sort intellectual depth. Consider the discussion when Kierkegaard's "leap of faith" is compared to Don Giovanni's life---it comes off a sophomore undergraduate philosophy discussion. It's almost as if the writers were out of their depth when tackling this subject matter.
Ultimately, I found The Tao of Steve unsatisfying. For all its pretense, its ending has no real revelation and I was disappointed (and if you read a lot of my reviews, you'll see this rarely happens). I do not recommend wasting your time on this one unless you're clueless about how relationships work.