I just saw Scott Pilgrim Vs. The World. I thought it was incredibly good. Honestly one of the best movies I've seen in several years. Cool special effects, interesting characters, unique story, cool soundtrack. Lots of late 80's early 90's references that I'm sure some of the actors and audience didn't get (the characters are in their early 20's, so I doubt any of them really know who Launchpad McQuack is without looking it up on Wikipedia). Lots of neat little gags and editing tricks. The Seinfeld part had me rolling. Very entertaining despite being a box office flop ($60 million to produce, only grossed like $15 million). It has pretty positive reviews online, but mixed reviews from professional critics. Totally worth checking out.

Anyway, Michael Cera plays the title roll, so of course he plays the same person he always does; the awkward young guy with strange mannerisms and nerdy tendencies who, for some inexplicable reason, ends up with a hot girl (several in this movie). I think this is a winning formula because everyone can relate to being the outcast loser on some level. Either you are there, or have been there at some point in your life. But the premise of these movies is so far detached from reality as to be laughable. Ever see Superbad? I didn't care for it for that reason. Take away the "loser gets the girl" paradigm and it's a shitty, hollow buddy comedy.

Pretty in Pink, the early 1980's comedy staring Molly Ringlwald is more in tune with reality. Again there is a "lovable loser" (named Duckie) pining for her affection. So she blows him off and goes out with the attractive rich guy. That's the plot of the movie as well; he's rich, she's poor, no one approves, etc. Duckie ends up friend zoned, as happens in real life.

Here's an article. Very insightful.
http://pulsotic.blogspot.com/2011/01/pr ... sited.html

I recently saw The Tao of Steve, and it's basically the definition of what you wrote. With some actual game and pick up techniques sprinkled on top. It's pretty good.