The legacy of Say Anything, in which a totally boring guy decides he should date the most popular (and also boring, but smoking hot) girl in school in order to somehow justify his own mediocrity, can be seen at its most full blown in Zach Braff’s Garden State. Other perpetrators are Wes Anderson, who generally throws the “foreign girl” wrench into the mix, Kevin Smith, who adds lots of homosocial gay subtext, and parts of Judd Apatow’s oeuvre.
I love all of those examples. When scripts are written by “normal” guys that have always been overlooked by the hot girl, you can bet a trend will develop.
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