The other day I sat down and watched an indie that came and went without much buzz a handful of years ago -- 2006's I'm Reed Fish. The film starred Jay Baruchel -- after the likes of Undeclared, but before the likes of Knocked Up and Tropic Thunder -- as the radio voice of the people for a small town called Mud Meadows. Trying to exist under the heavy arm of his dead father's shadow, Reed has it rough, being romantically linked (either in real life or his own art) with the following beauties: Alexis Bledel, Schuyler Fisk, Shiri Appleby, and Valerie Azlynn. Additionally, one of his only friends is played by DJ Qualls (the weird guy from Road Trip), who is engaged to A.J. Cook (Mary Lisbon from The Virgin Suicides) in the film. Another apt title for the comedy would have been: How Awkward Geeks Get the Hotties.
Of course, this is nothing new, though I'm Reed Fish stretched the idea to its limits. When lots of boy geeks/dorks/nerds/etc get successful in Hollywood, of course they're going to perpetuate the dream -- that they'll get the girl that Duckie lost all those years ago. And that's not the only reason. Certainly, unlikely matches happen in real life too, like the oft-used example of Julia Roberts and Lyle Lovett. But it's also a matter of beauty.
Hollywood is no longer comfortable with a female lead or love interest who offers a different type of beauty.