Owen Wilson's character

This was golden, character-wise. They have to convince the audience Reese would rather be with Paul than a rich good looking baseball player than Paul Rudd. Since it's a movie, both guys are attractive but you assume Owen is supposed to be the better eye candy catch.

Anyway wow. How NOT RIGHT were they for each other?! Owen DOESN'T GET how insulting and unacceptable the anonymous sex is. He has clothes for girls when they wake up and doesn't see how this is even out of place or what a serious girl might think of it. He has EVERYTHING some girl would want, except any connection with what Reese is even feeling.

The best part is HE'S A REALLY SWEET GUY! He just wants to know what he did wrong when they finally break up. He thinks cutting back on anonymous sex is some great compromise and he's doing his part. He echoes this sweet but unfortunate code throughout the movie.

Lastly, his best line. It went something like "Why do girls look so good when they're leaving?" Oh man. Perfect. He's basically saying "I only want you so much because you're running away" (obviously). But it's not spelled out! He's not even aware it's what making him like her! His attraction is based off convenience and mostly this fleeing. You feel for him b/c in his head he really likes her.

You could write one of these for at least 3 characters in the movie. It was pretty great.