Whatever It Takes (2000)

Synopsis
In this teen-oriented romantic comedy, Ryan Woodman (Shane West) is a socially inept high school senior whose idea of a good time is practicing his accordion, while Chris Campbell (James Franco) is a BMOC football star (and intellectual lightweight) at the same school. Ryan is hopelessly in love with Ashley Grant (Jodi Lyn O'Keefe), who is beautiful, popular, and entirely out of his league, while Chris has a serious crush on Maggie (Marla Sokoloff), a pretty but bookish friend of Ryan's. Chris and Ryan realize that they're in a position to help each other, and through a complicated arrangement of phone calls, e-mails, and double dates, they try to work out a system by which each guy will be with the girl of his dreams -- though things hardly turn out the way anyone expected. Produced under the title Got to Be You, Whatever It Takes also features Julia Sweeney and Colin Hanks. ~ Mark Deming, All Movie Guide