To date the stunning and popular Ashley Grant (Jodi Lyn O'Keefe), geeky, accordion-playing high school senior Ryan Woodman (Shane West) concocts a wild scheme with resident meathead and superjock Chris Campbell (James Franco). Chris, in the meantime, is pining after Ryan's best friend, Maggie (Marla Sokoloff), a girl with beauty, brains... and heart. Weaving a web of fake e-mails, plotted phone calls and contrived double dates, the two guys arrange to set each other up with the girls of their dreams