A nerdy teen, Ryan Woodman (Shane West) is smitten with the popular and gorgeous Ashley Grant (Jodi Lyn O'Keefe), who apparently has no interest in him. Meanwhile, dim star athlete Chris Campbell (James Franco) has his eye on Ryan's brainy and beautiful friend, Maggie Carter (Marla Sokoloff). The two agree to help each other in their romantic quests, but, as they come closer to their goals, both Ryan and Chris suspect that they might be pursuing the wrong girls.