Like most of the male population at Gilmore High, Ryan (Shane West) has a serious crush on the beautiful and popular Ashley Grant (Jodi Lyn O'Keefe), and he is willing to do whatever it takes to win her over. Ryan's best friend, Maggie (Marlo Sokoloff), meanwhile has attracted the attention of Ashley's cousin, Chris (James Franco), a babe magnet unused to rejection. Although they have never mixed in the same social circles before, the guys join forces and weave an hilarious web of fake e-mails, plotted phone calls and contrived double dates in order to get the girls of their dreams in time for the prom.
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