Whatever it Takes (2000)

Ryan Woodman has been in love with the most popular girl in school, Ashley Grant, for years. Chris, the school jock, has the hots for Ryan's neighbour and best friend, Maggie. So Ryan and Chris have come up with an outrageous plan - to weave a web of fake e-mails, plotted phone calls, contrived double dates and mistaken identities that will surely win them both the girl of their dreams.

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