Whatever It Takes (2000)

A nerdy teen, Ryan Woodman is smitten with the popular and gorgeous Ashley Grant, who apparently has no interest in him. Meanwhile, dim star athlete Chris Campbell has his eye on Ryan's brainy and beautiful friend, Maggie Carter. 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.

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