Whatever It Takes (2000)

Ryan (Shane West) is a bit of a geek with eyes for the school sex bomb, Ashley (Jodi Lyn O'Keefe), which induces cringing in his neighbor and best friend, Maggie (Marla Sokoloff), a cute intellectual girl. But popular jock Chris (James Franco) has his eye on Maggie, and he offers to help Ryan win Ashley if Ryan will help Chris with Maggie. So begins a two-headed variation on Cyrano de Bergerac; Ryan composes soulful e-mails for Chris, and Chris advises Ryan to treat Ashley like dirt, which seems to be the only way to get her attention. At first, neither finds it easy to change their ways; Chris comes on too strong, and Ryan is too nervous to be a jerk. But as they start to succeed, Ryan begins to see Maggie in a new light and wonders if he's pursuing the right girl. He realizes Ashley is not meant for him, and tries to convince Maggie about Chris's affection for her. Maggie is reluctant to take him "back" at first, but then realizes Ryan has a change of heart.