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 (play); 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.