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Ryan (Shane West) is a bit of a geek with eyes for the school sex bomb, Ashley (Jodi Lyn OKeefe), 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 hes pursuing the right girl. He realizes Ashley is not meant for him, and tries to convince Maggie about Chriss affection for her. Maggie is reluctant to take him "back" at first, but then realizes Ryan has a change of heart.
Ryans dreams for catching the eye of the goddess of the high school hallway has a chance of becoming true when her cousin (Chris) offers to make him a deal. All he has to do is help Chris to win the heart of his best friend, the beautiful enigmatic Maggie. This sparks off a damned cute comedy as boy helps boy to get girl
Shane West
Ryan
Marla Sokoloff
Maggie
Jodi Lyn O'Keefe
Ashley
Manu Intiraymi
Dunleavy
Aaron Paul
Floyd
Julia Sweeney
Kate Woodman
James Franco
Chris
Kip Pardue
Harris
Scott Vickaryous
Stu
Colin Hanks
Cosmo
Richard Schiff
P.E. Teacher
Kevin Ruf
Security Guard
Erin Champaign
Shower Girl
Rachel Zerko
Shower Girl
Eric Kushnick
Stoner
Christine Lakin
Sloane
Nicole Tarantini
Marnie
Shyla Lefner
Shyla
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