Geeky high school senior Ryan Woodman (Shane West) has no chance of getting the romantic attention of the "goddess of the high school hallway," Ashley Grant (Jodi Lyn O'Keefe). Popular athlete Chris (James Franco), however, has a crush on Ryan's best friend, the pretty and enigmatic Maggie (Marla Sokoloff), but his dumb jock persona stands in the way. Together, the two lovelorn young men plot to win their respective dream girls: Ryan does his best Cyrano to help Chris woo Maggie, while Chris convinces Ashley that Ryan is worthy of her attention. But the young men soon learn that their plan's apparent success has created a romantic nightmare of mismatched love. In the confusion, Ryan comes to realize the real love of his life may be closer to home than he thought.