Cassidy Merteuil (Kristina Anapau) is a beautiful, manipulative student at an exclusive Santa Barbara, California college. Jason Argyle (Kerr Smith) and Patrick Bates (Nathan Wetherington) are roommates there. They pull off a devious plan where Patrick beds Cassidy and disrupts a potential relationship she had been pursuing with a British prince. This then helps Jason win a bet he made with Cassidy (which turns out to have been Patrick's bet all along). When Patrick (who also reveals his awkwardness and social ineptitude to be an act) and Jason reveal their deception to her, she is devastated. She later encourages them to compete against each other. Jason has to seduce Sheila (Natalie Ramsey), who is in a steady relationship with Michael (Tom Parker (actor)), and Patrick has to seduce Alison (Melissa Yvonne Lewis), who is already engaged.