This film (as with the other two previous Cruel Intentions films) once again portrays seduction and betrayal among the teenage idle rich. Cassidy Merteuil (Kristina Anapau) is a beautiful, manipulative student who arrives in California to attend the exclusive Santa Barbara 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. However. 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), and Patrick has to seduce Alison (Melissa Yvonne Lewis), who is already engaged. Jason succeeds in his part, but Patrick is rejected by Alison, who says she does not want to cheat, and does not find him sexually attractive. However, when classmate Brent Patterson (Charlie Weber) shows an interest in Allison after being rejected by Cassidy, she succumbs to temptation and sleeps with him, not knowing Patrick is taking photos of the sexual encounter. Patrick blackmails Alison, using the photos of her cheating on her fiancé. He tells her how he succeeded before he throws her on her bed, pulls down her white thong and rapes her in order to fulfill his part of the bet. Meanwhile, Jason and Cassidy strike up a relationship, as Patrick is left unsatisfied and angry by the rape. He attempts to seduce Cassidy, but she rejects him. So, he convinces Cassidy that the man she loves, Jason, is only staying with her because he wants to win the bet he and Patrick had set up, which was to see who could sleep with Cassidy first. Seemingly angry with Jason, she succumbs to Patrick and has sex with him, and Jason walks in on them. Patrick snidely remarks that both Jason and Cassidy have been victims of his cruel game to show them that they underestimated the evil in themselves. They ask him if he has ever been a victim, and he tells them 'no'. However, Cassidy reveals that this had been her plan all along. She began the little charade so Patrick and Jason would seduce Alison and Sheila; before sleeping with Patrick, she took one of his sleeping pills (roofies), planning to tell the policemen that he had drugged and raped her. As Patrick is led away by the police, bewildered and protesting his innocence, he is warned that another victim (Alison) has come forward, and he will get the punishment he deserves for raping Alison. In the final scene, Jason and Cassidy are shown together at the swimming pool and making another bet with each other for Cassidy to seduce and corrupt another person at the college.
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