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|“||It's okay for guys like you and Court to f-ck everyone, but when I do it, I get dumped for innocent little twits like Cecile. God forbid, I exude confidence and enjoy sex. Do you think I relish the fact that I have to act like Mary Sunshine 24-7 so I can be considered a lady? I'm the Marcia f-cking Brady of the Upper East Side, and sometimes I want to kill myself. So there's your psychoanalysis, Dr. Freud.||„|
|~ Kathryn, explaining her frustrations to Sebastian Valmont|
Kathryn Merteuil is the main antagonist in the Cruel Intentions duology. She is based on Marquise de Merteuil from the Pierre Choderlos de Laclos novel Les Liaisons dangereuses.
She was portrayed by Sarah Michelle Gellar in the first movie, who also voiced Seventh Sister and the forthcoming NBC pilot, and by Amy Adams in the prequel movie.
Kathryn was born in New York, the daughter of the wealthy Tiffany Merteuil, who raised Kathryn to be manipulative as she is, though she did not openly approve this. When Kathryn was a teenager, Tiffany married Edward Valmont whose son, Sebastian, was just as manipulative and dangerous as Kathryn. After a long-standing rivalry, Sebastian joined Kathryn in her games of manipulating the student body of Manchester Prep and anyone else. However, little did Sebastian know, Kathryn was only using him as a toy.
That all changed when a girl, Annette Hargrove, moved into town. Sebastian and Kathryn made a bet: if Sebastian can get Annette to lose her virginity to him, he could finally sleep with Kathryn; however, if Sebastian failed, he would lose his vintage 1956 Jaguar XK140 Roadster to Kathryn.
Sebastian, along the way, fell in love with Annette and lost interest in Kathryn, who then manipulated him into breaking Annette's heart. After he came to collect his "prize," Kathryn finally revealed to him that she had been stringing him along all these years and that she doesn't "f-ck losers". After that, Kathryn manipulated Ronald, a mutual friend of theirs, to fight Sebastian. During the ensuing fight, Sebastian was accidentally hit by a car and died shortly after, telling Annette he loved her.
At Sebastian's funeral, Sebastian got his revenge from the grave when Annette published his journal, revealing all of Kathryn's indiscretions, including her cocaine use, to the student body and her parents. What happened after is unknown, but it can be assumed that she was kicked out of school, her squeaky clean reputations is ruined and sent to rehab.
The original script's ending differed greatly. Instead of Annette publishing the journal, she uses the threat of publishing it to blackmail Kathryn into becoming essentially her slave. Corrupted by the tragedy she has been through, Annette plans to use Kathryn as a pawn to upset the social establishments at school and "turn it upside down." After kissing Kathryn forcibly, Annette leaves, taking Sebastian's car with her and leaving Kathryn defeated.
Kathryn's personality is a very complex and elusive one; the few who know the real her believe she is emotionally unstable. She possibly suffers from borderline personality disorder; she's extremely manipulative, and her charming and brilliant persona seduces everyone around her. Though very intelligent, she has difficulty feeling empathy, sympathy, or conscience, and is completely self-absorbed, not even appearing upset at her stepbrother's memorial but making sure she looks perfect in the bathroom mirror. She also shows many narcissistic traits.
Even before the events of the movie, Kathryn is already accustomed to destroying her peers' lives and using sex as a means to control the men in her entourage, but still maintaining that she is a virgin and planning to wait until marriage.
Though Kathryn is self-obsessed, she isn't an actual sociopath (she does not have antisocial personality disorder), as she still has had feelings for a few men in her life, such as Court Reynolds, a jock from her school who broke up with her and later fell for Cecile Caldwell (which led Kathryn to set out to destroy Cecile's life), and Ronald Clifford, Cecile's music tutor who's romantically involved with her and with whom Kathryn openly sleeps with. After finding out she had been dumped by him, she seemed to look mildly upset. She also seemed to genuinely love her stepbrother back when he was on her side, and his transition to good was seen by her as a betrayal and caused her to hate him, although she showed a small measure of regret when saying "Goodbye, Sebastian" after their final meeting. She also cries at the end of the movie when reading Sebastian's journal which describes every hateful facet of her personality yet still has "My True Love" scribbled by her picture, showing how Sebastian truly cared for her even so.
Kathryn also suffers from bulimia nervosa, and is mildly self-conscious about her body. According to her, a great degree of her underhanded behavior is because of the double standard society places upon females and sex. Pretending to be a virgin and a good girl fills her with self-loathing, and she expresses that she sometimes feels suicidal as a result. Her cocaine addiction is her method of dealing with this.