History Film / CruelIntentions

* DoubleEntendre: Sebastian, asking Cecile about her Australia-themed t-shirt, causing her to look down at it (which causes her [[PantyShot knees to sag open even wider]]:

* {{Yandere}}: One way of looking at Kathryn. Kathryn offers herself to Sebastian after he wins the 'bet', but he rejects her, because he now only wants Annette, which leaves Kathryn enraged and jealous. After he breaks up with Annette for her, she turns him down and throws it in his face. Then when he still chooses Annette, she spreads lies to Ronald about Sebastian hitting her to get back at him for rejecting her for Annette. Things only get worst from there. See the ForTheEvulz entry for the other interpretation.

* WomanScorned: The story of [[ClingyJealousGirl Kathryn]]'s life. Halfway through the film, she delivers a MotiveRant about how she's [[NotGoodWithRejection sick of being dumped]] by guys like Court, Sebastian and Ronald for "innocent little twits" like Cecile and Annette. Annette isn't really a twit, but Kathryn would consider her one just for being a NiceGuy.

* WickedCultured: Kathryn speaks Vietnamese, French and has sashimi as a midday snack. Sebastian rides, is an expert marksman and quite well read. He also drives a vintage Jaguar, which Kathryn covets.

* WhamLine: Kathryn to Sebastian after he wins the bet: "Silly rabbit! My triumph isn't over her. It's over ''you''.". Also the start of her TheReasonYouSuckSpeech to him.
* WhamShot: [[spoiler: The journal Sebastian gifts Annette with, detailing the truth about him and Kathryn]].

* VillainWithGoodPublicity: Kathryn is obsessed with maintaining her wholesome reputation as the student body president who attributes all her success to her unwavering piety, and she'll go to any length to destroy anyone who threatens the image that she's worked so hard to create.
* VillainousBreakdown: In the musical, Kathryn utterly breaks down briefly before [[spoiler:Sebastian dies]], culminating in the ending of "Kathryn's Turn Medley."
-->''Fool me, fool me, love me, love me! Leave me...''

* UnholyMatrimony: Sebastian and Kathryn's parents. When she tells him that her mother suspects his "impotent alcoholic" father of diddling the maid he simply says “excellent”, while he calls her mother a "gold digging whore".

* TookALevelInKindness: When Kathryn and Annette meet again in the pilot Kathryn is far more civil and reasonable. She's also been sober for 15 years

* StepfordSmiler: Kathryn pretends to be an upstanding Junior League-type schoolgirl, when in reality she's an oversexed, scheming coke fiend who takes out her frustrations on her fellow female classmates by persuading them to sleep around and ruin their reputations as a result.
* StrawFeminist: Kathryn whines to an eye-rolling Sebastian about how the DoubleStandard between boys and girls [[InternalizedCategorism causes her to feel suicidal]] ([[SlidingScaleOfSillinessVersusSeriousness literally]] or [[{{Narm}} hyperbolically]]?). At least her more mature counterpart, the [[https://tvtropes.org/pmwiki/pmwiki.php/Literature/DangerousLiaisons Marquise de Merteuil]], fancies herself as a self-empowered 18th-century woman, albeit still a StrawFeminist, as she gloats to the Vicomte de Valmont about how cunningly she's learned to utilize her feminine wiles to outsmart men. The '90s teen counterpart, on the other hand, just comes off as pathetically [[EmoTeen emo]] and [[{{Wangst}} wangsty]].
* StrawHypocrite: [[IncorruptiblePurePureness Everything Kathryn professes to stand for]] is one big [[ConsummateLiar fabrication]].
* TheTease: Kathryn, at one point grinding on Sebastian to convince him to sleep with Cecile.

* SpitTrailKiss: The infamous strand of saliva in the lesbian kiss between Kathryn and Cecile was like this.

* TheSociopath: Kathryn and Sebastian both have elements of this: superficial charm, sexual promiscuity, lack of meaningful relationships, manipulation of others...

* SissyVillain: Sebastian, played by pretty boy Creator/RyanPhillippe, gets symbolically emasculated by Kathryn[["I'll fuck your brains out" - not the other way around]]

* SissyVillain: Sebastian, played by pretty boy Creator/RyanPhillippe, gets symbolically emasculated by Kathryn[[note]] "I'll fuck your brains out" - not the other way around [[/note]].

* SmugSnake: Kathryn spirals into this toward the end. For much of the movie, she's very competent and successful at manipulation, but she ''really'' overreaches when she turns on Sebastian, whose assistance was a big contributor to her past success.

* RepriseMedley: The musical has two.
** The Act One closer, "Only Happy When It Rains," concludes with all the main characters singing reprises of nearly every song in the act.
** Towards the end of Act Two, Kathryn gets "Kathryn's Turn Medley," which has her singing reprises of "I'm the Only One," "Genie in a Bottle," "Kiss Me," "Lovefool," and "Only Happy When It Rains," along with bits of "Bitch." (And "Losing My Religion," for Sebastian's part.)

* ShoutOut:
** According to costume designer Denise Wingate, Selma Blair's red hoodie was supposed to invoke ''Little Red Riding Hood''.
** Kathryn's reference to "parental units" is from the classic 1970s ''Film/{{Coneheads}}'' sketches on ''Series/SaturdayNightLive'' (1975).
** When Kathryn exits the church at the end of the film, a plaque to the left of the doorway says "Rosemond Chapel." "Rosemonde" is the last name of Valmont's aunt in ''Les Liaisons Dangereuses''.
** After [[spoiler: her public humiliation, Kathryn Merteuil's cross gets pulled open and her]] cocaine falls out, referencing the scene in ''Film/DangerousLiaisons'' (1988) in which the similarly disgraced Marquise de Merteuil (Glenn Close) sweeps a cloud of white powder off her dressing table.

* RichBoredom: Kathryn and Sebastian seem to have nothing better to do than lounge around their palatial townhouse -- or country estate if they feel like a change of scenery -- while placing bets on how many people they can sleep with and lives they can ruin just to pass the time.
* RoyalBrat: All the servants in the Valmont house live in fear of "Miss Kathryn," but they endure her wrath simply because the Fifth Avenue mansion is a "good address" at which to be employed. As the QueenBee of her school, Kathryn treats her GirlPosse much the same way, and they're afraid to fall out of favor with her.

* RevengeByProxy: The whole reason Kathryn sets Sebastian onto Cecile is to get to Cecile's current boyfriend, who is Kathryn's ex.
* RichBitch: Kathryn, Tiffany and Cassidy Merteuil come from a line of rich bitches.

* FunctionalAddict: Supposedly, Kathryn somehow manages to balance a hard drug addiction and alcoholism with an exemplary academic resume (by blackmailing all her teachers perhaps?).

* ReallyGetsAround: Sebastian. Kathryn notes the hypocrisy that nobody thinks any less of him for sleeping with everyone, but she has to keep her sexual liaisons a secret.
* ReasonYouSuckSpeech:
** Kathryn gives one to Sebastian after she tricks him into dumping Annette.
-->'''Kathryn''': Silly rabbit! My triumph isn't over her. It's over you. You were very much in love with her. And you’re still in love with her. But it amused me to make you ashamed of it. You gave up the first person you ever loved, because I threatened your reputation. Don’t you get it? You’re just a toy, Sebastian. A little toy I like to play with. And now you’ve completely blown it with her. I think it’s the saddest thing I’ve ever heard.… So I assume you’ve come to make arrangements. But unfortunately, I don’t fuck losers.

* RaceForYourLove: [[spoiler: Sebastian tracks Annette down at the train station where he professes his love for her and they consummate their relationship soon after.]]

* PracticeKiss: In a LesYay example of this trope, this is proposed by ManipulativeBitch Kathryn to the innocent Cecile, who is worried about making a fool of herself when kissing her boyfriend for the first time. After the kiss Cecile is left breathless, and unconsciously leans forward for more as Kathryn pulls away.

* OperationJealousy: Kathryn tries this on Sebastian using [[spoiler:Ronald]], but it blows up in her face.

* NotBloodSiblings: Right before Kathryn propositions her stepbrother for anal sex, she makes it a point to clarify for the audience that her mother only married Sebastian's father fairly recently.
* NotGoodWithRejection: Kathryn is not happy when Sebastian turns her down for sex and is more than willing to ruin both his relationship with Annette and both their reputations unless he dumps her for her.
* NotIfTheyEnjoyedItRationalization: Kathryn thinks this when Cecile admits Sebastian got her drunk and performed oral sex on her and she liked it even though she didn't want to and Kathryn encourages her to sleep with more people.
* OhCrap: [[spoiler: Kathryn, when she goes outside and sees that everyone is reading Sebastian's journal exposing the secrets about her.]]

* MirrorScare: Kathryn is using the sink and is shocked to see Annette looking back at her in the girl's restroom mirror.
* MoreExperiencedChasesTheInnocent: Kathryn invokes the trope as the premise of TheBet she makes with her equally morally and sexually bankrupt step-brother Sebastian: if he can somehow sleep with Annette, the [[IncorruptiblePurePureness exceedingly virtuous]] headmaster's daughter, she'll [[FlirtyStepsiblings sleep with him]]. Sebastian is a verifiable [[TheCasanova Casanova]], as part of his introduction in the film is him flirting with a girl one scene and [[InstantSeduction bedding her]] the next.
* MotiveRant: Kathryn states hers in one scene to Sebastian.
--> '''Kathryn:''' Eat me, Sebastian! It’s okay for guys like you and Court to fuck 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 fucking Brady of the Upper East Side, and sometimes I want to kill myself. So there’s your psychoanalysis, Dr. Freud. Now tell me, are you in, or are you out?
%%* MrFanservice: Sebastian.

* MadonnaWhoreComplex: Kathryn speaks against this, talking about the DoubleStandard of boys being able to sleep around while she must pretend to be a Madonna in order to avoid being classed as a Whore. Her whole game plan is to corrupt Madonnas Annette and Cecile and turn them into Whores.
* ManipulativeBastard: Sebastian and Kathryn both excel at manipulating people to their own advantage.
* MaleGaze: Kathryn's description of Cecile when making the bet with Sebastian: "She's quite cute, you know? Young, supple breasts. A tight, firm ass. Unchartered pooty".

* LightIsNotGood: Kathryn can't seem to stop telling people how fortunate she is to be a part of the Christian faith. She speaks as if Jesus Christ is her greatest ally and even wears a rosary as a necklace in public. But despite all that she is an insufferable elitist, and manipulative, spiteful and cruel, and stashes cocaine inside a hollowed-out crucifix at the end of her rosary.

* LaserGuidedKarma: [[spoiler:Kathryn's downfall comes about from people whom she screwed over. Her secrets are exposed by the journal of Sebastian, which was copied by Annette and distributed to the student body by Cecile.]]
* LeanAndMean: In the form of the rail-like Kathryn.

* LackOfEmpathy: Kathryn tells her maid she can empathize with Khmer Rouge refugees because she ''almost'' had to fly coach one time. She also tells her stablehand over the phone how badly she feels that he or she will just have to cancel his or her daughter's birthday to groom Kathryn's horse.