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6[[quoteright:300:https://static.tvtropes.org/pmwiki/pub/images/cruelintentions_9451.jpg]]
7[[caption-width-right:300:''[[{{Tagline}} In the game of seduction, there is only one rule: Never fall in love.]]'']]
8
9->''"It amazes me someone as charming as you can be so manipulative."''
10-->--'''Annette'''
11
12''Cruel Intentions'' is a 1999 American drama film written and directed by Roger Kumble, and starring Creator/RyanPhillippe, Creator/SarahMichelleGellar, Creator/ReeseWitherspoon, and Creator/SelmaBlair. The movie is a comedic and dramatic appropriation of the 18th-century French epistolary novel ''[[Literature/DangerousLiaisons Les Liaisons Dangereuses]]'' by Laclos, but unlike other modern film versions of the novel (''Literature/DangerousLiaisons'') is not set in the France of that time.
13
14The story follows a handful of wealthy teenagers living in modern New York City. Kathryn Mertueil (Gellar) wants her step-brother Sebastian (Phillipe) to seduce freshman student Cecile (Blair) in revenge for her boyfriend dumping her for Cecile. Kathryn offers him a bet: if he fails to seduce Cecile, Kathryn gets his vintage Jaguar, but if he succeeds, Kathryn will sleep with him, as Sebastian has been attracted to Kathryn since their parents wed and is furious she's the one woman he can't have. Sebastian initially refuses since he has his eye on the headmaster's daughter Annette (Witherspoon) who believes in remaining chaste until marriage, but when he learns Cecile's mother has already warned Annette about his womanizing ways, he agrees to Kathryn's offer. Thus the two begin spinning their webs of seduction, blackmail, manipulation, and betrayal, to get what they want - at least until Sebastian begins having second thoughts.
15
16The film started as an independent film with a much smaller budget, and was later picked up by Columbia Pictures. The film was released on March 5, 1999. It was later followed by two direct-to-video films: a prequel, ''Film/CruelIntentions2'', and a sequel, ''Cruel Intentions 3''. A pilot for a sequel television series set 15 years later was in the works for NBC, with Gellar returning to the role of Kathryn, but the network ultimately passed on the series.
17
18In 2018, the film was adapted into a JukeboxMusical of [=90s=] hits, which premiered Off-Broadway. The cast album is available for streaming on Spotify and Website/YouTube.
19
20----
21!!Tropes associated with this work:
22
23* AdultsAreUseless: The teenagers run the show and use their elders as pawns.
24* AgeInappropriateDress: Despite only being in high school, Sebastian and Kathryn wear power suits as loungewear. Although, for the Upper East Side in New York City, this is more or less TruthInTelevision. And let's not even get started on Kathryn's lingerie as daywear.
25* ArmouredClosetGay: Greg, a popular and wealthy football player at Sebastian and Kathryn's school, is in the closet and secretly hooking up with Sebastian's gay friend Blaine. Sebastian takes advantage of this, setting things up so that Blaine brings Greg to a hookup that Sebastian has access to and later photographing them in the act. Since Greg spends most of his time bragging to his teammates about his (female) hookups, Sebastian's threat to spread the evidence around school ''and'' show them to Greg's father is enough to terrify the boy into helping Sebastian with his scheme.
26* BoardingSchool: Technically, Manchester Prep is a day school, but it comes with the same tropes of spoiled students picking on {{Scholarship Student}}s and engaging in SituationalSexuality -- except for the one perfect and kind student, of course.
27* CampGay: You can tell Blaine is a DepravedHomosexual because his dye job matches his sweater vest -- it doesn't get much campier than that. Also, he displays mannerisms that are stereotypically associated with gay men.
28* CasualCarGiveaway: Either this trope or HeroStoleMyBike is the only plausible explanation for that bizarre closing shot of Annette [[spoiler:driving off into the desert behind the wheel of Sebastian's prized vintage Jag]].
29* CastingGag: Swoosie Kurtz appears in a modern day adaption of ''Les Liaison dangereuese'' after appearing in its seminal film adaptation a decade earlier.
30* CatholicSchoolGirlsRule: Though their uniforms are more drab and conservative than is popularly portrayed.
31* CelebrityCameo: A brief close-up of a family photo shows Sebastian and Kathryn with their parents alongside President Clinton and First Lady Hilary Clinton.
32* CheatingWithTheMilkman: Kathryn sarcastically remarks to Sebastian that her mother suspects that her stepfather is having an affair with the maid.
33* ChineseLaborer: Technically, Kathryn's handmaiden is Vietnamese.
34* TheCobblersChildrenHaveNoShoes: The psychiatrist is about to go on a book tour to promote her ''Great Parenting'' manual, however when she finds out her daughter was manipulated and had nude photos of herself put on the internet, her response is neither kind nor particularly constructive.
35* ColdHam: One of the pleasures of watching this film has to be watching and listening to Gellar take [[ChewingTheScenery frequent bites out of the stony surroundings]].
36* ColorCodedForYourConvenience: Sebastian and Kathryn wear black and other dark colors, while Annette prefers white and pastels. Cecile initially wears white and other light colors, but shifts to wearing red as Kathryn and Sebastian begin to corrupt her.
37** In the scene where Sebastian seduces Cecile, he's wearing dark green ("go") while she's wearing bright red ("stop").
38* ConsummateLiar: Kathryn, Sebastian. Annette's best friend, Greg, qualifies as well.
39* CoolOldLady: In the original story Madame de Rosemonde becomes a trusted friend and wise mentor to Madame de Tourvel. In this version, Sebastian's Aunt Helen is just an eccentric biddy who whips up [[UnsuspectinglySoused "iced tea"]] and pawns her charity duties off on her nephew and his girlfriend so she can go to the theater instead.
40* DeadpanSnarker: Sebastian and Kathryn both have mastered the art form.
41* DarkerAndEdgier: Of all the Les Liaisons Dangereuses adaptations, this modern version is definitely the edgiest and also arguably the darkest in the way that Kathryn Merteuil and Sebastian Valmont come across as even more brooding, nihilistic and emotionally disturbed than their 18th-century counterparts. Add the fact that all the characters are minors, and you've got an especially disturbing tale of sexual predation and death.
42** Also DarkerAndEdgier as far as teen flicks go. When ''Cruel Intentions'' came out in theaters, the film's ostensible target audience couldn't even get in to see it without a parent or guardian.
43* DepravedHomosexual: Blaine, who's openly gay, is eager to help Sebastian blackmail closeted Greg by getting him into bed so that Sebastian can walk in on the two men together and take photos of them in a compromising position. Though to be fair, the heterosexual characters are also depraved, so it doesn't stand out as much.
44* TheDogBitesBack: [[spoiler:Cecile is the one who photocopied the journals. And to further add salt to the wound, she personally hands one to Kathryn.]]
45* EstablishingCharacterMoment: needing to overcome the challenge involved in casting [[DawsonCasting a 26-year-old woman as an immature teenager]], the film introduces Cecile dressed as small child would, in an animal-themed t-shirt and schoolgirl skirt (in contrast to the [[LadyInAPowerSuit power suits]] worn by the more sophisticated villain protagonists). She [[PantyShot fails to keep her legs closed while seated]] and fails to recognize Sebastian's [[DoubleEntendre reference]] to her wardrobe malfunction. Her mother has to close her legs for her, signalling her sexual vulnerability.
46* EthnicMenialLabor: The film loves using this trope for comedic effect: The Caldwells have a Hispanic maid who says her one line, "¡Ay, caramba!" right on cue, while the Valmonts have two different [[ChineseLaborer Asian maids]] who give pedicures, an [[TheJeeves English butler]], a [[CreepyHousekeeper creepy German]] chef, an Arab driver who wears a turban, and two Swedish masseuses. Of course, all their personalities are [[FunnyForeigner stereotypical and over-the-top]].
47* {{Expy}}:
48** Cecile Caldwell is Cécile de Volanges.
49** Ronald Clifford is Chevalier Danceny.
50** Bunny Caldwell is Madame de Volanges.
51** Court Reynolds is Comte de Gercourt.
52** Helen Rosemond is Madame de Rosemonde.
53** Blaine Tuttle is Azolan.
54** Greg [=McConnell=] is Julie.
55** Mai-Lee is Victoire (sort of -- she's just Kathryn's maid, not an accomplice in her schemes).
56** Gretchen and Mora are both Emilie (in a deleted scene).
57** Sebastian's journal represents the letters Vicomte de Valmont possessed.
58* FanDisservice: Everything about the sexual relationship between Sebastian and Kathryn, once the audience realizes that they're actually step-siblings.
59** Sebastian getting Cecile drunk and then taking advantage of her state by coercing her into letting him perform oral sex on her. Albeit PlayedForLaughs.
60* {{Fanservice}}:
61** Selma Blair and Sarah Michelle Gellar making out for 47 seconds.
62** Kathryn lounging around in a pantsuit and lingerie that show off her CleavageWindow.
63** A shot of Sebastian's backside as he and Annette dress down to go swimming in the pool.
64** Annette stripping down to a blue swimsuit.
65** Sebastian and Annette's love scene.
66* TheFool: Realistically, Cecile seems to have more or less average intelligence for a 15-year-old girl, but she's treated as though she's mentally handicapped by her more sophisticated peers, which is continually PlayedforLaughs. More than anything, she's simply naive and lacks social graces. She gets better; at the end of the film, she finally understands the other characters' true motivations and helps to take down Kathryn.
67* FrenchJerk: Okay, technically Sebastian and Kathryn are French-''Americans''. But they're still jerks.
68* FreudianSlip: Mrs. Caldwell's racism slips out when her coffee arrives: "...Black! Brown sugar! No sugar!".
69* {{Golddigger}}: Sebastian sarcastically refers to Kathryn's mother as this, believing that she only married his father for his money.
70* GrandeDame: Tiffany Merteuil uses her status in the community to persuade NouveauRiche social climbers to "throw money" at her self-serving charity, as Kathryn puts it.
71* HairOfGoldHeartOfGold: Beautiful young virgin Annette.
72* HandsOnApproach: Cecile and her music teacher Ronald, with a Cello.
73* HeelFaceTurn: Sebastian, who's every bit as slimy as his stepsister at the beginning, just couldn't continue being such a jerk after Annette genuinely won his heart. [[spoiler:According to information on the television series, Kathryn by all appearances seems to have made one too following the film, even running a rehab movement for troubled youths like she used to be.]]
74* HighSchoolAU: Of ''Literature/DangerousLiaisons''.
75* HollywoodHomely: In ''Cruel Intentions 3'', Patrick's FreudianExcuse for being a sexual predator is that he isn't fortunate enough to be an Adonis, especially in comparison to one male character who's played by a former Abercrombie & Fitch model. He even says he feels like he has to "play up the [[HollywoodHomely homely]]" with [[NerdsAreSexy nerdy clothes]] and unstyled hair to trick girls into thinking he's a NiceGuy.
76* HookersAndBlow: Sebastian and Kathryn make drugs and debauchery look so glamorous.
77* ILikeMyXLikeILikeMyY: When Mrs. Caldwell's racism slips out, she tells the shocked waiter she was referring to how she prefers her coffee "--Black! Brown sugar! No sugar!".
78* InsultFriendlyFire: Sebastian drops a few "fag" and "fudge-packer" jokes after he catches Blaine and Greg together, then casually adds "no offense" with a look towards Blaine. Considering Blaine is pretty similar to Sebastian personallity-wise, and the entire thing was set up to manipulate Greg anyway, he doesn't seem to mind all that much.
79* IWantYouToMeetAnOldFriendOfMine: Sebastian hands Kathryn a magazine that has Jennifer Love Hewitt on the cover. Both Ryan Phillippe and Sarah Michelle Gellar had starred alongside her in ''Film/IKnowWhatYouDidLastSummer''.
80* TheJeeves: Naturally, the Valmont house has a proper English butler to manage a full staff of diverse EthnicMenialLabor stereotypes.
81* JukeboxMusical: The stage adaptation has classic [=90s=] songs, from "Genie in a Bottle" to "No Scrubs" to "Only Happy When It Rains."
82* KickTheDog: Why did Sebastian humiliate his therapist and his therapist's daughter in the opening? Because "[the therapist] was charging him too much".
83* LargeHam:
84** Ronald. "THE BLACK MAN IS GONE! THE BLACK MAN IS GONE!"
85** Cecile's mother, played by Christine Baranski.
86* LightFeminineAndDarkFeminine: Annette and Kathryn, respectively.
87* LoveIsAWeakness: The movie's tagline is "In the game of seduction, there is only one rule: Never fall in love." Kathryn and Sebastian (at first) both live by this philosophy, which she uses as the basis for her ReasonYouSuckSpeech against him.
88* MeaningfulName:
89** Sebastian's surname, Valmont, consists of the French words ''val'' (literally meaning "vale", the old-fashioned word for "valley") and ''mont'' ("mountain"). Sebastian starts out the movie "high" (cool and arrogant) but by the climax [[BreakTheHaughty has been brought low and made pathetic]].
90** Cecile:
91*** Kathryn and Sebastian succeed in making Cecile impure - which is ironic, because her name is the French form of "Cecilia" - the Catholic saint who is famously known as "The Incorruptible."
92*** More irony in that St. Cecilia is the patroness of music. Cecile, by her own admission, is a DreadfulMusician.
93* MyGodWhatHaveIDone: [[spoiler: After attacking Sebastian and inadvertingly causing his demise, Ronald, now remorseful after realizing he was manipulated, kneels in the street with Annette to tend to the dying Sebastian.]]
94* NouveauRiche: The Caldwells in contrast to the OldMoney Valmonts.
95* NoodleIncident: Cecile's mother about Sebastian: "I can't believe they didn't expel him after what he did to the school nurse."
96* OldMoney: The Valmonts in contrast to the NouveauRiche Caldwells.
97* PoliceAreUseless: The officer just seems dismayed that Sebastian rudely brushes him off after he repeatedly tries to point out that his car is in a no-parking zone.
98* PracticeKiss: Kathryn and Cecile share one after Cecile reveals she's scared of boys and has never been to first base with one, and Kathryn asks if she's ever practiced with a girl. Kathryn insists that this is how most girls learn.
99* ThePreciousPreciousCar: Sebastian's 1956 Jaguar XK 140 Roadster is his most prized possession. If he loses his bet with Kathryn, he has to hand it over to her. [[spoiler:After Sebastian dies, Annette somehow ends up with the car. Although, production stills from the NBC spin-off TV series appear to show Kathryn eventually ends up with the car in San Francisco. Apparently, she hands it over to Sebastian and Annette's [[BastardBastard son]], Bash Casey, once [[RightfulKingReturns he comes out of the woodwork to claim his family name]].]]
100* PrisonRape: If there's one decent thing about the ''Cruel Intentions 3'' script, it's this witty line from Kathryn's cousin Cassidy, alluding to another character's earlier complaint that his promiscuous sex life has become boring: "You're off to prison, where the sex is never boring."
101* RacistGrandma: Cecile's mother, Mrs. Caldwell, seems like a cultured philanthropist but barely conceals her decidedly ignorant views, no doubt carried over from her generation. When she learns that Cecille is carrying on a dating relationship with Ronald, she promptly fires him and bans him from having any contact with her.
102* RapeIsASpecialKindOfEvil: In ''Cruel Intentions 3'', [[spoiler:Patrick]] becomes the official villain of the movie when he crosses this line.
103* RepriseMedley: The Act One closer, "Only Happy When It Rains," concludes with all the main characters singing reprises of nearly every song in the act.
104* ScatterbrainedSenior: Since AdultsAreUseless anyway, it should come as no surprise that the residents at the nursing home that Sebastian and Annette visit are adorably senile.
105* ScrewTheRulesIHaveConnections:
106** In ''Cruel Intentions 3'', Cassidy's father founded an entire dorm hall just so she could have her own private suite, decked out in just about every standard college room code violation you can think of.
107* SecretCircleOfSecrets: Kathryn's many extracurricular activities include running the Manchester Tribunal, a secret society of cruel popular kids at her snobby prep school. Basically, it's a rip-off of the [[TheIlluminati Skull and Bones]] fraternity at Yale. Orders of business include such dastardly plans as [[ArsonMurderAndJaywalking ruining classmates' reputations, getting faculty members fired and scoring tickets to the Hole concert]].
108* SettingUpdate: Of ''Literature/DangerousLiaisons''. It takes it from 18th century France to 1990s New York City, changing all the characters to teenagers.
109* SevenDeadlySins: Both Sebastian and Kathryn have this:
110** Both are incredibly promiscuous people. (Lust).
111** Both mostly sit around and do little work. (Sloth)
112** Both come from a wealthy background. (Greed)
113** Kathryn is a drug addict and a bulimic. (Gluttony)
114** Kathryn envies her classmates. (Envy)
115** Kathryn and Sebastian despise others around them. Kathyrn in particular takes pleasure in manipulating others to cause as much damage or chaos to themselves and/or their peers as possible. (Wrath)
116* SexualKarma: [[spoiler:Sebastian and Annette's sex scene is depicted as [[IdealizedSex tender and heartwarming]] in stark contrast to the other instances of sexual intercourse.]]
117* ShamedByAMob: Near the end, as Kathryn gives a eulogy at Sebastian’s funeral, suddenly one by one of her fellow students start leaving the room abruptly. As she furiously questions their misbehavior, she decides to follow them and discovers that the students are reading the copies of Sebastian’s journal (handed out by Cecille) that expose the details of her schemes and manipulations all along. Cue, Kathryn receives a [[DeathGlare death glare]] from each of said students, humiliating her. To put the cherry on top, the headmaster single-handedly exposes the [[spoiler:cocaine hidden inside her rosary]] as well.
118* ShoutOut:
119** According to costume designer Denise Wingate, Selma Blair's red hoodie was supposed to invoke ''Little Red Riding Hood''.
120* SingleTear: After being exposed as a sinister in the end, Kathryn sheds a single tear, realizing her reputation is now ''indeed'' destroyed.
121* SinisterShades: [[spoiler:After Ronald is fired by Mrs Caldwell, he is met outside the elevator by Sebastian and Kathryn, who are both wearing sunglasses and smirking, with the intentions of using Ronald's affiliation with Cecile to further their bet.]] Also, Sebastian is seen wearing the same shades in his first introductory scene, driving to his therapy session with Dr Greenbaum, where it is revealed he had been [[spoiler:seducing Greenbaum's daughter to humiliate her.]] At the end, Annette's final scene [[spoiler:(after outing Kathryn) is her driving out of New York City in Sebastian's car, his journal beside her, and smirking somewhat deviously...while wearing Sebastian's sunglasses.]]
122* SocialClimber: Bunny Caldwell hopes Kathryn will take Cecile under her wing so her popularity will rub off on her socially awkward daughter.
123* SomeOfMyBestFriendsAreX: Cecile's mom denies disapproving of Ronald dating Cecile because he's black, citing the fact that she's donated money to Colin Powell's foundation. [[SarcasmMode Ronald is duly impressed]].
124* SophisticatedAsHell: Sebastian and Kathryn, being afforded the best education money can buy, mix phrases such as "[[GratuitousFrench au contraire]]" with adolescent potty-mouth language.
125* StealthPun: ''Cruel Intentions'' contains quite a few of these:
126** Just like the sterling cross in which Kathryn hides her drugs, she looks like a saint on the outside, but on the inside, she's filled with pure sin.
127** Sebastian sports a hunting jacket when he first meets his "prey", Annette.
128** Kathryn wears a snakeskin-print dress as she "slithers" seductively onto Sebastian's lap and hatches an evil plan.
129** Cecile wears a [[{{Literature/LittleRedRidingHood}} red hoodie]] when she sneaks out to go see [[TheBigBadWolf Sebastian]].
130** Sebastian has a bowl of maraschino cherries on his nightstand after he pops Cecile's cherry.
131** In the DVD commentary, the director points out that the way Sebastian suggestively points the [[DoesThisRemindYouOfAnything neck of the champagne bottle]] toward his face when he says he and Kathryn should celebrate was intentional.
132** The way Sebastian strokes the [[DoesThisRemindYouOfAnything handle of his tennis racket]] when he taunts Cecile isn't so stealthy.
133* ThereAreNoAdults: The few adults who do exist on rare occasions are clueless or indifferent to what the kids are up to. Either way, they are not individuals to whom the children can appeal.
134* TheThreeFacesOfEve: The three girls: Annette (wise and mature) as the wife, Kathryn (cold, manipulative FemmeFatale) as the seductress and Cecile (sheltered NaiveEverygirl) as the child.
135* TheyWastedAPerfectlyGoodSandwich: When Kathryn is meeting with Cecile and her mother, the maid Mai-Lee sets a tray of tea or something in front of them, which no one touches. When Sebastian arrives, he sets the tray aside and it's completely forgotten by the time everyone has left the room.
136* TitleDrop: Courtesy of Annette quoting a letter about Sebastian's manipulation: "Even more treacherous than he is attractive...he has never uttered a single word without some dishonorable intention."
137* TookALevelInJerkass: Again, Cecile, who gets more bitchy and slutty as the film goes on, just as Kathryn had planned.
138* TotallyRadical: Cecile's dialogue, particularly when she says goodbye to Ronald with "Peace out!" much to Kathyrn's disgust.
139* {{Tsundere}}: Sebastian pretty much accuses Annette of being this at one point ("Hot one minute, cold the next")
140* UnsuspectinglySoused: Becomes something of a running gag across the series. Provides the page quote.
141* VerbalBackspace: Mrs. Caldwell does this after a politically incorrect outburst.
142-->'''Kathryn''': She's so young, and he's so --\
143'''Mrs. Caldwell''': Black! Brown sugar. No sugar.
144* VirginityMakesYouStupid: Subverted with Annette, played straight with Cecile. Not that Cecile is any smarter afterward.
145* WhereDaWhiteWomenAt: Ronald Clifford is instantly smitten with Cecile as well as, as it turns out, [[spoiler:Kathryn]] despite that neither really seems like his type personality-wise. Suffice it to say, Cecile's mother does not approve of her daughter liking her men like she likes her coffee.
146** In a deleted scene, [[spoiler:Kathryn uses the scandalous nature of her relationship with Ronald to her advantage by manipulating him into believing that Sebastian is a violent racist]].
147* "YouDoNOTWantToKnow," Cecile says about being taken advantage of.
148
149----
150!!Tropes associated with the prequel, ''Cruel Intentions 2'':
151* {{Adaptational Dye Job}}: In the prequel, Kathryn (a Brunette in the first film) is an Icy Blonde while Sebastian (who had the gorgeous curls of Creator/RyanPhillippe ) has Brown hair. They both apparently started dyeing their hair different colors after the prequel.
152** Also, Danielle and Cherie (Annette and Cecile’s prequel counterparts) are a BrainyBrunette and a DumbBlonde in this version.
153* AdultsAreUseless: In the second film, Kathryn and Sebastian's parents are essentially middle-aged versions of their respective children. Responsible authority figures apparently don't exist in this universe.
154* AlcoholicParent: In the second film, Sebastian's mother is said to be "in rehab for the long haul," hence the reason why he moves in with his father.
155* AllGirlsLikePonies: The second movie uses a racy version of this trope where proper horse-riding technique is used as a metaphor for sex.
156* AmbiguouslyBi: Kathryn is going to date and fall in love with Court Reynolds at some point after the Prequel and before the first movie. However, she made out with Danielle when it was revealed they were accomplices to Sebastian.
157* AmbiguouslyGay: Danielle pretends to fall in love with Sebastian, but in reality she couldn't care less about him. She's also not shown seemingly having any crushes on boys at her school, but she does make out with Kathryn when they are revealed to be accomplices. It's implied she was involved with Kathryn in a threesome with Sebastian after they join forces, however it’s not made clear if Danielle has any real affection for Sebastian.
158* ArchnemesisDad: Edward Valmont and his son Sebastian have a strained relationship even though [[LikeFatherLikeSon they're exactly the same]].
159* BettyAndVeronica: This is reversed in the prequel where Kathryn is an icy blonde and [[SuspiciouslySimilarSubstitute Danielle]] is a warm brunette, and then [[spoiler:subverted in the plot twist at the end when Danielle reveals that she's really just like Kathryn]].
160* BitchInSheepsClothing: Kathryn and Sebastian are obvious. It's revealed Danielle is just as bad as Kathryn.
161* BrotherSisterIncest: A pair of girls (who claim to be cousins, but are played by real-life [[{{Twincest}} twin sisters]] share a kiss in the shower while the [[YuriFan male lead watches]].
162* ButtMonkey: Cherie in the second.
163* ChineseLabourer: In the prequel, Kathryn has another one who's a Cambodian refugee, but she's mistaken for Chinese and Japanese by her mistress.
164* CoveredInMud: In the second film, Sebastian pushes Kathryn in a pool of mud as a declaration of war.
165* DepravedBisexual: Gretchen and Sarah, who seduce Sebastian and maintain an incestuous relationship with each other.
166** Kathryn may be this; see Ambiguously Bi above.
167* DivergentCharacterEvolution: [[spoiler:An inverted example. In the prequel Sebastian is kind and considerate, and Kathryn is cold, calculating, and uses sex as a weapon; and frequently destroys other peoples lives for her own amusement or revenge. Both try to convert the other to their way of thinking, but Sebastian is broken by Kathryn and ends up becoming a male version of Kathryn.]]
168* DownerEnding: [[spoiler: The antagonists Kathryn, Sebastian and Danielle are all revealed to be cruel and manipulative by the end of the prequel, while the naive, spoiled yet good-natured Cherie has been seduced and recorded by Sebastian. It's heavily implied they are going to ruin Cherie’s reputation and get her expelled.]]
169* EvilMatriarch: Tiffany Merteuil shows her "love" for her family by being [[MyBelovedSmother controlling]] and [[ManipulativeBastard manipulative]].
170* FreudianExcuse: In the prequel, a sobbing Kathryn uses the [[AbusiveParents emotional abuse she endures from her mother]] as her excuse for being so mean.
171* IdleRich: Sebastian and Kathryn each get a weekly five-figure allowance. And no, they don't mow the lawn for it. Meanwhile, middle-class Danielle has an after-school job at a used bookstore.
172* KissingCousins[=/=]{{Twincest}}: The twins Gretchen and Sarah claim to be cousins, but they look very identical to one another and they were played by RealLife twins.
173* NegativeContinuity: In the first film Sebastian called Kathryn’s mother a "gold digging whore" which implies that Kathryn is the step-sibling who came from a poorer background. However, in the prequel Sebastian is the one from a poorer background. Many fans have noted this.
174* TheOmniscientCouncilOfVagueness: In ''Cruel Intentions 2'', the Manchester Tribunal convenes in the school's candle-lit attic with a a slide projector to discuss its plans to corrupt Sebastian and Cherie Claymon.
175* PervertDad: Although Sebastian's dad is certainly a sleazeball, in this case, it's actually Kathryn's [[DistaffCounterpart mom]] who tries to get a little too close to her new stepson in the prequel.
176* PreachersKid: Before Headmaster Hargrove takes over the position, [[SuspiciouslySimilarSubstitute Danielle Sherman]] is the same thing, only [[spoiler:she's [[BitchInSheepsClothing not what she seems]]]].
177* {{Prequel}}: ''Cruel Intentions 2''... [[InNameOnly sort of]]. It was [[PoorlyDisguisedPilot actually a pilot for a TV show]] that never happened.
178* ScrewTheRulesIHaveConnections: ''Cruel Intentions 2'' invokes this trope often to explain how the characters are able to pull off some pretty [[WillingSuspensionOfDisbelief unbelievable]] scams (e.g., Sebastian switching his high school transcript with a forgery; Kathryn getting her hands on the real one).
179* ShowerScene: ''Cruel Intentions 2'' has a shower scene with a pair of [[{{Twincest}} twins]] [[ShowerOfLove making out]] in front of Sebastian, which, incidentally, is the [[BestKnownForTheFanservice only thing people remember]] about the film.
180* SocialClimber: In the prequel, [[SuspiciouslySimilarSubstitute Bunny Claymon]] has the exact same hopes for her daughter [[SuspiciouslySimilarSubstitute Cherie]].
181* TeensAreMonsters: Especially in the prequel, and even more especially in the unaired episodes of the canceled television series that became the prequel. Almost every student at Manchester Prep turns out to be every bit as cruel as Kathryn and Sebastian.
182* {{Twincest}}: Gretchen and Sarah. A scene shows the identical twins make out in the shower to entice Sebastian. Rather ridiculously, in the scene the girls claim to only be cousins.
183* TwinThreesomeFantasy: Gretchen and Sarah (played by Alicia & Annie Sorell) tease Sebastian with this in the shower, invoking Twincest as well (even though the two identical girls claim in dialogue to only be cousins).
184* WickedStepmother: Kathryn's mother tells Sebastian in no uncertain terms that if he doesn't keep an eye on his philandering father, the two of them will both be [[GettingTheBoot kicked "out on the street."]]

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