I Rewatched ‘Cruel Intentions’ As An Adult & Now I Need Serious Therapy
I’m a sucker for late ’90s movies and you don’t get much more iconic than Cruel Intentions.
It’s wild that more than 20 years have gone by since this extremely horny movie first hit our screens, but as the years have passed, it still remains one of the most quotable films ever.
While I do remember loving this movie, aside from that, I’m pretty hazy on the details of what actually happens so I decided it was time to finally watch Cruel Intentions again.
I rewatched Cruel Intentions as an adult! Let the filth begin!
From the second the Placebo song starts strumming, I’m transported straight back to high school. We quickly meet our protagonist, Sebastian (Ryan Phillippe), who is driving his fancy convertible in New York City. Then suddenly he’s in his psychologist’s chair staring at the ceiling. Who has the money to pay someone to watch you stare at the ceiling? Oh yeah, he’s wildly rich. This is important.
Seb (that’s his new name) acts like a baby and speaks in a baby voice. He says he’s sick of only caring about sex but his psychologist dgaf, she barely listens and says she can’t see him again for a month as she is going on a book tour.
Seb pathetically asks for a hug, before he admires a photo of his psych’s daughter on the desk — it’s Tara Reid! Remember her?! Anyways, as Seb leaves the office, the daughter calls her mum in tears as Seb has put her nude photo on the internet. It’s baffling stuff.
Seriously Seb, is this the best you could do?!
As Seb leaves the appointment, the psychologist screams at him through a glass wall. He laughs before meeting some random woman who immediately agrees to go out with him. Umm isn’t he still in high school?? This is just the beginning of the confusion.
We then meet Kathryn (Sarah Michelle Gellar, playing Seb’s stepsister), who is helping a new student, Cecile (Selma Blair), to fit in at their school. Kathryn talks about her deep devotion to God before Seb stumbles in and peers up Cecile’s skirt. This fucking dude.
Once Cecile leaves, we finally get to see the real Kathryn, I’ll call this version Kath. She presents Seb with a challenge: after finding out her ex is now dating Cecile, she wants to turn her into a “tramp” and needs Seb’s help.
Seb puts his head inside a a piano, which I think is rich boy speak for ‘OK’.
The step siblings then almost make out (yes, this is our new normal for the next two hours) before Seb says he’s found his own challenge. He wants to deflower the new headmaster’s daughter, Annette (Reece Witherspoon). Kath strikes a deal, if he takes Annette’s virginity, she will have sex with him…her own stepbrother. Nice.
Kath then says this amazing line, sealing her status as the most iconic villain of all time:
That does sound painful but I’d volunteer as sacrifice to get the full Kath experience because I fucking idolise her.
Seb visits his Aunt Helen’s house where Annette (let’s go with Annie) is staying. They meet and he’s very full on with her. But she won’t take his shit, telling him, “You promise girls the world to get them in bed with you”. He is outraged and demands to know where she got this (very correct) info from but her lips remained sealed.
Seb visits a guy called Blaine and OMG I FORGOT JOSHUA JACKSON WAS IN THIS. He is gay and blonde and hilarious.
Seb decides that a school jock told Annie about his reputation, before Blaine reveals that he and said jock have hooked up before. Seb threatens to out the poor jock (this fucking dude?!) after he pays Blaine to set the scene so he’d find them in bed together.
Pacey Witter would never.
After all that mess, it turns out that it was Cecile’s mum who had warned Annie about Seb. Speaking of Cecile, we find out that she’s actually into her cello tutor: Ronald, played by the devastatingly handsome Sean Patrick Thomas.
While at the park, Kath is brushing Cecile’s hair, which sidenote: is not a thing women do together, ever. Anyways, Kath volunteers to teach Cecile how to go to first base, which I’m pretty sure is a scene that every teenage boy had to watch as some kind of heteronormative rite of passage.
This scene was so scandalous in its day. I remember it was the string of saliva that had everyone losing their goddamn minds.
The tea had never been more piping.
I’m sure when I eventually kiss someone for the first time I’ll look like the plant in Little Shop of Horrors trying to devour a man whole.
After the sexy spit kiss, Cecile is into it, telling Kath “That was cool!” It was cool! Kissing is cool! Kissing Sarah Michelle Gellar is always cool! She’s a fucking VAMPIRE SLAYER.
Anyways, back with Seb and he’s listening to opera so obnoxiously loud that he wakes the whole house. Annie confronts him as he sits in a wooden wheelchair beside an indoor pool. You know, teen stuff.
He is so desperate to get Annie’s attention. Boys are so needy.
“Are you aware this music is playing in every room of the house?” Annie tells Seb, who replies “It’s not just yours!”, which umm, is something a nine-year-old might say.
Later he gives her a backpack as a present (which tbh isn’t helping his cause) before spontaneously asking if she wants to go swimming (again, you’re not a tiny child?). As Annie arrives at the pool, he’s nude! He tries to sleeze all over her and she warns him that she’s seeing someone.
Back with Kath and Seb, as usual they’re exhibiting a totally normal family dynamic.
I AM VERY UNCOMFORTABLE.
After Kath tells Cecile’s mum about Ronald, she’s so furious (and very, very racist!) that she bans her daughter from seeing him again. Kath and Seb tell her to communicate with him via love letters and they offer to help.
Cecile sneaks out at night and visits Seb, who spikes her drink and then blackmails her into letting him give her oral sex. Have I mentioned this guy can fuck off? Back with Annie, she encourages Seb to volunteer with her at an aged care home.
While driving home she becomes possessed by some kind of dark force and her face contorts into these demonic expressions.
To this day I still don’t know what the hell this scene was about but it feels oddly familiar.
Whatever witchcraft Annie invokes seems to change things between them and they end up holding hands. Back with Cecile, she tells Kath about being sexual assaulted by her brother but this is quickly brushed aside when Cecile realises she had her first orgasm.
Kath tells Cecile to keep having sexual encounters with Seb, as well as sleeping with as many people as possible. Cecile replies that would make her “a slut”, but Kath tells her the real tea: Everyone does it but no one talks about it. Did I mention Kath is my fucking hero?
TFW you’re done with bullshit gender-based double standards:
Cecile and Seb have sex, he treats her awful afterwards and even at one point he actually pushes her off the bed — THIS IS FINE!
Seb continues to stalk Annie, in a scene he actually wears binoculars which seems like overkill. While Annie is sitting in a park (and minding her own damn business), Seb tries to aggressively kiss her, she pushes him away and he yells at her.
Later that night he comes to her room, calls her names and tries to emotionally blackmail her. She locks the door, kisses him (OK??) and starts unbuttoning her pyjamas. He freezes and flees. Seb looks in the mirror and says “Pussy!”, which is also my nightly routine although I’m usually holding my cat Chandler at the time.
As Annie leaves the aunt’s place, Seb tracks her down and this iconic Cruel Intentions scene plays out…
She says she’s “impressed” (by his stalking techniques??), he replies, “Well, I’m in love”. OK, sure.
They kiss, then all of a sudden they’re on a bed. Where is this bed? At the train station?? Anyway, they do the sex, at least I think that’s what’s happening?? It’s very dark. “HELLO, WHO’S OUT THERE?” I shout into the abyss. It’s all shadows and random body parts.
The next day Seb is in a chipper mood, he almost walks in on Kath and Ronald doing the sex stuff, but she hides him in a draw under the bed.
I need to get me one of these nifty men storage systems. I wonder if I can pick one up at IKEA.
Ronald leaves, as Kath knows that Seb banged Annie she tries to sex him up…but he rejects her! His own half-sister! HOW DARE HE?! She shouts at him, “I want to fuck!” and haven’t we all been there girlfriend.
Anyways, Kath mocks Seb and says that he and Annie ‘s relationship will ruin both of their reputations. Seb leaves and wanders the streets of New York. For how long?? I don’t know! Much to ponder! Women to stalk!
Seb dumps Annie and she does something I’ve been wanting to do all movie:
I usually don’t condone violence but this fucking dude.
After breaking up with Annie for the second time in the space of like 48 hours, he returns to Kath who quickly taunts him. She tells Seb that she manipulated him into breaking up with the love of his life, as she teases, “You’re just a toy Sebastian, a little toy i like to play with.” It is brutal. She finishes him off by telling him,”I don’t fuck losers”, which I’m adding to my Tinder bio asap.
Seb is devo and decides the best way to mend his relationship with Annie is to gift her his sex journals, documenting all the women he’s manipulated into bed.
I probably would have gone with a bouquet of roses, or maybe a nice card with a happy owl on it.
From here shit gets real. Kath tells Ronald that not only did Seb have sex with Cecile but he hit her (wut?!), so Ronald goes and starts a fist fight with Seb on the side of a highway — because, why not, you know?
Annie appears and somehow ends up on the road, Seb saves her but gets hit by a car in the process. He tells her that he loves her before dying. DYING?! HE’S DEAD.
Probably should have stayed at home, Annie.
Cruel Intentions ends with Seb’s funeral, where Kath gets exposed for all her deceitful and manipulative (and legendary) actions. Seb’s journal is printed out and hundreds of paper copies (in this economy?) are handed to Kath’s classmates.
Me reading my old tweets:
The closing shot is of Annie driving off in Seb’s car. She now wear’s cool girl sunglasses. Is she the new Seb? Has that car demon who possessed her earlier returned? What have we supposed to have learnt from all this?!
Who the fuck knows. Siri, play ‘Bittersweet symphony’.
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Cruel Intentions is available to stream on Stan.