Revisiting Cruel Intentions: The Most Toxic Teen Film of The 90s

I am optimistic that the world won’t end for at least another five years, but I’m willing to call it: Cruel Intentions is the most inappropriate movie ever made for minors. For the uninitiated, Cruel Intentions is a teen psychosexual thriller based on Dangerous Liaisons. Set in a wealthy Manhattan high school, I don’t think it’s inappropriate out of a pearl-clutching prudishness, but rather, because the sexual mores it models promote a gendered double standard – one I was sadly exposed to as a teen, when I saw this movie in theatres. I still think that trip to the cinema was the most scarring entertainment experience of my life…

Written for the screen and directed by a then thirty-something dude called Roger Kumble, Cruel Intentions is a film that suggests sexually active young women deserve to be publicly humiliated – and probably expelled from school. I’m not kidding you – that is the message of the movie, and if you don’t believe me, rewatch it!

The plot starts with Sebastian (Ryan Phillipe) and his stepsister Kathryn (Sarah Michelle Gellar) making a bet about whether Seb can bed the new headmaster’s daughter, Annette. Played By Reese Witherspoon, Annette has recently published an op-ed in a teen magazine vowing to remain celibate until marriage. As a viewer, it seems unlikely Sebastian could seduce her. I mean, why would anyone find this person charming? When the character is first introduced, it’s revealed he made a revenge porn website about his therapist’s daughter for….no reason. Sebastian is a sociopath, but I don’t think the movie knows that…

I’ve decided Cruel intentions never should have been made. Please do not show it to impressionable teens and tweens in your orbit. To explain my thought process, here are three issues with this movie that make it toxic (I could have written more but I doubt you have time to read a 15,000 word treatise).


  1. It’s Pretty Freakin’ Rapey

Sebastien spends the movie pursuing Annette, but that doesn’t mean he doesn’t have time for a side hustle! He also pushes sexual activity on a young girl named Cecile (Selma Blair) without her consent. But the film excuses this blatant example of assault, because Cecile has an orgasm. News Flash: That doesn’t make rape okay!


  1. It’s So, So Sexist

When we meet Kathryn, she explains the fundamental hardship of her life: she has to act like “Mary Freaking Sunshine” all the damn time. Indeed, while Sebastian can play the part of charming bad boy without becoming a social pariah, Kathryn has to be perfect to be a socially acceptable young woman. This film – probably unintentionally – illustrates the pressures double standards place on young women. Kathryn must hide her interest in sex and partying, and God forbid she ever gets mad in public! Her life is pretty taxing…

Despite Sebastian’s status as a rapist and revenge porn maker, he still gets to be this sexist film’s hero. After the guy’s admittedly tragic death (he’s still a child and I don’t want children to die), Annette publishes his sex journals for the whole school to see. This romantic gesture is meant to cement Seb’s legacy as the biggest stud in their school’s history. For some reason, Annette believes it’s better to have a legacy of being a total douchebag than to be forgotten by your prep school classmates. Okay then!

Photocopying Sebastian’s journal is Annette’s final act of love for the boy who seduced her on a bet, but then writes her a confessional letter about it and apparently redeems himself in her eyes. Anyway, before Sebastian and Annette can truly reconcile, he dies in a weird street brawl with another child. I get that Annette is sad about this senseless loss; however, her final tribute to Sebastian is problematic.

By ensuring her boyfriend’s creepy reputation is safe, Annette is actually selling out Kathryn, who is outed to her school as – gasp – a young woman who enjoys sex. Thanks to the journals, her peers and teachers also learn Kathryn keeps cocaine in her cross necklace. And, since this is the ‘90s, she’ll probably get expelled for her drug use disorder. Fundamentally, this movie believes sociopathic teenage boy sex criminals should be exalted, and girls who enjoy sex with multiple partners should be destroyed…


  1. The Male Gaze

This film courts The Male Gaze whenever it can. Case in point: There’s a faux lebsian kiss between Kathryn and Cecile that is obviously there to titillate straight dudes. Seemingly ripped from the plot of a bad adult film, Kathryn suggests she can teach Cecile how to kiss by making out with her on a picnic blanket. The scene is not meant to be an example of sexual fluidity;  however, it could explain why every heterosexual boy I knew in high school had seen Cruel Intentions multiple times.

Sarah Sahagian

Sarah Sahagian

Sarah Sahagian is a feminist writer based in Toronto. Her byline has appeared in such publications as Elle Canada, Flare, Bitch Media, The Toronto Star, and The National Post. She is also the co-host of You Do You: A Dating Podcast. Sarah holds a master’s degree in Gender Studies from The London School of Economics. You can find her on Twitter, where she posts about politics and live-tweets The Bachelor