Growing up in suburban England in the late '90s, my friends and I learned about adolescence mostly through movies that came shiny and direct from America. We ate up films like Never Been Kissed and Bring It On, but as we became more aware of our sexuality, the one that influenced us the most was 1999's Cruel Intentions. Because aside from hallway whispers, and in the absence of smartphones and instant internet access, we had limited info about sex. As such, the film’s racy content really piqued our curiosity, especially when it came to each female character's sexual journey.
The movie tells the story of privileged Upper East Side stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe), who form a twisted bet over whether or not playboy Sebastian can seduce Annette Hargrove (Reese Witherspoon), the virginal daughter of their prep school headmaster. The teen girls at the center of the film are meant to be archetypes; there's "the whore" (Kathryn), "the ditz" (Cecile, played by Selma Blair), and "the virgin" (Annette). Each character undergoes a different sexual arc throughout the film, and they all impacted how I — and probably countless other young women — thought about “it” in vital ways. Now, 20 years since Cruel Intentions was released, we can revisit those storylines in order to see just how each of them impacted the views on sex we have today, as adults.
Prior to watching the movie, I’d seen a few examples of sexually liberated female teen characters (Courtney in Bring It On, Michelle in American Pie), but Kathryn was different. In the film, she unapologetically owns and uses her sexuality to gain positions of power, putting it up as collateral in her bet with Sebastian and seducing Ronald (Sean Patrick Thomas) out of boredom and jealousy over his relationship with her pawn, Cecile. Kathryn genuinely loves sex, even saying, “I wanna f*ck!” to Sebastian after presuming she has lost their bet.
Seeing this kind of character was revelatory for me, as someone growing up in a place where slut-shaming was rife and the sex lives of girls rumored to have "gone all the way" were used as punchlines at school. If Kathryn, a beautiful girl with a strong sense of self and innate sophistication, enjoyed sex, how wrong could it be? Her actions also taught me that women could be sexually dominant if we so desired; up until Cruel Intentions, I had simply assumed the guy would always be in the driving seat in any given sexual situation.
I’m also grateful that Kathryn’s comeuppance in the film is not due to her proclivity for sleeping with people or her appearance, but rather her deep-seated meanness and skillful manipulation of others. This isn't exactly good behavior, of course, but it's great to see that the way Kathryn conducts herself in relation to her sexuality isn't her downfall. Instead, it's simply a positive example for viewers in need of a healthy dose of sexual confidence.
Cecile is treated horribly in Cruel Intentions. At Kathryn’s whim, Sebastian turns the inexperienced teen into his sexual play thing. In one problematic scene, he plies her with alcohol (“This sure doesn’t taste like an iced tea,” Cecile says, and Sebastian tells her it’s from Long Island) and tricks her into letting him perform oral sex on her. Even at 14, I knew this was predatory and vile behavior.
What Cecile and I shared, though, was both an innocence and a very adolescent need to be viewed as more grown-up than we were. Watching Cecile have her first tongue kiss and later, her first orgasm (and liking it!), made me feel hopeful, safe, and not alone in my emotions.
Cecile was also, at her core, a romantic; she delights in receiving love letters from music teacher Ronald, with whom she is deeply infatuated. It was refreshing to see their sweet courtship in a film full of duplicitous, emotionally abusive relationships. With Cecile, Ronald wants to take things slow and doesn’t use her sexual curiosity as an opportunity to take advantage. Watching them, I daydreamed about a future in which my crush and I could experience intimacy together at our own pace.
Even Cecile’s transformation from clueless to in charge of her sexuality (“Want a blow job?" she later asks Sebastian in an attempt to flip the power dynamic in the bedroom), despite the gross involvement of Kathryn and Sebastian, is endearing and plausible. If she can get through the awkward bits and emerge with a healthy relationship to sex, all while keeping things at her comfort level, then there was hope for me, too.
Annette’s story resonated with me most. She's principled and mature, confident not only in relation to sex but to who she is in general. I was impressed she was firmly in charge of her own sexual narrative, choosing to write about it in Seventeen despite inevitable backlash from peers. From her, I learned about the concept of waiting for marriage before having sex for the first time, a choice I hadn’t considered before. And although she defaults on this decision later in the film, it’s not due to pressure or deception from Sebastian. In fact, Annette calls him out on his #playerlife from the beginning, letting him know she's aware of his reputation and that his patented moves are futile. When they do ultimately have sex, it's totally her decision.
As a young viewer, I really responded to Annette’s lack of regret over the circumstances in which she had sex for the first time. There are no scenes where she beats herself up internally or a character calls her a slut. Her decision to be intimate isn't shameful, but powerful, and I knew that it could be like that for me, too. Annette's journey showed me it'd be OK if I changed my mind about sex, and that if I did, I shouldn't feel guilty about my choice.
These days, we're lucky to have the full gamut of teenage girl experiences portrayed on-screen, from the painfully realistic PEN15 to the nostalgically sweet To All the Boys I’ve Loved Before. Yet back in the late '90s, Cruel Intentions was one of the only films that didn't skirt around female teenage sexuality. As Gellar noted in a January interview with Entertainment Tonight, the film "was daring and edgy, and some people were against the movie [but] I think we always knew that we [the cast and crew] were doing something really cool."
The movie deviated from the wave of “frothy romantic comedies” that had cropped up in the late '90s, in which teenagers fell in and out of love but were never explicit about sex. In Cruel Intentions, though, Kathryn, Cecile, and Annette all got to experience sex on their own terms, which powerfully affected me and so many others as we were coming of age and figuring out our own sexuality.