If you’ve seen Cruel Intentions, then you’re bound to remember the kiss. It’s between Sarah Michelle Gellar’s wicked Kathryn Merteuil and Selma Blair’s Cecile Caldwell, the film’s sexually frustrated naïf. Kathryn, the student-body president at Manchester Prep, a fictional private school on the Upper East Side, is playing teacher to clueless Cecile, who will be starting at Manchester when summer is over. Kathryn doesn’t really give a shit about Cecile; she’s only hanging with the slack-jawed brunette to move along one of her several long cons. This one, a logically convoluted act of vengeance against her ex, involves turning Cecile into a slut—Kathryn need only teach her the tools of the trade, of which she is intimately familiar. 

First thing’s first: first base. Cecile is in love with her cello instructor Ronald (Sean Patrick Thomas), and she’s got to learn how to please him. It’s a sunny afternoon in Central Park, and the girls are lounging on a picnic blanket—Kathryn, a posh vixen in an all-black get-up (tiny dress, smart blazer, shades, and floppy hat); Cecile, playfully girly in a bubblegum pink top-and-skirt combo, a lime green sweater tied over her shoulders. The best way to practice is with your girlfriends, Kathryn insists, matter-of-factly. After the first gentle smooch, the camera zooms in on the girls’ faces as they try again with a bit of tongue. When their lips touch and part moments later, a string of spit clings between them, briefly. For this sapphic smooch, the two actresses nabbed the Best Kiss award at the 1999 MTV Movie awards. In the nineties, lesbian erotics were all the rage: think Neve Campbell and Denise Richards going at it in the pool in Wild Things (1998); or Gina Gershon and Jennifer Tilly, nestled in noirish shadows as they make love (and do crimes) in Bound (1996). 

Directed by Roger Kumble, Cruel Intentions is a high watermark of the teen-sex movie that takes its source material (Pierre Choderlos de Laclos’s Les Liaisons dangereuses, also adapted by Stephen Frears into the 1985 film Dangerous Liasons) and translates it to the world of Manhattanite rich kids. This demographic is well suited to the decadence of the original, also about aristocrats with little else to do but sleep around, look fabulous, and create palace intrigues. Kumble’s film, a true product of the nineties starring a roundup of the decade’s biggest teen stars, is also triumphantly, indifferently racy—perhaps that’s why it’s such a beloved object among the millennial set, with many of us all-too-eager to wax nostalgic over the days when sex in the movies was less circumscribed by political correctness. 

Sex had long entered the pop cultural mainstream by the nineties, but the decade saw the sexualization of teens on a whole new level. Consider young Drew Barrymore, playing a Lolita-style homewrecker in Poison Ivy (1992) or the rise of Britney Spears, who was only sixteen when she unleashed “Hit Me Baby One More Time.” Cruel Intentions followed this trend and placed it on the wavelength of a bitchy, broody daytime drama. Without it, we probably wouldn’t have aughts-era guilty pleasures like Gossip Girl and Pretty Little Liars (though the sex in these shows, reined in by the TV networks they originally played on, pales in comparison to that of its ancestor).

There’s real heat to the kiss despite their playing pretend—and Cruel Intentions is full of these kinds of interactions. Ronald is pretending to teach Cecile the cello as he straddles her from behind and moves her hand as it clutches the bow. Eric Mabius’s closeted all-American boy, Greg, pretends to be a straight football bro, though he’s “got a mouth like a hoover,” which he likes to use on Blaine (a peroxide blond Joshua Jackson). Good sex, in a sense, is about maneuvering the divide between performance and reality. You act out desires, unleash the animal side of yourself that you keep private from the masses—but then, is that the true you? How much you is inside the persona enacted when playing the merciless dom? The whimpering virgin? Being a teenager is about trying on masks, too, and working through identities as you edge into adulthood.