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Let's Talk About Sex: 20 Movies About Losing Your Virginity

The Playlist By The Playlist Staff | The Playlist July 26, 2013 at 12:05PM

You never forget your first time, they say. And even if you were to try very hard to expunge the memory, Hollywood will do its best to keep on reminding you anyway. With seemingly another R-rated comedy released every week, (this week's being "The To Do List" starring Aubrey Plaza, opening this Friday, read our review here), The First Time has become increasingly well-trafficked territory, and it's not hard to see why. Really it's a screenwriter's dream—an (almost) universally relatable life-stage conundrum (in the Western world, anyway) that is ripe with potential for misunderstandings, social embarrassment and awkwardness, and that's just within the more comedic end of the spectrum.
17
Where the Boys Are

"Where The Boys Are" (1960)
Over 50 years before "Spring Breakers," there was "Where The Boys Are." The 1960 MGM coming-of-age comedy may seem hokey to a modern audience, but it was groundbreaking at the time in its discussion of sex, pre-marital sex and date rape. The movie follows four female college co-eds on their group spring break, with each having a different approach to man-chasing and the value of their virginity. Don't get your Women's Lib hopes up; each girl still ultimately wants to get married and start a family. Oh the early '60s, when women were going to college just to land a man. Anyway, before the trip to the ethical no-man's land known as Florida, the leader of the group, Merritt Andrews (Dolores Hart), spouts a feminist approach and advocates "making out" before marriage, encouraging her pals to do the same as they hit the open road. Once down in Fort Lauderdale, Merritt backtracks a bit when she actually encounters a red-blooded man in the form of yacht-owning Brown student Ryder Smith (George Hamilton). Unfortunately, Merritt's friend and co-traveler Melanie (Yvette Mimieux) took her rhetoric hook, line and sinker and loses her virginity to a Yalie, mistaking sex for love to dire rapey consequences. The group is rounded out by Paula Prentiss who in all earnestness says, "Girls like me weren't built to be educated. We were made to have children. That's my ambition: to be a walking, talking baby factory. Legal, of course. And with union labor" (we're not sure whether to retch or clutch "The Feminine Mystique" to our bosoms), and goofy Angie (Connie Francis, who also sings the obligatory theme song/pop hit), who doesn't have a clue about romance but isn't as eager as Melanie to find out. With the exception of a traumatized Melanie who gave her *ahem* heart away too soon, the girls manage to find love with men who are willing to wait for them, which means until after the wedding bells chime like "good girls." A hit amongst teens, the film was refashioned for West Coast kids in the form of "Palm Springs Weekend" and "updated" in an unsuccessful 1980s remake involving Judy Garland's daughter Lorna Luft, "Where The Boys Are '84."

"Cruel Intentions" (1999)
Based on the 18th-century French novel "Les Liaisons dangereuses" by Pierre Choderlos de Laclos, "Cruel Intentions" uproots the story of social machinations and hypocrisy amongst the Ancien Regime and updates it to a high school set on the Upper East Side of Manhattan. At the center of the intrigue, grande dame Kathryn (Sarah Michelle Gellar) calculates the love lives and demises of her classmates with an icy, sadistic quality that would make Buffy bring out the trusty wooden stake. Kathryn herself is no virgin, but she manipulates her stepbrother and love interest Sebastian (Ryan Phillippe) into deflowering two women, the sheltered Cecile (Selma Blair) for revenge, and the upstanding Annette (Reese Witherspoon) for a sexual wager. Not that Sebastian is some wholly innocent pawn; he uses sexual and romantic blackmail to get his way. It is only when he falls for one of his victims that he gains some semblance of a conscience, although it's a bit too late in the game. Of course they each get their comeuppance, with Sebastian paying the ultimate price while Kathryn's dastardly ways are revealed by the virtuous (now virtue-less, in misogynist terms) Annette at his funeral by way of distributing photocopies of his very detailed and lurid diary amongst the student body. Suffering a ruination more damning than a calculated deflowering, Kathryn eats public humiliation while Annette drives away from it all with fond memories of Sebastian, ultimately not regretting her first time. The moral of the story is that sex isn't evil; it's the people who abuse and misuse it.

Weird Science

"Weird Science" (1985)
Another John Hughes classic, this time we not only do we have your typical (for the '80s) high school nerds trying to score with babes, but some weird science that gets downright surreal at times. At the beginning of the movie, it appears that the closest they've ever got to physical contact with a girl was being pantsed by a young and pretty Robert Downey Jr. but rather than waiting to meet kindred spirits in college, Gary Wallace (Anthony Michael Hall) and Wyatt Donnelly (Ilan Michael-Smith) take it upon themselves to use their nerd powers to create the "perfect woman." Combining some computer hacking, a Barbie doll and a passing lightning storm, they get Kelly LeBrock, who boasts, in addition to her obvious physical assets, superhuman powers including mind and matter manipulation, and actually liking the two dweebs. See, it's all very scientific. Although Gary and Wallace are too nervous to actually score with this fantasy woman outside of some kissing (at her insistence, believe it or not), the real reason they created this walking, talking teen fantasy hovers round the fringes of the film, never directly acknowledged but nonetheless entirely, well, duh-worthy. But this was John Hughes, after all, and he wasn’t so tone deaf as to have her snaffle their innocence: instead she helps them get age- and um, species?-appropriate girlfriends of their own, and assumedly become men. 

Stealing Beauty

"Stealing Beauty" (1996)
Directed by Bernardo Bertolucci, "Stealing Beauty" drenched in a kind of overly lyrical, romanced style that puts off as many people as it entrances (can you tell which camp we belong to?) is about a young woman grappling with her mother's suicide who goes to Tuscany to stay with family friends. Marking Liv Tyler's film debut as 19-year-old Lucy Harmon, the character hopes not only to get over her mother's loss but to reconnect with a boy she had met there four years before and possibly meet her father. It's a slower-paced "Mamma Mia!" of sorts, with fewer songs and way more mooning over Tyler's lushness in the late afternoon Tuscan sunshine. Lucy's father could be one of three men: an Italian war correspondent, an English playwright (Jeremy Irons) or an Irish sculptor (Donal McCann). While on her search for both "men in her life" (say what you will about father issues), she decides to lose her virginity (and not to that Italian boy from four years ago) and through that experience, she grows and learns about herself. Definitely one of the rare occasions on this list of a First Time that is altogether not played for laughs, though some unintended titters at the ridiculousness of the film's po-faced longing for transportative profundity may have escaped us. 

Saved!

"Saved!" (2004)
A neglected gem and a surprisingly funny "born again" satire, "Saved!" is about a "good girl" high schooler named Mary (Jena Malone) who becomes pregnant, and unlike her namesake, it isn't going to be a virgin birth. When her "perfect Christian boyfriend" Dean reveals that he's gay, she misguidedly thinks that she should sacrifice her virginity in order to "save" him. Unfortunately, Mary's action does not save Dean from Mercy House, a Christian treatment center for those off the "righteous path" (LGBT, pregnant unwed women, etc.). Through the help of the only Jewish student at school (Eva Amurri) and the only wheelchair-bound one (Macaulay Culkin), she manages to keep her pregnancy a secret from her former clique "The Christian Jewels," run with witchy piety by Mandy Moore's Hilary (Moore's never been better than here), the rest of the student body, her mother (Mary-Louise Parker) and her crush (Patrick Fugit) for just long enough. Though maybe a little shy of the pomp and circumstance surrounding Prince George Alexander Louis' birth a few days ago, Mary does go into labor during prom. But in a sweet and maybe slightly surprising turn, given the film's occasionally caustic tone to that point, after the ordeal of giving birth Mary's faith is restored, albeit not with the same phoney dogmatic dedication she had before—"it's like life is too amazing to be this random and meaningless consequence of the universe. There had to be a God... or something out there." 

And where else could we end a feature like this other than with a mention of God? Was that as good for you as it was for us? As we lean back, spark up a cigarette and bask in the glow of our newfound adulthood, we must admit that with a field this broad, we couldn't possibly hit them all. Here are a few applicable titles that fell by the wayside in the midst of our fumbling, often because we felt the virginity-losing did not form the main thrust (sorry—these inescapable puns!) of the plot: "An Education," "American Beauty," "Can't Hardly Wait," "Clueless," "I'm So Excited!," "Mermaids," "The Notebook," "Revenge of the Nerds," "Road Trip," "Puberty Blues," "Lolita" and "Splendor in the Grass." There are many more, and if we've skipped your favorite, feel free to tell us about it below— Diana Drumm, Kristen Lopez, Drew Taylor, Kieran McMahon, Jessica Kiang, Oliver Lyttelton

This article is related to: Features, The To Do List, Feature


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