‘Booksmart’ is Queering the Teen Comedy

A new movie about best friends going to a party the night before high school graduation delivers one of the best first same-sex hook-ups in history.
Booksmart
BooksmartAnnapurna Pictures

Sorry to sound like a horny 12-year-old boy, but Superbad is my favorite comedy of all time. I can recall every joke and detail from the movie, including my theater-going experience (I sat in the second row and my neck hurt the next day from craning to look up Jonah Hill’s nostrils). In Superbad, Seth (Hill) and Evan (Michael Cera) were absolutely clueless about girls and sex, which struck a chord with teenage me, a girl who was curious also about sex, confused about friendship, and terrified of a romantic future.

That being said, I’ve also re-watched the movies numerous times in the last year and come to terms with how problematic it is; how many times it punches down at people of color, women, and queer people (Seth calling his best friend Fogel “Faggle” whenever he’s mad at him is proof enough of the movie’s underlying homophobic worldview.)

Twelve years after my favorite comedy’s release, Jonah Hill’s younger sister, Beanie Feldstein, stars in a movie reminiscent of the best parts of Superbad. Actually, Booksmart is better than Superbad, because it's funny and led by two female characters, one of which is gay.

There have been a few loss-of-virginity comedies with a queer lead—I was wowed by Blockers last year, which featured Gideon Adlon as a closeted lesbian who enters a pact with her best friends to lose their virginity on prom night. Jamie Babbit's But I’m A Cheerleader was a teen sex comedy, to be sure, but it was no blockbuster—in its opening weekend in 1999, the satirical indie about conversion therapy played in four theaters. Booksmart, which opens in 2000 theaters across the United States this weekend, takes a classic mainstream film format and completely reforms it. The teenage sex comedy has officially been queered.

In Olivia Wilde’s directorial debut, the movie follows best friends Amy (Kaitlyn Dever) and Molly (Feldstein) on their last night of high school. Molly has the gutting realization that she and Amy wasted their high school years just studying, while everyone else studied and partied. So on the night before graduation, they agree to go to a house party and prove to their classmates that they are fun. One of the tenets of the agreement is that Amy has to hook up with a girl, something she hasn't done before.

BooksmartAnnapurna Pictures

I’ve never seen a movie so bullheaded in its depictions of that cumbersome, awkward fumble through a teenage girl’s first encounter with lesbian sex. I was raised on a series of trash movies about sex and virginity; raunchy sex comedies of the aughts like the American Pie franchise, which defined an era of movies for teenagers. Movies like Not Another Teen Movie, Eurotrip, and a few years later, Superbad. The kind that begins with “This is our last chance to party as high school kids!” and end with a cringe-worthy tumble through sex firsts. It’s no wonder I was so deeply closeted and repressed until my twenties—everything I knew about sex and sexuality, I learned from movies that were openly chauvinistic and grotesquely anti-gay.

Homophobia was one of the hallmarks of Steve Stifler’s personality, one of the more memorable characters in the series of American Pie films. With all his gay jokes, which were mostly aimed at men, but also at Jessica (played by Natasha Lyonne), the message was clear to teenagers in the '90s and 2000s: Gay men shouldn’t enjoy sex or the pursuit of such, but rather, they should be shamed for it. And women? Well, women wouldn’t pursue sex with another woman according to these movies—lesbianism was either wholly invisible or treated as an invalid, emotional ID. In American Pie 2, Stifler and his friends posit that two female neighbors are lesbians because they live together, and he tries to get them to kiss while he and his friends watch, and a group of men listen in on walkie talkies. The women were not lesbians, simply roommates who make it clear they've never been intimate before but find the scenario humorous and fun, not unlike most lesbian porn made by men. In "American Pie 2," lesbianism is only kosher if Stifler and co. get to witness it in a moment of hypersexual comedy.

These movies of the aughts were inspired by the slate of '80s and '90s teen sex comedies that blazed the trail for them, movies like Sixteen Candles, The Breakfast Club, Fast Times at Ridgemont High, and Dazed and Confused. If one throughline has ever remained in-tact in movies aimed at teenagers, it’s that teens want to have sex, desperately, which also rings true in real life. And that includes young queer girls—we just haven’t seen portrayals of such until now.

BooksmartAnnapurna Pictures

In Booksmart, the language Molly and Amy use is profoundly different from their predecessors. The girls joke often and vulgarly about the difference between sexuality and gender, but neither are the butt of the joke, nor is Amy. Molly encourages her best friend to embrace her inner-sex freak, just as we’ve seen so many times before in best friend pairings like Seth and Evan in Superbad, Stifler with Jim in American Pie.

In true Jonah Hill form, Molly asks her best friend, “Amy, do you know how many girls are gonna be up your vagina next year? Every time I come to visit you, you’re gonna be scissoring a different girl.” Amy responds, “Dude, scissoring is not a thing,” warranting her best friend to add, “Don’t knock it ‘til you try it.” Later, Molly says, “You’ve been out for two years and you haven’t kissed a girl. I want you to experience that.” That line of dialogue just about shattered my gay heart. Growing up, I never heard a teenage girl embolden her female best friend to hook up with another teenage girl—not in the movies, and not in real life.

Amy, though slightly coyer than her bossy bestie, is also brash in describing her sexual desires, telling Molly that she loves their sleepovers, but wants to have ones with “more vagina involved.” In Booksmart, the pro-LGBT sex-positive messaging is literally written on the wall— their high school’s all-gender restrooms are tagged with graffiti touting an “all gender glory hole.”

Molly and Amy are supportive of each other in everything they do, including figuring out how lesbian sex works—first by theorizing that it’s like masturbating, “but a flip” of the hand, then by watching lesbian porn to “get a sense of the mechanics." Amy’s complete lack of “how to do it” is so unbelievably relatable to me. Lesbian sex was invisible in my own sex education and any conversations about sex. I didn’t know “how to do it” until I was, well, doing it. Learning how to have sex lesbian sex is a very real and very intimidating experience that I’ve never seen illustrated in a sex comedy before, much less one for teens.

The most important and laughable—and by that I mean cringeworthy—scene of Booksmart comes when Amy finally takes a stab at lesbian sex with her classmate Hope (Diana Silvers). Amy struggles to take Hope’s pants off, and then her shoes, and also her underwear, saying she feels dizzy from it all. Again, this is a scene I’ve watched dozens of times. At first, it’s hot and exciting and pure and naïve, and then it quickly devolves into scary wrong-turns and “Oh no!"s and “Is she gonna throw up?” It’s McLovin saying “Oh my God, it’s in!” in Superbad; it’s Jim kissing Michelle and then getting a trumpet up his ass in American Pie. In Booksmart, Amy stumbles through her first sexual experience with another girl, and yes, throws up on her, but it’s still charming and sweet, and it’s so uniquely lesbian.

That sex scene between Amy and Hope is brimming with all the teenage excitement and nervousness of exploring new territories with new people. I have never seen a loss-of-virginity scene like that before—well, I have, 100 times between a boy and a girl. Booksmart is successful in that it doesn’t feel like gender-swapped sex comedy; it’s actually specific to female experiences, and that’s thanks to the four women who wrote the film, including Katie Silberman, who penned last year’s hit rom-com Set It Up, and Susanna Fogel, the woman behind other lesbian-friendly movies and TV shows like Life Partners and Chasing Life.

And just like in all the other great teen sex comedies, Amy actually gets a happy ending when her almost-first time sex partner, Hope, visits her before she embarks on a big summer trip. Hope gives Amy her number before walking away. Then, just like Judd Nelson raised his fist to the sky in Breakfast Club, Amy looks to the heavens, and says, “Yes!” That moment may be one small step for Amy as a lesbian, but one giant step for lesbian kind.

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