Brow Beat

Fact-Checking Booksmart: Could a Lesbian Really Confuse a Butthole for a Vagina?

Slate investigates.

A GIF of scenes from Booksmart
Photo illustration by Slate. Photos by Annapurna Pictures.

In the days since its release, Booksmart, Olivia Wilde’s sweet and bawdy directorial debut, has been hailed as a groundbreaking teen comedy and a victory for queer representation. The film follows two studious best friends on their last day of high school as they try to find their way to the cool kids’ party and win the affection of their respective crushes. One of the two main characters, Amy (Kaitlyn Dever), is gay. Booksmart treats her sexuality as both not a big deal and grounds for good-natured humor, making the movie a refreshing anomaly in a film landscape where queerness is usually either a site of tragedy or the butt of a joke.

Many of the plaudits for Booksmart’s treatment of non-normative sexuality have focused on the film’s one sex scene. After spending most of the film trying to figure out if her crush is gay, Amy drunkenly hooks up with a different girl, Hope (Diana Silvers), in a bathroom at a party. Vice’s Booksmart review credited the scene with exhibiting a “dose of empathy” for the queer characters and “a refusal to turn women into drunken objects to be coerced and conquered.” The New York Daily News said the scene was an “alternative” to typical Hollywood depictions of sex, which are “often steamy but less than realistic.” Screenwriter Katie Silberman told the publication the writing team was excited to make an “authentic” love scene, in terms of “how awkward it is.”

I have to say, as a queer woman, authentic and realistic would not be my first choice of descriptors for Amy and Hope’s sexual encounter, mainly due to one alarming mishap. After fumbling for a minute while trying to remove Hope’s shoes and jeans (authentic!), Amy, who’s never had sex before, proceeds to try to finger Hope, leading to the following exchange:

AMY: “Um, how is that for you?”

HOPE: “It’s OK.”

AMY: “Is there, like, another way you would prefer, or, or like … ?”

HOPE: [whispers] “I don’t think that’s the hole you think it is.”

As a woman who has had plenty of slapstick sexual experiences with other women but never managed to mistake a butthole for a vagina, I was confused. I wondered: Does this actually happen to people? Or was it the filmmakers’ graceless attempt at transposing bro-y sex jokes into a feminist film, as Slate’s own review suggests? I felt disappointed that the writers had inserted the laziest possible shorthand for clumsy sex into a film that otherwise avoided comedy clichés. But I was also genuinely curious if anyone involved in the making of Booksmart actually thought it was believable that a person with both a butthole and a vagina might feel a butthole—which has a very distinctive feel!—and think it was a vagina.

I came home from the screening and asked my partner if I was completely off base in my bewilderment. “Christina,” she said, slowly and patiently. “Not everyone explores their own body before they have sex with other people.” In other words, Amy might have never felt a vulva or vagina before she groped around for Hope’s. I then recalled some Booksmart foreshadowing that suggested as much: When Molly (Beanie Feldstein) tells Amy she’ll automatically be passable at sex because she can just do to a partner what she does to herself when she masturbates, Amy admits that she usually gets herself off by grinding on a stuffed panda, rather than stimulating herself manually. Amy also seems concerned that, once she does have sex, she’ll be approaching her partner’s genitals from a different angle than she’d approach her own. OK, fine, so maybe she’s not an expert at the female undercarriage. But hasn’t she ever wiped herself after using the bathroom?

It’s nearly impossible to find any data or anecdotes on the internet that might shed light on whether any lesbian has ever had a vaginal-anal mix-up, mostly because the scenario Booksmart plays for laughs appears to be a flourishing category of pornography. The appeal of the genre seems to lie in elements of surprise, pain, and non-consent. When I Googled “wrong hole movie” to remind myself of previous feature films that had made use of the plot device, I got pages and pages of results for videos with titles like “Painful Wrong Hole,” “Wrong Hole Accident Makes Girl Cry,” and “Wrong Hole! Please Stop! (Brutal Anal Destroy Screaming in Pain).” Some sites offered “wrong hole compilations.”

Funny or Die, Kanye West, the Wayans brothers, and The Mindy Project are a few of the many non-pornographic artists and cultural products that have featured jokes about “accidental” anal sex. Most of them include a mention of how unexpectedly tight the woman’s vagina (actually butthole) is, a comment about poop, and/or a winking acknowledgement that the “accident” might actually be a man’s cover-up for forcing anal sex on an unknowing or unwilling partner. There is no shortage of memes, GIFs, and commemorative memorabilia out there making the exact same joke: Men love anal sex, but it can be uncomfortable for women, so one way men can get some is to pretend they don’t notice when their penis “unintentionally” goes in the “wrong hole.”

It’s this context that for me places the Booksmart scene on the confusing-disturbing spectrum rather than the cutesy-clumsy spectrum. Why didn’t Hope say anything about the surprise anal penetration until Amy asked her for feedback two times? Why are we supposed to be laughing at a sex act that seems both unexpected and less-than-enjoyable? How can a sex scene be groundbreaking if it shows little, if any, sexual pleasure?

Also, importantly: Aren’t unsheathed fingers even more likely to perceive the difference between two fundamentally different body parts than a possibly condomed penis, which isn’t exactly known for its fine motor skills? The only thoughtful online discussion on this topic I was able to identify in the midst of all the porn was in Dan Savage’s sex column, Savage Love. In 2016, a reader asked how she could stop her boyfriend from repeatedly “accidentally” penetrating her anus during vaginal sex. “My own personal sexperience with anal led me to doubt claims of accidental anal penetration,” Savage responded, “as anal penetration always required focus, precision, and proper breathing techniques.” Appendages of all sorts would have greater trouble inadvertently slipping into a typical anus than they would a typical vagina, which creates its own lubricant when aroused.

Savage’s answer was unsatisfying to many of his straight readers. Tons of people spoke up in the comments with stories of perfectly innocent but often painful vaginal-anal miscalculations, mostly during heterosexual sex. Lube, which did not factor into the Amy-Hope tryst, was often named as an abettor of the slip-ups; once everything’s slick down there, the commenters said, the impossible becomes possible. One lesbian did pipe up with a claim that an ex-girlfriend had “missed a couple times. With her fingers, not a strap-on, even.” To that point, the Booksmart scene would have been a million times more believable had Amy been wearing a strap-on dildo, which has no nerve endings and would have been much less wieldy than her own fingers. (Then again, most dildos are thicker than most fingers, which would make it much harder to accidentally stick anywhere. I can’t stop overthinking this!)

But one comment on Savage’s column, from a user named Ankylosaurus, did much more to ease my qualms about the Booksmart sex scene than any of the conversations I’ve had with my partner or my co-workers, who, I assume, are filing HR complaints against me as I write this. Here’s that comment:

The variety of anecdotes remind us all of the many threads that make up the tapestry of life. It sounds like the likelihood of accidental anal depends greatly on the specific anatomy of parties involved, how those anatomies relate to each other, preferences, actions, etc., and here we all thought what we had experienced was what everybody experiences. We should know better by now.

Ankylosaurus is right. Who am I to presume to know what Hope’s body is like or how incredibly ill-informed and ham-fisted (ham-fingered?) Amy might be? The tapestry of life is broad, mysterious, and, sometimes, extremely lubed up. May Hope and Amy’s misadventure be woven into it with care.