Pegging. It’s seemingly everywhere these days—podcasts, TikToks, and even mainstream sex and love magazines like Cosmopolitan and GQ. Historically, however, the term is fairly recent, and only just beginning to shy away from societal stigma. Even though women have anally penetrated men for centuries, the word itself wasn’t coined until 2001, in the popular sex-advice column Savage Love. This is to say that, weirdly enough, many of the creators featured on #PegTok were born before pegging became what we understand it to be in pop culture.

The popularization of the term—and, to some extent, the concept—in heterosexual society at large can be traced back to the best 23 minutes in the history of television: Broad City, Season 2 Episode 4, entitled “Knockoffs.” In a flawless example of parallel narrative, the episode follows two best friends, Abbi Abrams and Ilana Wexler, throughout the course of a particularly chaotic series of events. Ilana spends the day hunting discount handbags with her mother before attending her rebellious Grandma Esther’s shiva; meanwhile, Abbi finally has a date with her neighbor and long-time crush, Jeremy. 

The date goes well, and, to Abbi’s delight, eventually ends in the bedroom. Everything is going perfectly, until she suggests that they try and mix things up—meaning, of course, that they should switch from missionary to cowgirl. Instead, she is shocked when Jeremy gets out of bed to retrieve a bright green, custom-made dildo, fully outfitted with a strap-on harness. The combination of horror and confusion in Abbi’s eyes, Jeremy’s unabashed enthusiasm, and the strangely sleek, abstract phallus is a total sucker punch—the first time you see it, and every time after that. The scene never fails to get a laugh.

Naturally, Abbi is completely freaked out. Whipping out a strap-on unprompted—and on the first date, no less—definitely goes against the standard rules of sex etiquette. However, to his credit, Jeremy realizes his mistake and urges Abbi not to do anything she isn’t comfortable with. Panicking, she runs to the bathroom to collect herself—and to call Ilana for advice. Always the more adventurous of the pair, Ilana encourages Abbi to break out of her comfort zone with an inspiring and infinitely quotable speech: “We are going to my grandmother’s shiva, okay? The reason I’m not sitting and crying is because that badass bitch did everything she ever wanted to. You want to go to the grave dreaming of Jeremy’s hairy, adorable little butthole? Or do you want to die knowing that you brought him pleasure by plowing it like a queen?”

As ridiculous as it may sound, I believe in this advice and I try to follow it every day. Not the pegging part, specifically—although I’m down to try anything once—but the sentiment behind it. We should all strive to be as ballsy as Grandma Esther was before we lose the chance. The passage of time waits for no one. And, I mean, the woman played for the Rockford Peaches, sang at the Cotton Club, and fucked Little Richard. Clearly, she knew something that we lesser beings are still trying to figure out.

Throughout the chaos of these past few months, I can’t stop thinking about all of the opportunities that I didn’t seize: the movies I didn’t see, the places I never visited, and the things I didn’t say, all because I assumed that there would be time to do so later on. But now, with much of the country still on lockdown, I have no idea when this mysterious “later” is actually going to arrive. I guess I never did; I just assumed that, eventually, it would. With every passing day of 2020, this belief seems more and more naive. I had no idea what was coming. And now, I’ve experienced enough turmoil to know that I still have no clue what tomorrow is going to bring.

This sudden emotional diatribe may seem a bit off topic from the subject of pegging, but that’s because this essay is about more than that: it’s about what the pegging represents. This is a call for everyone to peg their Jeremys, no matter how big or small. Have you been dreaming of getting a new tattoo? Go out and get it. Afraid to tell someone that you want to be more than friends? There’s no time like the present. More than anything else, that’s what “Knockoffs” is really about: finding the courage to buckle up your metaphorical strap-on and penetrate your fears head on. It’s what Grandma Esther, may her memory be a blessing, would have wanted you to do.

Second Illustration by Joy Velasco