In the wake of ‘Scammer,’ the memoirist joins Document to set the record straight—again

It’s a tribute to Caroline Calloway’s strange talent that I wondered, briefly, if I should refrain from taking a pink highlighter to the pages of Scammer, because my personalized galley could be worth something someday. This is an impression she consciously cultivates: The book is numbered, like an art print—mine’s 40/50—and comes with a handwritten dedication on the inside cover. Also in the package is a pink felted flower in a miniature mason jar, referring to Calloway’s failed creativity workshops, the first of several scandals that have come to define her career.

Until this point, Calloway has been a writer best known for the projects she never delivered. First, there was the memoir she sold in 2014 for half a million dollars, having leveraged her 300,000-person social media following to impress literary agent Byrd Leavell (though not without tricking him into accepting their first meeting, as she details in Scammer). The memoir, then called School Girl, was billed as an extension of the Instagram captions for which Calloway was known: romantic, highly-stylized dispatches depicting the glamorous life of an American undergraduate at Cambridge University, mixing and mingling with the British elite.

That’s not what Scammer is about. In the years since, Calloway has lived several lives: the one where she dissolved the book deal while in the throes of a crippling Adderall addiction; the one where she was the subject of public vitriol after a viral exposé written by her ex-best friend and sometimes-ghostwriter, Natalie Beach; the one where she mourned her mentally-ill father, found dead by drug overdose in his home two days later; the one where she paid back her hefty book advance by selling softcore porn on OnlyFans, and a self-made skin tincture she cheekily called “Snake Oil.” Then there’s the most recent scandal, in which Calloway was taken to court by her landlord after not paying rent for a year, instead channeling the money toward partying with New York media in Dimes Square. (“It was an investment in my reputation,” she writes in the book. “It girls are startups, and startups need funding.”)

In Scammer, Calloway tells all of these stories and none of them, dipping in and out of different timelines to deliver a 67-chapter memoir meant for fans and haters alike—albeit not one for those who haven’t heard of her. Neither is this article, for that matter. If you don’t know who Calloway is by this point, there are lots of things you could do with your one precious life. Touch grass! Have sex! Do your taxes! But if you have—like me—cultivated, over the years, a fluctuating fascination with her, read on.

“I’ve always had this fundamental belief that my only purpose for being alive was to make very specific books about a very specific world that I was not born into.”

Calloway took our first interview in a bikini, eating avocado toast. It was 2020, and she had just raised $50,000 for a COVID-related charity by paywalling a series of self-published essays about her friendship with Beach. Titled “I am Caroline Calloway”—a reference to Beach’s assertion that she was Caroline Calloway—the series was her first attempt to tell her side of the story. Scammer is the latest, but it won’t be the last—something Calloway continually reminds us of, referencing no less than three books to come over the course of the memoir’s 158 pages.

During that first hour-long Zoom call, we discussed Calloway’s relationship with performativity, self-authorship, and her enduring desire to be seen. I remember her eyes brimming with tears as she discussed the Natalie Beach exposé, then her father’s death. I also remember facing backlash from Calloway-haters online, claiming I had been too nice to her after the piece was published.

Calloway, however, doesn’t remember our interview at all: “I was so drunk,” she says, recalling how she spent the first six months of quarantine as a high-functioning alcoholic. (Ironically, she can now no longer even purchase alcohol, having gotten drunk and destroyed her only form of legal ID—but we’ll get to that later.)

The next time she answers my call, it is three years later, and her eyes are also red and teary—not with emotion this time, but due to the fact that she just accidentally sprayed chemicals in her own face. “I swear my next scandal is going to be how poor the working conditions are here at Caroline Calloway HQ—safety hazards out the wazoo,” she says, reclining in her bed in a plush fleece robe. “I’m doing everything myself, and I’m a very poor fit for the job: very physically clumsy, and not great with manual labor. So yeah, I sprayed it in my face like an idiot, and then I glued my own hand to my face trying to wipe it off. I was like, ‘I have an interview in ten minutes, and I am not prepared.’”

“Caroline,” I say, “Why didn’t you reschedule?”

“There was really a moment there, when my own hand was glued to my face, that I was like, I can’t do this—but then I washed my eyes, and I think it’s fine. But if I start crying during our interview, that’s why.”

How I act is so unnatural to most people that they assume it must come unnaturally to me. And I also look at people sometimes, and just think, I can’t even fathom what it’s like to be in your head, and live the way you live.

This kind of chaos is part of Calloway’s brand—a quality so evident that, at times, one might be tempted to designate her behavior as performance art. It’s what caused the writer of a recent Vanity Fair profile to conjecture that the details of her meeting with Calloway—the press-on nails painted to depict a fiery car crash, her accidental nip slip in a half-buttoned shirt—were all part of a master plan to command public perception. Calloway would like you to know that the answer is, emphatically, no: “That really took my breath away with how deeply wrong it was,” she says. “The journalist who wrote that, Lili Anolik, is so bright, and she sees me so clearly in some ways; I consider her a friend. But her thinking I had flashed her my boob on purpose made me wanna rip my hair out and scream, Do you even know me at all?

Calloway did not protest, however, to Anolik’s characterization of her as a Warhol-like figure: “Andy Warhol was a bit of a Caroline Calloway, if you ask me,” she quips, then turns serious. “But really, all jokes aside—I just think a lot of things about me are very contradictory, and how I act is so unnatural to most people that they assume it must come unnaturally to me. And I get it! I also look at people sometimes, and just think, I can’t even fathom what it’s like to be in your head, and live the way you live.

Among the contradictions of Calloway’s identity: She’s performative, but loves spending time alone. She’s self-obsessed, but compulsively generous with the people in her life. She’s conniving by nature, but is honest about her crimes. In Scammer, for instance, Calloway details the various creative liberties that paved her path to success, from buying Instagram followers and sponsored posts, to forging her transcript to ensure admission to Cambridge. (Though only after she was rejected from Yale four times—the maximum number, she says, before the university bans you for life.)

Attending a prestigious, Anglophilic university was always going to be part of Calloway’s story—even if she hadn’t written it yet. “It’s not so much that I felt I deserved to get in, as that I’ve always had this fundamental belief that my only purpose for being alive was to make very specific books about a very specific world that I was not born into,” she explains. “I don’t even think my purpose on earth is to enjoy my own life! I’ve always felt my life was about doing what’s best for my art.”

This might be “diet schizophrenia,” Calloway reasons—mental illness runs in her family, and it unsettled her that the only people to support her aspirations were her dad and his two clinically insane siblings. But from where she’s standing, it’s a reasonable response to realizing the singular nature of your ambitions. “The same way I can’t remember the moment I learned what my eye color or hair color was, I can’t remember learning what a memoirist was—but it’s always felt integral to who I am and what I wanted to do,” she says. So instead of a fig tree branching out with multiple possible futures, Calloway only saw one—all she had to do, she thought, was get the rest of the world onboard.

That proved more difficult than expected. When Calloway started to create content, it wasn’t called content; this was before the Instagram economy took hold, before ‘influencer’ was a profession, and before there was a clear path to becoming one. Calloway has always been ahead of her time in this regard: “I was trying to explain to people how this idea of living the kind of life you can write about—and leveraging my audience to do it—could be valuable. It’s not just about performing for the theater of the internet. It’s this theater of the self, the result of which is only fully realized on the page.”

For Calloway, sharing her life online comes naturally. It’s this process of realization, of putting pen to paper, that has eluded her for so many years. So when my book didn’t arrive for months—despite her texting me that I’d be “one of the first people in the world to hold Scammer in my hands”—I shrugged it off. After all, Calloway has publicly proclaimed that such promises should be treated with a grain of salt, writing in a now-deleted Instagram post in January 2021: “How will you expect me to deliver on writing when I am historically, famously, bad at doing exactly that?”

But then, lo and behold, I received a book in the mail—a slim, baby blue volume that starts with an unlikely confession: “I fuck to be fucked over. I’ve never had an orgasm, but I fake them all the time,” she writes, going on to describe languid days spent in the company of Florida men with “porn jobs,” like the pool boy she let fuck her for months without a condom.

Then, she intervenes on her own narrative, addressing the reader in first-person just when you think she’s drifting into a naval-gazing reverie: “I needed those first paragraphs to slap you like a dead fish to the wet face,” she explains; with so much pressure on how she’d open, she chose an approach that would knock readers back in their chair—simultaneously skewering their expectations, and setting the tone for the rest of the book.

“I got drunk and threw my passport in the ocean, because I wanted to clip my own wings and force myself to stay in Florida. I was just like, I’m not coming out of this state until I have multiple books published.

I ask Calloway the inevitable question: How did she finish Scammer, after so many years of stops and starts?

“I got drunk and threw my passport in the ocean,” she tells me, straightfaced. “I did that because I wanted to clip my own wings and force myself to stay in Florida. I was just like, I’m not coming out of this state until I have multiple books published!

This is only half of the truth, Calloway admits: she was also motivated by the fact that Beach was working on her own essay collection, rumored to center around her relationship with Calloway. “I know this because my friend leaked the proposal. It was so deeply frustrating to see that, four years later, she’s still using me like this—capitalizing off my life, my name, my brand,” she says. Calloway wasn’t about to let someone else publish a book about her life before she did: “Anger can be really destructive, but it can also be really constructive. I wasn’t going to let her control the narrative.”

Self-published by Calloway’s own imprint, Dead Dad Press, Scammer is a 67-chapter “daybook” meant to be read in one sitting. It’s not a complete and linear memoir, like her next one will be: “Instead of a photorealistic still-life, this book is a bowl of apples by Cézanne: the apples from every angle, all at once,” she writes.

Toggling between past and present, Scammer sees Calloway chart her trajectory from a child raised in a hoarder home to her salad days at Cambridge, to her continued attempts to grapple with the complexity of what came after. Because of its nonlinear format, the story’s darker elements—like the details of her deceased father’s autopsy—are punctuated with digressions and humorous anecdotes, such as her account of the crooked psychiatrist who appeared at each appointment dogged by a new physical malady, yet remained ever-ready to write her precious Adderall prescription: a genuinely funny bit, helped along by Calloway’s pithy one-liners and instinct for narrative flair.

Alternating between languid digressions and breakneck pacing, Scammer is a book where you can feel the hand of the author at play—proving that even without Beach as a foil, she is perfectly capable of captivating her readers. By the third page, she is teasing her next book; by the 10th, she is detailing her decision to change her name; and by the 19th, she is confronting her attraction to women, casting the tension between her and Natalie in a whole new light.

“I focused on that relationship in Scammer because it’s the book I need to write now, so that in the future, I can write a book that doesn’t center on Natalie,” Calloway says. “At the same time, I’m very interested in sapphic themes, so the topic of the book—this idea of a ‘lesbian gothic’—has dovetailed with what’s already on my mind.”

“People say all the time that I’m delusional and I ignore reality. And they’re not entirely wrong. But I always think to myself, How crazy can someone ever really be if they’re aware of their own madness?

Calloway’s tendency to fall into codependent female friendships predates the situation with Natalie; in Scammer, she describes the crush she had on her roommate as a teenager, and how she would crawl into her bed to cry about boys, sniffling with her nose against her neck—tears shed for a man who she “never could have loved as much,” had his disappointments not served to expedite the intimacy between the two women. “My affection for him was unsustainable without her emotional availability,” she writes, going on to describe how being attracted to both men and women made her complacent—plus, it didn’t suit her goals. “I liked presenting feminine, and I liked power. Being conventionally attractive to men catapulted me closer to it than being held by a woman ever would.”

The book is full of such lines: candid confessions of unflattering truths, though none quite as disturbing as Calloway’s admission that she found herself turned on while listening to Natalie describe her recent sexual assault. At the time, she ignored it, instead summoning up the right words to comfort her: “It’s one of the last times I can remember being a good friend to Nat before the drugs completely took over,” Calloway recalls, going on to recount how she later asked her boyfriend to reenact some of what had happened to her friend, to learn what had made her so aroused. It wasn’t the violence that made her wet, she realized, but hearing Natalie talk about her naked body.

Calloway admits that being turned on by her best friend’s trauma is fucked up—so fucked up that most people wouldn’t admit to it, much less write about it. But that’s what sets her apart; as much as she seeks to right the ways in which she was wronged, to correct the record of what happened between her and Beach, Calloway also owns her flaws—freed, perhaps, by having already ruined her reputation and rebuilt it from the ground up.

It’s something Beach herself admits in her own essay collection—recalling how she once stumbled upon an old first draft that was manic and self-indulgent, but also brilliant. It “read like Caroline was performing her own open-heart surgery,” says Beach. In contrast, Beach’s writing is self-conscious and considered; if she were to behave as Calloway does, it would be a master plan. But for Calloway, sharing herself with the world comes naturally—and much like the old adage that all press is good press, she doesn’t shy away from putting the worst parts of herself on display.

She alludes to this in the book, attempting to square her diametrically-opposed ambitions: “All my life I wanted to be a famous memoirist,” she says. “But we want our famous people to be role models. And we want our memoirists to be honest.”

This is the crux of Scammer: “It’s a book about the lies we tell to other people, and the lies we tell ourselves,” Calloway says. She’s no stranger to this: “People say all the time that I’m delusional and I ignore reality. And they’re not entirely wrong—but I also think I’m perfectly capable of engaging with reality when it behooves me. I always think to myself, How crazy can someone ever really be if they’re aware of their own madness?

For example, Calloway still believes her few months spent rubbing shoulders with New York media were crucial for rehabilitating her image—paying off in glowing reviews of Scammer. This is a relief for Calloway, not only because the shift in sentiment is beneficial to her image, but because it means those who ally themselves with her will no longer face public backlash: “For a long time, I had the feeling that if I were to get close to someone, I would inherently make their life worse because like people would just seek them out and bully them online,” she says. “The best thing about getting great press is not even the happiness I feel, because if you live for the rave review, you’ll die going viral as a scam. It’s the fact that I no longer feel that shame and guilt, because there are so many positive articles about me now is that the haters are working even harder than I am in the Caroline Calloway factory.”

As we speak, Calloway’s cat, Matisse, jumps onto her lap, peering outward at me benevolently. He has at least doubled in size since we last spoke, a time when Calloway was still in the thick of her public shaming: something she credits with helping her mature, and let go of habits that weren’t serving her. “I was dealt some really tough hands by life: the Adderall addiction, the cancellation, my father’s suicide. Pain has a real way of humbling a person. But also I got exactly what I needed. I could never go to another ball for the rest of my life, I’d still have the stories I need for my books. Living in Florida, I feel like I’m exactly where I need to be—because here, I can write.”

And, after all, she’d need a passport to go anywhere else.