She Got Famous Calling Herself a Scammer. Is She Finally Making Good?
This will be the last interview Caroline Calloway gives before she’s officially a memoirist. A scammer? Perhaps. Guided by grandiose ambitions? Definitely. But she’s about to have fulfilled the largest, most infamous promise she’s known for having broken: She finally wrote a book.
For those who aren’t terminally online, Calloway is a 31-year-old “It Girl” — or “satanic shroom trip,” depending on your persuasion — living in Sarasota, Florida who performs for “the theater of the internet” and enjoys pinning orchids in her hair. Before that, starting around 2014, she was an Instagram-famous influencer, gaining at least 800,000 followers for the wide-eyed optimism and whimsy of a self-described “well off” American studying at Cambridge University. (Whether and which of her captions were co-written or edited by her best friend — more on that later — has long been public debate, in warring essays in The Cut and on Calloway’s personal website.)
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I am, she claims, the only person in the world not affiliated with the book, aptly titled Scammer, to have read it, or to have yet discussed its contents with her in an interview. “I think it’s so good,” she tells me. “I know you’re not supposed to say that, but I’m so proud of it.” This makes a great deal of sense. She has for years endured what she calls the “skull-sickening” experience of telling her “best stories” to other writers instead of publishing them in a memoir, as has been her lifelong dream.
Now, on the eve of publication, she’s ready to have it all out there, in her own words. “I take pills for anxiety every single day,” she tells me, “and thinking too hard about what people would think about me — if I made the art I wanted to make — kept me paralyzed for so long.”
Let’s start at the beginning. The first book she was supposed to write came around 2015, after her wave of Instagram fame. In Scammer, she describes sobbing, “bereft,” at the success of the book deal for School Girl — or And We Were Like, as she calls it now. The version of her life she was selling, excluding her Adderall addiction and without a focus on her true self, didn’t feel authentic. She writes, “I didn’t know myself well enough yet to understand how this was breaking my goddamn heart. Breaking me.”
This was after 2013, when Anna Sorokin arrived in New York City and posed as a German heiress, but before Sorokin and Billy McFarland were convicted — in McFarland’s case, of defrauding Fyre Fest investors of $27.4 million. In short, 2017 was a bad time to renege on a deal, even though Calloway eventually paid back her $100,000 advance.
She still bristles at these comparisons, since she’s never been charged with a crime, but it wasn’t just the book. There was the controversial “national tour of creativity workshops,” which led to widespread criticism. The most searing coverage claimed she was charging her fans $165 a pop for little more than a boxed salad in a warehouse. During that tour, she infamously forgot to book venues and promised guests “orchid crowns.” In the end, Calloway only gave out a single non-orchid flower to each person. By 2019, she was posting content from New York’s West Village — trips to the sauna and pilates classes and her Matisse-inspired art and a skincare product called Snake Oil (some complaints were sent to the Federal Trade Commission, claiming that their paid orders never appeared). She used a literary-themed OnlyFans account to pay back the advance, and then some. Once she decamped to Florida, she was sued over the horrific conditions in which she left her New York apartment and the rent she owed to her landlord. (She has said she’s since reached a deal with the landlord to pay what she owes in monthly installments.)
Snake Oil is when she officially dove, unflinchingly, into the brand of scammer: “No one was going to give me $500,000 to write a book again, and I totally respect that,” she tells me. However, “In order to be able to afford to write a book on your own, think of all the things I had to sell that were not books. I had to do all this stuff that not only bolstered the ‘scammer brand’ but was also bringing in tens of thousands of dollars. That was more time I couldn’t be writing, but that was also more time that people saw me as Not a Writer, which came with its own consequences.”
She’d done all of this scammer branding, mainly in an effort to leave it behind and ascend to an upper echelon of famous, critically-acclaimed authors. But the ethics of this branding-as-performance art can be crazy-making; if you buy into a scam that’s called a scam, from someone identifying as a scammer, were you actually scammed at all?
Let’s look at the book itself. Calloway began accepting pre-orders in January 2020. Then the pandemic hit, and she took a long break from social media (though she retained 645,000 of followers, to date), and allegedly returned about half of that initial pre-order money, to everyone who requested refunds. “Over the next two years, people just very reasonably lost faith that this book would ever exist,” she says.
She claims the finished copies arrived at her home on Monday — and posted photos to prove it online — and now she plans to mail galleys out to a carefully chosen set of “blue-check” journalists, then a few days later, on a rolling basis to fans and probably some hate-readers who’ve paid a cool $65 for a “luxury first edition.” As she says, “I actually have one of the best publicists in the biz, and that publicist is me, and she works very, very hard.”
Now that it’s real, the question on many people’s minds might be, Should I believe any of this? I can’t tell you what to believe, but what I can say is that most of the 158 pages she crafted are delicious, even as much of the book is a rehash of what those paying attention already knew, or already assumed: Galas at castles; trips to Italy, France, Vienna; book deals; sex; her father’s suicide; her drug addiction; her depression. But some of it is new, like her exploration of her bisexuality, and her writing about the experience of actually dating women.
There are more confessions than I could count, including theft from an ex-boyfriend (“I physically stole from [him] the night he metaphorically took my virginity”); forgery (her Exeter transcript to get into Cambridge); cheating (“I kissed a Venetian count at his family’s palazzo”); and trauma (“I woke from my blackout to a boy fucking me”). Reading this book is like watching a mostly saccharine, giggly, and familiar bisexual rom-com — only sharper, more volatile, and a lot better written.
About one-quarter of the way through, the fictional Michiko Kakutani review of Carrie Bradshaw’s first book in Sex and the City popped into my head: “Bradshaw’s sharp, funny, finely-drawn world where single women rule, and the men are disposable.” The comparison is apt not because Calloway is surrounded by three soul-mate best friends — quite the opposite; Calloway writes from a world that feels deeply isolated. (As she says in the book: “At 30 I began writing and retired from the plot.”) Instead it’s because the men appear small in contrast to Natalie Beach, the most famous ex-best-friend and co-writer among extremely online millennials, who may have been the greatest love of her life so far, and her most desperate heartbreak.
She speaks about “Nat” more like an ex-lover than a one-time pal who she says “betrayed” her via a viral essay in The Cut, which claimed credit for editing some of Calloway’s most famous Instagram captions in an effort to pay her back for a litany of travel and food-related expenses. It was a cutting portrait of a former friend, and Calloway apparently hasn’t gotten over it. She says she was at one point “broken and in love with her,” and it shows: The sheer volume of space dedicated to Natalie, and their not-quite-romantic relationship, is huge. But it’s also deeply intimate (Calloway writes that the pair “braided our eternal souls together”) and angry (“Over my fucking dead goddamn body would Natalie put out a book before I did”).
Of course, there are plenty of non-Natalie subjects in Scammer too. The rawness with which she describes her depression — and her father’s 2019 suicide, and her own suicidal thoughts — is vulnerable and precarious. Suicide even comes up casually, like in her series of premonitions about her own life: She believes she’ll be a famous author, at some point a divorcée, a parent, and then, eventually, that she’ll kill herself. She frames it almost as if she doesn’t have agency, like she’s just another person along for the ride in Caroline Calloway’s Life.
And although trying to pin her down on the truth may be difficult, reading her is a pleasure. “I tried to make every single sentence a sugar high,” she says. The writing itself is Swiftian — sapphic and layered and annoyingly clever, even if you try not to bob along to the tune (“There had been a freak-blizzard while I slept, the kind that wonderlands the world with winter, and sleeves each twig in ice”).
Readers get a behind-the-scenes look at some of her boldest deceptions, like the incredible forgery she crafted in order to get accepted to Cambridge: She was desperate to get into Yale, to Harvard, to Cambridge. The first two failed completely, and her acceptance to Cambridge came on her third attempt. But only after, she says, she photoshopped her Exeter transcript to include better marks — and changed her AP exam scores. “I think I made the right choice then just as I am making the right choice writing about my lies now,” she says in the book. “It’s not about what’s best for the texture of my day-to-day happiness. It’s about what’s best for the art.”
“If you are a woman, people will pity your soulless addiction to fame,” she writes, admitting to craving popularity “with a bloodlust.”
I wondered if it was possible that she didn’t actually lie to Cambridge. What if the idea of lying to Cambridge itself was performance art? So, maybe the reading of the book was a little crazy-making too; these did not feel like the thoughts of a sane person. This is her performance art.
But just as you feel like you’re losing grip on reality, Calloway ushers in sections that are devastatingly self-aware. “If you are a woman, people will pity your soulless addiction to fame,” she writes. “Maybe it’s clinical malignant narcissism? Needing attention even at the cost of more controversy?” She admits to craving popularity “with a bloodlust.”
She handles trauma and sadness with relatability and deft skill, feigned casualness that mimics what it’s like to question your own experience of sexual assault: “It was rape. I’m overreacting! I don’t fucking know, okay? Stop asking me about it! Let’s never speak of it again. I don’t want my Mom to think she did a bad job raising me.”
Scammer is also self-aggrandizing, like when she muses, “Did [John] Mulaney plagiarize me?” or claims that a photo of her face was thumb-tacked to a mood-board in the HBO writers’ room for the reincarnation of Gossip Girl. And it’s hard not to balk at lines like “not everyone can remember the day they turned famous, but I can,” or the repeated mentions of being a Pretty Girl. But of course, her fame and her face and her hair are relevant to her story. “Internalized misogyny be damned!” she writes. “Hating Extremely Online Pretty Girls is the last guilt-free prejudice this world has left.” Her current plan is to publish two more books by the end of this year about her Cambridge-era Instagram captions. But in the end, I found myself wondering what her writing would look like if she came back out of plot retirement, as it were. If she’s now a memoirist and performance artist ostensibly trying to pay off her debts and make good on promises and shed the scammer skin she’s been wearing for all these years, what does that look like?
“Books and love,” she says. But to be clear, Calloway understands that she has a reputation for “canceling plans” and “being flakey,” which she agrees “was very well deserved in my Adderall days.” But now, she argues, “I’ve been reliable for the past maybe two years of my life, which is still a small fraction of my life…but from inside my body it feels so much like I’m trying so hard to change and that nobody’s believing me.”
She’s optimistic that eventually readers will see her as more human, once she finishes tying ribbons around all of the “luxury first editions” and gluing Italian marbled paper to the thousands of heirloom-quality copies of Scammer she hopes to mail out. These lavish plans — which include custom-designed bookmarks and wrapping paper and stickers and envelopes she intends to send to more than 3,000 buyers — raise concerns about whether she’s about to repeat those ill-fated creativity workshops. “They begin shipping to the public on [June] 16th,” she says. “It’s going to take throughout the month of July, at least.” But from that viewpoint, she seems much less like a scammer than a person who dreams big and then sometimes fails to make those ambitions a reality. And she does appear more clear-eyed about the commitment now.
“I’m not a fairytale, but I’m not a criminal either,” she argues in Scammer. “I’m a writer. Maybe now that I have a book, people will finally believe me.”
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