Caroline Calloway Isn’t a Scammer

Her Instagram account reads like Brideshead Revisited meets Twilight meets Vanity Fair magazine circa 1988, when greed was good and having money was a golden superpower.

Caroline Calloway stands in front of a pink backdrop looking straight into the camera.
Noam Galai / Getty

Updated at 10:10 a.m. ET on September 29, 2019.

Let us begin with the 45 servings of eggplant salad made in the tiny kitchen of a studio apartment in Greenwich Village, transported to a Brooklyn loft, and served as a homemade lunch to ticketed guests. It was so tasty that many people asked for—and were generously given, at no extra cost—second helpings. And let us acknowledge that if this labor-intensive, potentially money-losing endeavor were part of a “scam”—as many people insist that it was—its architect may not be suited to the life. If you are running a short con that involves driving eggplant salad to another borough, you might as well find honest work, because you lack the grifter mentality.

Now let’s back up.

Caroline Calloway came crashing into my awareness, and maybe into yours, this month when a former friend of hers, Natalie Beach, published a revenge essay in The Cut titled “I Was Caroline Calloway.” It was a sensation, as there are only two possible positions vis-à-vis this young woman: You’ve never heard of her, or you possess a nearly encyclopedic amount of information about her. She is an Instagram “influencer” with close to 800,000 followers, and it seemed as though within 24 hours every single one of them had blazed through the piece and made some kind of comment about it on social media. The majority of her followers are young white women, a demographic not underrepresented in the world of media, and so—improbably enough—this micro-event was covered just about everywhere, including in The New York Times, The Washington Post, NBC, you name it.

Natalie chose her moment wisely and kicked Caroline when she was down: First, Caroline had sold a book proposal for a large sum of money, then failed to deliver the manuscript and had to pay back the portion of the advance she’d been given. In January, she’d had the idea to host a series of “creativity workshops” for her fans, offering to spend time with them; giving them gifts, some of them handmade; and serving lunch—including that eggplant salad. But the organizational skills required to manage these events overwhelmed her. She ended up canceling most of the workshops, and the ticketing agency Eventbrite refunded everyone. For this, she has become known as an internet scammer, on a par with the men who organized the notorious Fyre Festival. Any time investors or ticket holders are given a prompt, full refund, you are not anywhere near the land of the scam, but the internet didn’t care.

All influencers live on the knife’s edge. To display the details of an appealing life is to gather fans and jealous toads at about a 5-to-1 ratio. Get big enough, and then make a mistake, and the toads will rise up. Female internet rage is not nearly as frightening as male internet rage, which can include threats of extreme violence and sexual harm. But what it lacks in physical threats, it can make up for in intensity. Once it is unleashed on a new victim, all she can really do is lie low and wait it out; although, this is not the way of an Instagrammer, who inevitably prolongs the attack by repeatedly posting about it.

The venom of Natalie’s essay in no way matches her claims against Caroline, which amount to these: For a short period, Natalie helped edit Caroline’s posts, a service for which she was compensated, and she ghostwrote the book proposal, for which she requested the astronomical fee of 35 percent. For the toads, this news of a ghostwriter was the last straw. Caroline’s creativity workshops had been a scam, and now it seemed that she herself was a fraud.

Grotesquely, two days after the publication of the story in The Cut, the bloated body of Caroline’s mentally ill father was discovered in his home, a possible suicide. He may have been dead for more than a week. Some of the toads announced, in what they seemed to think was a high-minded stance, that they would not discuss the death. Others felt no need to hold back. On the day Caroline announced her father’s death, someone commented on her heartfelt post: “Just fucking deleted your social media. Nobody gives a shit about your [sic].” I started to worry. With a gathering sense of unease, it occurred to me that these bitches might actually kill her.

Caroline Gotschall was born in the middle-class but by no means glamorous suburb of Falls Church, Virginia. “It, wasn’t one of those REALLY bougie suburbs,” she tells us, “where the politicians live, with the sweeping lawns and the azaleas.” Rather, it was more “parking lots and Best Buys and craft stores.” Falls Church is one of those American towns determined to think of itself, in terms both gently self-mocking and obviously self-congratulatory, as a Mayberry R.F.D. kind of place. In Falls Church, the ethos of swim teams and Little League games and Reunion Sundays prevails, and despite profound changes in the racial demographics of the Washington, D.C., metro area, it remains overwhelmingly white. Caroline was the only child of an unhappy mother and a mentally ill father. (Unless otherwise noted, all information about Caroline comes from her Instagram account. I don’t know if it is all the truth, but as we say today, it is “her truth,” and I read it as such.)

When Caroline was 7, her parents separated. Her mother moved herself and her daughter out of the family house, a place that quickly became a monument to her father’s illness, a site of hoarding and disrepair. It was in this house that his body was discovered. He had a terrible temper, which was surely frightening to the little girl who, in the way of all daughters, wanted only approval, protection, and love from the most powerful man in her life. She understood him to be profoundly intelligent—“a rain man savant”—and clearly his belief in the value of education pursued at the most elite and storied institutions was a preoccupation he impressed upon his daughter. He insisted that Caroline attend a fancy private school in Alexandria, 45 minutes away from Falls Church. Caroline’s mother objected, but she was worn down by him, and thus began a ritual, born of necessity, of the father driving the little girl to and from school. That so much of their private time unfolded in the course of pursuing an elite education is entirely fitting. It is the force that allied them most powerfully.

Once, Caroline asked her father what had been the happiest day of his life. It took him a long time to think of an answer, presumably not because there had been so many of them, but rather because the taxonomic consideration of “happiest days” was not one he dwelled on very often. Finally, he came up with the perfect answer: the day she was born. Of all of the things I have learned about this tragic man through his daughter’s various accounts of him, this was the most poignant. When an only child asks you about the happiest day of your life, there is only one right one, and he had found it.

Secure in her father’s affections, Caroline told him she wanted to hear a story that didn’t involve her, and he told her that the second-happiest day of his life had been the day he was admitted to Harvard. He’d sat on his bed with the course catalog, marveling at all the classes in all the many departments, the whole world revealed to him in this book of offerings. But her father did not simply love Harvard for the education it could offer him. He loved it for all the old reasons: its history and traditions and rituals. He told her that he had been “number two” at the Crimson, filling her mind with lore about the rivalry between the Crimson and the Lampoon. He had gone to Harvard from Exeter, a double cynosure. Only when she was a young woman did she learn from one of his boarding-school classmates that he’d been somewhat of a laughingstock there, nicknamed “Briefcase Bill” for the uncool way he carried his books and notes to class in an attaché case. Preppies can be their own kind of toad.

As a child, Caroline was sad and desperately lonely. She was bullied at school, upset about the divorce, and trying her best to contend with her father’s mental illness and depression. She became the kind of girl who rebelled against these things not by getting in trouble, but by building an imaginary world for herself and then moving into it. She filled her bedroom with art supplies and books about princesses and fairies and magic. She had a Union Jack on the wall, and she went through a Titanic phase. She loved Harry Potter, and she kept a framed photograph of her very favorite aristocrat, Empress Sisi of Austria, who was known for her great beauty, her slender figure, and her luxuriant long hair, into which she sometimes braided flowers. Caroline stared out her bedroom windows—which gave way only to a boring suburban street in boring Falls Church—and thought about her future. She spent all her time “waiting, waiting, waiting” for her life to begin.

She applied to Exeter, but she was rejected. It’s a delicate thing for the child of an alumnus to get rejected from the parent’s school. What most parents do is move on very quickly and settle the child in a different school, but Caroline says she was rejected over and over by the institution. That’s a punishing process, and one born of obsession. Whose was the obsession—Caroline’s, or her father’s? Or was it a shared obsession, one Caroline adopted to draw closer to her father? And how does a teenager ever gain a sense of real belonging at an elite institution—Exeter is widely regarded as the most prestigious boarding school in the country—if it has rejected her so many times? If you have to push harder and harder on the golden door until it is grudgingly wedged open just wide enough and long enough for you to dart through it, have you sullied the project? Finally, the door swung open just wide enough for her to dart in for her senior year. At age 17, she changed her name to Caroline Calloway—it sounded more like that of a writer, she has said. Maybe it also sounded more like that of someone who would have been admitted to Exeter the first time around.

Her college-admissions process, as she describes it, was similar to the failure-is-not-an-option war she waged on Exeter. She applied to Yale, Harvard, Oxford, and Cambridge not once, but apparently four times over four years. Finally, St. Edmund’s College—which she had strategically chosen, she says, because it was the least desired of the Oxbridge colleges and therefore gave her the best odds—waved the white flag and admitted her, a 22-year-old “first year student.” Life could begin.

Caroline characterizes the three years between boarding school and Cambridge as a series of gap years, which is straining the term of art to the breaking point, and also a flagrant denial of something that happened IRL: enrolling at NYU, which most people would consider putting an end to the gap years and starting college. Not Caroline. It was just one of those things that happened while you were staring out the bedroom window, waiting. But we must not pass over these years, because this is where she met her future, poisonous diarist, when both enrolled in a creative-nonfiction class. Let that be a lesson on creative-nonfiction classes.

And let us now admit Natalie’s essay to our list of sources. Here she is, telling us that Caroline arrived “late to the first day of class, wearing a designer dress, not knowing who Lorrie Moore was but claiming she could recite the poems of Catullus in Latin.” Not having heard of Lorrie Moore does not strike me as an especially black mark on the intellectual range of a college student, nor does knowing some Catullus seem wildly improbable for an Exeter graduate. But Natalie’s essay “I Was Caroline Calloway” is a small masterpiece of a certain form: an aggrieved young woman’s account of being repeatedly wronged, often by slights so minor that only someone very young could have nursed them so long and then decided that they demanded a public airing. One of her main beefs with Caroline is the amount of attention Caroline received from the world, when it was she, Natalie Beach, who had arrived on time and known about Lorrie Moore.

Both girls wanted to be writers, and they became fast friends, hanging out and getting high in Caroline’s West Village apartment, where, Natalie reports, the walls were painted Tiffany blue and the place was filled with “fresh orchids and hardcovers,” which is both an appealing way to decorate an apartment and a stylish way to describe it. You can already see, in this simple detail, how the girls could fuse together, one of them making a beautiful life, the other deeply attuned to its component parts.

Caroline admitted to Natalie that her heart had been broken when she was denied admission to Yale, which gave Natalie the inspiration for a gag gift. She was a New Haven townie, and her mother had once come across three plates stamped with the Yale crest discarded outside a campus building. Natalie took a Sharpie and wrote “Fuck Yale” on the back of each one, wrapped them up, and gave them to Caroline, who seemed pleased. But shortly thereafter, the plates disappeared from Caroline’s apartment. Natalie says that Caroline said they’d been stolen, which was obviously not true, as nothing else from the apartment crammed with valuable items had been taken. Natalie was miffed, and remains so to this day. But there is no sentiment Caroline Calloway is less likely to hold than “Fuck Yale.” Yale was the point; Harvard was the point; Cambridge was the point. Caroline once told Natalie that she would “rather die than go through life with an NYU alumni email address,” which is a very Caroline thing to say. It showed her devotion to prestigious institutions, and it was also thoughtless and cutting. Natalie wasn’t transferring; Natalie would have to make peace with a life lived in the shadow of a crappy email address.

Let’s make one thing perfectly clear: Caroline Calloway is the kind of friend who, even if paired with a relative equal, could atomize your ego in less time than it takes to order a double macchiato. Natalie’s fusing herself to Caroline was bound to end in her profound unhappiness. Caroline is self-involved, very pretty, able to bend strangers—especially male strangers—to her will; and Natalie, in her telling, is none of these things. Caroline is also very, very careless: with people’s emotions, with her belongings, with the opportunities presented to her. But Natalie is the one who forced herself into Caroline’s creative projects, out of envy and desire. She’s been seething with jealousy for a long time.

Natalie took a semester abroad in London, at the end of which Caroline joined her for a holiday in Sicily. Natalie initially recalled the trip as fun, but later she read a journal entry that revealed it hadn’t been such a good time. Reading her diary, Natalie “realized how bitter I’d been.” She’d written that she wished “something bad would happen … a humiliation, like the one I feel always,” concluding, “There has to be a price for getting everything you want. For never being embarrassed.” Years later, the essay in The Cut was the price.

While Natalie was abroad, Caroline did something fateful: She started an Instagram account. Right away, Caroline realized that it could be a vehicle for magnifying herself and her talents to a larger world. As terrible as she would turn out to be at moneymakers such as delivering manuscripts and hosting workshops, Caroline had a deep and intuitive understanding of Instagram. She realized that it could be more than what people were then calling it: Twitter for people who couldn’t read. She was far ahead of most in recognizing that the site allowed users to add long, novelistic captions to the images they posted. She was interested in becoming a writer and she was interested in herself—she was made for Instagram. She decided the account would serve as a venue for an extended work of creative nonfiction, and that the imminent start of her Cambridge education would be a perfect subject for it.

She paid for roughly 20,000 followers. Moreover, she was one of the early vanguard of users who understood that buying ads, if done correctly, could be a huge boost to an account. Imagining that her proposed subject would have particular appeal to the YA market, she bought ads on the fan accounts of successful YA books including The Hunger Games and The Fault in Our Stars.

Most important, she bought ads on Harry Potter fan sites.* That series is based on the great British boarding-school books, such as Enid Blyton’s beloved Malory Towers series and the novels of Angela Brazil, who all but invented the form. J. K. Rowling’s stories built on that popular tradition by adding the element of wizardry. Soon, the world discovered the pleasures of reading about growing up within one of those historic, tradition-bound places, with their elaborate rituals, their formal robes, their generations-long sense of continuity. In writing about Cambridge, Caroline showed a mostly American audience that the dream world they had encountered in Rowling’s series was not all invention and didn’t end at age 18. Her account presented followers with a beautiful female protagonist beginning at a storied and ritual-laden English institution not at 12, but at 22.

This is what made Caroline Calloway’s Instagram account famous: her Cambridge years, expressed as Brideshead Revisited meets Twilight meets Vanity Fair magazine circa 1988, when greed was good and having money was a golden superpower. She gave herself the persona of a rich, careless, happy American girl who falls utterly in love with Cambridge.

So here is Caroline, in ball gown after ball gown, sitting at candlelit dinners in great halls, her head inclined toward one handsome young man or another, or punting on the Cam wearing an orange gown and sunglasses and shielding her face from the sun with a pink parasol, a handsome young man in a dinner jacket sprawled at her feet. Here is the Henley Royal Regatta, and the Oxford Hunt Ball.

And here is the principal romance of the Cambridge years, Oscar, who opens his dormitory door to Caroline one morning, wearing only Ralph Lauren boxers, seeming to already know her, to have been waiting for her. And all of this—the languor with which she approaches her days, her apparent nonconcern about her future—takes her account out of time. Typically, an American girl who attends a top boarding school and then Cambridge is on the superhighway to becoming a “global leader,” a leaner-inner, a person who drives herself every day to get to the top. But Caroline’s attitude toward Cambridge, as presented on Instagram, is as relaxed as a pale hand trailing through the waters of the Cam.

She seems like a spoiled golden girl of yesteryear, someone whose life path and material comforts were so predestined that she could spend the days of her precious youth making flower crowns. She is in a dreamland of met desires, majoring in art history and writing her undergraduate thesis—if this were really a novel, not a writer in the world could have gotten this so exactly right—on the notebooks of Cecil Beaton.

But that is not the only thing that makes her Instagram account feel out of time. The other is that it is crammed full of ravishing images of great European paintings and architecture, as well as endless, admiring references to aristocrats—all without any attempt to place them within the contemporary concerns of race, class, and gender; all without any consideration of Europe as a malevolent and colonial force. Seeing an educated young person take in European art and culture with unconflicted admiration is so unusual that the first time I breezed through her account, I wondered if it was possibly an invention of someone from the “alt-light” world of young people who have taken about half of the red pill. But no, her politics turn out to be as doctrinaire as those of any other hyper-educated New York–dwelling Millennial. It seems, simply, that she’s the very last student to approach Western art not as the by-product of oppression, but only for its beauty, its power to move the viewer. She is eager to immerse herself only in the sensual experience of it; she is the Walter Pater of Instagram.

So here is Girls After the Ball, by József Borsos, and John Singer Sargent’s little girls with paper lanterns and a Pompeii fresco. Here is a Hans Holbein portrait, and the July page of Très Riches Heures. Painting after painting—not the greatest hits from a survey course, but rather works that show some range and hint at her tastes. Here, too, are the Great European Ideas and the Great European Families. Here she is wondering if hoarding might run in a family, “like hemophilia in the House of Hanover, and insanity in the Hapsburgs?” And here she is seeking to comfort herself by tending to her own garden and keeping her mind on “the Voltarian sense of soul.”

However unintentionally, she seems to be staging a one-girl defense of Western culture, territory she pretty much has to herself at this point. The West! What a fantastic back catalog!

To this day, she regularly posts works of art and pairs them with thoughtful and sensitive observations. It comes at you, perforce, interleaved with endless posts dedicated to her self-obsession; her various dramas; her endless, endless selfies. All of that is tedious. It’s the art and her ideas about it that get my attention and elevate her intentions.

Taken all together, her account is a kind of madhouse, which suggests that Instagram is pretty good at exposing the range of a young person. There’s the great Cambridge romance novel, the endless stories of hurt feelings and social triumphs, the selfies without number, and the glowing images of the greatest paintings and architecture in the history of the world—all of this is presented in the Instagram form, which is nonlinear, marked by short bursts of narration, and richly illustrated.

The 1990s introduced us to the idea that the “memoir” wasn’t the sole province of presidents and dowagers, and that any 26-year-old woman with a boatload of problems and a humanities degree could write an engaging account of her experiences thus far. But the published book, as a medium, is perhaps too much and too little for the life and times of an extremely young person. Instagram, like Baby Bear’s porridge, is just right. In this form, the past—which, let’s face it, is a pretty slim chunk of time in the life of a 20-year-old—repeats itself, amends itself, inscribes new details on old stories; it’s a form in which the triumphs and hurts of yesterday or yesteryear can be called up, reworked, reintroduced to the narrative as though they are as real and as present as anything happening in the actual moment. Just as important, the platform allows photographs to have equal weight with prose, which is essential for a young person who has grown up in the smartphone generation. All of it spools forward and backward, with no regard to linear time, like a postmodern novel.

But everything exacts a price, and Instagram is no different. It ends up flattening young women, taking whatever was original in them and slowly forcing it into the language and tropes of the site. In Cambridge, Caroline created someone out of time, sexually sophisticated but withholding of every secret detail. Lately, though, she is becoming like everyone else: She holds up her middle finger to the camera, posts about her great, “juicy” ass, decides that her signature phrase is “Suck my big fat cock.” Yawn.

Moreover, the successful Instagram accounts of young women inevitably develop a common, unplanned, and dull theme: the emotional toll that the online haters exact from them and how to cope with it. Always, these young women choose the same three approaches and cycle through them during periods of duress. There’s the badass: “Fuck people who don’t understand me.” There’s the Judy Garland: “All I ever wanted to do was sing ‘Somewhere Over the Rainbow.’ All I ever wanted to do was make people happy.” And there’s the spreading of memes by professional uplifters. When Caroline began posting the sayings of Schlockmeister General Glennon Doyle, it was a low day for her account. Where was Cecil Beaton? Where, for that matter, was Voltaire?

The publication of Natalie’s essay has been rich fodder for new content created by fans and toads, by journalists and tweeters. The two principals have been speaking to each other in oblique ways. To The New York Times, Natalie played the executioner’s song—“I haven’t been looking at her feed right now in part because I feel a deep guilt about causing her pain”—while also revealing that her inbox is so full of possibilities, she can hardly contend with it. And she offers Caroline a strange crumb of gratitude. “It’s a small thing,” she told the Times, “but Caroline was the one who introduced me to the man who did me the great honor of relieving me of my virginity. Which was very nice of her. And I’ll be eternally grateful.” Finding a man willing to take the virginity of a healthy, young NYU student hardly seems like one of the labors of Hercules.

As for Caroline, that Gatsby-like figure—the name changed to something less ethnic; the Oxbridge obsession; the conviction that you can transform your life and rewrite its origin story if you can just peg them to a few solid and impressive facts—she’s been rocked by the events of the past weeks.

When her father died, she wasn’t sure what to do. It had been so long since she’d known what to do about him. She ended up taking the train to Harvard, the only place the spirit of the man might linger. She met a boy and had “the most perfect date.” She toured the archives of the newspaper, where she made a shocking discovery: Her father hadn’t been “#2 at the Crimson.” He’d only ever gotten a single letter to the editor published in the paper. But Caroline is quick on her feet in such matters; Caroline will never be daunted by an unwelcome truth. “It turns out I misremembered,” she tells us. “My Dad was second-in-command at The Exonian, Phillips Exeter Academy’s student newspaper.”

She went to a late-night party at the Lampoon, and then two new friends took her somewhere she wanted to go: Adams House, where her father had lived, and where there were no records to check, no mean nicknames to be told. She could be in the present, and she could conjure the past; and she could fuse the two and make them beautiful and perfect, a daughter’s coda that could have come right out of Gatsby:

He died in the house I grew up in, in debt, in pain, alone, surrounded by his hoarded mess. But in Adams House he was young, bright, and still hadn’t done any of the things for which I have forgiven him.

As for Caroline herself, she’s back in her cluttered studio apartment, where the art supplies and candles and paper cutouts threaten to overwhelm the place, still pumping out posts that trade extreme self-obsession with considered comments about art. The toads think the apartment is a hoarder’s squat. The fans think it’s a gem. Caroline wants all of them to lift their sights.

“Shoebox? Jewel box?” she asks rhetorically. Neither is right for this dreamer, this girl who has seen Venice and endured Falls Church.

“Sainte Chapelle, anyone?”

* This article originally stated that Caroline Calloway bought followers from the fan accounts of successful YA books. She bought ads on these accounts.