Influencer Caroline Calloway Isn't a Scammer, Just a Self-Obsessed Mess

I was obsessed with her, until I saw firsthand who she really is.

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Jan 17 2019, 12:54am

Photo by Barcroft Media via Getty Images

“As you may or may not know, friends, I’ve had a teensy obsession with an Instagram blogger and author named Caroline Calloway for a while now. And by ‘teensy,’ I mean on a scale of one to Beyoncé, my love for Ms. Calloway comes in at a solid 9.”

The words above opened a piece I authored on May 25, 2015—three and a half years before Caroline Calloway would announce (then quickly dissolve, then re-announce) a now-infamous global tour of creativity workshops. At the time, I, like Calloway, was an American studying in Europe, and this particular post on my “blog” (a blend of personal stories and heavily filtered cityscapes, presented via Tumblr’s Accra theme) aimed to share the twinkling, fairy tale details of my experience at Cambridge Prom—a ball Calloway had thrown at the English university and invited 30 of her Instagram followers to attend.

Invitees had been given about five days’ notice, and I spent goodness knows how many Euros to fly from Prague to London and attend the event—borrowing a dress from a friend, booking a room at a cozy, Cambridge bed-and-breakfast, and, of course, scouring the Czech Republic for the perfect flower crown to wear. (Calloway fans are nothing if not dedicated to the art of the flower crown!) All Caroline had asked was that we arrive with a bottle of Prosecco and a £10 corkage fee— “If you really want to contribute something to the party”—but these were small prices to pay for the chance to meet my hero, I’d decided.

For the past several weeks, journalist Kayleigh Donaldson has been documenting Calloway’s antics surrounding her ‘Creativity Workshops’—a promptly launched event series, offering lessons in creativity, authenticity, and how to live one’s best life, as taught by Calloway—first in a Twitter thread and then in a subsequent, extremely thorough Pajiba piece. Attention grew, attracting responses from the likes of Roxane Gay, Seth Rogen, and numerous other critical Tweeters, all befuddled by the ways in which Calloway was able to convince hundreds of young women to purchase the pricey floor (literally, these women sat on the floor) seats.

Over the last 48 hours, countless internet users have asked themselves–and the ether–how and why Calloway was able to amass more than $30,000 from fans in just a few weeks’ time (she sold out at least four 45-person workshops in a matter of days). Why were 180-plus young women so eager to front $165 (plus fees!) to attend creativity workshops hosted by a woman who has seldom created anything, save for a carefully curated Instagram feed and a warped self-image? Well, once a die-hard Carofan myself, I may have the answers.

But first, a bit of background.

As a 2015 profile in Broadly explains, Calloway rose to Instagram fame by weaving a mouth-watering narrative around her life as a student at Cambridge University, pairing photos of the medieval town with lengthy captions about her adventures, friends, and her plucked-from-a-teen-movie love interest, Oscar. Calloway had cultivated a tight-knit community on the social network—one she affectionately dubbed her #AdventureFam—and quickly turned it into a $500,000 book deal. (At the time, she was represented by literary agent Byrd Leavell, whose client roster also includes Cat Marnell, Tucker Max, and Donald Trump.)

Before and after scoring a golden ticket to Cambridge Prom (evidence that Calloway is, indeed, capable of booking a venue!), I was a gleefully loyal member of the #AdventureFam, entranced by her prose and overall existence. She was equal parts intellectual and quirky, beautiful and awkward, social and bookish. I wanted to be just like her.

Between the summers of 2015 and 2017, however, Calloway’s narrative started to shift. Her self-deprecation appeared to warp into self-obsession. Her book deal crumbled. Her romance with Oscar quickly wilted. During the months of July and August of 2017, Calloway would post a series of bizarre Instagram stories, confessing that she’d pulled out of her book deal, cheated on Oscar, and suffered from an Adderall addiction.

(I should note that she had also—coincidentally—just finished reading Cat Marnell’s How to Murder Your Life.)

It wasn’t the wholesome, relatable content I’d once adored, but existing in Caroline Calloway’s bubble, even peripherally, was a thrill. She possessed all of the qualities of a cartoon princess dropped into the real world, including the ball gowns and utter lack of self-awareness. And, either out of Jonestown-level loyalty or my own voyeurism, I couldn’t turn away.

When Calloway began selling annotated “chapters” of her book proposal for $5 a pop on Etsy, I purchased each without hesitation (after sharing the first six or so chapters, Calloway abruptly shuttered the shop). When she started courting journalists and planning a series of media interviews, I dove into her inbox and begged for the chance to speak with her about Cambridge for a travel story.

“OMG GENEVIEVE OF COURSE I REMEMBER CAMBRIDGE PROM HOW COULD I EVER FORGET YOU OR THAT NIGHT,” she’d responded. “Do you want to be my first of all the interviews? They start Monday, but we could set something up for tomorrow afternoon. I have ~quite~ the scoop.” I would never hear from Calloway about this interview again, nor did I see any other stories come to fruition.

Just last year, when Calloway announced she’d be inviting “fans” to her art-history-themed birthday party in London’s Soho Square, I once again leapt at the opportunity to interact with her. I would land an invite to the party and watch guests buy her drinks upon drinks throughout the night. A few actively walked away from me when I’d shared that I’d gone to Boston University, not Oxford or Cambridge; “I have never felt like such classless trash,” I texted several friends.

All this to say, when Calloway announced she’d be going on a “world tour” late last year, offering attendees personalized care packages, hand-tossed salads, and a wealth of inspiration for just ( just!) $165 a head, I had no doubt that young, starry-eyed women like myself would gobble up tickets. And, more frustratingly, I had no doubt this tour would never come to be (as of January 14, it had officially been cancelled, only for Calloway to change her mind again and “uncancel” it on January 16).

In the five-plus years that I’ve followed Calloway, she’s promised followers stories she would never tell. Television (and, much later, Facebook) shows that would never air. Sponcon she would never promote. Books, then second books, then book proposals that would never go to print.

And yet, her cult-like following has carried on—creating fan pages, professing their admiration, purchasing $48 “Calloway House” t-shirts (a collaboration Calloway did with clothing brand Rowing Blazers, one of the few promised projects she completed). Like teenagers with crushes, every morsel of content Calloway offered—no matter how narcissistic—made us want more.

My guess is this: Much like a surrealist perfume ad, Caroline Calloway shows her followers, voyeurs, and fans (the majority of whom, I presume, are Millennial or Gen-Z-aged white women) a twisted look at something we all want to be—An American swept off her feet in a charming English town; a cool New York City girl with no responsibilities, but a whole lot of plants; a free spirit, dancing on the edges of volcanoes in Sicily.

But, more simply, Caroline Calloway also shows us what it’s like to be seen, allotted only in teasing doses. No matter the circumstances or setting of her misadventures, she is perpetually being watched—sometimes critically, yes, but also with admiration and envy—by thousands of individuals. She is undeniably noticed by those around her. And, from time to time, she offers her “fans” the chance to be seen, too. For the right price, and perhaps fleetingly.

Admittedly, I don’t believe Calloway intended to scam hundreds of women; I actually trust she had every intention of embarking on this tour. The trouble is, Calloway’s entire career (or lack thereof) rides on a cloud of good intentions and lack of follow-through, as evidenced above. And the moment she started accepting $165 payments from girls—maxing out credit cards for the sake of connecting with her—she, indefensibly, took it all too far.

“If I had known how hard it was, I never would've tried,” she told BuzzFeed News on Tuesday, only to change her tune on Wednesday.

“I canceled my tour because I was frightened and feeling worthless because if you read enough bad things about yourself on the internet you will start to believe they’re true,” she wrote on Instagram stories, her preferred medium of choice. “What else is there left to say, but life is a learning experience and I am proud to learn along side [sic] all of you on tour this spring?”

I was once repeatedly willing to shell out hundreds of dollars for Caroline Calloway. But in the wake of her latest capers and shortcomings I can now clearly view Calloway for exactly what she is—not a Writer, Art Historian, or Teacher, as her Instagram profile (THE FIRST OF ITS KIND!!!) proudly declares. Not even a cartoon princess dropped into the real world. But rather, a self-indulgent girl in far too deep, hoping to be seen as some unintelligible version of herself.

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Genevieve Wheeler is on Twitter.

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