Caroline Calloway — ‘con-artist’, influencer/OnlyFans star and as of last month, bestselling memoirist —seems a little annoyed. “Like, the question I keep getting asked by English journalists is ‘to what extent are you performing the character of Caroline Calloway?’” English journalists like me. She wrinkles her nose in distaste — she’s done with all that now, she tells me.
She’s in Florida, living in a house that once belonged to her grandmother, with her cat, Matisse (“Oh, my God,” she cries at one point, “Matisse is just causing problems, he literally just shattered a glass,” she stops and holds the cat up to the camera, kissing its head, “baby, why are you like this?”).
After cheating her way into Cambridge University, selling a ‘fake’ memoir, reneging on the contract, selling tickets to Caroline Calloway live events that never materialised, being branded a “one woman Fyre Festival” and scammer; after the OnlyFans years and the many cancellations, Calloway has emerged as the fully-integrated, real version of herself — and judging by her new memoir (the wryly titled Scammer), as one of the most mesmerising writers of the online age.
I spend 90 minutes talking to her and find that I love her — I suspect it’s hard not to. She is mercurial, smart and interesting, she laughs at herself but also insists on being taken seriously as an artist, which (con or otherwise), is what she is. At the moment she spends about 14 hours a day hand-binding $65, limited edition copies of the memoir. She’s been taking pre-orders for more than three years — and her fans are rabid with excitement to finally receive them.
There’s an element of ‘if you know, you know’ about Calloway — those who know are generally rapt with interest, those who don’t have probably never heard of her, couldn’t pick her out of a line-up and would struggle to understand the furore of headlines that engulf her every move. The two camps split along generational fault lines: if you came of age in the era of Instagram, then you get it. For those who were already fully-fledged adults by 2015 Calloway, now 31, might best be described as one of the world’s first truly successful Instagram influencers.
Born in Virginia, USA, she came to prominence around 2013 when she moved from New York to study at Cambridge University, cannibalising the black tie balls and champagne suppers for content to grow her following. Her dreamy, diary-like captions painted a picture of Cambridge as an academic idyll — part Brideshead, part Hogwarts — and eventually earned her 850,000 fans and a publishing contract worth $500,000.
Fast forward, two years, though, and she had reneged on said contract — admitting that the ‘memoir’ she’d sold was little more than a created-for-Instagram fantasy (“I found myself locked into a book deal for a memoir that wasn’t even about my life,” she tells me) and that during her time at Cambridge, she’d actually been in the grips of an addiction to the prescription amphetamine Adderall. Recently, she has also admitted that she falsified her school records to get into the university. As she writes in the memoir: “I began by photoshopping my Exeter [the elite American boarding school she attended] transcript. Was this difficult with their complex visual watermark? Yes. But I’m an art historian and artist.”
“My Cambridge friends have known for years,” she tells me. “And they’ve never told anyone — good on them for never betraying me, and selling that information to a tabloid in the UK. I am afraid that Cambridge will take my degree back, though. It would be a big blow to my ego. Even though I’d still have the things that count, which they can never take away from me — the friendships, the memories and the plots for future books.” By 2017, when it came to delivering a manuscript, she found that she simply couldn’t do it. “In that book I said that the worst things that had ever happened to me were breakups and bad hair days when in reality, at Cambridge, I was addicted to pills, and my father was struggling with suicide, and I was struggling with suicide,” she says. There was also a rape, which she writes about in sparse and moving prose in Scammer, “but I sold the idea two years before MeToo and I just knew that the truth wouldn’t have gotten me as much money - and I needed money.”
Still, a contract is a contract and she’d spent the $100,000 advance without delivering a manuscript. She resolved to pay the money back.
Even though my book deal fell through, I earned the $100,000 to pay them back in less than a year by selling topless photos
In yet another sign that she understood how to play the game of social media well ahead of the majority of us, she parlayed her influence into cold hard cash by selling tickets to Caroline Calloway live events. Over the years she’d inspired such damp-eyed devotion in her legion of (mainly millennial women) fans that they lined-up in their thousands to pay $165 for four-hour-long ‘creativity workshops’ with Calloway. As with the memoir, though, the wheels came, rather spectacularly, off. Venues weren’t booked in time, shows had to be cancelled or moved, promised elements never materialised. She was roundly decried as a ‘scammer’— though she did eventually refund all the ticket holders.
“The rules that apply to surviving a riptide apply to surviving getting cancelled,” Calloway writes in her memoir of that period. “Your first instinct is to struggle. You want to clear your name, set the record straight. Don’t. If you do, you’ll expend your energy too quick and drown. What you do instead is follow the current… If you’re me, that means leaning into your scammer identity.” She started selling ‘Snake Oil’ cosmetics through her website and announced that the title of her book would be Scammer.
She also signed up to OnlyFans, which was then still in its infancy, and paid the publisher back by posing as topless versions of literary characters. “My mom actually subscribed to my OnlyFans, which I love because it’s such a shocking sentence,” she tells me, “she was supportive. She didn’t go and look at it, but I did always have in the back of my mind, like, ‘I’m not going to do something that I would hate my mom to see.’
“Ultimately, I’m extremely good at earning money,” she says. “I mean, I got into this blockbuster book deal in my senior year of college — and even though that book deal fell through I earned the $100,000 to pay them back in less than a year by selling topless photos.”
Still, by 2019, after the creativity workshops had fallen apart, a deafening howl of schadenfreude followed Calloway around the internet — and it was compounded when her one-time best friend, Natalie Beach, sold a tell-all essay to New York magazine’s The Cut in which she claimed that it was actually she who’d written most of the captions, and the book proposal, which got Calloway her initial book deal. As Natalie explained in the essay: “My involvement was uncredited, as the entire selling point of Caroline was that she was an ingénue, and ingénues don’t have sleep-deprived collaborators living in deep Brooklyn.” The essay went viral — spawning reems of op-eds and Twitter take downs.
Calloway’s animosity to Natalie, and her anger at the betrayal, can be felt throughout Scammer, obvious enough that some reviewers have commented on it. Calloway doesn’t think she was being mean, though: “what’s an example of me being mean to her?” she asks. “I think I was really nice to her.
“I say that she got fat — or like I say that she has an adorable potbelly — and I’ve heard some people say that that is cruel. I actually think that’s more of a reflection of their own fatphobia — I think fat is a very neutral word, or at least it should be…I think some people read ‘adorable potbelly’ — especially people with a lot of internalised fatphobia - as really passive aggressive. But I think chubby is cute and bouncy and sexy…and the truth is that Natalie did gain like, I don’t know, 50-70 pounds since I knew her, like she’s fat now, and it’s not a bad thing. She looks beautiful. But I think a lot of women with body issues read just that descriptor and saw it as pure insult and cruelty.”
A few days after Beach’s essay went viral, Calloway’s father took his own life. In the period that followed Calloway began obsessively posting to her Instagram - most of the commenters implored her to step away. Her father, she explains, had struggled with mental ill health throughout his life - he was a hoarder (the passages in which she describes his hoarding are some of the most finely drawn in Scammer). “I think his mental illnesses got so much worse as he came closer to death. And I often think about the long goodbye — it’s strange, because like, whether someone is declining from say, dementia, or depression or alcoholism, it’s like you lose them years before they actually die…But it’s still very sad. He won’t walk me down the aisle - although at this rate, I’ll probably never get married [she is single, and with so many books to make has little time to date, she says] — but if I do there’ll be no father daughter dance. He didn’t get to see my first book come out. The Washington Post called Scammer a masterpiece - that was like his favourite paper and the paper we’d get delivered to our house every day, and I just, I would give anything to show him that.”
Many of the publications, in fact, which had lined-up to kick Calloway when she was down have now published repentantly glowing reviews of Scammer. It is very good, at times tipping over into brilliance. Calloway rushed the publication when she heard that Beach had a book of essays in the works (it published last month) - and you get the sense that with more time, a true masterpiece would have emerged. Still, it’s got pace, humour and depth.
Calloway’s story seems like a parable for our trick mirror age. A woman who dreamed of being a memoirist and in lieu of simply documenting her life as it was, decided to curate a life worth documenting. “I now consider myself fully retired from the plot, though,” she says. Like all of us who’ve lived through the birth of social media, she’s become exhausted by the constant need to curate the narrative.
With ‘the plot’ set aside, though, Calloway’s reality seems a painful one: “I don’t think I have ever expected to be happy,” she tells me at one point. “Maybe it’s a consequence of growing up with such intense, untreated depression. I spent the majority of my life, from ages zero to 28, expecting that I would always be unhappy, that it would always be excruciating to be awake.” Antidepressants have had a hugely positive impact on her, she explains. “The past three or four years have been the happiest of my life even though my life has objectively been at its worst. Like, everyone was dying — grandma, my dad — going viral as a scammer not once but twice, my ex-best friend selling me out and taking credit for my work. Objectively it’s been a sh*t time. But I’ve 100% been my most stable because I’m finally on the right medication. Every day, I take 60 milligrammes of fluoxetine — which is like Prozac — and 400 milligrammes of Gabapentin for anxiety, and it helps so much. But the truth is that I never expected to be happy and I still don’t see it for myself.”
My mom actually subscribed to my OnlyFans, which I love because it’s such a shocking sentence
There is a quiet tragedy to this sentiment, but Calloway seems sanguine: “I really see my life as like an act of service to the books. I want to make the most jaw dropping, compelling, long lasting, weird masterpieces that I can make.”
She’s on the hunt for a traditional publisher as we speak, she explains. The self-publishing was part of the business model — “if I can sell 10,000 handbound copies at $65, imagine how many I can sell when it’s just your average paperback,” she says (by the time this article publishes, she’ll have sold 6,000). Scammer will be part of a trilogy, “I actually have my next two books, finished and ready to sell. I really want to bundle them together in what I’ll call The Instagram Trilogy.” And after that, when Cambridge and Natalie and scammer-gate have been put to bed? “That I haven’t announced yet, and that I’m going to keep it a secret. But yeah, I have book four all planned out, and book five for that matter.” Still memoirs though? “One’s a memoir and the other one’s nonfiction, but it’s relevant to my life.” Her real life.
