Caroline Calloway is at it again.
The notorious ‘scammer’ who made her name a decade ago as one of social media’s first ‘influencers’, charting her idealized adventures as an American at Britain’s Cambridge University, is back with her most audacious venture to date.
Yes, more brazen even than her outings as a ‘slutty’ Jane Austen on the pornographic OnlyFans site which she claims made her a quarter of a million dollars!
Calloway is self-publishing a book that is not entirely self-authored. Instead, she has drawn heavily on another advice memoir written 20 years ago by the late, acclaimed writer Elizabeth Wurtzel.
The result – outrageously entitled Elizabeth Wurtzel & Caroline Calloway’s Guide to Life – is an odd mash up of what others can learn from the highs and lows of both women’s lives.
In an exclusive interview with the Daily Mail, Calloway, now 33, is at pains to point out that she has footnoted, edited and attributed all the passages of her book that are cleaved from Wurtzel’s self-help tome, Radical Sanity.
But even if she manages to evade the ire of copyright lawyers or plagiarism charges, hitching her herself to Wurtzel – who wrote the 1994 globally best-selling confessional memoir Prozac Nation about her battles with depression and addiction – feels like a scam too far. Not to say distressing for Wurtzel’s loved ones.
It is, however, perfectly on brand for a woman increasingly regarded as the literary world’s equivalent of con artist and fraudster Anna Delvey (aka Anna Sorokin) who scammed New York society and the art world.
Caroline Calloway is at it again. The notorious ‘scammer’, who made her name a decade ago as one of social media’s first ‘influencers’, is back with her most audacious venture to date. (She is pictured during her Cambridge University days).Â
Yes, her newest venture is even more brazen than her outings as a ‘slutty’ Jane Austen on the pornographic OnlyFans site which she claims made her a quarter of a million dollars!
Certainly, they share a penchant for generating headlines.
In recent months, Calloway has claimed to have slept with a high-profile murderer – more of which later – and ‘risked death’ by refusing to evacuate from a hurricane zone.Â
She survived – and now, the Wurtzel furor.
In person, Calloway is petite and childlike, fussing with her waist-length brown/blonde hair, curling it round and round her fingers as she chatters on.
She is casually dressed in an outfit that is as eye-catching as it is casual – black sweats peppered with prints of purple, white and pink orchids, and a boat-necked black top emblazoned with an oversize, blush version of the flower on the front. Orchids are Calloway’s favorite bloom.
‘I realize that in doing this, you know, maybe me and Wurtzel’s ex-husband or her aging mother would never be close friends, which would have been very nice for me because of course she is my favorite writer,’ Calloway tells me.
‘But I really think I’m in a better position than anyone who is formally part of the work’s estate to generate publicity and get her name back in the cultural conversation where it deserves to be.’
So far, so shameless – and so true to form.
To recap: in 2013, Virginia-born Caroline won a place to study history of art at St Edmund’s College, Cambridge.
By 2015, her enchanting Instagram posts and blogs of student life – from sipping champagne while punting on the River Cam to May Balls and black-tie dinners – had garnered 300,000 followers who delighted in photographs with lengthy, witty captions showing Caroline at work and play in the idyllic surroundings of the historic university town.
‘I feel like I’m in Harry Potter, turning up for dinner in the grand hall in my robes and having beautiful three-course meals,’ she told the Mail at the time.
At just 23, her social media fame won her a publishing deal – reportedly worth between $375,000-$500,000.
The book, however, never materialised. Indeed, what cemented Calloway’s fame – or rather her notoriety – was a 6,000-word essay published in September 2019 in the online magazine The Cut that quickly went viral.
Headlined ‘I was Caroline Calloway’, it was written by her former best friend Natalie Beach who revealed that she was the unpaid collaborator who concocted and edited Calloway’s social media content, creating the persona that won her such a following, and who co-wrote the book proposal that secured the lucrative publishing deal.
Calloway is self-publishing a book that is not entirely self-authored. Instead, she has drawn heavily on another advice memoir written 20 years ago by the late, acclaimed writer Elizabeth Wurtzel.
Beach’s essay painted Calloway as a self-absorbed, self-serving nightmare – high on the amphetamine-based, prescription drug Adderall (for ADHD) and utterly unapologetic for all manner of terrible behavior during a relationship that left both young women damaged and distant.
Beach’s decision to reveal all seems to have been prompted by Calloway’s return to the spotlight following her failure to deliver on the book. Now billing herself as ‘artist and historian’, she was also a fully-fledged influencer with 800,000 followers who’d been busy for much of that year promoting her $165-a-head Creativity Workshop to help attendees ‘architect a life that feels really full and genuine and rich and beautiful’.
It seems they got rather less than they paid for – not even the ‘orchid crown’ she promised.
In fact, Calloway ended up being dubbed ‘a one-woman Fyre Festival’ (referencing a notorious and fraudulent music festival in the Bahamas in 2017) and Instagram’s ‘worst influencer’.
She’d known Beach’s essay was coming and hit back even before it was published, lamenting the betrayal and saying how hurt and ashamed she felt.
However, Calloway is nothing if not resilient. In 2023, she bounced back with her first self-published book, Scammer, in which she admitted lying about her qualifications – upping a grade D+ to A- for example – to win her place at Cambridge after two rejections. She felt ‘no guilt’ because it was ‘what’s best for the art’.
Now, two years on, her second book – with, it seems, a lot of help from Elizabeth Wurtzel.
Calloway had no relationship with Wurtzel, who died of cancer aged 52 five years ago.
Ironically, that article in The Cut may have been the only time Calloway actually registered with her literary crush. Beach described how, when visiting Calloway at Cambridge, she saw someone very different from the image conveyed in the carefree posts and not, ‘someone I wanted to be but a girl living with one fork, no friends, and multiple copies of Prozac Nation’.
A day after the story was published, Wurtzel tweeted: ‘Who is #carolinecalloway and why does she have so many copies of #Prozacnation? People keep asking me what I think of this. Hmmm @TheCut @NYMag.’
Indeed, Calloway’s only other link appears to be an obsessive fandom that saw her snap up items of the author’s estate at auction – a mink fur coat and ‘ephemera’ which included old debit cards. Nor has she received permission to use Wurtzel’s work or present it along with her own in this ‘pseudo’ collaboration.
What might Wurtzel have made of Callloway’s latest publishing gambit?
One who knew the author well has told the Mail that she would ‘have had a fit,’ at the very idea of Calloway ‘editing’ her work. (We have learned that Wurtzel’s estate has pre-ordered a copy of the book.)
‘Maybe it’s foolish to think that I’ll make great work and that it won’t be embarrassing for her legacy to be associated with me,’ Calloway concedes. ‘Maybe that’s wishful thinking but that feels very realistic to me.
‘But I think I have something a lot of even more traditionally well-respected writers don’t have and that’s an audience and this sort of spotlight of the internet that’s pointed at me.
‘So even a conversation of someone being outraged about me taking advantage of her legacy is still a much needed conversation about Elizabeth Wurtzel’s legacy.’
And there Calloway gives the game away. No attention is bad attention for this woman who shamelessly admits that fame is her goal.
With close to 700,000 Instagram followers now, she knows that millions more have loved to ‘hate-watch’ her over the past decade.
It’s a reputation she leans into and exploits. In October last year, she posted a video to social media in which she tearfully claimed she was not evacuating her home in Sarasota, Florida despite it being in the path of Hurricane Milton.
Then in December, she set the internet on fire with her claim that she’d slept with 26-year-old Luigi Mangione, the man accused of the cold-blooded execution of father-of-two, United Healthcare CEO, Brian Thompson, 50.
In October last year, she posted a video to social media (pictured) in which she tearfully claimed she was not evacuating her home in Sarasota, Florida despite it being in the path of Hurricane Milton.
In December, Calloway set the internet on fire with her claim that she’d slept with 26-year-old Luigi Mangione (pictured), the man accused of the cold-blooded execution of father-of-two, United Healthcare CEO, Brian Thompson, 50.
Today, Calloway won’t be drawn on whether that is true, batting off the question with: ‘No comment.’Â
But, of course, the truth is something with which the writer has often had a glancing relationship at best.
The ‘Cambridge Captions’ were, she admits, more Cambridge fanfiction than an accurate account of her life.
‘I really started my Instagram account in 2014, the summer after my first year at Cambridge. This is hard to remember but the ecosystem of Instagram was so different then. Remember a normal post then was like an aerial photo of your avocado toast and your caption would literally be like “#Valencia” and here I was writing like 3,000 characters of what was revolutionary for the time for social media.’
She says she loved the ‘radical vulnerability’ she poured into the posts at first, but as she sank deeper into a full-blown Adderall addiction – the drug is a stimulant – she says she lost sight of who she was. She became hooked on another, perhaps equally potent, drug – the ‘likes’ her posts generated.
‘I understood as I got more feedback from the algorithm that what performs well in an Instagram post is aspirational. And so, with this feedback loop, with my increasing dependence on stimulants, I just lost sight of who I wanted to be.’
But while Calloway pumped out those ‘fairytale’ posts about Cambridge – a process she describes as creating her brand – her real life was imploding.
‘Suddenly it’s my senior year at Cambridge and I get an email [saying the fee for my] tuition hasn’t been paid,’ she says. ‘I called my dad, and it turns out he has an enormous credit card debt and overnight I had to come up with $30,000.’
It was then that she decided to cash in her ‘brand’ – and a scammer was born.
Calloway says she secured a meeting with a literary agent at United Talent Agency by pretending to his assistant that she was an existing client and so landed that jaw-dropping first book deal.
The agent concerned, Byrd Leavell, has since referred to Calloway as ‘unwell’. She wouldn’t disagree.
‘It sounds crazy saying it now but, on enough stimulants, you really believe that everything is possible and that you can fix it.
‘There’s sort of the conscious voice in your head… It’s like, “Listen, you’re going to be able to graduate from Cambridge. You can figure this out. This book’s not due for two years”.
‘But then there’s the wordless, deep knowing in your bones and in that sort of languageless space of the body, I literally knew as I was signing this contract what an enormous mistake it was.
‘It’s still strange to me but you can’t fight it. You think I’m a scammer? Okay I’m a scammer… I got half a million dollars my senior year of college to write a book I had no intention of delivering.’
She says she paid back the advance by starting an OnlyFans account during the pandemic and selling topless photographs of herself dressed as literary heroines.
‘So, like Jane Austen vibes, but slutty Jane Austen. It was very niche, but it did well. I was in the top 0.03% of online creators.’
She estimates that she made $250,000, adding: ‘I use humor as a defense mechanism.’
She’s needed it over the years. Within 48 hours of the publication of Beach’s take-down essay in The Cut, the body of Calloway’s father was found inside his ‘hoarder’ house in her hometown of Falls Church, Virginia.
It was so badly decomposed that an autopsy was necessary to establish if he had been murdered. Instead, he had taken an overdose after a long descent into despair.
‘Talk about a good plot for a memoir,’ she says wryly.
In person, Calloway is like her prose – breathless, buzzy and scatty with the air of someone in a perpetual rush. It’s there in her smudged glitter eyeshadow, the dark unblended lines of contour make-up visible beneath her chin and her hurried gestures.
But the sense that she lacks all filter is deceptive. She may be an unreliable narrator of her own life but it is all much more calculated than people might think.
‘I would say it’s a lot more deliberate than people give me credit for… I always knew how complicit I was in this relationship [with the press] and I felt terrible. But on enough stimulants… you can feel numb.’
The way Calloway tells it, the public version of herself is an intentional creation – a mixture of imagination and guile. It’s a reality that oddly renders her both scammer and mark, perpetrator and victim of the scam she can’t quite shake-off.
In this respect at least she is better placed than most to offer advice on the downside of it all.
‘If you guys ever go viral in a bad way you need to survive it the way you would survive a riptide. You need to swim [with] the current.
‘If you struggle too much against what everyone is saying, you’ll expend all your energy too soon and too quick. You have to swim in the direction you’re being carried until the current subsides then you can make your way back to land.’
So, has she made her way back to land?
It is hard to escape the sense that she’s yet to regain whatever equilibrium she had before her world publicly imploded after The Cut essay in 2019.
Calloway is a contradiction: both fragile and resilient, part inspiration, part delusion.
Calloway (pictured in Cambridge) says she secured a meeting with a literary agent at United Talent Agency by pretending to his assistant that she was an existing client and so landed that jaw-dropping first book deal.
Calloway (pictured during her Cambridge University days) is a contradiction: both fragile and resilient, part inspiration, part delusion.
‘I want to be a famous writer,’ she insists. ‘I like including the word “famous”… because I think any writer wants their work to touch the maximum number of people.
‘There was a time when I was a fairytale for about five years from 2014-2019, then there’s a four maybe five-year period when people thought I was just Anna Delvey. I love that I’ve entered a new era of my career now.
‘You know I’ve been online for ten years and going into the next five year stretch I love that it’s now the literary Anna Delvey.
‘I just think about all the years where literary would never have been included in what someone thought of me.
‘But maybe I’d like to be literary Caroline Calloway… really I don’t want to be anyone else. I want to be the first of people like me.’
