‘Why not get actual human blood involved? I mean if I haven’t been cancelled at this point, I think it’s safe to say I’m uncancellable. Let’s get some ISIS vibes up in this bitch’, Calloway’s voice rings provocatively at my suggestion she shave my head live on her Instagram story. I wonder if there’s a lag in the call and she’s misheard me or if she’s just misinterpreted my proposal. Either way, I’m worried what she’ll say next.
I had wondered which Caroline Calloway I would be interviewing: the bright-eyed Cambridge student, obsessed with black-tie dinner and boys? The ambitious scammer willing to do whatever it takes to get her name on the cover of a book? Perhaps the fame-hungry, self-obsessed mess, as portrayed by a particularly damning Vice article?
I was not expecting this.
The thing about Caroline Calloway is you either know her or you don’t. You either know obscure facts about her life – the incident with the Yale plates, the rumours circulating about her kneecaps, the fate of all 1200 mason jars she once ordered to her Brooklyn apartment in a chaotic haze, or you get her confused with Kellyanne Conway.
Calloway’s rise to fame has been a slow-burner, dating back to 2013 when she gained popularity on Instagram for her ‘memoir in real-time’ captions, documenting the adventures of an American Girl in England, which subsequently earned her an alleged half a million dollar book deal. A book she never wrote.
Her next foray into the public eye came in the shape of her infamous ‘creativity workshops’, which cost attendees $165 and lead to her being publicly labelled as a scammer by various journalists, most notably Kayleigh Donaldson in a scathing Twitter thread.
The most recent addition to the saga is an essay published by her former best-friend and supposed ghost writer Natalie Beach for The Cut, a tell-all about the two’s friendship and working relationship, which took the Internet by storm when it was published back in September, inspiring countless think pieces and Calloway’s own response essay, I am Caroline Calloway.
She has 705,000 followers on Instagram and Reddit communities dedicated to trolling her.
She is in the top 0.37% of creators on OnlyFans and regularly receives death threats. Even Jameela Jamil has weighed in, stating a desire to ‘kick her arse’. Praised by some for her ‘no fucks attitude’, criticised by others for her lack of self-awareness, Calloway is a polarising figure. I, for one, don’t quite know how I feel about her. But I do know that I feel it very strongly.
In what feels like a typically Caroline Calloway move, she’s seven minutes late to our interview, apologising profusely that her therapy session overran and complimenting the British-ness of my name. We make polite small talk while she pets the cat lying at her feet.
‘Everyone told me that I would kill these cats,’ she says.
Calloway is a self-proclaimed artist, but trying to pinpoint exactly what her art consists of is something even she struggles with. ‘I myself am trying to advocate for the legitimising of an art form that even I don’t have a complete enough command of language to verbalise’, she admits.
Her ‘Internet art’ does not refer to the individual posts or stories she uploads, but rather her curated online presence. When I finally grasp this, she gives me a relieved, but exasperated ‘Yes!’ With my arms flailing and a look of manic excitement on my face, she likens me to the Pepe Silva conspiracy theory meme. ‘You look like you are actually, personally the guy in the meme solving the Caroline Calloway mystery,’ she adds.
Her incessant, seemingly compulsive, social media updates give the impression of a woman on the verge of a very public break-down. This is far from the truth. ‘The stuff that I put online and the way I build my persona and the way I capture and keep people’s interest with me is very intentional,’ she assures me.
Browsing her timeline, I wonder how much of her is a persona, her creative voice seeming to flitter between the ironic (see her ‘POSH DICK ONLY’ tweet) and the intimate, such as her moving reaction to her father’s suicide in her most recent essay. I ask her about this and she teases me playfully, saying ‘What if I was just like, no, I was being serious when I tweeted POSH DICK ONLY? No, of course a lot of what I say is satirical.’
This juxtaposition of the serious and the satirical is a facet of her art, she tells me, a way of engaging with and mocking the ‘astonishingly tone-deaf, classist person’ her critics make her out to be.
The Internet’s shared fascination with Calloway is a testament to the success of her art. Though I question whether some fans have crossed the line between enthusiasm and obsession, whether there’s a difference between taking an interest in her online presence and learning the intricate details of her life. ‘When [building an online persona] is done well,’ she explains, ‘you build a parasocial relationship with that online creator, and you end up not only knowing all these random details, but caring.’
She views her art as an escape for her ‘parasocial friends’ and part of this escape is The Mystery of Caroline Calloway, the desire to crack her. This a recent phenomenon that she’s ‘leaned into way more’, claiming ‘it would just be silly to ignore that strength.’ It’s certainly something she benefits from, with people paying $2 a month to access her ‘close friends’ story on Instagram and $500 for a one-to-one skype call with the woman herself. A section of her website reads: ‘I am mysterious and hard to reach.’ Like much of what she says, it’s laced with irony, but it is indicative of the role she plays in perpetuating her own myth.
For every fan referring to Calloway as their ‘problematic fave’, there are five tweets ridiculing her. This ‘snark’ ranges from criticism of her apparent self-obsession to cruel remarks about the shape of her face, which prompts my next question, why do people hate her with such vitriol?
She thinks it has something to do with the change in her online content. A cursory glance at her original Instagram posts will show this – captions narrating her grand adventures at Cambridge, exploring the safe, well-trodden themes of love and heartbreak, set against a backdrop of castles and balls, with impossibly beautiful men serving as the supporting characters in her bildungsroman. Her comments section is filled with admiration, young women longing to live vicariously through her. It was, by her own admission, a ‘fairy tale.’
Her most recent essay, however, is a frank account of addiction and mental illness, both hers and her father’s, who committed suicide in early September, accompanied by images of the house he killed himself in. They’re difficult to look at. In her own words, her father was ‘a hoarder who loved cleaning supplies’.
Many influencers choose to portray a sanitised depiction of mental health. But not Calloway.
‘What is still quite a grey area of online ridicule is when you talk about the actual nitty gritty, day-to-day texture of experiencing mental illness, and especially mistakes that can’t be fixed and regrets that you may have as a consequence of being mentally ill’, she says. She cites this as a reason for being ‘easy to hate’, an expression she readily brandishes throughout our conversation.
Though it would be untrue to say that all her criticism is a result of toxic Internet culture and snarling trolls. Calloway has come under fire recently for posting an anti-semitic cartoon, which references her relationship with her ghost-writer Natalie Beach. When I bring this up, I’m expecting her to be elusive, perhaps skirt around the issue. Instead she offers a sincere apology: ‘My own privilege led to blind spots that made me post this cartoon which was actually anti-semitic. I take full responsibility for those blind spots caused by my privilege. And I’m sorry.’
She’s less apologetic about another tweet I raise, one in which she questions whether she is the only person on OnlyFans with a degree from Cambridge. She immediately faced backlash from her followers, being accused of classism. However, she argues that it was a genuine question, and didn’t phrase it as such because she doesn’t ‘ask for feedback from the Internet anymore’.
‘If people can have compassion for sex workers who receive so much hate from the world, I would hold them to the standard of being able to feel compassion for what I’ve been through with my cancellations and have enough compassion to see why, with the trauma of public shaming that I’ve been through, I wouldn’t phrase that as a question,’ she says.
I’m sceptical of her justification, but can’t help but sympathise when she asks me, ‘can you imagine if you just got feedback on every micro decision you made, that was mainly negative, because you are a very safe person to hate on the Internet?’
‘Even without asking people to respond to me, I get violent messages about how I should kill myself, about what’s wrong with my personality, about how awful I am, every minute of every day, and I will for the foreseeable future.’
After the immense criticism she faced, ranging from sensitive and thought-provoking discussions of celebrity privilege to abusive comments, I wonder if her critics, and perhaps her fans too, have placed Calloway in a position wherein she can only fail, if they’re rooting for her downfall. ‘I know when I post something anti-semitic, it’s a lot more damning than when someone else does,’ she says, claiming that intense scrutiny follows after being cancelled because ‘you lose the benefit of the doubt.’
Just as Calloway’s followers were sucked into the romantic tales of her ‘#adventuregrams’, it’s easy to be consumed by the media’s portrayal of her. There is something eminently clickable about the story of a narcissistic New York scammer, captivating her followers through flower crowns and fraud. ‘We’re all part of the problem,’ she tells me, ‘if I saw an article about a scammer influencer I would have clicked on that too. Anyone who likes a sensationalised story feeds into it.’
Despite being many people’s go-to punch bag, Calloway continues to live her carefully filtered “no-filter” existence. When I ask her how she wants the world to see her, her response is simple.
‘I think for the people who follow me, I absolutely want to be seen as Caroline Calloway, the real person.’
And the rest?
‘Fuck what other people that don’t know you think about you.’
This is an attitude she’s developed from ‘the politics of BNOC-ery at Cambridge’, an environment she claims has served her well for real life.
‘There’s perhaps no more environment bitchy enough to prepare a person for that sort of judgement than the bubble that is Oxbridge.’
I ask her what she thinks lies ahead for those same Oxbridge students in the current climate and her response sounds exactly like one of her Instagram captions. ‘It’s one thing to like castles, it’s another to assume that you can actually predict the future in a global pandemic. Boy do I love a good castle, but I have no idea what comes next.’
We talk about her cancellation and she prides herself on being one of a handful of people to survive social cancellation, twice. Her advice is characteristically tactical, ‘even your cancellation can become material for why people should buy your stuff’; her creativity tour was later renamed The Scam, the title of her new memoir is Scammer.
I appreciate the plucky sentiment but there’s one comment that jars with me: ‘I’ve been dealt this hand of being a controversial figure and I would be remiss to try and avoid it or not lean into it.’
There’s a fine line between embracing scandal and seeking it out, between wearing your controversy on your chest and using it to sell t-shirts. Recalling her previous comment about ISIS, I wonder which side Calloway is on; to what extent her chaotic charm relies upon her audience’s hunger to see which scandal she’ll embroil herself in next. Controversy for the sake of controversy? You’ll have to read her book to find out.
Calloway has built her Internet empire so meticulously, I can’t help but wonder how she would react if it was suddenly taken away from her. As we finish our conversation, I ask her how she would feel if she wakes up tomorrow, goes online and discovers that both fans and critics have no idea who she is.
‘I’m feeling…,’ she says, reflecting for a moment, ‘like it’s time to start an Instagram account.’