“This will be the only press I’ll be doing from bed,” announces Caroline Calloway, when I finally join our Zoom call, late and flustered. “I just got the most intense deja vu,” she continues. “I was like, man, being THIS hungover for an interview with the British press – what is this, Cambridge 2015? Oh my God, it’s happening all over again!”
Caroline and I are talking because she’s just, finally, published her long-awaited, much-anticipated first book; a memoir titled Scammer.
I first came across Caroline the same way as millions of others; via I Was Caroline Calloway – a 6,000 word essay on The Cut, written by her former best friend and collaborator, Natalie Beach. Having never heard of her before, much of the article washed over me, but the gist was: Caroline Calloway was a narcissist, a bad friend, and the beauty, rather than the brains, behind her brand.
Interest piqued, I set to Googling, and soon discovered I had a lot of catching up to do. I’d completely missed her first incarnation as an early Instagram influencer – posting about her seemingly fairytale existence as an American ingénue at Cambridge University, where she was studying at the time. I’d also missed her first scandal – when she reneged on the $500,000 book deal she signed off the back of her Instagram success. And then her first cancellation – which saw her labelled a ‘scammer’ and ‘one-woman Fyre festival’, after supposedly botching a series of $165 a head creativity workshops she’d set up to raise the money to pay back her $100,000 book advance.
Natalie’s article – which resulted in Caroline being cancelled for a second time – came out just a few months later. And, in a twist of fate which Caroline writes is – ‘just bad writing! The kind of bad first draft I spent my whole life trying to avoid’ – two days after that, her father’s dead body was found in her childhood home. He’d taken his own life.
“For so long, it just felt like life kept getting worse and worse,” she tells me, from her grandma’s former flat in a retirement community in Sarasota Florida, where she’s been living since turning 30 last year. “Like, you know, as soon as I got over the Adderall addiction I was in the debt; and as soon as I saw a way out of the debt with the creativity workshops, I went viral as a scam; and then as soon as I went viral as a scam, Natalie pitched that piece to The Cut; and then as soon as her piece came out, my dad’s body was found. And it’s just like, I could not catch a fucking break for like seven, eight years in a row.”
Oh yes, Caroline’s Adderall addiction – something she is keen to point out doesn’t get a mention in her ex-friend’s lengthy essay. ‘Natalie erased my Adderall addiction from the record and no one even blinked. She presented the symptoms of my disease (mania, prioritizing pills over people) as the smokey poison core of who I am.’ she writes in Scammer.
Natalie is still a sore point – and this comes across clearly in the book. When I put this to Caroline, noting that she seems to have broken her own rule for posting online – “never share something you haven’t healed from,” – she pushes back, telling me: “I think the rules for what you can put in a book and what you post are different. There are things I would put in the book that I would never put in an Instagram caption; the response is so much less thoughtful, it’s just a totally different beast.”
But there’s no denying Natalie’s betrayal cut deep – and is something that, four years on, Caroline’s still processing. “It’s not a lot of my life, but thinking about her is a lot of my healing currently,” she tells me. “So much of the narrative about who people think I am has been defined by her, and whether or not I like that – spoiler alert, I don’t – it’s a reality I have to grapple with. So I’m doing that. I’m undoing a lot of the damage that she’s done in my life over the past couple of years.”
Later, when I offer the reflection that her and Natalie’s relationship reminds me a lot of female friendships I had in my 20s, Caroline again pushes back, telling me: “I find it absolutely fucking infuriating when people say: ‘oh my god, your friend who tried to take credit for all your work, who sold you out for $5,000 to The Cut and publicly humiliated you on an international scale – it reminds me so much of my friend and what happened with us.’ It is not like other female friendships. And the fact that you think that is just because we live in the fucking patriarchy, and we just haven’t had the luxury of seeing enough women talk about their experiences with other women, because the patriarchal culture doesn’t like stories that don’t centre men.”
I have to admit, she has a point.
If I’ve made Caroline sound bitter or confrontational, I can assure you, she’s anything but. Warm, thoughtful, open – my interview often feels more like a therapy session, with her in the role of the therapist. “I don’t like seeing you putting yourself down like that,” she tells me, full of genuine concern, when I reflect that unlike me (who is all grand plans and very little follow through), she seems to pursue her dreams with dogged determination.
In fact, it was largely this energy that drew me to her in the first place. Following her shenanigans (of which there were many during 2020 and 2021) from lockdown in London, she seemed to be everything I wished to be; brave, impulsive, free, and completely in touch with her creativity. As it turns out, that wasn’t exactly the case. “When I turned 30 I had to get very honest with myself, and be like: if book is priority, what is working, and what is not working, to produce book.” she says. “I’ve been doing the plot gathering part of my job for, arguably, far too long. Like I actually overdid it. I think it would’ve, could’ve, should’ve been better for me to make this book sooner. But the reality is, I didn’t.”
I don’t remember when I started following her on Instagram, but at some point I started noticing her content… and liking it. Which, in turn, made me feel conflicted. I wasn’t the kind of person who followed influencers. I felt embarrassed… ashamed… maybe even a little bit dirty. “Yeah, my brand was very bad. It made people feel worse about themselves to like me,” she says, matter of factly. “There was a real chapter there, where my brand was so bad that it actually lowered a person’s self esteem to enjoy anything that I made – I’m very aware of that.”
Given everything she’s been through, it’s unsurprising that Caroline – who has suffered from suicidal depression since her teens – has had some pretty dark moments over the last few years. “I’ve felt very low and like a burden to anyone I knew,” she reflects. “Even just tagging someone on my story meant, you know, a small nightmare for them. And I just felt like I made everyone’s life worse – all the people who I loved were just worse off because they loved me, and I felt like such a failure.”
Those days are now, thankfully, behind her. Finally a published memoirist – which, she explains in Scammer, is a dream she’s held since her teens, and was her goal all along – her days of shame and sadness are over. Well… apart from the fact that she’s never orgasmed (a recurring theme in the book), which she tells me she feels “deep shame around” – but only when men enter the equation.
In fact, while a lot of what she covers in Scammer is new takes on old news (which, believe me, does nothing to dampen the deliciousness of the book), one of the new revelations is that she’s currently only dating women. “Maybe I’ve just never had an orgasm because I’m not even bi? Maybe I’m just a lesbian, and my problem is that I’ve been fucking men this whole time,” she says. Adding: “But goddam is Ron DeSantis so fucking homophobic – it’s making very difficult for me to fulfil my sapphic dreams here, in the sunny state of Florida.”
But anyway, back to me. I mean – my journey as a Caroline Calloway fan. Because at some point, I went from sceptical onlooker, to full-blown stan – even sending hundreds of dollars to her via PayPal for her latest ‘grifts’. And I’m not even sorry about it – even though the rainbow portrait of my face, which I ordered in June 2021, still hasn’t arrived (DON’T WORRY! She made sure to make good on all outstanding orders before publishing Scammer, so it’s in the post, and is coming with a bonus treat apparently). The Snake oil I ordered a month later (it was the pandemic, give me a goddamn break!) finally arrived in March this year (beautifully packaged, in typical Calloway style) with a bonus body oil, Caro Card, Scammer stickers, grift (not gift) cards, and a knitted cat hat (if you’re familiar with her cat/ best friend, Matisse, you’ll know what I’m talking about).
Like most of her fans, I’m not bothered by the delay. In fact, it’s all part of her chaotic charm. And although I did have moments during the intervening years where I wondered that I had genuinely been scammed, another part of me always knew she’d make good on the deal. “I’m very sorry it’s taken me so long to get your portrait,” she says, when I mention it on our call. “To be totally honest with you, the scammer allegations made me a worst person – in terms of what sort of decisions I made with my life, like not paying rent, or just not being more organised with these portraits. I honestly thought to myself: ‘well, what’s the worst they can call me? A scammer? Oh no, how will I survive?’ And in a weird way, those articles made me more reckless than I would have been otherwise.”
And anyway, these extra projects were never anything more than a way to pay off debts while she procrastinated on a grand scale. “I enjoyed making the Snake Oil and the Caro cards and the grift cards, but like, I don’t wanna be Kylie Jenner. It’s not my dream to have a skincare line – it’s not the goal.”
No, the goal was always to write a book. This book. The one I’ve just devoured in six straight hours.
“What did you like about the book?” she blurts out, suddenly. “I know I’m not supposed to ask this question – but outside of people who made it, you’re probably like, I dunno, number fucking five in the world [who’s read it]. So what did you like about it? What did you think?”
I don’t want to gush (well, any more than I already have), but let’s just say, it’s a good read. A great read, even. Beautifully written, it’s juicy, shocking, relatable, touching, funny, clever, insightful – and at times, as much a manual for creativity (and, I guess, hustling) as a memoir. It skips around – between Cambridge and New York, her complicated childhood and chaotic adulthood. It’s sweet and bitter and confessional and coy – in short, it’s everything any of us (as in: her hundreds of thousands of fans) could have hoped for.
But really, I should be the one asking the questions here. So how does it feel, now she’s finally done it? Now she’s reached the top of the mountain, I ask. “Honestly, it feels soooo good,” she smiles. “It’s just nice to be happy, if only for a little bit.”
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