I first read Caroline Calloway’s name in 2013, when it was widely reported that a young American woman who studied at Cambridge had landed a $500,000 book deal, based in part on her Instagram account. At the time I ached with jealousy.
Now, nearly seven years later, Calloway and I have arranged a phone interview to discuss her new book. Early on, I mention my jealousy to her, mostly as a joke. But she responds with genuine concern. ‘I’m sorry I made you feel that way’ she tells me. ‘For what it’s worth, when you were so jealous of me getting my book deal, I was suicidal, depressed and addicted to Adderall.’
If I was talking to any other internet celebrity I might have been surprised at the candour. But this is Caroline Calloway, and before she became famous for being publicly shamed online twice in one year (once by her erstwhile best friend), she was famous for sharing her inner most thoughts with the internet.
In case you managed to miss the saga, Caroline went from a bit famous to very, very internet famous after she planned a 'creativity workshop' in 2019, for which she ordered thousands of mason jars. It went awry on quite a grand scale and was covered by international news outlets. ‘I don’t dispute the fact that I ordered too many mason jars’ she tells me, ‘1,200 Mason jars in a studio apartment is not the hill that I will die on.’
Anyway, the drama about her workshops quieted as people lost interest, and various participants said they'd actually really enjoyed them, and it seemed like the storm had passed. ‘After that I thought "surely the worst is done, surely I won't go viral again this year"' Caroline laughs. ‘And then The Cut article happened{
The Cut article was a piece written by Natalie Beach, a personal essay titled, ‘I was Caroline Calloway’, which explored the period during which Beach co-wrote the captions for Calloway’s Instagram account. It detailed Calloway’s mental health issues and struggles with addiction, and included the allegation that Calloway had once purchased Instagram followers, portraying her as a captivating but cruel rich girl who specialised in deception.
Scammer, Calloway's forthcoming book, is the story of the year that all of this happened. It opens on 1 January 2019, when she was ‘on top of the world’ having almost sold out her creativity workshop tour, and follows the year during which she was dubbed a scammer, made an international synonym for organisational failure, and endured the death of her father (which she writes beautifully and painfully about on her Instagram feed). The book will, she tells me, deal with what we do not see of Calloway on screen; the people in her life who are not on her Instagram.
In naming the book Scammer, Calloway has leaned into her reputation. I ask her why she chose that title, given that she didn’t actually scam anyone.
‘I was excited to explore the ways in which I can build something with the digital architecture which exists around my name and the concept of scamming,' she says. 'I thought it would be more interesting to repurpose that invisible structure than to try to raise it to the ground and build something new. I was more excited by the idea of building on top of it rather than fighting to my dying breath "but people enjoyed the workshops! It was a niche event for a nice community!"'
Surely it must hurt to hear your name used in the same sentence as actual scammers like Anna Delvey, the fake German heiress who stole hundreds of thousands of dollars? ‘It did really, really, really bother me.’ she says. ‘It bothered me to the point that I was considering antidepressants because the pain of the public shaming was so intense. You Google my name and there it is, alongside people who are on trial or in jail.’
Back when Instagram was a different place I wrote long captions. Now long captions are de rigueur. I post against every single social media rule.
The hardest part of the whole thing, she says, was trying not to believe what people were saying about her. ‘How do you hold on to the idea that you are good and kind and deserving of love when the whole world thinks you’re evil? It’s really disorienting to see this character with your face and your name and your details catch internet wildfire. It really bothered me.’
Why, I wonder, has she chosen to self publish Scammer? [{href='https://carolinecalloway.com/products/scammer-pre-order' target='_blank' rel='noopener noreferrer'}.) Presumably publishing houses all over the world would have bid for a book written by a woman with 717K Instagram followers, even though she did default on a previous book contract (It's important to note that Calloway still has a contract with Flatiron, her original publishers, and still plans to publish her work with them). She tells me that she likes the immediacy of self-publishing. ‘I’m really excited by pushing the envelope of how things are done. Back when Instagram was a different place I wrote long captions. Now long captions are de rigueur. I post against every single social media rule.
‘I know people think that having a regular publisher is more prestigious, there is even this idea that self-publishing is a result of being snubbed. But self-publishing really appeals to me. The publishing world has been very slow to adapt to the digital world. I thought, why not do it myself? Why not forge my own path?’
There are those online who seem to think that Scammer will not be delivered. I ask her how that feels. ‘It’s really exhausting to have a real-life Greek chorus that follows me around chanting at me that I’ll never achieve anything and everything I’ve done is bad. It sucks to hear strangers say the things that I have to quiet in my own mind. But it teaches you to be very strong in your ability to quiet them within your own mind.’
Sometimes, when I go to write up the things she said to me during our conversation, I lament that they look different written down. There is something about the way that Calloway talks which is so painfully sincere that I would challenge anyone to dislike her.
Calloway says she might send the Scammer manuscript to Natalie, to get her approval over the way she is represented. I am surprised to hear this, and ask if they still speak. ‘Oh yeah,’ Caroline says. ‘You can read all about that in Scammer.’
Like everyone else who has followed their saga, I’m fascinated to hear how Calloway feels about Natalie Beach.
‘Everything she wrote about me was true’ she says, calmly. ‘The only way she lied was by omission and by not placing my behaviour [against] the backdrop of my addiction. But that’s not to say she printed anything untrue about me. Her essay is immaculately true.
‘The people who were closest to me suffered the worst consequences of my addiction. Something I really struggle with is that I can’t take back all the hurt that I caused her, and nothing I ever do will be able to change that. That guilt is so heavy. At what point does she deserve to hurt me back? Or deserve to pull herself up by using that hurt? At what point do I deserve it, or is it a fair punishment? If anything I struggle with being too forgiving towards Natalie because nothing I do will ever change the way that I failed her as a friend during my addiction.’
I ask the her how Instagram affects her romantic and non romantic relationships, assuming that she will tell me that it is hard and that privacy is a right that anyone who dates her should expect. She does not tell me this. Instead she says, lightly, ‘No one is warning John Mayer that he’s never going to get a date again because he writes about the girls he fucks.'
I wouldn’t date someone who forbade me to write about them. If I couldn’t write about my own feelings I would be like, "I am not the right girl for you."
‘I only write things which delight the person it’s about, and I’m very good at having that conversation with people who haven’t had this [Instagram fame] before. I’m really good at leading a partner through a conversation, asking whether there are parts of our relationship of their background which are too identifying.
'I wouldn’t date someone who forbade me to write about them. If I couldn’t write about my own feelings I would be like, "I am not the right girl for you. I am good at my job, I love my job, we are not a good fit." I want to be with someone who doesn’t see my career as a nuisance, but who is like "damn you have a skillset", who wants to be with a partner who is talented and passionate about what they do.’
It’s not the only time in our conversation that without attempting to convince me of anything, Calloway totally subverts my perspective. I ask what she would do if someone she liked romantically was anti-Instagram and she tells me that it would be a deal breaker.
Towards the end of the call, Calloway tells me that she is going to follow me on Instagram. Boldened by this, and the fact that we’ve been talking for over an hour, I tell her that I am going to be in New York in a couple of weeks and ask if she wants to have a glass of wine. To my surprise, she invites me over for dinner at her apartment. I accept without hesitation. I wonder what my 22-year-old self would make of the fact that ** seven years later, I am having dinner with the object of my book-deal jealousy and that we have both learned that significant success does not necessarily make you any happier.
Afterwards I think about the invitation and feel somewhat shocked at her ability to be so open to meeting new people and making new friends – after so much mocking, so much name-calling. This is the thing about her, I realise. She seems entirely unbroken by things that would destroy other people. I resolve to be more Caroline Calloway.
READ MORE: Why is the internet so obsessed with Caroline Calloway and Natalie Beach?