Interview: Caroline Calloway talks May Balls, The Pitt Club, and why she (now) loves Tab readers

She’s either your chaotic fave or a trainwreck you follow out of morbid curiosity. Either way, you’re obsessed

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Caroline Calloway, a Cambridge grad, Instagram influencer, and self-described memoirist, belongs to a breed of internet celebrity whose celebrity itself is difficult to define.

It’s as hard to place exactly why I should be writing about her as it is to look away from her seemingly endless stream of turquoise-coloured content. She first rose to prominence as a Cambridge undergraduate, with her lengthy Instagram captions landing her a contract with the literary agent Bryd Levell, whose clients included Donald Trump. Only after securing a book deal worth over $500,000 did this shiny, pretty facade begin to crack; Caroline was desperately and entirely addicted to Adderall and unable to write the book, the deal fell apart, the centre couldn’t hold.

In January 2019 her name resurfaced, labelled a “scammer” following a series of poorly organised creativity workshops. In September of the same year an article in The Cut written by her ex-best friend Natalie Beach, “I Was Caroline Calloway”, went viral, detailing how Calloway bought Instagram followers, employed Natalie as a ghostwriter for her book proposal and treated her friend poorly, which Calloway claims was due to her addiction. A side effect of the article is the rash of think-pieces that have emerged after the fact, portraying Caroline in various degrees of villainy and sainthood, or using her story as a springboard for grand, sweeping judgements on the state of influencer culture, white female privilege and even Art Itself.

Calloway remains a controversial figure, seemingly unable to stay away from scandal for long; most recently her posting of an antisemitic cartoon on Twitter caused outrage, followed by a swift apology from Caroline, who claimed that she was unaware of the cartoon’s problematic messaging.

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When I first encountered Caroline’s profile last summer, before I was aware of the layers and layers of scandal and conversation, her general schtick seemed attractive; a typical easy breezy beautiful ambiguously liberal Instagram influencer, but, like, she reads? Ah mon dieu, oui oui, s’il vous plait!

She made the university I was about to attend appear full of possibility, a dreamy, misty castleland. But at the same time, her depiction of a Cambridge full of lords and aristocrats, princes and polo players, has always left a bad taste in my mouth, especially given that all the people of this sort who I’ve encountered at Cambridge have been unspeakable at best, and dangerously backward thinking and misogynistic at worst. 

When I ask Caroline how she feels about her romanticisation of the most elitist and conservative elements of Cambridge life, such as the infamous Pitt Club, her response is slow and considered. “If you counted the amount of times that I’ve posted feminist content, or anti-racist content, or anything from supporting abortion in the United States to supporting climate awareness, and you counted up all the times I’ve ever mentioned the Pitt Club, it would be like five mentions of the Pitt Club versus thousands and thousands of posts.” 

She jokes about this lingering elitist perception of her in the media. “If I wanted to integrate into the royal family I would not fucking make an OnlyFans page!” 

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I’m a model now, don’t look at me

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She is unapologetic about her tendency to limit her depiction of British society to the uppermost of the uppermost echelon. “It just sucks that because I’ve had success talking about Cambridge that people put this pressure on me to write about the Cambridge that they want to see. That’s not my fucking problem, as an artist!” Is “people” me? I think “people” might be me. 

Caroline is quick to clarify that she doesn’t want anything she creates to feel exclusive or to perpetuate white supremacy. “I just think there’s a lot of humour in an American narrator who goes to England and who only sees Oxbridge! That’s the art I want to make. I’m not a National Geographic reporter trying to recreate Cambridge with objective specificity. The very premise of memoir is to make the most subjective thing possible!”

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In person, Calloway is very different from her Instagram presence; softer, more thoughtful, and open. I am most surprised by her willingness to make fun of herself, which can sometimes get lost on her Instagram; she finds herself and her situation as ridiculous as everyone else does, and when I ask about her creative process, she is quick to mock herself. “First, apply to Cambridge, get rejected. Then, apply to Cambridge, get rejected again. Apply a third time, get in, immediately become addicted to prescription amphetamines intended for third graders. Spend three years building a brand on Instagram that will haunt you for the rest of your life. And then wake up and begin making art from there, is my creative process!” Wow, this interview is truly beginning to feel like one of Calloway’s creative workshops, except it didn’t cost me $165 and there are no flower crowns in sight.

 

We talk about Caroline’s previous Cambridge Tab interviews, which both took place while she was still a student. She tells me that “this is the first Tab interview I’ve ever given in a fully honest way”.

During the first two interviews, she continues, she was “high off my fucking face on amphetamines”; if you actually read the interviews you will find this the least surprising news of all time (the interviewer’s repeated references to her “crazy eyes” are particularly jarring). 

I ask how she’s changed since those interviews. “You know what’s so fucking funny? Now, after having been cancelled twice, I’m like fuck The Tab! I wish I’d gone into those interviews with a bit more of a ‘fuck The Tab’ attitude, which I just did not have access to when I was younger. I just cared so much what people thought.” 

She laughs at her assertion in this article from the time that The Tab comment section was “the meanest place ever”. “Little did I fucking know – I fucking love The Tab readers now! Tab readers – thanks for being the real ones, I was wrong. That was my bad, turns out there are much, much meaner people out there than Tab readers!”

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Confusingly, although Caroline was a student at Eddies (though when I tell her I’ve never visited, she tells me I’m “better off not going”), she lived in Downing during her second year and King’s during her third. She is honest about her superficial reasons for this decision. “I really fucking wanted to live in a beautiful part of Cambridge, and I really wanted to live in a beautiful college”, and jokes about how “I spent the summers calling up every beautiful college, just being like ‘do you have any vacancies, do you have any housing vacancies?’ and then I’d just call back the next week”.

Caroline talks about May Balls in the same way that a Catholic priest would talk about the seven sacraments; with an almost misty-eyed wonder and reverence. “From a purely aesthetic point of view, I really think that people are drawn to certain things in the world. Like why did Gauguin like Tahiti and why did Monet like the gardens of Giverny? I showed up in Cambridge, and I was like’“Oh, this. This is the aesthetic that sets my insides on fire.’ It’s so fucking lame to be excited about May Balls, but there’s something about 18-year-old lords in their great-grandfather’s ill-fitting white tie, checking their DMs on their phone while they pull out a shitty fruity iced bottled drink from a punt full of melting ice, that I just think is so fascinating! I just feel so drawn to Cambridge as an artist, and I really feel that it’s just my calling to express this world through the prism of my imagination”.

In Calloway’s view, her expression of this world has been successful, essentially legitimised by her recent invitation to speak at the Union via Zoom later this term. “So many people in my class, who looked down on my Instagram as I was making it, I think a lot of them were surprised that I was the first person from my graduating class to be asked to speak at the Union”. When I ask my Union hack contact/college husband to verify this claim, he helpfully replies that “it’s a fair guess tbh”. The Union president is also not entirely sure, but thinks it’s “probably true”.

In the grand tradition of Caroline Calloway interviews, I must ask about Natalie’s article, which she is currently responding to in a three-part self-published series “I Am Caroline Calloway”. At the time of interview, she has not finished the final part, and tells me she is going to work on it as soon as we hang up. I ask her why she still feels the need to respond seven months later, and her answer is well-rehearsed and cutting; she has been asked this question many times before. “If you recall, my dad overdosed on painkillers the week it came out, and so I think it’s really cruel when people ask me why I didn’t respond sooner. How mind-bending, to see a version of your life go globally viral, in which the thing which almost killed you and has just killed your father, evaporates!”

I ask her whether she still feels love for Natalie, as she often claims, or just anger. She is slow to respond. “Forgiveness… is not a stagnant thing, you know, and I experience that every day. It fluctuates, it’s not linear”. 

She tells me she feels both love and anger towards Natalie, to different degrees at different moments. “I’ve been very careful about not going into detail about how much she knew about my father, because honestly I don’t want to make her vulnerable to the character assassination to which she made me so vulnerable, but sometimes I do feel angry because she knows exactly what she did. As you’ll read in Part 3 of “I Am Caroline Calloway”, Natalie and I finally get on the phone together, and she tells me that she wrote that piece with a lot of anger, which is the closest she’s ever come to apologising for it”. 

Almost immediately after Beach’s article was published, Caroline signed with UTA and performatively undertook a series of meetings with film executives in Los Angeles, about which little has been heard since. I ask if a film or TV series based on the essay is on the way, and Caroline lights up in excitement. “Oh my god! I am so not allowed to talk about this, my manager will slaughter me in cold blood because there is so much money involved in this, it’s going to be fucking huge! It’s going to take up the next four years, and it’s happening and it’s changing my life. Oh my god, the very famous people involved!”

Although she tells me this is all she is allowed to say, I push for more, asking if she herself will be involved in the writing process. She tells me she won’t be. “They have a very fancy writer, who I honestly idolised when I was at Cambridge. It’s a little nerve-wracking putting my life story in someone else’s hands, but it gives me tingles, having a woman write the story of me writing my life story, whose life story I based my life story on, does that make sense? It’s like a mirror facing a mirror, but in terms of writing relationships”. 

As it has become hard to write about Caroline without bringing up Natalie, it is equally hard to avoid mentioning the various groups of “snarkers” that have arisen on Reddit and Twitter, a microcosmic world in itself (there is even a podcast!), with the sole purpose of discussing Caroline’s flaws, mistakes and, from their point of view, her general all-round untenable awfulness. She tells me that she never looks at these threads, but that her management checks in on them from time to time. “If someone has a problem with the way I’m behaving, they can text me. And if they don’t have my number then I don’t care about how they’re affected by my behaviour. Unless it’s something like, for example, posting an antisemitic cartoon, by accident, or anything that perpetuates violence, or climate destruction, or hate crimes, or anything like that, then I will obviously be aware of that behaviour. But stuff like they just don’t like my personality, that’s just not my fucking problem!” 

I ask how she differentiates between trolling and fair criticism, and she tells me that this is a difficult task in itself. “I don’t have time to go through the thousands of comments, and tweets, and DMs, and story tags that I get every day, and sift through ‘who of these people do I think are whole-hearted, sane human beings with joyful lives, from whom I should take advice, and who are very sad people sitting behind their screens in their mother’s basement, from whom I don’t want to be taking advice on how to live?’ If you live from the random compliment from a stranger, you’ll die by the random Reddit page”. 

Then, to my surprise, she asks me what the Reddit threads about her are like. “I’m kind of curious now. Is it as scary as I think it is?” I reply as truthfully as possible, describing how easy it is to get sucked in. How much thoughtful discussion I have found there, about Caroline but also about wider themes. The obsession with tiny details of her life (yes, I hint at the fabled teapot, and yes, of course, Caroline quickly brushes over it). And the parts of it I find uncomfortable, such as the incessant and almost surgical body shaming, inch by inch, one pore at a time. Caroline sighs. “I’m glad to hear that there are nice discussions happening in a larger sense around other themes. The body-shaming stuff has really been rough. Especially when they were calling me a Nazi, oh my gosh! That was a tough week with a lot of ‘go kill yourself’ messages”. As an indication of how fast these things move, the week she’s referring to is actually only the week before this interview takes place.  

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I am struck by a quote in “I am Caroline Calloway”, in which Caroline describes choosing Art History as a major because it feels like the “kind of subject that the character of Caroline Calloway would major in”. Is there a difference, then, between Caroline Calloway and the character of Caroline Calloway? Not any more. “Now I don’t think about it like that at all. I used to. Now I think about it more in terms of watching my life as it happens, not making decisions about how I live in order to have something to write about. I find myself always as an observer of my own life, though, taking notes about details that would make a poignant ending to a paragraph”. 

So, let me get this straight. Natalie wrote an article about Caroline that was really about Natalie and now Caroline’s writing an article about Natalie that’s really about Caroline and all these journalists are writing articles about Caroline that are really about all these journalists and now for some reason, I’m writing an article about Caroline and Natalie and all these journalists and wow I’m getting a headache!

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Zoom photoshoot with @arihassanali 🍒

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Even after the interview is over it remains hard, if not impossible, to know who Caroline Calloway is. In the same way that it is hard, if not impossible, to know who anyone is. And yet journalists and snarkers alike have set themselves on this fool’s errand, inadvertently giving Caroline exactly what she craves: a personal myth.

As you find yourself drawn further and further into Caroline’s world its multitudes are revealed to you; the vaguely intellectual musings of a chirpy art enthusiast become a messy tale of incompetence, Twitter threads and badly organised workshops, which morphs into a revenge drama of a toxic friendship, a tragic story of family and mental illness, a parable of the dangers of being Extremely Online, a very public meltdown, a very public life, and the whirlpool sucks you in without you ever really knowing why.

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Much like Ring Pops and disposable razors, memories deteriorate with use. It’s science. According to a study by Northwestern University, every time we access a memory we tamper with it, editing the past with our feelings in the present. Or to put it like this: the only way to preserve our most precious memories is to forget them. Sometimes I worry that I’ve revisited my first weeks at Cambridge so often that the real story is too damaged to tell with accuracy—that something about the star-struck, devastated, bewildered way I felt when I arrived has been permanently paved over. I know now, for example, that Oscar and I will end up dating. We will spend Valentine’s Day in Paris and weekends at castles and untold hours of our lives watching movies on laptops. Cambridge will not always be a beautiful but hellish maze. I will, eventually, learn the street names; the college names; where to buy falafel at 3 AM (Gardies). I will even become friends with Josh after many upbeat and infrequent lunches in Manhattan. Once—and only once—Josh will say the name Oscar by mistake. “George,” I will correct him quickly. “The royal baby’s name is George.” But in the moment that this photo happened I couldn’t have imagined what was to come. And in fact, at this moment now, it’s hard for me to imagine how this photo felt. During the past week I’ve asked so many friends (spoiler alert: I make friends) what Cambridge was like at first and they all say it was a whirlwind. They cite Bambi-like awe. And sure, I get it. But when I look at this photo I see a staged kind of fun. Where is my jacket? Did I throw it out of frame, but keep the champagne? Why am I looking off into the distance? I had definitely asked for this photo to be taken. What I’m trying to say is that wonder can often run parallel to loneliness. And while the emotional sum of my first weeks at Cambridge would eventually add up to happiness, this photo was probably not the extraordinary moment it looks like. Sneaking past the porters wasn’t actually that hard. Conversation that afternoon with Oscar lulled. Things were real. And they would only get surreal-er. To Be Continued… #adventuregrams

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Is there a floor to this churning sea, does all this lead to an ultimate endgame, or a pithy answer, as it somehow feels it should? No, of course not, no more than any life has an answer or a simple storyline with a prefigured crisis, climax, and resolution. Caroline is a person among all people, and she lives a life among all lives, a messy and incongruous stack of days, as much as she and everyone else invested in her tries to find some intrinsic meaning in them. Which is ultimately a flawed way to see things. Caroline is fascinating as every person would be fascinating if they laid out their entire life before us, with all their flaws and insecurities and thoughts archived so that any contradiction and statement can be fact-checked and fact-checked again by the thousands waiting for her to mess up so that they have something to complain about over coffee.

Especially as we are all shut up in our boring houses, these seemingly innocuous distractions become an escape. It is fun to revel in the small but intriguing details and controversies of another person’s life; the failed attempts at veganism! The post-irony ironic Twitter presence! Questionable teapot-based activities! The Yale plates, goddamn it! The pointlessness of the exercise becomes the point, even, a distraction as the world spins dizzily. 

Featured image: Wikimedia Commons, Creative Commons license