“I don’t fully understand who Caroline Calloway is to be totally honest,” a friend revealed when I mentioned that I would be interviewing the Instagram socialite over the phone. “You know? I don’t either,” I responded, realizing that I couldn’t explain why the world was so captivated and simultaneously filled with a burning rage over a young woman that posted on Instagram during her every waking hour.

The social media starlet has been the subject of headlines for years now. In early 2019, when a Twitter user went viral after calling Calloway’s workshop event series a scam through a series of posts, Calloway did too. Calloway first rose to fame by Instagramming her career as a student at Cambridge University. The posts were romantic and innocent, shown through the lens of a young woman so obviously trying to be part of a world she had not grown up in. Photos of picturesque Cambridge University were accompanied by lengthy, fairytale captions written with a type of naiveté akin to looking at the world through rose colored glasses.

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When it comes to parties I’m a quitter. I tell myself it’s because over all years I’ve built up what can only be described as an junkie’s high tolerance for fun, but the truth is that I just don’t know what to do with my arms. How to stand. What to say. And not in the quirky J-Law way that’s rapidly becoming the new cool. When I stop having fun at parties I ponder my own mortality and chew on my hair. Then I go home. As Oscar set our drinks down next to me on the bench, I stood up. “Thank you very much, Oscar. This looks like a really great alcohol. Just super. But I’m afraid I have to go now.” I felt scooped out from being surrounded by strangers all day. Oscar picked up one of the crumpled flowers and tucked it leisurely behind his ear. Leaning back he smirked. “Prior engagement?” “Um. No.” “Then stay,” he shrugged. I watched in silence as he tipped his head back, closed his eyes, and smiled in the sunshine. “What happened to your shoes?” I asked. He grinned. “I wanted to go barefoot. Kindly remind me to get my riding boots from the bushes on our way out?” I looked around at the rest of the party. Several girls were watching Oscar over their friends’ shoulders, but no one else was barefoot. By the time I looked back at Oscar he had stretched out across the bench, eyes closed with the same smug smile. There was something about his confidence that was terrifyingly attractive. He wasn’t just self-assured, he carried himself with the attitude that nothing could possibly be more fun than whatever he was doing, wherever he was. He squinted at me in the sunlight. “You stayed. Good girl.” “I… I actually just wanted to say goodbye. I’m going to go explore Cambridge now.” As I watched him sit up and start to down his drink I added hastily. “Don’t feel that you have to come with me. I’m totally okay if you want stay here and enjoy the party! Really!” He finished his drink and took in a long breath. “Of course I’m coming with you. What if you get lost and never come back? I’ll have to answer to the police. They always think it was the neighbor.” To Be Continued @oscar.frans #adventuregrams

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But behind the veil of a carefully curated Instagram grid stood a young woman in the throes of an addiction to prescription amphetamines. “After I quit Adderall and got clean I took about two years off from all forms of social media and I didn’t even return to Instagram posts until April [2019],” Calloway says. “When I came back I definitely improved in my ability to express myself authentically online. I definitely consider that December of 2018, right before I went viral as a scam, to be when I began posting with the intention not of selling myself as a product or even getting people to like me, but in making content that I felt was meaningful,” she says.

Today Caroline Calloway is much less synonymous with the dream-like Instagram posts that made her famous as she is with the unpredictable rawness that she operates under today. The one-dimensional character that once graced the feed of hundreds of thousands of Instagram users has now been replaced with a multi-dimensional character that values authenticity over likability. The performance of Caroline Calloway, today, is experimental and unpredictable, though grounded in a strategy that Calloway has long been perfecting from the back end of her public-facing persona.

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Team meeting! Everybody huddle the fuck up! We gotta talk about mental health and the carelessness with which we use certain medical terms. I have noticed lately that even some of the reporters who have written about me have described my personality as “manic.” I know exactly what they’re talking about. It’s my Pomeranian enthusiasm. It’s the way I was able to hide an Adderall addiction from the world FOR FOUR FUCKING YEARS. How do you think I went so long without anyone noticing?! My baseline personality is PRETTY GODDAMN UPBEAT, which is unrelated and unhelpful to my chronic depression. When I was high out of my mind on amphetamines my British friend were like, Yeah maybe Caroline is acting a little weird, but (italics) that could just be HER BEING HER. I am not above misusing mental health vocabulary. I grew up saying things like, “Don’t be so paranoid,” or “Haha I love organizing things in rainbows because I’m so OCD.” No more. Paranoia and Obsessive Compulsive Disorder and Mania and Hypomania all refer to real conditions and when we use them to describe “fear” or “particularity” or “exuberance,” we trivialize the experiences of people whose lives are affected by these conditions every day. I have been diagnosed with Generalized Anxiety Disorder and Chronic Depression. I had no obligation to share my medical information with Instagram, but I have. If I were diagnosed with mania or hypomania I would owe y’all exactly NONE of that info, but—let’s be honest ppl—I would probably weave it into some fire fucking captions!!! “Anxious” and “depressed” refer to me in true ways. “Manic” does not. Please join me in being more mindful of the ways we mislabel certain peoples’ mental illness and erase others’ experiences with our sloppy vocab. I’m trying to do better. Please do better with me.

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Not long after initially going viral in early 2019, Calloway’s former best friend and co-writer, Natalie Beach, wrote a lengthy personal narrative for The Cut detailing her friendship and subsequent falling out with the influencer. The article, which recounted nearly every interaction that the two had shared throughout their multi-year friendship, revealed that Beach worked alongside Calloway on the Instagram captions and subsequent book deal that launched Calloway into internet stardom back in the mid-2010’s.

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Do you guys have any friendships that have ended that still bring you pain? This afternoon I found out that one of the two people I have hurt the most in this world will be publishing an essay about our friendship for The Cut. I don’t know when this essay will go live. But it will be different than the articles that called me a scammer for clickbait. Everything in Natalie’s article will be brilliant and beautifully expressed and true. I know this not because I have read her essay but because Natalie is the best writer I know. I still love her. Our friendship ended 2 years ago, but I still walk around New York sometimes, listening to music, running errands, thinking about her. Amsterdam. I’ll let her tell you about that trip because it put her in danger—not me—so maybe it is hers to tell. Maybe she has custody of that story. Sometimes I all but gag with guilt. Sometimes I write emails to her in my head. Sometimes I imagine a future where we’re friends again! Natalie suffered all the consequences of being loved by an addict and none of the benefits of being loved by the woman that recovery made me into. In early August Natalie liked one of my Instagram photos by accident. I knew it was by accident because I know Natalie. But still! I thought: Maybe she is checking in on me because she still wants to be friends! Maybe she still loves me, too. I realize now that she must have been working on the article about us that will be published soon by New York Magazine. My team asked two things of me: To ignore this essay in my posts so I don’t drive traffic to it and to give them Natalie’s email so they could reach out. This is the first time I’ve disobeyed them. You should read Natalie’s article when it comes out. I’ll post a link when it does. Go leave a comment on nymag.com even if it’s insulting me. Every digital impression will be another reason for The Cut to hire Natalie again and to pay her even more next time. And The Cut doesn’t have access to the audience most interested in hating and loving Caroline Calloway. I do. So start anticipating this article. Get excited. Read it. I hope I can support Natalie now in ways I never did during my addiction.

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During the same week that the article was published, Calloway received word that her father died, a grim milestone that would later reveal itself to have been a suicide. “After [Natalie’s] article I didn’t get that many more followers—probably only twenty or thirty thousand—but I felt like that twenty or thirty thousand really, really hated me,” says Calloway of having to navigate a sudden onslaught of cyber-bullying while grieving her father’s suicide. “They just expected the worst from me,” she says.

Months later, Calloway’s cyberbullies are still as present as ever. Thousands of accounts dedicated to vilifying the Instagram blogger have taken to communities like Reddit, where each of Calloway’s posts on platforms like Instagram, Twitter, and now OnlyFans are picked apart with enhanced scrutiny. From how dirty her socks are to accusing her of pedophilia, Calloway’s trolls seem to be no less obsessed with her than her biggest fans. “I’m just really sad about it,” she says. “Last week they were picking apart my body and calling me a nazi and this week they’re calling me a pedophile. The body stuff really taps into the way they ridicule every inch of me and make me seem so repulsive. It just preys on the sort of internalized misogyny that we all have, as women,” says Calloway. Despite the enhanced lens that Calloway’s followers have put her under, she continues to share her every move on social media because, she says, it’s what makes her feel happy.

Of her father’s suicide and the damning essay published in The Cut, Calloway processed both experiences in great detail on her Instagram feed. Photos of her day to day antics, navigating a newfound fame and recognition in the real world, differed from her once fairytale life online. Unfiltered photos of Calloway in a bikini were coupled with introspective stories about what it’s like to be a young woman grieving, understanding, and thriving all at the same time. “Personally I really hate the word oversharing. I think it’s such a gendered verb. I mean when was the last time you ever heard of a man oversharing?,” Calloway says. “There’s lots of ways that English itself is very sexist. The language through which we understand the world has the patriarchy baked into it,” she says.

People hate Calloway the way they hate Kim Kardashian—because it’s the sophisticated thing to do and because, historically, vilifying women for taking unconventional, provocative routes to success is so nuanced in our culture that we seldom recognize when we’re doing it. “There’s no male equivalent for spinster,” Calloway says. “Bachelor doesn’t mean the same thing. There’s no word for a man that ends up alone in a sad and pathetic and sinister way, similar to [words] we have for women [who do the same]. Similarly, to that noun, oversharing is a really useful verb for devaluing female stories,” Calloway says of her latest strategy for Instagram: authenticity. “The language with which we describe female storytelling is really important. [Deeply rooted misogyny] is the poison that we all breathe in. Does anyone ever say men overshare? Don’t they just [get to] tell their stories and people just consume them at face value? But with women there’s this vulgarity to it,” Calloway says.

Her tendency to share the fine details of her personal life on social media are not unlike the reality TV stars of the early 2000’s that made careers out of performing provocatively in the public eye. Regardless of whether people appreciate figures like Kim Kardashian, Paris Hilton or Snooki, their success compounds each time someone mentions their name—both on and offline. That success, however, did not come by accident. “I really admire Paris Hilton and Kim Kardashian so much. No one wakes up with half a million followers by accident—unless you’re like me and you buy them. That was a joke. No one wakes up with sustained notoriety. No one keeps waking up day in day out with notoriety by accident. That takes intelligence. That takes ambition. That takes resilience,” Calloway says.

“This past year, especially coming off of a two year period where I just focused on getting securely sober, I really just wanted to shed those followers that I gained [after Natalie’s essay was published],” says Calloway. “I used to be really concerned with being liked and getting big numbers and getting a book deal that would make more people like me and that would pull big numbers from a publisher. I’m very lucky that all of the attention—positive and negative—has kept my publishers interested in me, but what’s the point of being liked if you don’t like yourself? What’s the point of making content that other people like if you, yourself don’t enjoy it? I’m trying to get rid of those followers. I want to have an audience that enjoys what I make,” she says.

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I block people for any of these three reasons: 1.) They LEAVE a mean comment. 2.) They LIKE a mean comment. 3.) They follow an account that is part of the ‘CC snark community,’ which is a nicer name for cyberbullying. Recently an account has popped up that is reposting my Close Friends content and my essays for FREE. In response I am getting @instagram to take it down for copyright violation. BUT FIRST I AM BLOCKING ANYONE WHO FOLLOWS IT. Instead of running adds (selling access to YOU) I give my audience the CHOICE to buy the things I make. Close Friends content. Merch. Dreamer Bbs. Books. Tittáys. Essays. OnlyFans posts. You don’t **have** to buy any of this stuff. But it breaks my fucking heart when you betray my trust by getting it for free. If you see something you want in a store: Your options are paying for it or stealing it and paying the consequences. The recent round of blocking people is the same thing. That being said, I understand if some genuine fans followed accounts reposting my monetized content for free without thinking about it too much. If that’s you and you comment down below and you seem like Not A Troll, maybe I’ll ask @brigidrduffy. Maybe not. I’m pretty upset. If I haven’t blocked you YET and you follow any accounts that repost my monetized content for free, this is your chance to unfollow it. Otherwise you will be blocked. If you paid for my content, thank you for being a good citizen with a good heart. I see you. I appreciate you. And you should be very proud of yourself.

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These days, Calloway posts on Instagram as often and as excitedly as someone would text their best friend something exciting that happened to them throughout their day. Just like any other social environment, Instagram has a set of unspoken rules that dictate how often someone should post, and what kind of content is ‘instagram-friendly.’ For Calloway, pushing the boundaries of what it means to create good content is precisely part of her latest schtick. “I plan degrees with my social media strategy in advance,” she says. “I’m going to do some more multi-grid things with the last part of my Natalie essay. Then I’m going to do this big content push over the summer to get down into the 690,000’s, and then next fall I’ll probably return to something a little bit more normal to how other influencers use it,” Calloway says.

Unsurprisingly, the bizarre nature of Calloway’s posts are, likely, precisely how the Influencer has canonized herself as Instagram’s favorite ‘spiral.’ “I try not to hold onto any social media rules. [There is] this idea that you can’t post too many selfies or that something has to be this certain aesthetic to be gridworthy, or that you can’t post two times in two minutes, or you can’t, you can’t, you can’t, you can’t. Because Instagram has become such a vulnerable, nuanced place I think people forget that, although they’re posting more freely than they ever have, they’re still following so many rules. I try not to listen to any of those rules and I try to post what I feel like posting. I don’t think about likes at all,” she says. “I don’t even know if i’ll always post this way but I think i’ll continue it until [my followers] get down to the 600,000’s. Then I’ll maybe start posting in a way geared toward growth,” Calloway says.

Today social media followers are treated as capital. The more followers someone has on social media, the more valuable they are to brands. With a little under a million followers on Instagram, Calloway’s presence on the platform translates into a cash flow comparable to some of the world’s most successful celebrities, but not in the way of the traditional influencer business model. “The normal business model of an influencer has never sat right with me [for my brand],” Calloway says of how she’s monetized her social media following. “Both because—as you know—I paid for fifty thousand of my followers in the beginning of my career and I don’t know how much Instagram has culled those bots over the years, [so] I have no way of knowing what my actual follower count is. I would feel so—so scammy—selling an advertiser a sponsored post on my page. Combined with that, it’s so weird to me that, of all the influencers, I’m the one associated with scamming people when everyone else in my industry feels so okay with selling their audiences’ attention span,” she says.

“It’s so tough because we all need to pay our bills. I don’t want to vilify anyone, especially women—get your coin ladies,” Calloway says. “My feelings of support for those women exist side by side with my feelings of betrayal when I see an influencer post something that might not be totally in line with their values, but also my uneasiness at the thought of maybe falling into that trap myself,” says Calloway. “I just didn’t want to do that. But I need to be my own patron and I need to make my own art. And I need to keep the lights on and pay the bills like everyone else so it just seemed obvious to make whatever I do sort of an optional, ‘if you want it, buy it’ business model—you know? I feel like I’m mansplaining capitalism to you now. If you want it, you buy it,” she says.

Calloway describes the sort of renaissance we live in today, where everyone is creating, in the real world, content for the virtual world. We live in an era of artists, musicians, photographers, painters and story tellers that depend on the capitalization of their audience in order to continue making. The symbiotic relationship between capitalism and this renaissance both allows artists to create and trains them to hate their own trade—a relationship that also hinders the trust that their audiences have toward them in the first place.

Photo courtesy of Caroline Calloway

We are not so much in an era of dismantling capitalism, but dismantling the relationship we have with capitalism and what it means to live in a world where capitalism is both a hindrance to society in so many ways and a path to artistic freedom in others. While many scoff at the idea of their favorite artist “selling out,” shaking their heads in disappointment that a creator sold stake in their audience to a brand, the reality is that capitalism is the inevitable, necessary evil that allows creators to grow at all. Without capitalism, there would not be room for everyone.

“When the camera was first invented all of the criticism on it was that it was science and technology and too democratizing. [The argument was] that anyone can buy a camera but to be a real artist you have to go to school and learn how to paint,” she says. “I think the criticism of social media is identical. This is technology. This is science. This is too democratizing! Anyone can have a Twitter account. I’m not saying that all Tweets are the next great american novel. But I’m not saying that all novels are the next great American novel either. I just think that social media—as much as dance or sculpture or pastels or oil paints—has the potential for human creative expression. In addition to creating my own content and working in more traditional mediums like painting or making collages, or even just digital graphic design and social media, I would love to get the necessary certifications to become a leading voice in art criticism that brings social media into the fold of what is considered canonical fine art,” Calloway says.

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Turns out I could use more power

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Capitalism, the very thing that allows for Calloway to monetize her social media presence by selling access to her Close Friends content, posting to OnlyFans, and selling watercolor paintings of boobs, is also why people associate Calloway with being a scammer in the first place. Americans are hyper-productive, by nature, thanks to the decades of capitalism that told us that our value is based on our output.

Many of Calloway’s trolls and critics latch onto the idea that because the book deal she got years ago has yet to come into fruition, or because the other self-published book (the one literally titled “Scammer”) has yet to see the light of day, that they are correct in thinking that Calloway is scamming her followers out of their hard-earned money. Perhaps, in that regard, Calloway is her own worst enemy to promise deadlines that are almost never met on time.