Caroline Calloway On Messing Up and Being Human
Internet celebrity Caroline Calloway reflects on her time at NYU, art history, OnlyFans, and healing.
The first time I call Caroline Calloway, I’m sent straight to voicemail. When I call again, a few minutes later, she picks up quickly, and lightheartedly explains that she had forgotten she had an interview. She was busy researching her next OnlyFans set — a softcore porn photoshoot that will see her dressed in a chocolate brown pantsuit in order to portray Dagny Taggart, the protagonist of Ayn Rand’s Atlas Shrugged.
The somewhat chaotic tone this sets for our conversation is exactly what I’d expected from Calloway, an NYU student turned Cambridge alum turned Instagram celebrity turned viral scammer turned philanthropist, essayist, and now OnlyFans user. She’s perhaps most famous for the viral hit piece about her, written by her ex-best friend Natalie Beach and published by The Cut in September 2019. The piece details the author’s friendship with Calloway, from the two meeting at NYU to Calloway transferring to Cambridge to Beach acting as a ghostwriter for many of Calloway’s Instagram captions. It paints Calloway as a shallow, vindictive, thoughtless person who mistreated her friend and lied to her followers.
Calloway has responded with her own side of the story in an as-of-now three part essay titled “I Am Caroline Calloway.” In the response, Calloway takes responsibility for mistreating her friend and acknowledges years of mistakes and poor behavior, but also elaborates on many aspects of the story she feels Beach omitted, like her years-long Adderall addiction, her history of mental illness, and her father’s suicide. Calloway has donated the proceeds of“I Am Caroline Calloway,” to COVID relief efforts (the essay is normally behind a paywall, costing $10 in order to read Part One, though it’s currently free to read at time of publication). The essay paints a picture of a deeply flawed but complicated human being, working to grow and learn even as she deals with the repercussions of her mistakes.
The first thing I ask Calloway, after I mispronounce the word Cambridge “cam-bridge” (which she makes fun of me for), is whether she thinks her life would be different if she’d stayed at NYU. This, she informs me, is a weird question, because of course her life would be different, just like her life would be different if she hadn’t gone to Cambridge, or hadn’t gotten addicted to amphetamines, or made any number of other choices. “But,” she tells me, “you could just as easily ask ‘do you think your life would be different if you had never gone to NYU,’ and the answer would be yes. I mean, I never would have met Natalie… like, she’s one of the reasons I became a writer — because she believed in me.”
We spend a while talking about the NYU Creative Writers House. One of my personal favorite sections of “I Am Caroline Calloway” is the paragraph where she describes the house, a “brownstone…with built in shelving and pre-war molding…students chatting on the stoop, holding books, throwing their heads back in laughter,” and we both agree it’s one of our favorite places on campus. She says she didn’t realize how ready she was to “riff about the Creative Writing House,” until she started writing that paragraph and “it turned into 10 paragraphs, and had to be cut back down into one and a half.” The house, where Calloway met Beach, and where I’ve spent more than one evening frantically finishing an overdue short story, really is a gorgeous place.
Calloway is emphatic about wanting to dispel any idea that she hates NYU, which she worries Beach’s article suggests. She may have left NYU for Cambridge — she tells me she felt that it was her “life’s calling to make art about elitist educational environments in the same way Monet was inspired by the lily pads in the gardens of Giverny,” — but she reminds me that she studied art history at Cambridge, not creative writing, and in fact “didn’t take a single creative writing class” during her time there. NYU, she says, is where she became a writer — where she found her purpose in life.
NYU is also where she met her friend Lauren Singer, an environmental activist, in a Poetry 101 class she enrolled in because she refused to take Writing the Essay. Her advisor at the time protested the choice, but she held fast, sure in her belief that she would be transferring to Cambridge. She says Singer turned in a poem titled “One Year Stand,” (“like one night stand,” Calloway is quick to point out, in case I missed it). “Much like how I met Natalie,” she says, “she turned in some writing, and I was like, this girl is a genius. I cornered her after class, and I was like, you’re going to be my friend.” Singer has since gone on to found Package Free and Trash is for Tossers, two philanthropic efforts to reduce waste and help the environment. When I ask if they keep in touch, Calloway laughs. “Are you kidding me? We’re going to FaceTime this week. She’s still one of my best friends.”
She does, however, have a bone to pick with me. At one point in our conversation, she doesn’t hear my question because of a technical problem, but tells me that “it honestly wouldn’t have made any difference because I was just going to, like, bulldoze forward with my end of the conversation.” She makes good on that promise and bulldozes away, telling me that she’s upset with NYU Local for running an article titled “I Lived Like Instagram Trainwreck Caroline Calloway for a Week.”
The title itself is not the problem, as she says to me, “no one can roast me better than I can roast myself.” Instead, she’s frustrated by what the story is about — not, as she expected, a recreation of her life at its worst, at “peak addiction,” when she would “stay up all night buying $7,000 worth of furniture on eBay without sleeping.” Instead, the author emulates Calloway by going to spin class, talking about therapy, and posting on Instagram a lot.
The article is familiar to me, although I suspect at the time that it may have been written by Washington Square News, not NYU Local. I tell her this, and she says she’s pretty sure it was Local, but that I’m welcome to check her on it. (Ever the responsible journalist, after we talked I went and checked, and I am happy to say: Caroline, WSN wrote that article, not us.)
Beyond giving me the opportunity to dunk on our friends across the park, the problem Calloway has with the article is that what it portrays as a “trainwreck” was a week in her life where she was “sober, healthy, and happy for the first time.” It was demoralizing, she says, to feel judged for being open and honest about her emotions and mental health.
We talk for a bit about the importance of therapy — Calloway goes three times a week — and eventually I get around to asking about Natalie. Calloway’s relationship with her ex-best friend is one that has always felt close to my heart. Unfortunately, I, too, can relate to looking back at the last few years and realizing I’ve really hurt someone I care about. I ask Calloway the questions that have been floating around in the back of my head for the past nine months: How do you move forward? How do you trust that the new you is better, and that you’re not just repeating the same mistakes?
She tells me that the answer, as disheartening and intimidating as it may sound, is “that you really have to make peace with the fact that you’ll mess up again, and that messing up is human.” You can’t live life waiting to become some sort of idealized self,” she says. The truth, which is much more nuanced, is balancing a commitment to establishing new patterns of behavior with the simultaneous knowledge that “you will fuck up again, and again, and again.” Calloway tells me she wishes she had a more inspiring answer, and I wish I could tell her how inspiring the one she’s given is.
I finally get the chance to ask about art history (you know, the subject she went to Cambridge for), and I ask her if she considers her work online art. The answer is an emphatic yes, with the caveat that she’s excited for the day she can stop being asked that question. She compares the treatment of social media today to the treatment of photography in the late 19th century. Art critics at the time hated photographs, she says.
“They just derided the idea that photography could be art with claims like: cameras are science, they’re technology, they’re too democratizing, anyone can buy a camera,” Calloway says. “And I really see a lot of parallels with the intellectual and emotional biases we hold towards social media as art. You know: it’s science, it’s technology, it’s too democratizing. Anyone can make a Twitter account.”
Not all tweets are the next great American novel, she admits. But then again, not all novels are the next great American novel. She doesn’t think everything on social media is her best art — just that every artistic medium has “the potential for sublime human expression,” and that “when I get lucky and when I get disciplined…my social media art is not just art — it can be among my best work.”
Calloway even considers her OnlyFans account a kind of performance art. She tells me she finds it exciting to explore how to “command the architecture of the internet,” and to play with the idea of being smart and sexual, which she says stirs up a lot of internalized misogyny in people. The performance art is also about the medium itself, and how people are willing to pay $50 a month for access to her account — which she admits, is not “the best place to see naked women.” In fact, she says, “my OnlyFans is actually a really terrible place to go to jack off.” It says something about the value of celebrity, she continues, that her content can command that price.
“What people are paying for is access to a certain person,” Calloway says. “And what is it that makes my content worth that much? I don’t even have answers to these questions. They’re just questions that I’m interested in asking with the stuff I make.”
Her OnlyFans has garnered her some criticism, namely that, as an affluent influencer, she’s taking money away from less fortunate sex workers who need the money more than her. Calloway argues that she has as much right as anyone to earn money from sexualizing her body under the patriarchy, to explore how voyeurism excites her in terms of her own sexuality, and to “march forward into the ups and downs of capitalism and try to make good business decisions that bring in income.” People who tell her otherwise, she says, are just “singling me out when I am not the problem.”
She tells me that she resents that people feel so “righteous” in their hatred of her. “I think I’m one of the safest people to hate online,” she says. “You know, it’s not really a hot take to say that I don’t deserve money, that I shouldn’t have what I have or should have less.”
The day after we talk, Calloway texts me a picture of her own tweet (classic CC), where she argues, in response to an Elle article, that if she had opened a bakery, nobody would be telling her to stop competing with other bakers who might need the income more. To me, the Elle article seems to be drawing an arbitrary line between Calloway’s work and “real” sex work, just because she happens to have other sources of income. I tell her this, and she heart reacts my message. We’re best friends now.
The debate in response to her tweet rages on as always, but as one sex worker on Twitter says, “… as long as [Calloway] continues to stay open to valid criticisms of [her] privilege as a white cis het(? lmao) woman in a community where underprivileged folks often flock out survival, I don’t see an issue.”
As our conversation wraps up, I ask Calloway, writer to writer, how she found the voice she equips in “I Am Caroline Calloway,” a voice that feels so easy, natural, funny and serious at all the right times. She tells me that it’s about escaping fear of judgment. “The way that anyone makes something new and fully their own,” she says, “is from a very quiet place where they cannot hear the self-doubt born of other people’s judgment.”
She tells me to read without fear, and to read the stuff you actually want to read. For her, that’s Ender’s Game, and Harry Potter, and other adventure pulp (I am ecstatic to learn that she likes one of my favorite books, The Secret History by Donna Tartt — something I already suspected based on her love of the East Coast tweed aesthetic).
“Read and write without fear of judgment, she says, “without fear of being too serious, of being too anything, and just see what comes out of you when you can silence those fears.” It’s a lesson that, along with remembering that I will continue to mess up (and that’s ok), I think I’m going to take very close to heart.
I tell her that it means a lot that she took the time to talk to me. “Thanks,” she says. “I’m gonna go shoot some softcore porn now.”
