I Finally Understand Why People Care About Caroline Calloway

Last week, I wrote an opinion piece, updated an article in real time, and read countless Instagram posts from Caroline Calloway, the influencer who, in 2019, became known for her series of failed seminars. I kept getting asked the same question by my friends, family, and coworkers. The question was not whose side I was on. It was not if I think Caroline took advantage of Natalie. The question was this: why do people even care about Caroline Calloway? And, truthfully, I couldn’t really answer. It wasn’t her pictures—even though Instagram is a photograph-driven platform, Caroline’s posts look like anything you would see on a Facebook album from 2014. They are not perfectly composed, they barely appear filtered, and there is not a unifying aesthetic behind any of them. It’s not her IG stories, which also lack any real design element and are similarly frantic in tone. I knew, logically, that her captions were what made her popular, but I still couldn’t figure out who, especially in 2019, actually wanted to read Instagram captions that spanned hundreds of words.

That changed Sunday night.

Around 9pm, long after most people, myself included, had cared about “who was right” in the pseudo-feud between Caroline Calloway and Natalie Beach, I found myself on Caroline’s Instagram. Mere days after the Cut article heard ’round the world came out, she revealed via (what else?) an Instagram caption that her father had passed away. True to form, she made this confession about an hour after she received the news, and mere minutes before she was supposed to give an interview to NBC News. In 2019, when every influencer is only presenting a very carefully curated version of their life that conveniently leaves out all the less-than-desirable aspects, I can see it be refreshing to see someone with a big following just lay it all bare.

Following her father’s death, Caroline visited Harvard, where he attended undergrad, and was documenting her trip with her signature unimpressive pictures and lengthy captions. These posts made me stop:


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I just had the most perfect date. He’s one year older than me and has long hair and is from Australia and most importantly: He’s so fucking funny my face hurts. In one of the galleries of the Fogg art museum I decided to invite him to come visit on me in New York for a weekend. So I guess we are doing that now. Walking over to the museum we talked about his full-ride art history PhD scholarship and my Instagram. “Are you going to tell your followers about how handsome and suave and charming I am?” “No,” I grinned. “But I’ll write that you asked me to say exactly that.” “Ah,” he said, steepling his fingers with mock seriousness in the dappled sunlight of the Yard. “Very meta.” “Very,” I replied. When we got to the Fogg I turned to him and said, “This is what I want. I want you to use your beautiful art historian brain that got you a fucking full-ride scholarship for a SIX YEAR PhD program and I want you to take all of your experience working as an art critic in Australia and all your memories of being an art history professor back in Sydney and I want you to say gorgeous, intelligent things to me about the art here.” He laughed. Then paused. “I understand that’s what you WANT, but let me tell you what’s going to HAPPEN. I’m NOT as smart as you think I am and I WON’T have all these lovely things to tell you about art and you and I are going to go into these galleries and have EXACTLY the sort of boring conversations that boring people have in galleries. You’ll say ‘I’d steal that one.’ And then I’ll say ‘I’d steal that one.’” He paused again. Grinned. Added: “And then we’ll steal them.” I haven’t laughed this hard in months. The Lampoon and jokes and art history and joking art historians are exactly what I needed.

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The only problems with the Lampoon party was no one there had any drugs and they have a strict no photos rule inside all of the rooms I badly wanted to photograph. Surprisingly, I respected their rules. Unsurprisingly, I was able to crowdsource some drugs from Instagram (jokes). I probably won’t do that again and I don’t recommend it, but I really just needed to forget about my life for one night. Other than those two problems, it was a perfect party. And I don’t say that lightly!!!!! I have been to some pretty fucking great parties and my area of specialty is is fucking great parties in castles attended by genius college students. The Harvard Lampoon blew me away. I wish I could have taken a photo of the inside to show you when the party was in full swing. I’m not even sure if it would be okay to describe it with my words or if that’s being disrespectful, too. I’m hoping maybe I can find some art or photographs that OTHER people have taken of parties at the Lampoon and share them with you, but I’m just not sure what’s good. I need to send some texts.

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Between the drug mentions and shameless tone, I was immediately reminded of one of my other favorite writers, Cat Marnell. If you don’t know who she is, I highly recommend stopping whatever you’re doing and taking a quick crash course on her writing, because it is f*cking incredible. She was a beauty editor at Lucky (RIP) and XoJane (double RIP), and she would write articles that were basically like, “Being in a mental hospital is crazy because everyone’s so strung out and you aren’t allowed to do anything except stare in a corner, so anyway, if you want hair that’s full of volume and not lifeless when you get out of the mental hospital, try this Bumble and Bumble volumizing cream.” I’m paraphrasing a lot, but basically that was the gist: her columns would start out as these larger-than-life crazy tales of her nights/general exploits and weave, like, smoking angel dust in with the newest glitter eyeshadow somehow. She was the beauty and health editor who’d talk unabashedly about popping 30mg of Adderall like Pez candy. It was incredible, and it was not being done by anyone else.

So when I read Caroline kidding-but-not-really about buying drugs off of Harvard kids on Instagram, or asking people not to offer her Adderall out of respect for her addiction (adding that she’d “totallyyyyyy do a little coke or microdose some acid”), I was instantly reminded of Cat and how she would, in her own words, “write about deep-throating dicks the size of pine cones and foot cream in the same story.” Of course, it’s not entirely the same. Cat Marnell was disrupting the beauty space, a historically conservative industry, for an established online publication. Caroline, on the other hand, bares it all on her personal Instagram. But they both share this shameless confessional style of writing that offers a picture into a seemingly glamorous world—on the one hand, a beauty editor in New York, and on the other hand, an American abroad. And they both did something new and inventive, whether it’s talking about drugs in a less-than-glamorous way as a vehicle to plug a beauty product, or writing novels on Instagram when people mostly come to Instagram not to read a lot.

I’m definitely not the first person to make this comparison, and Cat and Caroline know that people see them as similar figures. They’re also both very aware of the other’s existence, which first manifested in a sort of Instagram feud when Cat accused Caroline of being on Adderall, and Caroline got mad (even though she probably was on Adderall). But eventually they came to some sort of understanding and now engage in public displays of affection, commenting on each other’s Instagram posts.


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Ok now we’ve BOTH publicly over-assumed how much Adderall the other person is on. Fair. I made the same mistake when I first posted about Cat and corrected myself in a second post. For the record, Cat just takes one stimulant a day and it’s really working for her and I haven’t touched Adderall since May 2017 and never will again. I realize now that Adderall was such an attractive drug to me in the first place because it clipped into my Caroline brain like a puzzle piece. First and foremost it mimicked the enthusiasm of my actual personality, thus allowing me to be high-achieving and normal-seeming while deeply depressed and under a lot of stress at Cambridge (money, book deal, Instagram, brand—plus all the normal college stuff like friends and homework and love). Ok maybe normal is the wrong word. My friends and enemies at Cambridge can attest to the fact that I was pretty fucking strung-out and jumpy in college. But here’s the kicker: All my behavior still fell within the range of what an exuberant weirdo might do. If I had been railing downers—mumbling and listless—people would have been like, wtf. But when I showed up to a ball two hours late because adjusting and readjusting yellow roses in my bun felt so fucking good on speed that I lost track of time and I hugged my friends while screaming YOU ARE SO SPECIAL TO ME, people were like: Caroline. So I guess it kind of makes sense that people see my personality now and think: Adderall. THAT’S WHY CHOSE IT IN THE FIRST PLACE, DUMMIES. The second reason it was such a perfect drug for me was because it heightened the most enjoyable part of being awake for me. Caring about details! Getting lost in a new project! You think I got into Cambridge without razor-like focus? Adderall exaggerated my outward facing personality, but it also ramped up the best experiences of my interior world. Not-high I can care and care and care about a turn of phrase or a plot twist or the passage of a painting. But on Adderall I never finished anything. I either needed help from a non-addict or I stayed up all night alone making minor tweaks to the first line. Closing thoughts: I love Cat. I love plants.???‍♀️?‍♂️

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As someone whose college creative nonfiction essays were barely reimagined snapshots from my own life, I was beginning to get the appeal of these long-ass captions that, a week ago, I did not have the patience to read. It took me back to a time when I would just write for the sake of writing, and then sit around in a circle of my classmates and just marvel at other people’s writing. When you read Caroline’s captions, there’s a feeling that you’re included in this literary world, appreciating art for art’s sake. No matter how unbelievably pretentious that sounds, Caroline refers to her captions and her feed as her art all the time. And it is pretentious—this feed appeals to the exact type of person who calls their Instagram their “art” and wants to participate in something “cultured”, even on a platform as common as Instagram. You feel ~artsy~ and ~cool~ because you can ~appreciate something~ for its ~literary value~ and not because it’s a picture that someone slapped a brightly colored preset filter over.

Obviously her captions don’t just attract writers, though. Caroline basically explains her own early appeal in the caption of the post about her dad’s death. She writes, “For many years (2013-2018) I tried to BE my online persona. I tried to make myself seem happier, prettier, more interesting on the internet and then I tried to be that girl in real life.” People probably came to Caroline’s Instagram initially because her life seemed glitzy and they coveted it from afar. There’s still this element in some of her posts, like the story about her “perfect date”. Wouldn’t we all love to meet a hot, smart Australian who makes us laugh? Alas, we are not all whimsical, beautiful creative types who charm the pants off of foreign men. So instead of living the life we want, we settle for reading about someone living the life we want. (Or, claiming to live it.)

Now, though, the sheen has worn off and Caroline is showing us what goes on behind the curtain: Adderall addiction and the ensuing recovery, a messy, plant-filled apartment, DMs from people who hate what she’s doing and declare her “over”. I think people were enthralled with The Cut article because we all like watching someone’s ego being cut down a peg. We especially love when influencers are taken to task. But as for why people follow Caroline in the first place? Certainly, a chunk of her audience now are newcomers who want to watch this manic train wreck unfold in real time. (It’s half my reason for being there.) But she clearly has a not-small amount of people who come precisely to read these meandering, lengthy captions. I won’t be the authority on whether or not it’s good writing, but I will say that when she’s at her best, Caroline makes me feel something. Reading about her chronicle her father’s death and his last moments is a bit of a yikes for sure, but it is also unflinchingly honest, and something you simply don’t see on Instagram. It’s messy, it’s either necessary catharsis or a bad idea, depending on who you ask, but it is at least interesting.

Caroline is clearly very into herself and takes her writing seriously, which is grating, for sure. But the thing is, she’s also not wrong. She writes of “blurry August nights drinking rosé in the park”—not blurry just because of the distorted accompanying photo she uploaded—and I can picture exactly the type of night, feel the energy in the air, taste the rosé poured into a Solo cup. So I scrolled through her feed, reading these little pieces of flash memoir. And honestly? When it was good, I enjoyed it. Two gin-scented tears trickled down the sides of my nose. But it was all right, everything was all right, the struggle was finished. I had won the victory over myself. I understood Caroline Calloway.

Images: Caroline Calloway / Instagram