NEW YORK MAGAZINE: When I was a sophomore in college, I took a creative-nonfiction workshop and met a girl who was everything I wasn’t. The point of the class was to learn to write your own story, but from the moment we met, I focused instead on helping her tell her own, first in notes after workshop, then later editing her Instagram captions and co-writing a book proposal she sold for hundreds of thousands of dollars. It seems obvious now, the way the story would end, but when I first met Caroline Calloway, all I saw was the beginning of something extraordinary.
Today Caroline is a 27-year-old Instagram influencer with almost 800,000 followers. A self-described “writer, art historian, and teacher,” she first became internet famous for diaristic captions chronicling her misadventures as an American undergrad at Cambridge University and was later known for the mysterious dissolution of her big book deal. After that, Caroline fell out of the public eye for a year but returned this past January on a tour to promote her “Creativity Workshop,” which was billed as a tutorial to “architect a life that feels really full and genuine and rich and beautiful” but ended up being compared to a one-woman Fyre Fest. She charged participants $165 a head and sold the tickets before booking venues, made promises she couldn’t deliver on (orchid crowns, “cooked” salad), and, true to form, posted the whole fiasco in real time. It seemed like the entire internet saw a pallet of 1,200 Mason jars delivered to her studio apartment and her pleas for ticket buyers in Philadelphia to just take the train to New York. She became a symbol of, as journalist Kayleigh Donaldson put it, “The Empty Mason Jar of the Influencer Economy,” which prompted Caroline to begin selling T-shirts that read “Stop Hate Following Me, Kayleigh.”
More recently, her Instagram has been filled with emotional posts about this very article, which she knew was coming. For almost a week she’s been posting constantly — how much she misses our friendship, how hurt and ashamed she is about whatever she thinks I’ll say here, how relieved she is that I broke the trust in our relationship so she can now write about me, too. It’s been surreal watching this unfold from my desk job in Los Angeles, but I’m not surprised she’s taken an essay of mine that didn’t exist yet and turned it into a narrative for herself. Caroline was the most confident girl I’d ever known. We were both 20-year-old NYU students when we met, Caroline arriving late to the first day of class, wearing a designer dress, not knowing who Lorrie Moore was but claiming she could recite the poems of Catullus in Latin. She turned in personal essays about heartbreak and boarding school, had silk eyelashes, and wore cashmere sweaters without a bra. She seemed like an adult, someone who had just gone ahead and constructed a life of independence. I, meanwhile, was a virgin with a meek ponytail, living in a railroad apartment that was sinking into the Gowanus Canal.
Caroline first took an interest in me after I wrote an essay about growing up in New Haven. Yale was an obsession of hers; she’d been rejected and never got over it. The fact that I was a Yale townie won me an invitation to her West Village apartment, a studio painted Tiffany’s turquoise and filled with fresh orchids and hardcovers. “This is my Yale box,” she told me, sitting me on her white loveseat and showing me a shoe box of Handsome Dan and Beinecke-library memorabilia. It was that same day, as we split a joint, that Caroline informed me I was beautiful, which no one outside my family had ever said. Soon I began going to Caroline’s after every class, then just any chance I could. To my other friends, I described her as someone you couldn’t count on to remember a birthday but the one I’d call if I needed a black-market kidney. What I meant was that she was someone to write about, and that was what I wanted most of all. “You’re a sharp writer,” our professor told me — he would soon be played by Jesse Eisenberg in a movie, and Caroline and I were both a little obsessed — “but what you’re limited by right now is where you’ve walked through yourself — you’re limited by your itinerary.” Caroline had no such limits. Her life was a cycle of adventures and minor crises. We dashed in and out of as many clubs as we could in a night, attended a Wet Hot American Summer–themed party at a secret society, and went to Cyrano de Bergerac on Broadway, which Caroline wept through as if it were a religious experience. We’d go out to eat all the time, and soon I was broke but didn’t care. I was now part of her life, a conspirator and confidante. At the Minetta Tavern, I told her that her fantasy of going out with our professor was dangerous and predictable. “It’s like a movie,” I said between bites of lettuce wraps. “This is Act I. Soon he’ll invite you over to his bachelor pad, fuck you, and in five months you’ll read all about it in The New Yorker.” MORE