When I sat down to face Caroline Calloway in the garden of a café in Chelsea to interview her and give her a tarot card reading, I had the impression suddenly that I was looking at a moving Instagram portrait. She wore a white blouse dotted with small blue flowers and mismatched earrings—a glossy, twisted peach seashell dangled from one ear, a pale, sand-colored one from the other—as if to suggest carefully curated whimsy. Unnaturally shiny, I wondered briefly whether the shells were fake or real but just so heavily shellacked that they seemed artificial.
Calloway, 27, an Instagram influencer who achieved notoriety in early 2019 when her pricey creativity workshops very publicly unraveled in what can only be described as the perfect illustration of Instagram vs. Real Life, again went viral last week. Her former friend Natalie Beach published an essay in New York magazine's The Cut, revealing she’d collaborated on many of the lengthy, diaristic Instagram captions that first garnered Calloway a following in 2015. The essay circulated widely, and Calloway’s name trended on Twitter. No one seemed above the drama—articles appeared about Calloway in the New York Times, the Washington Post, the Atlantic. Celebrated memoirist Roxane Gay even shared the article and commented, “This was...quite a white girl journey.”
Calloway has a knack for simultaneously sharing the minutiae of her life and leaving wide swaths of her experience unexamined. Depending on your opinion of her, this could be evidence that she lacks integrity, or it could be evidence of her expertise in crafting an alluring image. No matter how much of herself she shares, she has a knack for leaving her audience with the impression that there is more to her story than meets the eye.
In the days leading up to the release of Beach’s essay, Calloway hyped the coming controversy on Instagram, drumming up anticipation and helping to create the cultural storm that she now finds herself at the center of. Through it all, she’s been excessive in her praise of Beach. Following its release, she called Beach’s essay “a masterwork of art.” (Beach returned the praise. In an interview with the New York Times, Beach called Calloway a “fantastic writer.”)
When I pointed out how all the public social media love directed at someone essentially calling you out as a fake might be confusing for people, Calloway reflected. “It just seems sort of at odds for us to still be praising each other given what a toxic role praise had in our relationship at times,” she said. “I think the honest truth is that when I was an addict, I was a really shitty friend. And I failed her in a million ways. I think we got into this pattern where I really, like, weaponized my praise for her…. I did genuinely think she's so talented and still do. But I think weaponize is a great word for what happened to that praise, because it was really, in the depths of my addiction, like flattery was the only thing I had left to give her at a certain point. I didn't have a lot of self-awareness to offer her or even compassion…. I didn't even have compassion for myself. I hated myself.”
Calloway’s current recovery (she’s spoken characteristically openly about her struggles with mental health and, formerly, an addiction to Adderall) includes going to therapy three times a week. “I spend a lot of time unpacking the pain surrounding my addiction—both my own and the pain I caused other people,” she says. “I see recovery, as a professionally supervised healing process, paired with unsupervised conscious internal work.”
I ask what’s changed for her internally. “That's such a huge question,” she gasped. “Oh my gosh, I feel so unprepared to answer it.” She thought for a moment and then added, “I mean, I guess the number one thing is that I no longer live with, like, a veil of amphetamines separating me from every single moment of my waking life. And I mean, the trickle-down effect of of living in reality and not living in, like, an amped-up fantasy. I mean, it's—I don't even think I could enumerate all the far-reaching repercussions of that, you know?”
After a heavy lull in the conversation, Calloway changed subjects. “Let’s do a tarot reading!” When I told her that I think of tarot as a tool for storytelling, her face lit up anew. “Joan Didion!” she exclaimed. “We tell ourselves stories in order to live.”
She handled the cards carefully as I explained that I enjoy readings as a way of combining intuition and symbolism to give ourselves permission to tell new stories about whatever is happening to us at the moment. She nodded frequently, punctuating her nods with “I love that.”
I instructed her to pull five cards and then I organized them into a diamond pattern. The central card was “judgment” reversed. Calloway gasped. Not only had she seen the card as she was shuffling, it had come up in a reading a friend had given her on the day she received the news of her father’s death. Her friend told her the card meant a decision would be made, and it would be final.
I had a different take: Judgment is a card that represents a wake-up call. “When this card comes up, it’s time to tell the truth,” I told her. “It represents seeing your past truthfully and clearly, in a way that creates freedom to move forward.”
Calloway admired the other cards as I explained their meaning—the star, for hope and healing, the four of pentacles for control over material resources. “I find this process so relaxing,” she said. Then she snapped a picture of the cards and asked if I wanted her to tag me on Instagram.
As we closed the reading, I asked her about her aggressive optimism—where had it come from, was it a conscious choice, and had she always been this way?
“I would ascribe it to my fundamental extraversion. Even at my most depressed and low-functioning, as soon as you put another person in the room with me, I would perk up and be happy to see them. It's not that I don't experience absolute sadness, which is very unentertaining, but I think—when I'm being really honest about myself—I think there's, like, a really performative streak in my personality. Like, I wouldn't find it so meaningful to be so open if there wasn’t that part of my personality that enjoys entertaining.”
I asked her if acting had ever been a dream of hers. “You know, when I was little, I actually did want to be an actor,” she said. “But I only wanted to play myself. So Instagram is sort of perfect for me.”
And then, like an actor recalling her exit cue, she asked me if we had everything we needed, grabbed her things, and vanished.
Nayomi Reghay is a Brooklyn-based writer who covers women, wellness, and technology. She writes about how social media impacts our relationships in her advice column, Swipe This! You can follow her on Twitter.
Originally Appeared on Glamour