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The messiness and meaning of Caroline Calloway

Caroline Calloway at a New York City event in May. The Instagram personality drew media attention well beyond her previous fame when a former friend penned a tell-all about their relationship. (Astrid Stawiarz/Getty Images for Shorty Awards)

For reasons I cannot explain and nevertheless felt bashful about, I spent the better part of the week sporadically scrolling through the Instagram feed of a person named Caroline Calloway and trying to figure out why I was scrolling through the Instagram feed of Caroline Calloway.

This is an Internet celebrity who most of the world had never heard of — a social media “influencer” whose nearly 800,000 followers were apparently drawn to her globe-trotting, life-is-a-sparkler-and-I’m-the-match photos and captions. She wore a lot of flower crowns; she’d once gained some notoriety after scheduling and canceling a series of “creativity workshops,” for which she charged $165 a ticket and ordered 1,200 Mason jars.

“Why did she promise people Mason jar gardens?” a friend emailed me on Wednesday, because my friend, too, had fallen into a Caroline Calloway vortex and could not claw her way out.

It was all a lark until suddenly it wasn’t, until suddenly it was a meditation on the nature of grief and fame, creativity and complicity.

Here’s what happened to launch this obsession: Last week, New York magazine published a very long, very viral essay written by a former friend of Calloway’s. Natalie Beach alleged that she had ghostwritten many of Calloway’s successful Instagram posts. And that Calloway may have purchased some of the account’s followers. And that Calloway had promised her a never-materialized portion of a $375,000 book advance. And, and, and.

There were a lot of privileged problems, a lot of friendship drama. The spikiest distillation of the essay I heard was an acquaintance claiming that reading it was like boiling six seasons of HBO’s “Girls” into a teaspoon, and injecting it into your veins.

Was Beach’s essay petty? Yes. Was it embarrassing and painful? Yes — especially because Calloway documented her response in real time. “When we were still best friends I don’t think I even saw [Beach] clearly enough to love her,” she wrote online. “You may . . . say that I’m manic or spiraling or melting-down . . . I know what I am making and I have a creative vision.”

And, while observing all that in the moment, was it still inexplicably tempting to scroll all the way back to the 2012 beginnings of Calloway’s Instagram feed, to examine a mundane photo of an ice cream cone and marvel over the fact it garnered 1,873 likes?

Well, here we are.

Ever since Nick Carraway wandered into one of Jay Gatsby’s parties, ever since the talented Tom Ripley went to Italy to collect Dickie Greenleaf, America has been a sucker for stories of middle-class souls drawn into friendships beyond their pay grades.

First, these wealthy benefactors dazzle with incomprehensible charm. They bestow gifts and experiences, and they allow their new friends to bask in their reflected glory. Then, after a while, the middle-class friend begins to realize he is not being shined upon, he is being sucked in.

At that point, resentment builds to a revelation: There was never anything particularly great about Gatsby. The scenery was lovely but the conversation was banal; the books in his library were fakes. Money and fame can mask a whole manner of dullness while prompting a whole range of envy.

The publication of the Caroline Calloway essay launched an immediate wave of armchair analysis, at least in the rabid little corner of society that cared about it: Was this a story about toxic friendship? Was this a story about the vapidness of young, millennial white girls? Should we all feel embarrassed for reading such a frivolous thing?

To me, it wasn’t vapid. It wasn’t girly. It was F. Scott Fitzgerald reworked for our Instagram age; it was Patricia Highsmith with the comments function enabled.

Why did Caroline Calloway promise people Mason jar gardens? Because this is how we update our modern classics for 2019. The rich remain as inscrutable as they ever were, and we remain just as disdainful of them, and just as taken in.

Why are social media influencers always in the news for bad behavior? Hannah Jewell explores the multibillion-dollar global industry of influencer marketing. (Video: The Washington Post)

Anyway. These were my thoughts about Caroline Calloway, until Thursday afternoon, when she put up something else on Instagram — a sharp departure from rehashing the Natalie drama.

Her father had just died, she wrote. She’d learned only an hour before. She posted a photo of herself as a toddler gazing up at a dark-haired man wearing Coke-bottle glasses.

Even in grief, she’d considered the optics of posting this news: “I’m worried that by even telling this I will cheapen the truth. That I will make this moment into another ‘notorious misfortune’ of mine as the New York Times called them.”

Suddenly, writing about Calloway only as if she were a character in literature felt odious — even as she continued writing about herself that way, spilling every thought onto the page. Two hours after she got the phone call about her father, she gave an interview with NBC. It was already scheduled, she said, and she didn’t care if people judged her for doing it. It was how she was processing her grief, she said, and the format wasn’t anyone’s business but hers.

“Just don’t tell me how to f---ing grieve,” she wrote.

Suddenly, writing about Calloway at all took on a level of deeper meaning. Too big for a column, really, or even for a long, viral essay written by a former friend. Calloway had gone from being a cartoonish symbol to a hurting, complicated human.

It had become a story about what is real and what is fake, and what is livelihood and what is life. And what is fame, anyway, when the currency is likes and not dollars, and the role we all play in that.

Social media had made her a celebrity and then made her into a villain, and now, in an in­cred­ibly dark and painful time, it had simply made her. She seemed to cling to it, for better or worse. Only now, there was less of the applause she usually received; instead, there were baffled readers telling her to just log off, already, just stop creating.

Nothing about this felt mockable. It felt, instead, like a sad, strange, painfully real and in­cred­ibly bizarre world we’d all helped build and now were all watching teeter. And it all started to feel gross.

Enough with mining her Instagram, enough with trying to understand what made her more viral than lots of other more talented people, enough with the week of obsession.

The last post of hers that I read was one in which she talked about figuring out how to move forward after everything that had happened last week. “I don’t know how to be Caroline Calloway right now,” she wrote.

And then, since she wasn’t logging off, I did.

Monica Hesse is a columnist writing about gender and its impact on society. For more visit