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Who Is Caroline Calloway, The Instagram Influencer No One Can Stop Watching?

Either you know who Caroline Calloway is, or you don't.

Theoretically, that could be true for just about anything (you either know apples, or you don't), but in the case of Caroline Calloway it's somehow more true than usual. Either you're aware of her collapsed book deal, her special brand of vulnerable Instagram posts, and her 1,200 mason jars, or you just... don't.

"Who?" more than one colleague asked me.

So who is Caroline Calloway, the influencer no one* can stop talking about?

The reason she's in the news right now is because her former friend published a highly-anticipated essay on their friendship in New York Magazine's The Cut -- but we'll get to that in a minute.

*If you know her, that is.

Who is Caroline Calloway?

The short version is, she's a 27-year-old Instagram enthusiast in New York City trying to make it as a writer. So far, she's had one failed book deal, one published article, and typed thousands of words for her Instagram account, pushed out to nearly 800,000 followers.

She's not an influencer in the way we've come to define influencers -- diet tea, bikini shots, and a heavily curated aesthetic designed to show her #sponcon in the best light. She describes herself as a "writer, art historian and painter", and documents her day-to-day life complete with crying selfies or her Pilates socks.

She first rose to prominence -- if that's the word here -- in 2013 as an American student attending Cambridge University, documenting with wide-eyed fascination the Hogwarts-esque romance of the institution. Her life was a fairy tale: midnight balls, champagne on rooftops, and a romance with an English boy straight out of your teenage diary.

As it turned out, things were not as peachy as they appeared on Instagram (what is?). Caroline later said she was battling an addiction to Adderall, a medication usually used to treat attention deficit hyperactivity disorder, but all-too-often misused by students studying for exams. Caroline would later reveal she'd stay awake for three days at a time.

By 2015, she'd amassed 300,000 Instagram followers, and had secured a book deal for somewhere between $251,000 and $499,000. Her book, And We Were Like, was intended to be an extension of the stories she told on her Instagram page. She missed her deadline. And then apparently another. By 2017, Caroline announced she was no longer interested in writing it, because it was about her relationships and she didn't want her first book to be defined by the men around her. She said she owed her publisher $100,000 of her advance that she'd already spent.

Caroline's book that was never written.

But that's not where the story ends. Or, as Caroline would say back in her Cambridge days, "To be continued".

Why is she being called a scammer?

After her book deal collapsed, Caroline went quiet... sorta. She continued posting on Instagram, but only via Instagram stories, which disappear after 24 hours. She archived many of her old posts. Unless you intentionally followed her, you wouldn't see her day-to-day content.

Then, in late 2018, she began planning a series of 'creativity workshops'. They were billed as an event for her fans to talk creativity, writing, and being your authentic self (online) -- for the price of US $165.

Caroline's workshops promised to teach fans the 'secret' to her orchid crowns. The real secret? She just put them in her hair. Photo: Instagram.

Unfortunately, due to Caroline's chaotic personality things went wrong. Like, everything. She failed to book most of the venues for her nationwide tour, she asked attendees to bring a packed lunch instead of the salad she promised, and she ordered 1,200 Mason jars to her studio apartment and didn't know where to put them.

"If you are coming to this event for the salad and expecting a corporate level of event planning I will refund you because honestly I just want you to be happy," Caroline wrote on January 13.

"I'm just one human being learning and trying her best and if you haven't understood that by now WHERE HAVE YOU BEEN."

Journalist Kayleigh Donaldson documented the entire thing in a Twitter thread that went viral. Kayleigh called her a scammer. Caroline released t-shirts as merch that read "Stop hate following me Kayleigh". (She's since removed them from her store.)

Photo: Twitter.

Caroline was being compared to a one-woman Fyre Festival.

What happened next?

A handful of the creativity workshops went ahead, with attendees providing media with mixed reviews. The rest were cancelled; Caroline said she issued refunds. Several dozen articles were written about the whole debacle. And then things.... faded.

Unless you followed her on Instagram. There, things really picked up.

The thing you have to understand about Caroline is she will post anywhere from 10 to 100 stories to Instagram per day, usually edging towards the latter. She creates 'in-jokes' with an audience that only has a one-way communication with her, and yet somehow draws you in. She'll post about going to therapy five days a week, waking up for the 'blue dawns' in her apartment, her love and support for friends around her (some of whom seem to be genuine friends, others... less so), and will address 'The Scam'. She's vulnerable and laughs at herself and if she seems a little bit more intense than other people you know or follow, then who cares, right?

Around mid-2019, she began posting regular, permanent posts to Instagram again, to show reporters writing about her who the REAL Caroline was. She continued to live a hyper-visible life, documenting every high, low, and mundane moment. She began selling colourful paintings of breasts for US $80, calling them "tittays" or "bbs". She held a 'Scam' workshop, which was basically her creativity workshop rebranded. (It apparently went okay.)

Mostly, she fell back into the role of Instagram personality, a reality TV star airing her life in real-time.

Who is Natalie and what is this article?

Last week, Caroline shared that an article from her former friend, a woman called Natalie, was going to be published on The Cut.

"This afternoon I found out that one of the two people I have hurt the most in this world will be publishing an essay about our friendship for The Cut," she said.

"Everything in Natalie’s article will be brilliant and beautifully expressed and true. I know this not because I have read her essay but because Natalie is the best writer I know."

Caroline waited. Her followers waited. The internet waited.

There had long been rumours and unreported gossip that Caroline had a ghostwriter for the Instagram captions that made her famous and the "significant" book deal she couldn't deliver on.

Finally, after a week, we got some answers: Natalie Beach, who met Caroline when they were 20-year-old students at NYU, was the former friend, ghostwriter, and the person with the ultimate Caroline Calloway content.

Her piece, titled I Was Caroline Calloway; Seven years after I met the infamous Instagram star, I'm ready to tell my side of the story.

It detailed a one-sided friendship ("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") that saw Natalie act as photographer, supporting player and "punch-up writer" to Caroline's leading lady.

The pair travelled together, Natalie caught up in the orbit of Caroline's presence, ignoring how Caroline ditched her at the bar, lied to her face, said her apartment "made her too sad", reneged on promise after promise, and, climatically, left her alone during an accountable terrifying night in Amsterdam. A trip to Italy was recounted by Natalie: "I should have been having the time of my life in paradise, but Caroline had a way of making me feel small, as if I had folded myself up like a travel toothbrush so she could take me along for the trip."

Natalie wrote that Caroline's Instagram origin story -- of a post making it to the 'favourites' page -- was a lie, and she bought followers instead. But she insists Caroline isn't the scammer the media reported her to be.

"If it was just money and fame she was after, all she had to do was be quiet and let me do the work. She could have been paid hundreds of thousands of dollars, gone on the tour she always wanted, and recorded the audiobook in that beguiling voice of hers. But she had to be the one to tell her own life story, even if she couldn’t. Caroline was caught between who she was and who she believed herself to be, which in the end may have been the most relatable thing about her. This is why, when people ask me if Caroline is a scammer, I try to explain that if she is, her first mark is always herself."

The internet exploded.

The takes are still coming in. People are arguing over Caroline's white privilege, whether Natalie deserved to write the story, if this is all meaningless and if it is, then why do we care?

It's probably something to do with schadenfreude and the allure of seeing people fail, but if you think you're too high and mighty to care, then SORRY, but you've read this far. Why are you still here?

Caroline decided to 'set the record straight', and re-uploaded all of her old Instagram posts, saying which were written by her, and which by Natalie. Occasionally, she paused to observe the media coverage of The Cut's essay.

Apparently, she's writing a rebuttal.

What happened to the Yale plates?

Natalie wrote about giving Caroline -- who was obsessed with the Ivy league colleague -- a set of Yale plates, worthless to anyone else but apparently worth so much to Caroline that she cried. Later, Caroline claimed they were stolen from her apartment.

Natalie thinks Caroline was lying. So does everyone else.

Apparently, Caroline has answers to that, as well.

We don't have them yet, though. To be continued.

Contact the author: abrucesmith@networkten.com.au