In this day of social media mayhem, Instagram “influencers” with massive followings and a widespread platform to sell a certain lifestyle have come out as some of the most powerful people around. Caroline Calloway is (or maybe now was) one of those people. Self-described as a “Writer, Art Historian, Painter, Cool,” what really earned Caroline her notoriety was her fabulous jetset lifestyle. But while her followers were wishing their lives looked more like Caroline’s — none of it turned out to be true.
Caroline Calloway and Natalie Beach Meet
The last seven years of Instagram infuencer Caroline Calloway’s life have admittedly been an absolute whirlwind. Luckily, Caroline’s close college friend, Natalie Beach was there for every step of the way. According to Natalie, she and Caroline met when they were both 20-year old students at NYU. But as Caroline arrived, fashionably late no less, to the creative-nonfiction workshop Natalie was in, it wasn’t necessarily an instant connection.
However, as Caroline’s Instagram followers know all to well, she was obsessed with Yale, the university that had rejected her, and being a New Haven native was enough to earn Natalie an invitation to Caroline’s apartment. Just like a story one of their classmates might have read out in their workshop, the first chapter of their friendship had just begun.
A Friendship Starts to Form
Natalie Beach arrived to Caroline Calloway’s West Village apartment, and later recalled being completely dazzled by how chic everything was — especially in comparison to her tiny Gowanus apartment back in Brooklyn. Eager to talk to Natalie about all things New Haven, Caroline turned to Natalie, showing her a “Yale box” of university memorabilia. The girls spent the day together, and it was clear they had a connection.
Months later, for Caroline’s 21st birthday, Natalie got her new best friend a cute gag gift – a callback to their first time hanging out together – three Yale University plates, with a jokey line written in Sharpie on the backs. Caroline started crying when she opened the gift, and Natalie couldn’t believe how moved her friend was. Although Caroline’s reaction would make what happened next all the more puzzling.
The First Red Flag
Just a few short weeks after Caroline had had such an emotional reaction to Natalie’s gift, she casually informed Natalie that the plates had been stolen out of her apartment. Natalie was shocked. The plates weren’t valuable, and all of Caroline’s expensive electronics, and antique furniture had been left untouched. Why would someone break in to steal nothing but three Yale plates with a personalized message on the back?
Years later, Natalie recalled the moment vividly, saying “It was the first time I felt sure she was lying to me.” But thinking about what she could lose in confronting her closest friend over a seemingly strange lie, Natalie said nothing. Swallowing any possible disappointment or distrust, the two got even closer, and Natalie was more and more entranced, or perhaps blinded by, Caroline’s charisma.
Dreaming of the Future
The two girls were fast friends, hopping from swank bar to bar, indulging in fancy dinners and luxe leisurely breakfasts. Natalie Beach and Caroline Calloway could spend all day strolling through New York City, imagining what their lives would look like when they were published writers.
Natalie somewhat shamefully admitted in her diary to often feeling a little like the sidekick to the more outwardly glamorous Caroline. And even after the apparent lie about her stolen birthday gift, it wasn’t until a year after they first met that the dynamic of their friendship shifted. And although Natalie didn’t know it at the time, they would never be the same.
Natalie Meets Caroline Calloway the Instagram Influencer
Natalie went to study in London for a year, and as her year abroad wrapped up, Caroline was en route to meet her for a girls’ trip to Sicily. It was then that Natalie met with someone slightly different from the friend she’d known – she met Caroline Calloway, the Instagram “Influencer.” Apparently her social media following had blown up while Natalie had been away.
The small amount of celebrity she had amassed had made Caroline even greater figure of grandeur in Natalie’s mind, and had made her feel small in comparison. In her diary Natalie wrote, “I found myself wishing something bad would happen…a humiliation, like the one I feel always,” and adding, “There has to be a price for getting everything you want.” But in that moment, neither of them could see what the consequences would really look like.
Natalie and Caroline Strike a Deal
As Natalie tried to make her way back to New York, her fast-living and loose-spending in trying to keep up with Caroline had begun to catch up with her. After a series of missed flights meant Natalie was stranded in Italy, Caroline offered to pay for her ticket back home.
Natalie didn’t know how she would repay Caroline the $800 cost of the tickets, but she had an idea. The two agreed that Natalie would help ghostwrite the captions on Caroline’s Instagram posts for the summer. However, as they watched their social media following grow, their real lives couldn’t have drifted further apart.
Things Fall Apart — And Come Back Together
That fall, still short on cash and coupled with a roommate who wasn’t paying his half of the rent, Natalie was evicted. She asked Caroline if she could stay in her unoccupied apartment, but she declined. Natalie finished up her last semester and moved back home. Meanwhile, Caroline had transferred to Cambridge University in England.
Their summer deal had expired, and without sharing in Caroline’s rapidly growing internet celebrity, their friendship was all but extinct. According to Natalie, Caroline was off having adventures abroad with her new friends, while Natalie was itching to get back in on the action. So she reached out. Time passed and Natalie heard nothing. But then, Caroline sent her a message – she was back in New York and needed Natalie’s help. ASAP.
The Book Proposal
In the time that Caroline had continued to grow her “brand” as an Instagram Influencer, she had found an agent who was interested in having her write a memoir. It was going to be the true story of an American girl abroad, having adventures, falling in love, and traipsing through city squares at midnight.
Caroline told Natalie she needed a book proposal, and she didn’t just need it fast, it was due by the end of the weekend. Thrilled to be of use once again, Natalie grabbed her toothbrush and laptop and headed straight over to Caroline’s help. Staring down the start of a series of sleepless nights, the two friends set to work.
Watching Their Writing Dreams Come True
Writing frantically all weekend, Natalie guessed that the two worked for some 35 straight hours. It was around then that Caroline asked Natalie to come on board as a paid editor. Natalie enthusiastically agreed, even though nothing they had written that weekend had been usable.
Caroline blew her first deadline, but they decided to keep working. Natalie worked off of Caroline’s raw notes and eventually, they had a 103 page proposal. Flatiron Books agreed to buy the book for $375,000, and Caroline, in a verbal agreement, told Natalie she’d get 35% of all proceeds. The girls celebrated, all their dreams were coming true! But, after Caroline returned to Cambridge, things quickly started to crumble.
Natalie First Sees the Truth
Natalie flew out to Cambridge, where, she later confessed, she had the entirely unexpected realization that Caroline’s life was largely a fraud. She didn’t have loads of fabulous friends, she was on the brink of academic ruin, and she couldn’t cope with any of it. What’s more, Caroline admitted to Natalie an addiction to Adderall, and was awake for days at a time.
It was then that Caroline confessed that her Instagram followers weren’t all real – she had bought thousands of fake followers. Her celebrity had been built on a lie, and Natalie realized with dread, that they had sold the promise of a book, based on a girl who didn’t exist.
Everything Goes Wrong In Amsterdam
Still, Natalie couldn’t help but trust Caroline, this girl who seemed to have easy ways out of everything, and so she decided to stick it out. Together, the girls traveled to Amsterdam for the weekend. Despite the Instagram content they got out of the trip, Natalie reported the reality to have been so much worse.
After going their separate ways after a night out, Natalie ended up locked out of their AirBnB. While Caroline slept through all of her frantic calls and texts for help, Natalie was out on the street, all night. By morning, everything looked different for Natalie. She had been scared and alone and she knew that they needed a change. A big one.
A Fractured Friendship
After Amsterdam, Natalie returned with Caroline to Cambridge but she couldn’t look at her friend in the same way, she later wrote. With Amsterdam still swirling around in her mind, and the truth about Caroline’s academic and social life being less than she’d made it out to be, too many seeds of doubt had been planted in Natalie’s mind.
A few weeks later, Natalie left to return to New York and some time later, she relocated altogether, moving to Los Angeles. Although their friendship had been fractured, all the while, they worked on the book. It may have been built on a lie, but they had a deadline. And it was fast approaching.
Everything Comes Crashing Down
The book was going to be titled “And We Were Like,” and the two writers hoped against hope that it would change the course of their lives. As they tried to write the book together over Skype, Caroline couldn’t bring herself to contribute anything publishable. Still, Natalie tried her best to carry on.
She bought them time by writing a quarter of the manuscript herself. Caroline found the process of writing practically painful. As Caroline would eventually explain to a fact checker from New York Magazine, she had hit an absolute low. Overwhelmed by the memoir she couldn’t write, and her Adderall addiction, Caroline contemplated suicide.
Caroline and Natalie Meet One Last Time
The last time Natalie and Caroline would see each other was in New York during the winter of 2016. As an early birthday present, Caroline gave Natalie some used makeup and a check that ended up bouncing. Too worn out from all the fighting and deceit, Natalie was ready to finally give up on their shared dream, and on whatever was left of their friendship.
Having pulled away from the entire ordeal, Natalie watched on Instagram as Caroline counted down the days until her final deadline came and went. And with it, her book contract was canceled. Having spent most of her advance money, Caroline owed over $100,000.
Caroline’s “Creativity Workshop”
Seeing as she owed quite a bit of money, and her most marketable asset was herself, Caroline Calloway decided to put together a “creativity workshop” — a seminar-style few hours where she would teach her fans how to “architect a life that feels really full and genuine and rich and beautiful.” It could almost be something like her second act.
The cost of admission was $165, and attendees were promised a lot. Caroline advertised that the workshop would be a nationwide “tour” and that she’d even be taking it to Europe. As soon as journalist Kayleigh Donaldson caught wind of the “workshop,” her suspicions were raised. Journalist Andrea Park over at W Magazine was similarly skeptical. The two went on to record everything that happened next.
Caroline Gets in Over Her Head
Kayleigh Donaldson tracked and exposed as one by one, every promise Caroline had made to those who had bought tickets to her creativity workshop came apart. Caroline had sold some fairly expensive tickets to events across the country, but hadn’t booked any venues. Caroline too recorded everything on her social media.
Despite being honest about the unexpected difficulty of putting together such an event, Caroline insisted it would all be worthwhile. She told her social media followers that she just couldn’t pull off the event as promised — she was in over her head. In the end, only two workshops took place, and the writers were there to report on what they imagined would be every disastrous detail.
Caroline is First Accused of Being a Scammer
According to the two journalists, the first “creativity workshop” kicked off at an event space in Brooklyn, and for the first hour, Caroline wasn’t even there. Personalized gift bags, flower crowns made with orchids, a gourmet lunch, all of the things Caroline had advertised — none of it was as advertised.
Even as ticket buyers expressed disappointment over the New York-based “workshop,” Caroline conducted another in Washington D.C. Caroline’s seminar didn’t include much teaching, and according to attendees was just her retelling stories she’d already written about in detail on her social media. Within no time, the story of Caroline Calloway’s supposed scam had caught in the media, and was spreading like wildfire.
Trying to Turn it All Around, Again
In an attempt to quell all the bad press, Caroline canceled her “creativity workshop” tour, even though only two workshops had actually taken place. Hoping to restore a little good will, she issued refunds for every event. In fact, journalists Kayleigh Donaldson and Andrea Park both confirmed that Caroline hadn’t even booked event spaces in any of the cities she’d said she’d be traveling to.
Meanwhile, ticket company Eventbrite, which Caroline used to sell the tickets, wrote on Twitter that she was under investigation by their Trust & Safety department. With her reputation in tatters, Caroline had yet another idea to try and turn it all around.
Caroline Calloway Creates “The Scam”
Not long after her first “creativity workshop” failed and was billed as a scam by the press and public, and with the money owed to her former publisher for her memoir that wasn’t, Caroline created a new creativity workshop — still convinced she could pull it off. This time, she called it “The Scam.”
Having fully leaned into the shady personality the press had given her, and despite everything, “The Scam” sold out too. According to a writer who managed to make her way into the event, it was more of the same. Again, the internet went wild, and the backlash was too much for Caroline to bear. She had to speak out.
Caroline Tries to Explain it All
In the wake of her canceled book deal, canceled creativity workshop tour, and the bad press that followed “The Scam,” Caroline kept trying to explain herself to her followers – and the public at large. She wrote on her social media, and did her best to apologize.
Caroline wrote, “I was overconfident in believing that I had something to offer people that was worth $165 dollars [sic] and this experience has been incredibly humbling.” But while trying to take back the narrative of what had happened over the last few years, Caroline was confronted with something scarier than viral bad press — an email, from Natalie.
Natalie Comes Back to Caroline With Some News
Two years after they had stopped all communication between them, and two years after she was first declared a scam artist by the press, Natalie reached out for the last time. Natalie informed Caroline that she had written about their friendship, about ghostwriting portions of the Instagram that got her famous, and the book that almost was. She was revealing everything.
Caroline anxiously counted down the days on her Instagram along with all her followers, until the tell-all article was set to be released. And then, on September 10th, 2019 — the article went live. Almost immediately, the reactions started pouring in from everywhere all at once.
Caroline Reacts to the Article in Real Time
As has become her custom, Caroline continued to react to the news of the exposé in real time, online, for everyone to see. Veering wildly from quiet acceptance of her part in the series of “scams” and apologizing to anyone she misled, to trying to defend her actions, and back around.
The one thing Caroline maintained was praise of Natalie’s article, admitting that everything she wrote was true. As for Caroline’s almost 800,000 followers, many of them seem to have one of two responses: they either confess to feeling lied to and disillusioned, or plead with their former favorite social media star to take a step back, and just stop posting. But still, Caroline continued to post.
Money Troubles Comes to the Surface
Trending on Twitter, and with her name everywhere in the press, journalists can’t help but keep digging into Caroline Calloway. In addition to everything included in Natalie’s article, one journalist uncovered four civil suits against Caroline, two from 2017, one in 2018, and one in 2019.
Each civil suit was over non-payment on her rent. Caroline did pay back the rent she owed, and avoided eviction, but with this latest piece of information out in the open, it seemed, to her followers, that there was no way to keep denying the truth. It seemed Caroline had never been what she appeared to be.
Working on Her Response
In the aftermath of the article, and even with so many feelings of hurt and betrayal brewing between them, Caroline Calloway and Natalie Beach, while being brutally honest about the uglier side of their friendship and work relationship, have still been able to admit to admiring the other. In her initial email, Natalie signed off the message by telling Caroline she couldn’t wait to read her response to her article.
Mere days after the article went live, Caroline announced that she’d already gotten to work writing her response. But many fans have expressed the difficulty they face believing Caroline’s version of events. After everything they now know, and everything that turned out to be untrue, can Caroline’s fans trust her?
They say there’s three sides to a story, the two sides of the people involved, and then the truth. While Caroline’s 800,000 followers, the press, and everyone who’s gotten caught up in the shocking aspects of her story wait for Caroline’s version of events, lots of unanswered questions still linger.
What actually happened to those Yale University plates Caroline had claimed were stolen? And why would she have lied about them? Had she ever intended to book event spaces for her creativity workshop? And will Caroline and Natalie ever patch up their friendship? Guess we’ll just have to wait and see what happens next.
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