Inside twisted life of ‘world’s worst influencer’ who conned cult-like followers in scam dubbed ‘Instagram’s Fyre Fest’ | The Sun

SHE built a “cult-like” following of online fans who dreamed of being her friend and living out her glamorous Instagram lifestyle.

But in reality, Caroline Calloway was a self-confessed scam queen who exploited her 850,000 followers for her own gain. 

Instagram fans felt duped after she lied about her life and backtracked on meet-and-greet tour dates, which she flogged for $165 a ticket.

After being slammed as a “scammer”, Caroline shamelessly adopted the title and even went on to sell products branded “snake oil” – referring to her sneakiness. 

The 30-year-old, from Falls Church, Virginia, has now quit social media, but her wild life is being retold in the BBC Three documentary My Insta Scammer Friend. 

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‘Targeted Harry Potter nerds’

Caroline was described as “the first Instagram Influencer” by followers after becoming one of the first users to cash in on her "fairy-tale life” online.

She studied at the University of Cambridge and quickly amassed a wealth of American fans who dreamed of taking in the breath-taking British scenery depicted in her snaps.

In posts, she spoke about longing for “readers to grow old with me” and to watch her fall in love, get her heartbroken and get married.

It led to a “cult-like obsession” from fans, including Genevieve Wheeler, who admitted: “I was 10 out of 10 obsessed with Caroline Calloway.

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“She would like your posts and it felt like Christmas morning, it was the greatest thing in the world.”

Caitlin Vickers added: “I would definitely say I was addicted, I wanted to be living that life so much.”

Little did they know, they had not found her account accidentally – it was all part of Caroline’s plan to grow a following. 

“I bought 20,000 followers and then I bought ads before ads were even a thing…” she told Matt D’Elia’s Confused Podcast in 2019.

“I targeted fandoms of books like Harry Potter, Divergence and Hunger Games, since I wanted more readers, not followers.”

Harassed ex she lied about cheating on

At university, Caroline dated a polo player, Oscar, for around three years until 2017 and filled her posts with romantic tales of their time together.

When they broke up, she relentlessly posted about her heartache – despite it later emerging that she cheated on him at least once.

Eventually, Oscar asked her to stop talking about him and to stop tagging his new girlfriend, who was being targeted by the social media star’s fans.

He wrote: “Caroline, it is more than a year since we broke up, and so I think it’s really inappropriate that you keep writing about my life, including outing the name of my girlfriend.”

Oscar signed off his comment by stating: “This isn’t art, it’s cyberbullying. Please stop”. But she didn’t and continued to mention him in future stories.  

Frittered away book deal money

At 23 years old, Caroline’s large following helped her to land a book deal worth $500,000, which came with a $165,000 advance.

However, her memoir never materialised and when publishers cancelled her contract, she admitted to having already spent all of the money.

Later, Caroline tried to sell access to the 34 pages she had written for $20 a time and began charging $1,000 for a shout-out in her Instagram stories. 

‘Fyre Festival-esque' tour scandal

After graduating with a 2:2 in 2016, Caroline moved to a plush apartment on New York’s West Village. 

In a bid to repay her publisher, she started selling art, which was described as “two dots of paint and smiley face boobs” by New York writer Sophie Ross.

She added: “She was charging more and more every time she was dropping these paintings.”

In 2018, Caroline launched a US tour where she would spend time with fans, making flower crowns and talking to them during a six-hour “creative workshop”.

She sold tickets for $165 each, which follower Abigail Scott admitted “was quite a bit of money”.

After she bought one, the star began to backpedal on her promises.

No longer would Caroline provide food or handmade gifts as promised. She cancelled tour dates and tried to persuade fans to travel to different states to attend. 

Abigail added: “When I realised the lack of planning, I was in disbelief. What Caroline promised, she failed to organise 99 per cent of it.”

Concerned, she sent messaged Caroline, who promised to refund her but seconds later blocked her instead.

“It was this sickening feeling, I couldn’t believes she was that cold,” Abigail said. “A lightbulb went off… she was just looking at her fans as a way to make money.” 

The infuriated fan wrote an open letter branding Caroline a “scammer”, which went viral, and as her life was picked apart she tried to sell $20 t-shirts calling them out for “hate-following”.

The event was later compared to Fyre Festival – the infamous fraudulent luxury music festival founded by con artist Billy McFarland that became the subject of a Netflix documentary.

Scam workshops and snake oil

Eventually, Caroline refunded those who were not able to attend her event.

But she then tried to capitalise on being branded a ‘scammer’ by restarting her workshops, which she named The Scam and sold ‘snake oil’ online.

In 2019, while reflecting on her tumultuous time in the spotlight, she said: “History will always have scam attached to my name so I may as well f***ing own it.”

“My hobbies include scamming and I’m the best at it because I’ve never been caught. Lots of scammers are in jail, not this one that’s why I’m the best.”

As Caroline’s financial situation deepened, she claimed to be too poor to afford public transportation, which at the time cost $2.75.

She shared posts to her merchandise – including a $95 jumper and $48 t-shirt – which she captioned: “I really ned you guys to buy this stuff.”

Caroline also launched an OnlyFans account where she reportedly earned $100,000 to pay off the six-figure advance she owed to her former publishers.

Vice News discovered from court documents that she wasn’t paying rent on her fancy apartment and owed more than $40,000.

Ghostwriter shock

Another twist emerged when Caroline’s former friend Natalie Beach wrote an article stating that she was paid to write captions.

The influencer later admitted that some of her content and her book proposal was written by the pal between 2013 and 2018.

It was the final straw for fans who posted attacks online including “She’s truly repulsive” and “God, I hate her”.

Caroline’s followers continue to drop and even after posting that her dad took his own life, former followers didn’t relent in their attacks. 

Disappeared from social media

Prior to quitting social media and deleting all of her posts in 2021, Caroline shocked fans by revealing her true intentions for posting. 

She vented: “Do you know hard it is to conjure fame and money out of thin air? And I’m f***ing killing it. 

“It’s a bummer to be misunderstood and definitely a bummer to be trolled, cyberbullied or cancelled. It’s toxic. 

“But, big picture: I want fame, power and money and people talking about me is part of that.”

Former mega-fan Genevieve, who met Caroline once after winning a competition, admitted it was hard discovering the truth about their ‘friendship’.

“She didn’t value me as a person or friend, she valued me as a commodity that she could use to brands and publishers,” she said. 

It’s unclear what Caroline is doing now, but Genevieve speculates she is likely planning her next “reinvention” or trying to write another book.

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She added: “I have a feeling we haven’t seen the last of her.”

My Insta Scammer Friend is available to watch now on BBC iPlayer. 

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