European summers, fleeting romances, Cambridge University and the kind of social media presence that enraptured us all, Caroline Calloway was one of the influencers that dominated Instagram in its early days.

If you haven’t heard of Calloway – or perhaps if you need a refresher on her Instagram adventures – she was the paragraph-long caption-writing influencer who revealed every little detail of her life to her followers and quickly became the talk of the internet. It wasn’t just her personal life that we all became obsessed with, it was also the increasingly alarming stories that were coming from her followers. Calloway turned her hand to a number of different money-making ventures: workshops, merchandise, her well-known ‘snake oil’ and a book all about her scammer persona. Many of which fell flat with her followers or became a laughing stock on the internet.

She became the un-cancellable influencer, who instead of shying away from the scandals that were coming out about her, turned them into her new online identity.

And she’s the focus of brand new BBC Three documentary, My Insta Scammer Friend. The one-off film explores the social media marvel in all of her unlikely glory.  

As the synopsis reads: “In this era of social media, we are given more access to the private lives of celebrities and influencers than ever before. But how well do we really know our favourite online friends? This film explores the murky and, at its worst, toxic, relationship between one influencer and her followers.

“The infamous viral scandals of pioneering internet sensation Caroline Calloway have captivated audiences across the globe, with some of her followers left feeling duped and scammed. But why did Caroline’s actions garner so much attention? And what do influencers owe their followers who built the very foundations of their success?”

If you’re getting Inventing Anna vibes from the premise alone, you’re not far off from Calloway’s own escapades. By 2016, she was a firm Instagram hit and had nearly six times the amount of followers as Dua Lipa did at the time, according to the documentary. She went on to reveal an addiction to prescription drugs, the fact she cheated on her boyfriend, why she rejected her first book deal and promised authenticity on the platform going forward. 

Lest we forget the time she cut up patterned paper to make Matisse-inspired collages that her followers would rush to buy from her Instagram Stories, as well as annotated copies of her previous book proposal and line drawings that resembled doodles more than contemporary modern art. The price increased each time she dropped these paintings but her global tour of events – dubbed ‘creativity workshops’ – were to become Calloway’s road to infamy. Many of her fans were excited at the prospect of meeting their internet idol for the first time but they were charged $167 (£138) for the privilege.

The events promised flower-crown-making, as well as discussions to be held on the floor of a loft with tea or coffee and homemade salads. “Almost immediately after selling the tickets, she started to backpedal on her promises, posting these stories that would, all of a sudden, take something away from the workshops,” one follower reveals in the documentary.

For one workshop, she even posted an Instagram Story asking if those attending could bring a packed lunch in exchange for her extending the workshop by another 30 minutes. She was still in the planning process for other tour cities, promising to refund fans at the last minute and, essentially, it all became a bit of a disorganised mess. 

“When I realised the lack of planning, I was just in disbelief. Of what Caroline had promised, she failed to organise 99% of it, I would say,” the same follower describes and then details how Calloway went on to block her on Instagram after she requested a refund.

The mess of that situation is just one insight into how Calloway moved around unashamedly on the internet, transfixing us all. And when it aired last night (Thursday 28 July), viewers and previous fans of Calloway’s were quick to react to the new documentary.

The legacy of Calloway is one that this documentary most certainly highlights.

The documentary was the kind of deep dive many avid internet users had been wanting for years.

But really, it also brings up questions about influencer culture, proximity and the overuse of Instagram.

What My Insta Scammer Friend promises is to leave you surprised at Calloway’s actions but will also leave you questioning our relationship with Instagram and its influencers in an increasingly online world. So whether you’re familiar with Calloway or not, this documentary will certainly leave you thinking about a lot.

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

Images: BBC