The only person Caroline Calloway is scamming is herself

Three weeks ago, I had no idea who Caroline Calloway was. Like most of you, I was busy living my actual life in New York, not socially following around an influencer online.

If you’re part of the 782K (it was 784K when I first wrote this piece) Instagram fans of Caroline Calloway’s, or are a member of the Reddit subgroup in Blogsnark (known intimately among the group as “Snarkers”), you can’t actually imagine know what a day in your life would be like without her. Because of Caroline Calloway, you live and breathe Instagram. You’re there in the morning to see what boy she is posting about that day, or what nude of herself she is posting, or watching her make cheap replicas of Matisse cutouts whilst crying over a pending expose that her ex-best friend is writing. It’s a lot to take in, and for most of you non-Snarker hate fans, you won’t ever fall into a Calloway rabbit hole. So let this just be the only one you read, while waiting for that dreaded article to come out on The Cut.

Caroline Calloway is a 27 (almost 28) year-old influencer living in New York—with the rest of the celebrity-wannabe crowd that considers themselves too “real” for LA. She came to fame about six years ago, when she went to Cambridge for uni, and turned her Instagram page into a full-on travel blog, akin to if Culture Trip and Seventeen had a white, American baby.  

So, like any good journalist, I started there.

I scrolled to the bottom of the page to read her stories about finding love in Oxbridge, fancy parties with full dress, and a very small sprinkling of art history— which is what her purpose of coming to England was rooted in. I later learned from the “snarkers” that a lot of her posts were archived.

If you recall the culture of 2013, Instagram was just starting to be wildly used, many of us were still using those awful built-in filters to look edgy, and we had no idea how to use a hashtag. I also was in England around that time, and sure as hell didn’t find that kind of fame. But, I digress. Whether on purpose or purely accidental, Caroline learned how to navigate this new platform—and used it to tell aspirational stories of using quintessential English fairytale as both her muse and her backdrop.

New York City publishers caught on, and one of the big five offered her a publishing deal to produce a memoir. She couldn’t have been any older than 24. She hired a ghostwriter (i.e. her ex-best friend) to do the legwork—many think that the verbose posts on Instagram were also the work of a ghostwriter—and blew through her advance. Which, let’s be honest, we all probably would have done at that age. 

The book, however, never surfaced as she claimed she didn’t want to write a book about boys as she is more dynamic than that. 

Fast forward to present day, where many of her newest round of followers are from a recent “scam” she orchestrated—in which she sold ‘creativity workshops’ for $165, ordered an insane amount of mason jars and orchids, cancelled the workshop, un-cancelled the workshop, and held it in a Brooklyn loft where for the first hour she wasn’t even in attendance. The majority of the workshop was her gabbing about her addiction to Adderall and regurgitating the content found on her Instagram.

The media loved this — New York influencer turned scam artist, à la Fyre Festival adjacent. Because, historically in New York, there are few things that New Yorkers love more than seeing the mighty fall.   

After the media fiasco that caused her to go “viral because of a scam,” Caroline has stayed afloat with her gaggle of other New York influencer circle, but on the inside—and to those who have known her longer than a New York minute—she is falling apart. Her way of making income is selling “tittay” paintings and Matisse rip-offs, not fulfilling orders, writing freelance articles for culture outlets like Refinery29, and capitalizing on a very loyal, and rabid fanbase through Patreon.

This is when I was introduced to her. A new friend who was passing through New York to attend one of those famed creativity workshops, had recently told me about Caroline Calloway. She was also a fan of Caroline’s from her Cambridge days but is quickly noticing (and struggling) with how dramatic and awful her downfall is. And, we are all watching it in real time.

The only thing worse than seeing the mighty fall, is seeing those fall and watching as they have no conscious mind as to what is happening. Those who are narcissistic enough to delete comments on Instagram from people who are wondering when their “tittay” painting will be mailed, and post semi-artistic nudes to their stories, but have no idea that half of the people watching just want her to fail. And, it’s easy to fail when the empire you built is crumbling thanks to the vapidity of both the New York social scene and Instagram culture.

Living in New York City is hard enough— with friends, employers, and lovers who all want a significant piece of you—day and night. We are constantly consumed with flashy things—engagement rings on people’s fingers worth more than our family homes, fancy parties at the top of the Standard or William Vale, casual run-ins with models and celebrities, apartments with skyline views and marble countertops. It’s a lot to take in, and even harder to stay somewhat normal surrounded by the madness. When I was Caroline’s age, I also ran in heightened social circles, attended parties in famed spaces in the Lower East Side, and spent a lot of time building my “brand.” The only difference between us is that I didn’t become insta-famous. And, looking back on it, I’m really happy I didn’t. Because, good riddance, the appearance is a lot to keep up with, and self-care, mental health, and having solidly decent friends is a lot more important.

In five or ten years, when there is a next new platform or thing to engage with, when influencers are replaced with the next new thing, the majority of us—including the snarkers—will have moved on to new jobs, marriages, creating companies. But a lot of these social media influencers, who built their brand at a young age on YouTube or Instagram, will step away from the madness, and realize they don’t have many real friends, or an idea of who they are deep inside. And, that is a problem. Who really cares if you never receive an $80 “tittay” painting or that the creative workshop you attended was a glorified meetup, what is most important is that the scams being created are the ones by social and influencer culture, convincing these people that who they are, and what they are doing, isn’t a lie. Which, let me be clear, it is.

It’s possible to live in New York with money and a decent circle of friends and not cry on your floor making art that defies intellectual-property laws, because you’re young, blonde, and have no idea who you are.

Image from Caroline Calloway’s Instagram

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