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Caroline Calloway: The Influencer Who Turns “Scams” Into Success Stories

Caroline Calloway is a woman of many identities: Instagram influencer, art historian, writer, Swiftie, flower crown connoisseur, and—what she perhaps the most known for—scammer.  

If you’re not familiar with Miss Calloway, buckle in. 


Her resume goes like this: 

  • Caroline abandons Virginia’s suburbs for Greenwich Village.  While at NYU, she meets Natalie Beach, who we’ll talk about later.  

  • Instagram is an up and coming platform, and Caroline is one of the pioneers.  She has now transferred to Cambridge and people adore her lengthy captions about boys with accents and castles at dawn.  This is where Caroline’s scammer story begins.

  • Her Instagram followers aren’t the only people who loved her prose-filled captions—in 2015, Macmillian Publishers gave Caroline a $375,000 advance for a memoir she would never complete.  $375,000 is an absurd amount for an advance, especially for a novice writer. When Caroline lost interest in writing the book, Macmillian naturally asked for the advance back. Today, she still owes the publishing house $100,000.

  • Next up: Caroline’s creativity workshop tour, which has been dubbed as the one woman Fyre Fest.  For a mere $165, Caroline promises her fans four hours of oak milk lattes, lectures on self care and the creative process, homemade lunch, personalized letters, and a photoshoot where one can learn the secret to making flower crowns.  Soon, the plan unravels: handwriting letters and cooking lunch for 50 people is too much, she sold tickets before booking venues. Caroline cancels the tour. Two days later, she un-cancels the tour. However, she reduced the original 11 events down to only two: New York and Washington, D.C.  She refunds everyone’s money, including people who actually went to the workshops.

  • Earlier this month, Caroline’s former bestie/ghostwriter/editor, Natalie, wrote an exposé meets personal essay for The Cut.  It reads like a plot lifted from a Donna Tartt novel: unreliable narrators, stolen Yale plates, toxic friendships, over 1,000 mason jars, an obsession with aesthetics, and a nightmarish trip to Amsterdam.  Since the article’s release, everyone and your mother has written a think piece about their relationship.  (Also: expect a movie about the duo in the next few years!)

Caroline Calloway has a knack for being resilient.  

In the midst of her time at NYU and Cambridge, Caroline was struggling with an Adderall addiction.  Despite this, she still managed to churn out delightful prose and photos from around the world.

Remember Caroline’s creativity workshop tour?  She didn’t stop there. Afterward, she embarked on a new set of creativity workshops, these ones cheekily called “The Scam”.  

It’s hard not to admire her honesty and self-awareness.  Caroline is messy. She knows she’s messy and she leans into it—it’s a vital part of her online persona.

Let’s be real, Caroline’s so called “scams” may have helped her gain a few thousand followers, but the reason why she’s popular is because of her writing.

There’s something so refreshing and intoxicating about her trademark mix of realism and escapism.  

Caroline described the sensation of reading her work best in an interview with Buzzfeed News on Wednesday: “I make stuff that is deceptively smart, that is emotionally addictive…[I have] a writing voice that is so easy to swallow and goes down so easy on the throat that you blink and 20 minutes have passed and you’ve been binge-reading my captions”.

I don’t think Caroline Calloway is a vindictive mastermind intent on scamming the world.  I think she’s a twenty-something trying to manage numerous business endeavors and just got way over her head.

Yeah, maybe Caroline hasn’t made the best choices in life, but haven’t we all?  What twenty-something hasn’t acted in a totally selfish, idiotic way?  

It’s not like she’s Anna Delvey or Elizabeth Holmes.  The worst thing Caroline Calloway has done is sell overpriced “tittay” paintings via Instagram stories.

This blog post was written by Milly McKinnish, General Body Member.

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