Buckle up because you’re about to dive into the wild, unfiltered life of Caroline Calloway — the girl who somehow managed to make fame, scandal, and pure chaos an art form. From the moment she was 17 — and decided to change her last name to Gotschall Calloway because it “looked better on books” (classic move, right?) — she’s been on a mission to build her brand at any cost. And what’s that brand, you ask? Oh, just the self-proclaimed “It girl” who sees herself as a start-up — because, as she famously said, “It girls are start-ups, and start-ups need funding.”

Her workshops have been compared to a one-woman Fyre Festival. She’s been called the literary Anna Delvey. From questionable book deals to questionable life choices, this timeline is a masterclass in chaos. So grab your flower crown and your bottle of Snake Oil because things are about to get real messy, real fast.

Caroline Calloway Controversies: A Comprehensive Timeline

2012 – #Beginnings

Caroline joins Instagram with the help of her NYU classmate Natalie Beach— remember that name, it’ll be important later. The account documents her life at Cambridge, complete with long, rambling captions. To boost her following, she buys 40,000 followers and runs ads.

She quickly becomes barf-inducingly known as the “Gatsby of Cambridge” for the lavish parties she throws in rented rooms at other, more Instagrammable Cambridge colleges — ones she considers prettier than her own, St. Edmund’s. Caroline later admits to forging her academic credentials to get into Cambridge, claiming she “couldn’t stand to live the rest of her life with an NYU email address.” She also opens up about her Adderall abuse and addiction during her time there.

2015 – #AuthorGirlie

She’s going to be an author, supposedly. Caroline announces that Flatiron Books has offered her a $500,000 book deal for a memoir, and she’s already received 30% of that as an advance — for my calculator-dependent girlies, that’s $150,000.

April 2016 – #TheBook

More on the book deal: Caroline plans to publish a memoir titled, And We Were Like about her time at Cambridge with Flatiron Books (an imprint of Macmillan Publishers) and with the help of literary agent Byrd Leavell.

During her final year at Cambridge, Caroline hires Beach to co-write the book and proposal. She lands an initial meeting with Leavell by allegedly claiming to his secretary that she’s already one of his clients. Sorry, but from a fellow wannabe author? That’s low-key iconic.

Years later, she’ll admit she never intended to write the book. “I got half a million dollars my senior year of college to write a book I had no intention of delivering.” Less iconic.

July 2017 – #ConsciouslyUnCoupling

Change of plans! Caroline announces on her Instagram Stories that she’s withdrawing from her book deal after failing to fulfill the contract — so, kinda like when you say you’re leaving a relationship after being dumped. She cites creative differences, while others blame missed deadlines and a total lack of manuscript progress.

Natalie Beach later reveals that the deal was actually for $375,000, and Caroline only received a $100,000 advance, which she now owes back to the publisher after pulling the plug.

To make back some of that money, Caroline puts the book proposal, with personal annotations, up for sale on Etsy.

December 2018 – #TheChaosIsTheArt

Caroline launches an international Creativity Workshop Tour. In her original announcement, she promises tutorials on building an Instagram brand, developing ideas, and exploring “the emotional and spiritual dimensions of making art.” The price? A whopping $165 per person — so yeah, you’d expect to leave knowing how to build a Kardashian-level following.

Right away, things go off the rails. A bunch of the tour dates are canceled because Caroline fails to book venues. She claims refunds are coming, though some will never see one. Attendees show up at Airbnb apartments with no AC and not enough chairs. Someone finds her workshop outline on Google Docs titled: How to be a snake oil salesman. You legit can’t make this shit up.

Caroline declares she’s reinventing herself as a performance artist, insisting “the chaos IS the art.” Most tickets are eventually refunded after the media storm kicks in.

Reporter Kayleigh Donaldson creates a viral Twitter thread comparing the tour to Fyre Festival, which gains traction and later becomes an article on Pajiba.

In response, Caroline briefly sells t-shirts on Threadless that say “Stop hate-following me, Kayleigh.” Threadless pulls the shirts for violating their targeted harassment policy.

She eventually holds two workshops in New York instead. She promises “mason jar gardens,” then has 1,200 jars delivered, with nowhere to put them. She also promotes “orchid crowns” but ends up handing out a single sad, non-orchid flower per person.

August 2019 – #JournalistsStayOut

She holds a second creativity workshop in New York, cheekily titled The Scam. Press are banned from attending, and Caroline even refunds tickets bought by journalists. On Instagram, she openly shares her distrust of the media, saying she prefers podcasts for any kind of engagement.

A VICE reporter buys a ticket under a fake name and sneaks in. The subsequent article claims Caroline seems more focused on creating material for her Instagram captions than offering any real creative guidance. The workshop ends with a photo op with Caroline.

September 2019 – #IWasCarolineCalloway

Natalie Beach writes an essay for The Cut titled I Was Caroline Calloway. It chronicles her friendship with Caroline and reveals that she ghostwrote a number of the Instagram captions credited to Caroline and helped craft the book proposal for the now-abandoned memoir. Natalie also alleges she co-wrote parts of that memoir. The article goes viral and becomes The Cut’s most-read story of 2019. This is the controversy that launches Caroline into widespread internet infamy.

Caroline doesn’t deny Natalie’s claims — instead, she leans all the way into the drama, framing herself as an artist who’s unafraid of chaos and mess.

Late 2019 – #InHerArtsyEra

Caroline started selling watercolor paintings with text overlays inspired by famous works like Matisse’s Blue Nude II, pricing them around $140. Throughout 2020, she keeps marketing her art, sparking both criticism and support for her pricing and artistic choices.

It seems girlie really needs some extra cash because she also starts selling personal items on eBay and Etsy — think art supplies, partially used candles, and other odds and ends.

Then comes VacuumGate: Caroline lists a used Dyson vacuum cleaner on Instagram for over $200. The listing gets dragged online and quickly becomes a punchline across the internet.

2020 – #SelfObsessedMess

Caroline keeps the money-making schemes rolling by fully embracing the “Scammer” label and launching a line of merch and content. She sells sweatshirts boldly printed with the word “SCAMMER,” caps with “Self Obsessed Mess,” signed nude prints, and more. She even promotes an OnlyFans Masterclass, promising to teach others how to monetize their personal narratives and cultivate a charismatic online persona.

She also introduces Gift (not gift) Cards and Caro Cards—basically Tarot, but make it Caroline.

April 2020 – #NakedLiteraryInfluencer

In a tale as old as time, Caroline starts an OnlyFans account, promising videos, photos, and nudity. She describes her sex work as “emotionally poignant, softcore cerebral porn.” According to her, she’s a “naked literary influencer.”

What does this look like? Cosplay of characters from children’s movies, like Matilda, Harry Potter, and Beauty and the Beast — but, like, not Matilda, girlie. She also shares partially undressed photos of herself, often captioned with grim details from her father’s autopsy. I’m sorry… what?

She’s also accused of crossing ethical lines by mentioning past romantic partners without their consent.

But the plot thickens. In interviews, Caroline claims that entering the adult entertainment industry was a plan in collaboration with Playboy, even saying the magazine had commissioned a photo shoot of her dressed as a student in a library. When Playboy is asked, they respond firmly: “Playboy does not have and did not have any photo shoot planned with Caroline Calloway.” (Did she think no one would fact-check this?).

In an exclusive interview with MailOnline, Caroline explains that the OnlyFans account was just a way to pay back the book advance she still owes.

April 2020 – #MuseVisionaryNotWriter

She finally addresses the infamous essay by Natalie with a response titled I Am Caroline Calloway. It’s self-published behind a paywall, with the goal of raising funds for Direct Relief, which supports medical workers and first responders treating COVID-19 patients.

Caroline confirms most of what Natalie said but emphasizes that Natalie had “agency” and was “complicit” in the lifestyle. She also claims she was always the “muse” and “visionary,” not the one behind the pen.

Within a month, Caroline raises nearly $50,000. According to The Guardian, she celebrates by putting her phone down, pouring herself a glass of bubbly, and eating two whole jars of caviar — “like a Russian oligarch.”

April 2020 – #TakingSuggestions

Each time I think it can’t get worse, it does.

Caroline posts on Instagram asking her followers which literary hero she should dress up as on her OnlyFans. Someone suggests Anne Frank — seriously, dude? Caroline likes the comment and shares a screenshot on her Insta stories. As you can imagine, people quickly call her out. This isn’t the first time she’s been accused of antisemitism… that week! She also shares a cartoon that many perceive as a subtweet aimed at Natalie Beach, her former bestie. The image is filled with antisemitic tropes, and people waste no time calling her out. Caroline later apologizes, claiming ignorance.

April 2020 – #FameHungry

​In an interview with The Irish Times, Caroline Calloway expresses her love for fame, stating, “I love fame. I love being written about.” She also discusses the challenges of being scrutinized, especially regarding her mental health, and likens the backlash against her workshops to being diagnosed with cancer. Shockingly, people do not appreciate that comparison in the slightest. ​

May 2020 – #MakingItRain

Caroline boasts on Twitter about her projected yearly income of $223,800 from her OnlyFans content. She is criticized for failing to acknowledge the struggles of sex workers and continuously distancing herself from sex work, despite literally using OnlyFans.

July 2021 – #SnakeOilSalesWoman

Caroline teases a new skincare line called Snake Oil — very on-brand. She promises it’ll be based on historical beauty treatments (like ancient Roman olive oil). She offers small jars of what she claims is her personal moisturizer blend for $75. She is two steps away from selling moon juice and MLMs.

She explains her journey to the product in detail, listing her motivation as “When I was addicted to Adderall, I didn’t sleep for three years. There’s really nothing that bad for your skin in Amphetamines Salts per se, but staying awake for that long will fuck your face up real fast.”

She also urges buyers to “Stop supporting Big Oil and shop from your local Oil Baroness!”

If you’re somehow convinced by this sales pitch, I am so sorry to tell you that it is all sold out! Who knows if Caroline will make more, maybe there’s a 3-year preorder list?

March 2022 – #GirlMathRent

Caroline is sued by her landlord for unpaid rent totaling $40,844.56 on her West Village apartment in New York City. The lawsuit claims she hasn’t paid rent since September 2020, at a monthly rate of approximately $2,734.64. She’s also accused of subletting the apartment without permission and leaving it in a deplorable condition when she moved out.

In response, Caroline files a countersuit in July 2022, including a personal statement detailing her emotional attachment to the apartment and her reasons for not paying rent. She argues that she made significant improvements to the property, including installing a Murano-glass chandelier and enhancing the communal garden, which she believes should offset her rent obligations. That’s a very unique form of girl math.

She tells Vanity Fair, “At a certain point, I realized I could either live luxuriously or pay my rent.”

In 2023, a faux historical plaque appeared outside the apartment, commemorating her decade-long stay and referencing her rent payment history. Caroline denies any involvement with the plaque, but it conveniently coincides with her return to New York and the settlement of her legal issues.

May 2023 – #LemonsAndMushrooms

In an interview with Vanity Fair, Caroline drops several little truth bombs. For example, she says, “For months, I let a pool boy who is also a plumber fuck me without a condom. I haven’t used a condom in years.” When the journalist suggests she should probably use one, she simply responds, “No.”

The journalist mentions that during a different Zoom call, she notices Caroline sucking on a lemon wedge.

“She’s just taken mushrooms, she explains, and the lemon enhances the mushroom’s potency. I express irritation because I’d blocked out two hours for this interview, and now she was going to be too high to answer questions. No, no, she assures me, she won’t be too high to answer questions. Five minutes later she whispers, ‘I’m too high to answer questions.’ I sigh.”

At a different time, sans mushrooms, Caroline also discusses her reaction to Natalie’s sexual assault in more detail.

“I’m thinking that there’s something really sad about it but also fucked up and hot,” says Calloway. “I’m with someone. It’s very trusting, lovey-dovey. I say to him, ‘Okay, I’m going to get blackout drunk. Let me be very clear with you about what I want.’ And then he did to me some of what that guy did to Natalie. I never told Natalie that.”

I’m not really sure what to say, but maybe that was a story to keep to yourself, Caroline.

June 2023 – #SpitefulGleeAndGloating

Her first book, titled Scammer, is finally out, three years after she started accepting preorders. Reasons given for the delay include her mother’s cancer, excessive partying, and solidarity with Black Lives Matter. (For context, preorders typically open 3-6 months before a book’s release.)

It’s only sold through her website and is comprised of 67 vignettes, repurposed material, and reflections on her life and controversies. Initially, it had been marketed as an “at least” 400-page memoir.

There are various versions available, including Scammer (For Peasants) for $30, which is hand-signed and numbered. It lacks the ribbon, decorative stickers, Ex Libris bookplate, and Italian paper inner covers found in Scammer (Luxury First Edition!) for $65. The luxury version includes 14 pages of acknowledgments. The book is dedicated to Lena Dunham, who bought her life rights in 2019 (though the option has since expired). Caroline plans to dedicate the next two books to Greta Gerwig and Sofia Coppola, hoping all three will make movies about her.

It receives some positive reviews, including from The New Yorker, Dazed, and The Washington Post.

Caroline shares the New Yorker article that mentions both her and Natalie’s books, captioned:

“GOD, MAKE ME THE BIGGER PERSON — JUST NOT YET!!!!!! GIVE ME THIS ONE LAST DAY OF SPITEFUL GLEE AND GLOATING, AND I SWEAR TO YOU, I WILL WAKE UP TOMORROW AND NEVER MAKE ANOTHER MENTION OF AN ARTICLE THAT RAVED ABOUT MY BOOK WHILE TRASHING NATALIE’S.”

A more critical review by Charlie Squire for i-D describes Calloway’s attempts to clear her name and address her scandals as “unstimulating,” adding that the book is “fatally mediocre in the middle.”

A journalist who later interviews Caroline discusses their first read of the book, saying, “Her descriptions of Beach are harrowing — in one anecdote, Calloway graphically describes being turned on by Beach’s description of being sexually assaulted. In another, Calloway sets out to have sex with a woman but instead has sex with a pot-bellied man who she says looks just like Beach, down to the B-cup breasts.”

Scammer is just one of three books that Caroline refers to as her “juvenilia.” The Cambridge Captions and I Am Caroline Calloway, which will complete the trilogy, are both available for preorder at $65 each, without set release dates. It’s unclear why The Cambridge Captions is taking so long, considering it will literally be a compilation of Calloway’s Instagram captions from her days at Cambridge. Someone needs to explain copy and paste before she types each one out.

January 2024 – #NoPodcastNoProblem

Caroline promotes a new podcast, claiming she was filming the first episode. However, no podcast is ever released. The end.

October 2024 – #SaveMatisse

Hurricane Milton hits Florida, and Caroline refuses to evacuate from her home in Sarasota, where she lives with her cat, Matisse, despite a mandatory evacuation order. This prompts both criticism and concern from fans. Caroline and Matisse survive Hurricane Milton, and in an Instagram post, she quips, “If I actually do die in this storm, my books will go way up in price,” a comment that many find distasteful given the storm’s severity.

She also seizes this moment to promote preorders for a new advice book, titled Elizabeth Wurtzel and Caroline Calloway’s Guide to Life. In her words: “It’s about to come out if I survive.”

This book draws heavily from an advice memoir written 20 years ago by the late, acclaimed writer Elizabeth Wurtzel. However, Wurtzel’s loved ones are not part of this agreement or receiving anything for her included work.

“I realize that in doing this, you know, maybe me and Wurtzel’s ex-husband or her aging mother would never be close friends, which would have been very nice for me because, of course, she is my favorite writer,” Caroline tells MailOnline. “But I really think I’m in a better position than anyone who is formally part of the work’s estate to generate publicity and get her name back in the cultural conversation where it deserves to be.”

Caroline’s closest interaction with the esteemed author was when Wurtszel tweeted about Natalie’s article, specifically the reference that Caroline was not “someone I wanted to be but a girl living with one fork, no friends, and multiple copies of Prozac Nation.”

A day after the story was published, Wurtzel posted: “Who is #carolinecalloway, and why does she have so many copies of #Prozacnation? People keep asking me what I think of this. Hmmm @TheCut @NYMag.”

December 2024 – #NeverHaveIEverBoinkedAnAssassin

I can’t quite believe I’m writing this, but we’ve come this far. Remember when Luigi Mangione was initially accused of shooting the United Healthcare CEO? Yeah, the one everyone thirsted over. Well, Caroline claims she had sex with the 26-year-old prior to the crime. Luigi has yet to comment on this, but he might have other more pressing issues at hand.