Pretty Caroline Calloway and the lovebombing of Vanity Fair
A journey into the heart of darkness known as the snark communities of Reddit
I am nothing if not an internet anthropologist. My primary tool is Reddit. I like to find niche communities of people with extreme beliefs. I think of it a little like the BBC show Weird Weekends with Louis Theroux. Instead of being a faux-naïve English dude blundering onto the scene, I am a disembodied pair of eyes watching. Sometimes I interact, but mostly I lurk.
One of my latest obsessions is snark communities. I originally stumbled into these almost exclusively female spaces in December 2020. Hilaria Baldwin had just been outed as having faked her Spanish identity for over a decade. A few people knew that Hilaria Baldwin from Majorca was really Hillary Hayward-Thomas from Boston. But it had never gone viral enough to make it into the mainstream tabloids. It was one of those inside baseball secrets that are the currency of Hollywood power brokers.
The entire saga is bonkers and came at the perfect time. The world was exhausted at the end of the COVID year. All of the PR and reputation management people were out of the office over the holiday. If you want to take a deep dive on how Hilaria was outed for being Hillary, here’s a giant Reddit thread. Make sure you have a spare 5 hours.
So the winter of Hilaria’s discontent was my first introduction to these very funny, very mean female spaces. These ladies are sharp and witty. More recently, I fell in with a rough crowd who follows a certain anti-influencer named Caroline Calloway. reddit.com/r/smolbeansnark is the subreddit devoted to chronicling the Caroline Calloway saga. Most of the people who follow Caroline were once fans. They became disaffected along the way. But they stayed to watch the endless car crash.
Caroline became Instagram famous for posting about her college experience in Cambridge. And for being conventionally beautiful and con artist charming. A superficial charm like a character in a Bret Easton Ellis book, if you catch my drift. Caroline would write about the balls and parties she would attend amongst the old money crowd in England. She cast herself as some sort of fairy-tale princess mixed with a Joan Didion wit and eye for detail. Something about the internet age allows a person like Caroline Calloway the access to all the great works of the world, but not enough bandwidth to digest them. Never enough time. So if she had any of the Didion eye for detail, it was only in microdoses.
I came into Caroline’s world by finding a profile on Reddit of someone who I thought had written an insightful comment. It was on a subreddit for mid-century modern furniture. I find a lot of interesting communities from this technique. You find people who have something interesting to say, and then you see what else they are into. I had no idea what “Smol Bean Snark” meant, and really I still don’t, but I was interested and I started reading. And reading. And reading. And an entire weekend whipped by and I found myself reading late into Sunday night, thinking about how fucked I was going to be waking up the next day, drunk on Caroline Calloway shitposts.
In summary, I learned that Caroline got a book deal for $500,000 for a memoir of her Cambridge years. A memoir for a woman not yet out of her mid-20s. A woman who was addicted to Adderall and social media. Really, she was cross addicted, like one becomes addicted to the rituals of drug use. Caroline was a wreck and her friend Natalie Beach, a woman with real literary talent but without the effortless charm, had to come to Caroline’s rescue. Together, Natalie and Caroline created Caroline’s book proposal. They collaborated on Caroline’s social media.
Then the book never materialized. The Cambridge era was ten years ago now and Caroline’s book deal was signed in 2015. Caroline blew deadline after deadline and eventually her publisher Flatiron Books dropped her. The entire saga is so drawn out, it takes up two full primers laden with links to other material that took me hours to plow through on Reddit. Eventually Caroline would go viral for attempting to put on creativity workshops. They flopped spectacularly as Caroline was so scatterbrained she hadn’t booked venues until the day of the events.
Caroline became known for fucking things up in a madcap way more than for her writing, which was not forthcoming. She became a living meme for ordering 1,200 Mason jars. Caroline’s convoluted idea was to make flower arrangement for each participant in her workshops. A pallet of Mason jars arrived on a truck outside her apartment and Caroline had nowhere to store them. The Mason jars were never used to make flower arrangements. Whatever became of those 1,200 Mason jars? Only God and Caroline Calloway know. Here’s part one of the primer if you want to catch up. Be forewarned that you might feel like you were abducted by aliens and spit out of a timewarp after entering the Calloway zone.
Caroline’s ex-best friend Natalie Beach wrote an article for The Cut, an online publication, about the vampiric relationship she had with Caroline. Natalie’s piece was one of the most deeply affecting things I have read in recent memory. I identified with Natalie Beach on a molecular level. As much as it is possible for someone from another generation and another sex. Beach came across as an awkward introvert. A brilliant writer who has had to struggle to find her place of belonging. Never secure. The contrast with Caroline, and the way Caroline used and discarded Natalie, made for an engrossing tale:
To my other friends, I described her as someone you couldn’t count on to remember a birthday but the one I’d call if I needed a black-market kidney. What I meant was that she was someone to write about, and that was what I wanted most of all.
https://www.thecut.com/2019/09/the-story-of-caroline-calloway-and-her-ghostwriter-natalie.html
I’m not really sure why, but after burning a weekend reading page after page about this woman, I posted a thread on the subreddit about my journey into the Caroline verse. I normally am more circumspect. I was punch drunk from reading hundreds of pages. I felt a sort of secondhand confidence from the insanely overconfident Caroline Calloway. Here was a woman who had written only a handful of Instagram captions and had schmoozed her way into a $500,000 book deal and internet fame and then infamy. There was a lot that I could take from this creature, however loathsome.
The thread I posted ended up being an incredibly interesting experience. It was well-received and remains one of the highest rated posts from the last year on the subreddit. Over 30,000 people read it, which is insane for such a niche subreddit. People recommended me a bunch of other things to explore. Included in this maze of new links was a genuine internet mystery. One moment I was laughing at how messed up Caroline was and the next I was decoding ciphers. Mapping out a web of fake accounts, an elaborate troll scheme that took years to create.
A user in the thread I posted about discovering Caroline Calloway commented about if they should introduce me to the dark parallel universe. I felt like I was being let into a special club. I accepted the red pill, and I was on my way through the looking glass. There were moments that jolted me upright and I had an episode of déjà vu for the first time in many years. What began as an interesting tunnel into a fun new world became something much more transcendent.
whispers Should we introduce OP to the dark parallel universe of 🦔 and LVS?
Caroline has come back up because Vanity Fair has just published a profile on her. Caroline has declared that she is finally releasing a book next month. Conveniently, it is scheduled to be released a week before Natalie Beach’s debut book Adult Drama. Caroline is obsessed with Natalie because of the expose that Natalie wrote in The Cut. It must have felt like a world-rending affront for Caroline to be criticized by an ex-best friend and eviscerated in print.
https://www.amazon.com/Adult-Drama-Essays-Natalie-Beach/dp/1335914021
I have actually preordered Adult Drama on the strength of Beach’s article about Caroline in The Cut. The Caroline experts in the snark community are highly dubious that Caroline’s book will actually come out. She has said it was coming out dozens of times before and it never has. Maybe the jealously of Natalie eclipsing her will finally inspire Caroline to actually release some writing.
The writer who profiled Caroline for Vanity Fair, Lili Anolik, seemed to fall for Caroline’s high-powered love beam of glib charm. The profile was alarmingly puff-y for someone who has been taking pre order money from her fans and stiffing landlords for years and years. Anolik strikes some notes of caution about the scandals that Caroline has been involved in, but also seems to act as a co-conspirator. Anolik whips up a new excuse matrix for Caroline for never actually writing anything despite calling herself a writer.
Yet it could also be argued that Calloway is a writer. A new kind of a writer. A writer who’ll never finish a book because to finish a book is to kill the story. And a book is already a dead thing since it can’t change or adapt, be revised or edited or added to or commented on—not without a cumbersome reprinting, anyway. (Books even look like little coffins.) Digital media allows for an ongoing, interactive story, and maybe that’s the future and Calloway’s it.
The phrase “Books even look like little coffins” has been swimming around in my head all day. It’s one of those beyond batshit crazy things that you hear from someone, and it takes years to process. I’ve said the phrase so many times I’ve achieved semantic satiation where the sounds of the words stop making sense. Why is it in a parenthetical? Do books really look like little coffins? I guess both are vaguely rectangular, but then a 12-pack of La Croix looks like a coffin. And a toaster. And a tupperware container.
Books. Even. Look. Like. Little. Coffins.
In the piece, Anolik tries to brand Calloway as some sort of avant-garde figure. Someone with an outsider’s perspective. It made me think again that there was something I could learn from this sort of self-mythologizing and also something I could steal. Really, I consider myself avant-garde. Or at least I do now. I wrote avant-garde along with the definitions, noun and adjective, on a post it note and taped it to the back of my phone. I am really out here on the edge getting into the weirdest shit I can find, so if this basic shitbag is avant-garde, then I must be the weirdest person in recorded history. So I added that phrase to my substack description. For whatever that is worth.
https://www.vanityfair.com/style/2023/05/caroline-calloway-scammer-interview
I find it baffling that Lili Anolik got taken in by Caroline Calloway. Calloway is a hybrid of all the worst parts of a F. Scott Fitzgerald character and Patrick Bateman from American Psycho. She is the ugly reflection of the social media age and the way it corrupts and deadens the creative impulse.
Anolik also wrote a piece for Vanity Fair about Joan Didion and Eve Babitz that I really enjoyed. Now she is getting conned by a non-writer “writer” who appropriates the fashion literacy of Joan Didion with none of the substance. I wish Didion was still around to describe this mess. Although it was jarring to read late-period Didion stories where Didion would talk about googling shit. It’s so beneath Didion to sully herself with a search engine.
https://www.vanityfair.com/style/2022/08/joan-didion-letters-eve-babitz
If Joan Didion were to describe Caroline Calloway, I envision something like the mediated experience in Didion’s short story, Pretty Nancy Reagan. Didion watches television newsmen watch Nancy Reagan. This was in the 1960s when Ronald Reagan was governor of California. Didion describes the scene of the news cameraman directing Nancy on what flowers to cut. Then Didion watches the rehearsal of a contrived sequence where Nancy puts fresh-cut flowers in a vase for the television audience.
Calloway to me is a modern sort of Nancy Reagan type. For all my mixed feelings about the Just Say No blithe ignorance of Nancy and Ronnie, at least they were competent and did something. Caroline, like Nancy, was a bit actress in her youth. I’m surprised that Caroline didn’t pursue acting in that she is such a contrived figure, but then again to be a writer is to be a contriver. Lili Anolik mentions Caroline’s acting background in this piece filled with strange parenthetical asides that feel like Caroline’s co-authored comments:
She thought she belonged on the big screen and so climbed up there with Daniel Craig and Nicole Kidman, delivering her single line—“Sir, this was on our roof”—with conviction in 2007’s The Invasion. (“Yes, I was a child actor—a key piece of my villain origin story.”)
Pretty Nancy Reagan and Pretty Caroline Calloway are both obsessed with flowers. Calloway has flowers strewn everywhere in her chaotic apartment. And orchid crowns in her hair. Nancy tells the newsmen in the Didion story, “Did you know there’s a Nancy Reagan rose now?” Didion envisioned Pretty Nancy Reagan as something like a flower, too, being mostly there for appearances, an adornment. This passage from Pretty Nancy Reagan could have just as easily been written about Pretty Caroline Calloway:
Nancy Reagan says almost everything with spirit, perhaps because she was an actress for a couple of years and has the beginning actress’ habit of investing even the most casual lines with a good deal more dramatic emphasis than is ordinarily called for on a Tuesday morning on Forty-fifth Street in Sacramento.
After reading Lili Anolik’s piece and marinating on it for a day, I’ve been thinking about the epic profile by Gay Talese from 1966 called “Frank Sinatra has a Cold”. It is unfair to compare any celebrity profile to Talese’s masterpiece, but to compare and contrast them is still illustrative. Anolik’s piece, “Caroline Calloway Survived Cancellation. Now She’s Doubling Down” has no distance or boundary from its subject. In some metaphorical sense, Anolik was consumed by Calloway. “Frank Sinatra has a Cold” is written from a remove, with no access. Talese found a way to draw Sinatra without his subject sitting for him.
Both Talese and Anolik followed their subjects for months. The reactions of the celebrity subjects to the profile writers demonstrates a sharp contrast. Calloway love bombed Lili Anolik, sending her care packages and corresponding with Anolik since at least September 2022. Frank Sinatra, prickly and press averse, famously would not meet with Gay Talese so Talese spent three months interviewing hangers on and people in the orbit of Sinatra to conjure up a portrait. That Anolik spent three times as long to write her gushing profile feels like an artifact of this distracted age. Anolik may have spent much longer as she mentions contacts with Calloway going back to March of 2022. I cannot imagine being trapped in the Caroline Calloway edition of Groundhog Day for that long.
The Anolik piece also made me feel gross in that there was often too much information and no boundaries that would not be broken to gin up a buzzy detail. It felt calculated to outrage the Caroline Calloway detractors. In that, it was successful to some degree, but this spin cycle has played out many times before and the print has completely fallen off of the t-shirts at this point. Anolik acknowledges at one point that Caroline has no boundaries. In the same breath, as if completely oblivious to her own involvement and hypocrisy, Anolik shows her own lack of boundaries.
She can be sweet and funny and charming, yet she has no respect for boundaries, personal or professional. In the middle of a conversation, she’ll fasten her eyes on mine, say breathily, “I’ve always thought I’d meet a journalist that I’d be friends with. I really hope it’s you.” Last March, she randomly sent me a video of herself getting ready to go out for the night. She was wearing a minidress and kept flipping it up, flashing her Red Scare thong, and doing this obscene darting thing with her tongue. My sons, then nine and seven, were constantly stealing my phone to watch.
The part about Lili Anolik’s son’s “stealing [her] phone” to watch Caroline perform lewd acts is really gross and concerning. Anolik positions herself as if she has no free will and her sons have the responsibility in this situation, despite them both being pre-teens. Caroline, in her care package full of hairballs and the detritus of her Grey Gardens-esque condo, had sent Anolik a handwritten doodle that included the text “I’m sorry your children are boys!!!!”
There is no professional distance in this profile of Pretty Caroline Calloway. No cool and impassive observation. Anolik fell victim to Calloway, like a hunk of raw meat into the maw of an insatiable narcissist. I see some of the dynamics of a domestic violence relationship or a high control group. Calloway, if she was a little less lazy, could easily be a cult leader. Caroline Calloway is some kind of awful admixture of Pretty Nancy Reagan and Keith Raniere, the now-imprisoned guru of the sex and multi-level marketing scheme NXIVM. I think we all know how this story will end.
Your insight and observations regarding Calloway, the VF article and its author are brilliant. I wish this piece had been the one that had been used or, better still, that it was published . Well done! Thank you .
Didion's story was not a short story but an essay.