Caroline Calloway's Long Good-bye

“This is my whole 20s,” Caroline Calloway tells me wistfully, gesturing around her messy burnt-sage-scented West Village apartment, littered with plant dirt, wine bottles, flower petals, dozens of matchboxes inscribed with her name, and, in an odd gesture toward conventional orderliness, a color-coded closet. Caroline turned 30 in December, and, like many manically charismatic young people who schmooze and shitshow their way through New York right out of college, she has decided it’s time to pull back, take stock, and — at least for now — leave town. In other words, good-bye to all that clout-chasing. As such, she was hosting a series of not-quite-dinner parties in her studio apartment, the seat of her reign of shamelessness for the past decade (for as long as she’s had an Instagram), and mostly inviting other members of the status-thirsty-monde, many of whom, like her, are young women without boundaries.

Maybe you’ve been to this apartment for one of these “salons” yourself, or just feel like you have, having seen images of them in her apartment online. For years she has DM’d writers, artists, influencers and anyone with something to offer to come over so she could hold forth. This was the second time I’d been invited to her place after getting to know her the way thousands of people have, over the internet, where everyone obsesses over her, hates on her, or both at the same time. Calloway is, of course, internet famous for being internet famous. (Her Wikipedia entry describes her this way: “Caroline Gotschall Calloway is an American internet celebrity known for posting Instagram photos with long captions.”) Then she became even more famous for being betrayed — or possibly just described — by her ex-best friend Natalie Beach, who wrote a tell-all essay in 2019 about their relationship for the Cut, taking partial credit for her influencer success. At the time Beach’s piece came out, I was new to New York and didn’t understand at first why I was supposed to care about these two Instagram girls and their melodramatic friendship meltdown. But soon enough, her mess roped me in too. That she became an object of trollish fixation on Reddit seemed to prove she was for some reason significant culturally and therefore worthy of my attention, if for no better reason than that she was attracting that of so many others. Or so I told myself. But she was undeniably entertaining.

I first met Caroline in person last summer, when I followed her around for a party at Russian Samovar hosted by the Drunken Canal and Ion Pack for this newsletter. Unsurprisingly, she was an excellent person to party with — determined to have a good time, she brought genuine smiles to the faces of those around her. That party (and her being in New York again) was part of her post-Natalie game plan to stay relevant. She also started an OnlyFans, sold a $75 skin-care oil called Snake Oil — yeah, maybe too obvious, but she’s proud of her “scammer” reputation — and could be found around town trying to do the whole Dimes Square thing, systematically making friends with the influencers, writers, and artists who would accept her invitations to hang out, including me.

The thing I discovered about Caroline after I met her is that you just can’t easily say no to her; she sucks you in. Through the screen, you can dismiss her as a crazy disaster, and maybe in so doing reassure yourself that you comparatively have it together. In person, she traps you with her big doe-eyes and a flurry of compliments and scams you of any ability to deny her what she wants from you, whether that be validation, a bottle of wine, or your attendance at her party (or all three). It’s hard to say no because you think that you might just be witnessing something important — what that is you’re not sure — even though, deep down, you suspect it’s probably inconsequential.

Still, the manic charm doesn’t work on everyone. After being heckled at a sceney lit reading last summer, Caroline supposedly fled to the U.K. (she started her influencership by posting about her posh-looking undergraduate life at Cambridge University). But by the New Year, she was back in New York, showing up at the events you show up at if you want to be a part of the elusive scene, such as the artist Annie Hamilton’s one-woman show at the Jane and Sean Thor Conroe’s book launch in Ridgewood. But in November, she went dark on social media and “Is Caroline Calloway alive?” became a question I heard often.

She is, I can assure you.

In February, Caroline reached out to inform me that she’d soon be leaving, for real this time, moving to Florida to take care of her 99-year-old grandmother and focus on “her masterpiece,” her memoir. She wanted to invite me to one of the many farewell dinner parties she was scheduling at home, all organized in a hand-drawn calendar in her notebook.

It is a Caroline Calloway custom that when you go for “dinner” at her apartment you eat from paper plates in the middle of her floor, the drinks served in an assortment of mugs and jars. The menu is always the same: either take-out sushi paired with Aperol spritzes or salads paired with wine (wine that you bring). I was there first for salad night, with two 20-something influencers. When I showed up, there were four plates already on the floor, her cat, Matisse (she says he’s from Ukraine), wandering among them. They tasted like Sweetgreen (arugula, apples, avocado, Za’atar bread crumbs, seemingly no dressing) and had clearly been purchased earlier that day, then left out. The meal was served around her “altar”: a tableau of art supplies, animal skulls, flowers, vases, terrariums, and taper candles in the middle of her potting-soil-covered floor.

One of the influencers brought shrooms, and suddenly the very polite dinner, mostly spent talking about Caroline’s New York run and the “iconic lines” she can’t wait to write down in her book, turned into a trip. Before I knew it, I was agreeing to let Caroline razor off the top coat of my nails to superglue French-tip acrylics to my fingers (“I have no idea how she stuck these on there,” my nail lady told me a few days later during the three-hour appointment it took to remove them), while the other two took selfies around the studio, on her bed, and in front of her walls, lined with hundred of books — mostly classic novels, memoirs by women, a couple of collections with matching green-and-red slipcovers, and one clearly visible copy of Play It As It Lays. Caroline declared the night the beginning of the end of a “historic” era.

At some point, she asked us all to share what we like about her, and when I shroom-stumbled my way through an answer, she asked me, “What do you mean?,” forcing me to try again. For a couple of hours, we drank wine and talked about Caroline. Despite the self-interest, she’s warm and maternal in a way that reminds you of your one friend’s crazy mom. For a while, she spent her monologue telling each of us how special we were and handing out gift bags of Caroline Calloway matchbooks, Snake Oil, and vases of purple-hyacinth bulbs. Shortly before 2 a.m., she put her cat into a tote, and we set out down Sixth Avenue for Paul’s Baby Grand. You might think it’s animal abuse, but I have to admit I’ve never seen an animal so happy and docile, passed around the dance floor by kids who clearly couldn’t believe they’d run into Caroline Calloway, not to mention her cat. (The next morning, it was on Twitter: “I walked into a bar in NYC looking for a lowkey night and saw Caroline Calloway holding a cat and I left.”)

Over the next two weeks, the going-away parties continued, attended by Vogue editors, designers, Canal kids, Spike editor Dean Kissick, Fuccboi author Sean Thor Conroe, and Meg Superstar Princess. Caroline claimed to have invited Kaitlin Phillips, Victoria Paris, Serena Kerrigan, Emily Ratajkowski, and Alison Roman, but if she had, none of them appeared to show. Caroline told me Cat Marnell would be attending one of these parties, though Marnell denied to me that she ever agreed to go.

This past Monday night at 8 p.m., Caroline FaceTimes me again from the bathtub, boobs out, just like the first time we ever spoke. She tells me it is finally her very last night in New York and that a number of people she admires will be coming over, including Julia Fox, Serena Shahidi (a.k.a. @glamdemon2004), Cat Marnell, the writer Honor Levy, the poet Rachel Rabbit White, and Real Housewife Leah McSweeney (by FaceTime).

When I arrive shortly after 9 p.m., I find her once again on the floor, with Honor, Serena, and a number of other young people, drinking Martha Stewart’s Chardonnay collab with Snoop Dogg and trying to piece together 3-D flower puzzles Caroline bought for them.

“Don’t I look like an alien empress? Alien empress is what it’s giving,” Caroline says when I walk through the door, running around the room in a powder-blue silk dress and with flowers in her hair before sitting crisscross applesauce and exposing her white panties, which read “HONEY.” She talks mostly about the same things she did the last time I was here: the memoirs of Catherine the Great, “the time I lost my cat at KGB Bar” (at Rachel Rabbit White’s wedding: “The cat was doing coke with the bride and groom!”), the books she’s working on, the movie supposedly being made about her by Lena Dunham, possibly starring Maude Apatow and Emma Corrin, and about all of the things she wanted to do before leaving the city, like eating at Via Carota, drinking at Bar Pisellino, and meeting up with a guy she likes to fuck.

“I know we’re about to see one of the most famous people in the world,” she tells the group, referring to Julia Fox, though the only people to arrive after me are Rachel Rabbit White, (British) Vogue’s resident astrologer, and a sexy, beefy man who, she tells me, is 59th in line to the British throne and brought Cheez-Its and four Ferrero Rochers to the party (believe it or not, from what I could tell from Googling later, he actually is the queen’s first cousin, twice removed; Caroline refers to him as a “former lover”). At some point, Caroline FaceTimes Leah but she doesn’t answer.

Caroline plays Taylor Swift, talks about Kurt Vonnegut, and gives away more flowers and Snake Oil. “When I was creating my brand, Blair Waldorf was on my mood board,” I hear her say before giving us all pep talks about our respective careers (“You’re one of the great minds,” she tells Honor). Unlike last time, she has made an attempt at ambience in the bathroom by filling her tub with a foot of water and floating real daisies on top. On the ledge sits a Coca Cola can, more candles, and every product Glossier has ever made.

Shortly before Midnight, Caroline opens a bottle of port that she says belonged to her father, declaring it a very special evening, though I also drank it at the last dinner, also from a dirty glass. Rachel braves the detritus in the pond/tub for a photoshoot, still wearing her ripped tights and six-inch Giuseppe Zanottis, and Caroline shows me how she can contort Matisse’s face into a number of personalities: first a bunny rabbit, then a vampire, then President Franklin Pierce, then bunny Franklin Pierce. It’s at that moment that she tells me she’s on acid. “Who needs to leave next?” she asks the room, because she wants a private moment alone with everyone before they go.

“I can’t wait to be in open air, where I can’t catch on fire and none of my limbs fall asleep,” Serena says, after the second puzzle box catches on fire from one of the three dozen lit candles on the floor. Caroline commands us to “pretend” this is her real going-away party, which is confusing because I thought that it actually was. “Isn’t Julia in Milan?” Rachel asks when it starts to become clear she won’t be joining us tonight.

As people start to head home, Caroline, now somehow with a green juice in hand, declares that she’s going to the Waverly Inn for a martini and to “read her lover’s book,” but with an 8 p.m. flight the next day, she decides to head out to Art Bar instead with the distant Royal, Serena, and a sweet gay boy who has spent most of the evening trying to put the 3-D flower puzzle together. “I came, I saw, I conquered,” Caroline calls behind her on the way out the door, encouraging Rachel and me to stay for awhile, soak in her famous apartment, and shut the door on our way out.

Thinking her bottle of “acid” to be just more snake oil — “I bet it’s some herbal shit,” says Rachel — we drop it on our tongues and wander the littered apartment, looking for clues as to how someone becomes Caroline Calloway, catching glimpses in bowls of unidentifiable pills on the counter and the books and art, including a painting of herself, on the walls. “This is like a horror movie,” Rachel says. Having determined the acid really is just CBD oil or something, we take some more.

We spend the next hour or so listening to Lana, screeching “I’ve been tearing up town in my fucking white gown like a goddamn near sociopath,” gliding around the room, tripping, and searching for something, we’re not sure what — “talismans,” as Rachel calls them, that would explain who this woman is and what has happened in this apartment over the past ten years. It’s crazy, not to mention probably irresponsible, but both of us agree that the studio is intoxicating in itself, altering our behavior as much as the acid. We put on Caroline’s perfume because we can’t help it.

Around 3 a.m., I leave Rachel curled in a ball on the bed next to the cat, curled up in the same position. At 5:45 p.m. the next day, Rachel meets Caroline again before her flight, and she hands over the keys to the apartment so that Rachel can move in. Later that evening, she misses the flight and ends up at the Jane Hotel. Meanwhile, on Instagram, Julia Fox posts a video: “I had full dinner plans last night and decided to take a power nap and woke up the full next day. Forgive me @carolinecalloway.” Rachel texts me, “Look we were taken over by her spirit. Something happened there where she like brought us on on a psychic level to her vibrations.”

It is one of Caroline Calloway’s greatest wishes, among many other definitely grand and probably delusional things, that one day, when you arrive at her 55-unit apartment building in the West Village, there will be a metal plaque next to the front door commemorating her ten-year residence there. It was the decade she became, as she once told me, “professionally, Caroline Calloway,” and it ended this week — or at least her time on West 12th Street did.

What this hypothetical inscription would read will take time to determine. Maybe it would say “Caroline Calloway, Notorious Scammer” or “Caroline Calloway, Internet Celebrity.” If Caroline got her way, she’d be memorialized like Edith Wharton: “Caroline Calloway, Literary Sensation,” “Caroline Calloway, Best-Selling Author,” “Caroline Calloway, Downtown It-Girl.” Of course, most likely, there will only be a buzzer that the landlord still hasn’t fixed.

As of today, Rachel Rabbit White and her husband, Nico Walker, are in the apartment. Caroline says she’s staying off social media “to make prose that explodes over you like your favorite confetti,” though she did return to TikTok briefly this week to mark the “the end of a fucking era.” In the last video, she signs off with a quote from Joan of Arc: “I was not afraid. I was born to do this.”

If you enjoyed reading ‘are u coming?,’ smash that forward button and share it with a friend. Or, sign up for The Cut newsletter, a daily digest for stylish minds covering news, fashion, and power.