Caroline Calloway Is Cleaning Up Her Messes — EXCLUSIVE

Caroline Calloway has been called many things: an It girl, a socialite, a temporary OnlyFans superstar, and an agent of chaos. A self-proclaimed “PR savant,” she pivoted from aspirational influencer to controversial internet celebrity before rising from the ashes with her literary debut Scammer, which was released in 2023 to positive reviews. Now, she’s back with a new book she describes as “a never-before-seen type of conversation between two depressed downtown darlings across time and space.”

Titled Elizabeth Wurtzel and Caroline Calloway’s Guide to Life, the experimental memoir combines new essays with heavily annotated excerpts from Wurtzel’s 2001 advice book and one-liners from other notorious figures like Julia Fox and Cat Marnell, alongside illustrations by designer Sam West. It also functions as a posthumous collaboration with Wurtzel, whose unfiltered work predates the internet and laid the groundwork for future generations of essayists and bloggers — even if, as Calloway tells NYLON, she was never able to reap the benefits after being pushed out of publishing for being “too much of a loose cannon.” “We say that we like messy women,” Calloway writes in the book, “but we only act like it once they’re gone or dead.”

Calloway knows the idea of her giving advice will “bait rage online,” but she says she doesn’t believe in the oft-circulated quote to only receive counsel from someone you would happily trade places with. “That really doesn’t give enough space for specialization and expertise,” she says. “Obviously, if you wanted to learn how to pole vault, you’d go to an Olympian. So if you want to be a manic pixie nightmare, you’re going to go to the world expert on that.” But at the same time, she’s quick to point out that the guide isn’t a substitute for going to rehab; rather, it’s a “fun, flirty book you should read if you’re down bad for someone who’s not texting you back,” the exact situation she was in when she first picked up Wurtzel’s Secret of Life. “If you’re just, like, spiraling about something, having a book by someone you trust can be so helpful,” she says, citing Cheryl Strayed and Emily Gould. “I just think it’s really nice to spend time on the page with women who have had it worse in their own ways and have come out the other side.”

If you want to be a manic pixie nightmare, you’re going to go to the world expert on that.

The same could be said of Calloway. When I first interviewed her in 2020, she was navigating the fallout from an exposé written by her ex-best friend, in which Calloway was painted as a fraud “living with one fork … and multiple copies of Prozac Nation.” “My reputation was in shambles. I owed my publishers $100,000. My dad had just killed himself. I just felt like my life was one big f*ck-up and that there was no way to make it right,” she remembers, noting that the book’s frontispiece depicts her as a tarot card labeled “the f*ck-up,” petting her cat while the background goes up in flames. “For a long time, I struggled with the idea that maybe if you make enough mistakes, you create an irreversible situation … That’s some negative self-talk I’ve had to rewire in my brain. What I tell myself now is that I used to be someone who made a lot of messes, but I’m cleaning them up.”

After leaving her West Village apartment to care for her grandmother in Florida, Calloway sold literary-themed topless pictures on OnlyFans, earning the money she owed her publishers and former landlord, who sued her for skipping out on rent for a year while she was busy investing in her role as a woman-about-town. While she addressed her spending in Scammer — “It girls are startups, and startups need funding” — in Elizabeth Wurtzel and Caroline Calloway’s Guide to Life, she “tried to stay in my goddamn lane: no financial advice, no advice on delivering a book on time,” she says. Instead, her essays take on a range of (mostly) lighthearted topics, from overlining your lips to surviving cancellation.

“No one person has it all figured out, but many people have some things figured out,” she says, invoking another Olympic-athlete metaphor in which she compares high-altitude training to the extreme conditions “crazy women survive” to be able to dispense their hard-won wisdom. That disarray is what drew Calloway even closer to Wurtzel, after she purchased some of the late author’s possessions at auction, including her signature mink coat and boxes of her books. Inside, Calloway discovered love letters from men written on the covers, notes from Wurtzel’s friends urging her to pay her back taxes, and no less than two debit cards. (“Proof,” says Calloway — who once told me she threw her passport into the ocean — “that she’s a bitch after my own heart.”) Together, these details paint a vivid, familiar picture. “I almost feel like she’s drunk-dialing me from beyond the grave, you know? She lived her life with a degree of chaos that absolutely fascinates me.” (Before her death in 2020, Wurtzel tweeted asking who Caroline Calloway was and why she had so many copies of Prozac Nation.)

“They work in similar ways,” says Calloway’s publicist Mitchell Jackson, who was also Wurtzel’s editor at Vice. Describing Wurtzel as a perfectionist who fought him over every comma, he recalls how she attempted to serve him a moldy Edible Arrangement he himself had sent her weeks prior. “Similarly, at a business meeting, Caroline fed me a salad consisting of Whole Foods arugula and weeds she pulled from the side of the highway,” he says. (“Purslane is very safe to eat, just so everyone knows,” she responds by text. “Rich in folate and vitamin B!”)

What I tell myself now is that I used to be someone who made a lot of messes, but I’m cleaning them up.

Calloway says she likes to believe she and Wurtzel would have been friends, two kindred spirits who’ve been through it all — and are disarmingly open about it. “Messy women and women who have it together all have different things to share,” Calloway says. “And I think life advice from messy women can be particularly interesting.” But even if you don’t learn anything from Elizabeth Wurtzel and Caroline Calloway’s Guide to Life, at least you’ll be entertained.