On Her Majesty's Scammer Service

An unusual alliance with Caroline Calloway

Photo of Caroline Calloway from her recent Vanity Fair profile (Photograph by Martin Schoeller; Styled by Samantha Gasmer)

On the first day of March 2022, I published the roast of Matt Gasda’s Dimes Square play—the piece that marks the start of my “New York era,” the start of Crumpstack season 1, the spring from which all the rest of this drama flows—and a week later, I got an Instagram DM from the infamous Caroline Calloway. I’ll assume you’re already familiar with Caroline’s lore—plenty has already been written about that, all of it from before my time here. “What's your phone number? I want to befriend u,” she wrote, and so I gave her my phone number and got a facetime call the next day. She recognized that I was also from Virginia from the 703 area code in my number. Caroline was calling me from Florida, where she had recently moved to take care of her 99-year-old grandmother. Just days before I set up camp in my own first NYC sublet, Caroline had thrown a big going-away party in her notorious West Village pad and got out of Dodge right after, and New York magazine ran an article about this party on the day Caroline messaged me. Caroline and I had a nice conversation, and I appreciated her lovebombing. She told me that the review I wrote had “made the rounds in New York,” and had gone viral enough to reach her in her new subtropical exile. It wasn’t that she had a particular axe to grind with Gasda or anything, she could tell that the piece was about more than Gasda and his play. At that time, I didn’t actually know much about the social landscape of the downtown scene at all, aside from what I had read about online, so I welcomed her interest as a sign that I was on to something real. She’s clouted, and the tabloids call her an it girl. Caroline told me that she wanted to facetime me regularly so that I could keep her updated on what’s happening in New York, because she had no intention of returning to the city “for many years, if ever.” She said she was writing a book, a memoir, and that she needed to be away from New York—from Dimes Square, from the parties and the drugs and all the small-minded socialites who are destined to be mere footnotes in a narrative far greater than any of them. That was what most of those 1960s Warhol Factory kids really were, she said, mere footnotes. She wished me luck, and I thanked her, and that was that.

Caroline hit me up again after the “Fear and Loathing on Planet Urbit” piece. This was about two months later, and by this time I had also written the review of Betsey Brown’s film Actors. Caroline told me she was drunk the last time we facetimed, even though she almost never drinks anymore, and she confessed that she couldn’t remember most of what we had talked about. In fact, she had nearly forgotten my existence entirely. But now, she said, she was actually impressed. My newsletters were still coming up on her radar. She told me she wanted to be friends, “for real this time.” She wanted me to tell her what’s the deal with all these “fascists.” She’s met a lot of these people herself, she’s familiar with all the reactionary edgelord posturing, the whole Red Scare thing, this provocative new femininity, but she could never really understand what it really meant, other than that it was trendy (for example, she asked me to define terms like “Frogtwitter” that I often use without any elaboration). I was portraying these familiar characters in a different light. “Most of these people are idiots, mere footnotes, but Honor Levy? She’s a real good friend of mine, surely she can’t be a fascist…” I admitted that I had a soft spot for Honor, since she seemed to have an ounce of talent and self-awareness beneath her quirked-up nihilist persona, but also that I’d be lying if I said that Honor wasn’t an edgelord (edgelady?). I said that I was drawn to that same promise of edgy avant-garde mayhem, after all I’m basically just another white male bourgeois social-climbing writer passing through this titillating high society that copes in various ways (most of them bad) with the centuries of settler violence that makes it possible. A lot of blood had to be spilled for this. As for Caroline, she’s a white woman who’s always been mesmerized by aristocracy and the glamorous whimsy of all these rich kid poetry readings, but she’s still a liberal, she said, a feminist, she’s afraid of abortion rights being taken away, and she doesn’t care if that’s cringe. She’s livelaughlovecore. An unusual ally for this “communist” project, perhaps, but I’ll take it. She said she was going to promote my Substack on her Instagram, first of all because she fucks with the vision, but also because she wanted to test her own power, she wanted to see how just much clout she could conjure out of the ether. So she made a very perceptive and articulate endorsement of my Substack to her 650-thousand Instagram followers, and it tripled my Substack following. After this, I understood that I owed her a favor, a potentially risky debt to such a chaotic figure, but that’s just playing the game. Caroline’s one request was that I don’t write about her (I agreed to this and had no intention of betraying that promise to her, but I also knew that she did want me to write about her, at some point at least). Her parting advice was for me to always remember—whenever I’m out at all these events, being “seen” and photographed and whispered about and whatnot—that these people are far more afraid of me than I should be of them.

I heard from Caroline again in August, after the humiliation ritual piece, the climax of that summer. At first she was speechless on the facetime call, it’s hard to know where to begin with that one, and then she finally asked me how I could’ve sat through hours of all those people being such haters to my face. I told her that I had kept in mind her advice from the last time we spoke. She said that I was better at following that advice than she is herself. She confided in me some stories about being heckled and disrespected by some other characters in the scene, basically being treated as a fake and dilettantish writer by others who are just as fake and dilettantish themselves, and that she had taken it personally because she had foolishly sought their approval and let that approval define how she saw herself. She said it was satisfying to see this kind of behavior get such immediate comeuppance, and I got a better understanding for why she wanted to be friends in the first place, which I always sensed had to be deeper than mere opportunism (though I have no problem with her simply joining the winning team). Even though she towers over pretty much all the other scenesters in quantitative internet clout, she said she still felt like an outsider to the cool creeps and their pick-me cool girl accomplices (who were ironically probably just envious/threatened by her apparent “mass appeal” anyway; the heartland normies don’t give a fuck about all these Club Kids and wannabe Vincent Gallos, of course they’d prefer the narrative voice of the bubbly horse girl who goes to the big city to live out her naïve bohemian dreams, those delusions are more charming and relatable…). Caroline said that she now trusted me, so I now had her permission to write about her—she had been testing me by making me promise not to. She also added that she was relieved to read Honor coming across relatively well in the humiliation ritual piece.

In the following months I got texts from Caroline every now and then (and sometimes I was caught up in other stuff and would take forever to respond to her), but it wasn’t until April 2023 that I got the next big update. She was calling in the big favor. “Mike, mark your calendar. APRIL 11 IS THE DAY I WILL SEND YOU THE SCAMMER MANUSCRIPT. DO NOT SHARE IT WITH ANYONE. DO NOT EVEN TELL ANYONE YOU HAVE IT. Of everyone I’m asking for edits, you’re the person I know least, by far. Part of me is very worried you will leak it. But if you give me your word that you will keep this all private, I will trust you.” And then there were more details about the specifics of the task she was giving me, which was an utterly impossible editing deadline (line edits for the entire book by 5PM the next day). I told her she had my word I wouldn’t leak anything. “Ok you’ve officially made the cut Mike / I swear to god if you fuck this up for me I will hunt you down with my dying breath / But welcome aboard :)” By the time the 11th came around she messaged me again saying that the drafts would be coming out the 12th or the 13th, and then on the 13th I got another text saying that Vanity Fair loves the profile they’ve done on her—and they’ll be expanding it by 2,000 words for the July/August issue of the magazine (rather than the June issue). This means that she has another month to finish the book (which is supposed to come out at the same time). I ended up getting the first tranche of the draft on May 22.

Fortunately, I wasn’t very busy that week in May, so it wasn’t a problem to be roped into this unpaid and time-consuming task. I guess that’s now just part of my responsibilities as this recognized scene-figure, to offer myself to the it girls: Dasha slaps me for her own satisfaction, Caroline makes me edit her book, and so on. Besides, I intended to read it anyway, might as well enjoy this opportunity to subtly influence it. My edits were mostly standard mechanical edits and lightening/polishing certain sentences so that they’d be a little more elegant, so that they’d “pop” more. I didn’t do anything structural or substantive, I wasn’t telling her to cut or rearrange entire paragraphs or chapters, and I didn’t think the manuscript needed it. After all those years of anticipation and false promises, her book pretty much speaks for itself. Caroline is a crazy ass white girl with a knack for self-mythologizing her messy drama—some of it silly and shallow, some of it genuinely tragic and brutal, all of it fascinating—and that’s all her readers could ask for anyway. And I guess that’s already more than what the other “footnote” opps have to offer. I can’t really say that I’ve been scammed.