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Sloane Crosley: On Writing Humor and Friendship

Author and essayist Sloane Crosley talks about her new novel, Cult Classic, writing with humor, and the tangled romance of friendship in this interview from the July/August 2022 issue of Writer's Digest.

Have you ever talked about a movie or a book you’re interested in, only to have your social media accounts serve up ads for those very items, almost as if they were listening?

Now imagine the same social media accounts could be harnessed by NSA data scientists, upscale influencers, and leisurewear-clad zealots to deliver the most frightening package of all to your doorstep: your dating history.

Therein lies the central tenet of author Sloane Crosley’s new novel, Cult Classic, which debuted June 7. Much like her first novel, 2015’s The Clasp, Cult Classic finds its protagonist, Lola, coming to terms with the people and friendships of her past at a time when she’s embarking on a new life stage, namely an engagement to her fiancé, Boots.

But as Lola navigates her ambivalence about her pending nuptials, and her friendships with former coworkers from a psychology magazine, the past comes rip-coiling into her present in the form of one ex-boyfriend in her corner of Manhattan and then another and then another. Before long, Lola is besieged by the ghosts of relationships past, seemingly drawn to her at random, but then more nefariously by a shadowy group with a keen interest in her personal life.

Cult Classic wields the same rapier wit that Crosley has come to be known for not only in fiction, but also notably in her essay collections I Was Told There’d Be Cake, How Did You Get This Number, and Look Alive Out There, as well as an established career in magazine journalism.

Crosley recently spoke with WD about her new book, writing with humor, and how she navigates the differing approaches between writing novels and narrative nonfiction.

Where did the impetus for this novel begin and how long did it take to formulate?

I think I’ve been avoiding, for a very long time, writing about romance in any sort of direct way. Because when you are a writer and you are a woman and you live and write about New York, people assume you’re doing that anyway. … friends will often—especially with my writing narrative nonfiction for so long—say either, “I have a story for you. You should write about it,” or “Don’t write about this.” … I finally felt that I had the maturity, both as a writer and a person, to tackle what could potentially be a very cliché or trite subject in what is hopefully a new way and just go for it. … I guess I would say that my first novel, The Clasp, actually has some similarities to this novel, only in the fact that you have this group of people that are about my age engaging in their sort of social machinations. I almost wish for them more than chatting in a bar in Manhattan or Brooklyn. That’s sort of what this book does.

In both The Clasp and Cult Classic, it feels like the protagonist is approaching the end of a life stage and is trying to reconcile the relationship with some of the folks that were in that previous formative life stage. Do you find that’s an interesting part of a narrative to explore?

Any kind of conflict is, of course, interesting to explore. I think you might be getting at something that I really wanted to do with this book, which is in order not to just make it a litany of men—there’s a certain point in which the heroine jokes about not being able to pass the Bechdel test with herself—the container of it is about friendship. And I actually hear myself say that out loud and it sounds so hokey … But there is this complicated friendship that Lola has with her former coworkers, especially her former boss, Clive, and there is [this] telling thing where she feels like they almost should have dated at some point and that ship sailed. And that is not an experience that I personally have had with anyone I’ve worked for, but I can feel that for her, that sort of complicated friendship that you see more of on the page than you do, let’s say, on the screen. …

I wanted to make sure that … it was clear that there was sexual tension, but now it has calcified into something that is deeper. That is actually one of the most important relationships in the book and one of the greater reasons for writing it even … even though, quite clearly, it’s a book about ex-boyfriends.

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When you’re approaching the interactions in each scene, was it difficult to craft the humor in that?

… I think that if anything, it’s not that my humor is always successful, but that muscle is one that I’m used to exercising. Therefore, it is the one that has to be reined in. It comes pretty naturally to me—again, I’m not suggesting everything I say is uproarious—but it’s not the humor that I had to work on so much as the pathos. … It’s not hard to inject pathos or sadness or moments of poignancy into a funeral scene, nor is it hard to inject humor into it. I think as you go through your life, when you’re thinking about people you used to date … there’s some sort of spike and clarity in your memory, and so all emotions rise for those moments.

It’s been seven years since The Clasp was published. Has the process of writing a novel gotten any easier or changed from that first experience to now?

… I had written a novel when I was much younger that will never be published. It’s very bad, but part of the reason it’s so bad is because I had started it in college and then tried to expand it and was just sort of injecting chapters into it. But I already knew what the last 20 pages looked like, and it was just a miserable experience to know to that degree exactly where I had to go.

With The Clasp, I thought, Well, let’s not do that again. It was a little more feeling around, letting the characters take me where they wanted, but not quite knowing where it was going to go. With Cult Classic, it’s not easier, but I think I have figured out at what point I need to develop that North Star and just be headed there. … I was so afraid of it for so long because knowing the ending so much in advance really killed that first novel that will never be published. I had to figure out how to find that room to know where I was going, but still be able to surprise myself.

I read a few previous interviews where you talked about your essays and recognizing when a lived experience has the potential to be an essay, such as your first essay in The Village Voice where you were twice locked out of your apartment on the same day. How do you know when something as random as that could be an essay?

[Laughs] I always bring my keys now. It depends on the kind of detail or story or the size of it. So, first of all, details. Something sort of tiny and hilarious happens, something that could be a piece of dialogue, an analogy. You travel somewhere and you notice something, something in the natural world that moves differently than you would ever notice before. That kind of detail is a real free-for-all. …

For nonfiction, I think one of two things has to happen. It has to be a great story, an objectively good story. … I’ve told a couple of people the same story, and it sort of starts to congeal or calcify in my brain. Then it stays put for a while until I figure out if it’s bigger than me. Then the other way to do it is to look around and think, Is there some sort of theme that keeps on coming up, and do I have a story to support that theme? Both techniques really are—at least in my mind and in my process—in place … so that you’re not just telling cocktail party stories to people. You have some sort of system of checks and balances.

Sloane Crosley | Writer's Digest July/August 2022 Interview

This is your second novel and you have three collections of essays. Do you think you’re going to be returning to the novel as form again soon?

So, sometime next year, I will have my first full-length, narrative nonfiction book out, which sounds weird because it seems like that’s already happened. But, the essays are not fully connected. It’s a five-part book about grief that’s hopefully also bizarrely funny, called Grief Is for People, and that will be out next year. I just handed in the first draft. So you’re actually catching me at a very weird time, because I have the novel on June 7, I finished the nonfiction book, and it’s very rare that I just sort of look around for a couple weeks and right when you finish something I always think, Well that was fun. I’m never going to think of anything new again. I guess it’’s time to finally open that bed & breakfast.

And then it doesn’t last long, but it’s like a strange time period where like I’m sure both fiction and nonfiction will come. But for now, I just finished the next nonfiction one. I’ve got to do laundry and take a nap.

Does the process change how you approach your writing overall, moving from nonfiction to essays to journalism to fiction?

… There is a sort of humor of exasperation or that feeling of “I’m stuck in the middle with you” with nonfiction, where there’s less of an impetus to create an entire world. Whereas with fiction, you’re just on the back foot when you start because it’s not true. … The approach is always how do I both beautifully and efficiently get to the point where the reader forgets that I’m writing it? That is a question that you actually want to avoid when writing narrative nonfiction. You never want the person to forget that there is someone speaking to someone for whom the following things have happened or who has these opinions.

Is there anything I’ve neglected to ask you about?

The one thing that is funny that I will add is that … the kinds of conversations I’ve had with [Farrar, Straus and Giroux] and with booksellers, anybody in the media even, they tend to talk about the magic realist elements of [Cult Classic] … where if you just pay enough money using data from the NSA, Instagram, intense meditative thinking, general mind control, and influence, this organization [can put] ex-boyfriends in front of our heroine.

I feel like that’s not magic, that’s marketing. … We talk about it as if it’s this crazy thing … But I feel like if I had all the money in the world and access to the kind of technology that we have in our complicated day and age, I can put you and someone you dated in the same spot anywhere on this planet—and it would not be hard—using sheer influence and power of suggestion. So it’s actually very funny that everyone is using the shorthand about magic realism, and I’m like, “I think this is real.”  

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