BooksSeptember 2025In Conversation

CHLOÉ CALDWELL with Hannah Burns

CHLOÉ CALDWELL with Hannah Burns

Chloé Caldwell
Trying
Graywolf Press, 2025

The pressure was on, what with my ex-girlfriend texting me, curious what I would ask Chloé Caldwell. My friend, who gave me their copy of Women just before the reprint, said, “Please tell her I love her.” When I had the chance to chat with Chloé over Zoom, I had too many questions. Looking at my freakishly annotated ARC, deciding that I could never lend it out, I texted my ex back something about structure. I told myself not to stress about finding the right words, thinking, “It will come to me.” And it did.

Trying is a sticky, sprawling glimpse at a life impossible to slice up. Each vignette is connected through intuition, while Caldwell’s colloquial voice captures the milieu of modern love and the agency needed to alter your narrative.

Hannah Burns (Rail): I want to talk about the part where you were conversing with “Riley” in the Venmo comment section. It made me think of the Vogue piece that you did on blocking. And of course, being blocked on Goodreads is a classic from Women. I was wondering if that was a callback for fans.

Chloé Caldwell: I know blocking is a lot more common now, and it’s part of our day-to-day lives, but in 2014, when the book came out, it wasn’t. Like, I didn’t even have an iPhone when I wrote Women. So when I was writing Trying, and I was in act three, the Venmo thing happened. I was kind of, like, “That’s funny.” But it wasn’t so much blocking. It was just the ways we all communicate with each other and the ways our world is set up. It ties into some of the other stuff about consumerism and the emails I was getting from makeup brands or fertility clinics or whatever, and it’s all about buy, buy, buy, buy, buy. So to be on Venmo is just a money-driven thing, and yet we’ve brought emotion to it. I thought what the Riley character did was very creative and sort of romantic.

Rail: In our consumerist landscape, that is romantic.

Caldwell: I like including a lot of modern technology from our day-to-day world, because it’s so ridiculous, and we forget because it’s super normalized. But, like, it’s not normal to get an email from a sperm bank telling you that you can get 20 percent off. It’s not normal to open your period app, and have it be like, “Hey, it’s a Memorial Day sale.” It’s so fucked up.

Rail: I was wondering about that—those details about getting drawn into Trader Joe’s, and selling pants, and the ads for the sperm bank—if it was addressing subliminal messaging, about the pressure of expectations, both internal and external. Like when you talk about mimetic desire—how our desires are reflective of other people’s—then in the same breath you say you want to have a child of your own accord. And it feels like you’re saying both things are true. It’s a strong desire, maybe strongest, but it’s within a context of these other desires as well.

Caldwell: Yeah, exactly. I don’t think this is in the book, but I once came across this list in a journal from my twenties, and it was so sad. It’s like “things I want before 30.” And it was like, learn to cook, financial independence; and then it was like, black jeans, black boots. It’s these huge things, like financial independence, and then it’s the specific kind of Levi’s. And I think that’s what you’re talking about, because there’s the desire for the child, but then it’s like, “All right, well, if I’m not pregnant, I can get a manicure and a pedicure, and I want this kind of food, and I want to watch this show, and I want to drink cold brew, because everyone’s telling me not to right now.” So you’re right, there’s the core want, and then there’s all these other wants circling it.

Rail: Right, and there’s this feeling of, “Where do you put this desire when you don’t get what you want?” But on the topic of desires and expectations, you had a lot of these meta passages addressing audience expectations in Trying. You do this with the birds and the groundhogs and other images that feel inclined towards metaphor—you have a resistance to it, but then also an awareness of the attraction towards it. So at the end, whenever you return to these earlier images that you had set us up to reject, you embrace them, but then you complicate them by adding in another image—the image of the fox.

Caldwell: It’s sort of wild. I did not do that on purpose. I struggled with the ending of this book. It didn’t come for a while, but I’m a very intuitive, “trust the process” kind of person and writer. So I don’t really stress about that stuff. It comes when it comes, and it doesn’t have to be this big ending. I was just writing, and then that happened. I saw a fox. And when I put that in, I was like, “Would it be crazy to just end with that?” But I didn’t put it together until my editor, Yuka Igarashi, later said kind of what you were saying: “It’s so funny how you make fun of animal motifs in female memoirs. And then you’re like, ‘Fuck you, I’m gonna end with a fox.’” And I was like, “I did not think of that at all.” So this book is literally scary. There was some weird sorcery going on. Like, my subconscious wrote this book. It actually freaks me out a little bit. And that part where I have all these dreams and then they come true—that happened. I had a dream that I ran into Emily Gould on the street; and then, a year later, I ran into her on the street, in a place I don’t live. So all these things are more subconscious. It’s just a series of random, random things, but of course, they’re all connected, right? Because it’s me and it’s my life. So of course they all end up being connected in unexpected ways. But I don’t think I’ve ever had this happen in a book to this extent.

Rail: And I think it’s that same page that you’re talking about all of your dreams coming true where you say that people think God is a woman, but you think God is a writer. I loved that so much, because it’s a very human thing to think in terms of narrative, but for writers in particular, we don’t even date somebody unless there’s a story to it. Like, it has to feel it’s playing into a larger narrative somehow. And I think that you put that succinctly by saying, “God is a writer.”

Caldwell: I love that. Until the very end it was really back and forth, like, “Should we take it out? Should we keep it in? Is that pretentious?” But that was the mood I was in. I was just like—when you have this kind of experience and you try to control a narrative as I was doing—“Okay, I’m now going to get pregnant in two months.” And then life just laughs in your face. “God” laughs in your face. So when that all went to shit, I stopped trying to control anything—and I’m not controlling anyway. But with the fertility stuff, you kind of fall into that, because they tell you if you do this, you’ll get this. So if you take Clomid, you’ll get pregnant. If you do intrauterine insemination, you’ll get pregnant. If you do IVF, you’ll definitely get pregnant. None of it’s true.

Rail: That’s the whole unexplained bit.

Caldwell: Right, right. And that’s actually something that we can’t control, although culture and modern medicine make you believe you can. And it’s so humbling to say, “No, I can do everything right, and I can be on the right medicine and get sperm inserted into me and still not get pregnant, and no one will know why.” There’s something beautiful about it, because you just give up. You know what I was thinking about yesterday? This is really wild: my last book, The Red Zone, which was about premenstrual dysphoric disorder and my period, is definitely my book that sold the worst. You know, there’s people that like it, and it got read, but it didn’t really strike a chord. It was a really challenging book for me to write. And I think—I know—I was forcing that book into a narrative. Because at the end of the day, you do have to sell your book and publish your book and make it marketable or whatever. And I made it this memoir with kind of a happy ending, and I thought that that was my narrative.

Rail: And this is the one where people said that your ex-husband seemed perfect in it.

Caldwell: Yeah. Hmm. So isn’t that interesting, that the book ended up not being honest? I didn’t know it wasn’t honest, but readers did. My belief is that readers are picking up on the dishonesty that I didn’t even know was there, but something was wrong with that book. Something wasn’t quite landing. And I really think it’s because I didn’t have the agency to actually know the truth. So I was writing a totally different narrative that I thought I was living underneath. And then Trying just ended up so perfect, because it’s with Graywolf, which is already a publisher that lets you be experimental. So I basically got to do whatever I wanted with the book—resisting all of those things. It’s resisting narrative. It’s resisting conclusion. It’s resisting form. And that’s more me. So I just feel like that’s such a lesson for me. I didn’t know I was forcing the ending of The Red Zone, but I think it’s interesting that that’s my most concrete ending, and look what happened.

Rail: That makes me think about when you mention struggling with whether to leave out or include specifics about your ex-husband. And you talk about the emotional honesty that’s needed to write. I wonder if you feel like the calling to emotional honesty is kind of fraught? Like, what level of protection are you supposed to give to your friends, lovers, ex-lovers? What are they owed?

Caldwell: I have this theory that people—maybe it’s just me, but I would find that hard to believe—write differently when they are in a relationship. Because I did. I wrote The Red Zone, and I think subconsciously I was like, “Okay, I have in-laws now.” If I think about my first two books, I was free. It doesn’t really affect anyone, what I write. I really see that in my writing. I think I was really holding back. If you had asked me then, I would have been like, “I’m not holding back. I’m writing about my period and PMDD and blood clots.” And, you know, that’s also true. I think we make ourselves smaller to make other people feel comfortable. And honestly, I know we just do that, writing aside. That’s just how many women are, and it really doesn’t work for writing. If you do that, your writing will suffer.

Rail: Right, you’re going to self-censor. But I feel like that’s just a constant tension of writing about the people in your life.

Caldwell: Sheila Heti talks about this a lot: that writing a book is just a series of decisions, one after the other. And that’s what I did. It was only when the divorce happened in my real life that it became confusing. Honestly, I think writing act one and act two—that was just me alone all the time. I’m thinking even now to those days, and I wasn’t sharing with people. I was super isolated. I felt so much shame. I was depressed. And I see that now. So then the divorce happened, and what’s interesting that my editor picked up on, is that I started to use names after the divorce. We talk about the book as going from black-and-white into color, because I was suddenly naming concrete people and places, like Riley and Ridgewood. And that’s kind of cool. When I read act one and act two, I’m like, “This person’s really depressed.” And I think it reflects that I didn’t really have support and community. I was just on Reddit and Discord. And my conversations with people were awkward and painful. So then in act three, yeah, I brought in characters, and then you start to see support and—

Rail: Yeah, that beautiful intimacy with your friend who calls you every morning.

Caldwell: Oh my God. I was just with him right before this. Yeah, thank you for saying that. Yeah. That still makes me cry to this day more than anything.

Rail: And the time that you spent with your parents—that was kind of bringing the world into color, entering the third act. Saying, “Okay, this is what intimacy is, actually: watching Are You There God? It’s Me, Margaret. with your dad.” You know, that’s intimacy.

Caldwell: That’s so sweet. Yeah, I feel the same. I’m really, really glad …

Sorry. My dad passed away.

Rail: I remember the dedication. I’m sorry for your loss.

Caldwell: Yeah, and it was already dedicated to him, which was really cool. And he knew that. I sent him a picture. I just feel like that was the summer when life exploded, and you’re so in the present moment because everything’s gone. Like, “I don’t have to go to the fertility clinic. I’m not parenting anymore. I don’t have a house. Let’s go see a movie.” You know? We were in New Orleans, and it was so hot, so we went to see Are You There God? It’s Me, Margaret. So yeah, I’m glad it’s coming through. I love how community and friends kind of become the support system, because in the first acts, they’re not really there. And that’s partly on me, because I wasn’t leaning on people and asking for help.

Rail: I’m thinking more about your idea of God-as-writer, and the feeling of act three coming from black-and-white into color. This is a bit more of a, if-we-were-drinking-margaritas-and-not-coffee question, but you say that “some delays are protection.” And that made me wonder if you believe in fate, or just intuition?

Caldwell: Yeah, that quote helped me at the time, though I didn’t know what I was being protected from. I really believe in it. I mean, I believe in it too when people submit their books. Like, if you’re not getting published, there might be a reason. I really believe in timing now, and I’ve seen it happen with my own books. So I don’t know about fate, but I definitely believe in instinct and intuition, in ways that I think can be disturbing to people. But it’s all I have, you know? And I heard this quote recently too, that “decisive people are lucky.” And I was like, “Oh, that’s cool.” Like, my dad’s line, “Lean forward and run down the hill”—that’s kind of saying to be decisive. So, yeah, it’s cliché, but I think that’s what’s cool about getting older: you see the way things play out, and it’s so relaxing, because yeah, bad stuff happens, but a lot of great stuff happens too. And you can see more patterns the older you get. You can begin to see, you know, if X hadn’t happened, then Y wouldn’t have happened, and then I wouldn’t have Z. And it’s so soothing. For me, this thing of wanting to get pregnant so badly—not knowing why it didn’t happen and thinking it was the worst thing that could possibly happen to me—ended up being the best thing that has ever happened to me.

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