The last time I saw Daniel Mallory Ortberg, author of the New York Times-bestselling Texts from Jane Eyre, co-founder of The Toast, and Slate’s Dear Prudence columnist, we spent a glorious afternoon coasting via aerial tramway to the top of a serious mountain, then rode something called a “mountain coaster” back down—which did not surprise me, because Mallory is the kind of friend and the kind of person who makes me feel like I can do new and brave things. With The Merry Spinster: Tales of Everyday Horror, Mallory has created something new and brave; it’s a gorgeously witty, frequently dark, consistently satisfying collection of tales that could only have come from this author. Like all the best fairy and folk tales, the stories offer surprises and sly winks to keep you in thrall, while illuminating all the vulnerability and deep complexity of relationships between family, friends, lovers, and enemies. It was a joy to chat with Mallory last month about the work of imposing shrewd new twists on beloved stories and characters, the unique challenges and pleasures of the short story form, and what it was like to write this new anthology while transitioning.

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Nicole Chung: I’m always happy when we talk, and today I’m glad to have such a thrilling excuse to talk to you. Congratulations on your book! How are you? What’s been going on?

Daniel Mallory Ortberg: Well, today has been a very big day. When you called, I was finishing up at the gender clinic, where I got my very first injection of testosterone!

NC: Oh, congratulations, I am so excited for and proud of you!

DMO: Thank you! As you know, I was on patches at a low dose for 90 days, in part because I was operating on a theory (that theory being: maybe I am trans; I don’t know really know what sort of trans experience this is; I don’t know how much of this I want), and that experiment went so very, very well. When I took a pause, it was very clear to me that I wanted to continue. So I decided to switch to injections. I just got my first shot at the clinic, and it felt fantastic.

NC: As your friend, I’ve felt really glad that there has been joy in each new step for you, which is not to minimize the challenges at all.

DMO: It was a little over a year ago that I first started asking myself, consciously, “Am I trans?” I was finishing the book at that point. So much of the last year has been painful, isolating, frightening—but the moments of clarity, joy, and excitement that have come from being around other trans people and accessing medical transition have helped me realize this is not just about what I’m afraid of; this is also about wanting something, desiring something, excitedly looking toward the future and visualizing real possibility. Letting myself experience the joy of transitioning, and not just the fear, feels really powerful.

I’ve been so anxious with the idea of going on book tour. I know I’m going to look different than the last time I had a lot of public appearances. But as much as one can be certain of anything, I know that I want to go do this book tour as an out trans person.

“This is not just about what I’m afraid of; this is also about wanting something, desiring something, excitedly looking toward the future.”

NC: I can’t tell you how much I’m looking forward to seeing and being in conversation with you on your tour next month. I do have some book-related questions—we should do those, right?

DMO: We should! We should talk about what I wrote.

NC: But this is also kinda transition-related, because my first comment was going to be that I thought the way you wrote about gender in these stories was so interesting and important.

DMO: Well, Nicole, that’s because I was transitioning at the time. (It feels so good to say that!)

About half of the stories were written before I had a conscious understanding of the trans question in my head, and about half were written during the early parts of it, when I was thinking: Can this be true? Can this be real? Is something happening to me or am I uncovering something about myself? So it felt very natural for that to come into play in the book.

I would say there are a few characters in the book that I felt a real connection with, which is not to say any of them are supposed to be me. One of them is Paul in “The Thankless Child,” one is the boy in “The Frog’s Princess,” and one is Sylvia, the little brother in “The Merry Spinster.” I relate to these characters for many different reasons, and one is that sometimes they joke about things that are very important; they joke about wanting to be whisked away and have something done to them so that they don’t have to articulate their own desires. Paul in particular is a person who feels unable to speak in a lot of ways—they’re hounded by something that other people can’t understand or help them with. Writing that story felt deeply moving to me.

NC: How else was writing this book different from writing your last book? (I always just want to register my awe when anyone writes a second book.) Was it harder to get this one started?

DMO: Absolutely. It was so different from my first book, so there was the question of whether there would be an audience for it. And then I had to ask myself, Will I be able to write it? People sometimes say things like, “I have a novel in me,” and I was like, “No, I do not. I have no novels in me at present.” I don’t mean to suggest short stories are easier to write than a novel, more that I was looking in the back storage room and it was like, Nope, no novels here, but we have a collection of short stories!

NC: You’ve written many short stories, of course, not just for this book. What do you like about the form?

DMO: God, I love short stories. Some of my favorite books are short story collections. I think they’re beautiful and brilliant. Because they are short, you have to be really specific about the details you want to include and what you want to hint at. Being able to build something complete in a compact form is difficult and challenging and exciting and a lot of fun.

I love Angela Carter’s The Bloody Chamber and Shirley Jackson’s collections; I revisit those all the time. I love P.G. Wodehouse’s compendium of stories—I think some of them are absolutely brilliant examples of what you can accomplish in a short story. And Carmen Maria Machado’s book, Her Body and Other Parties, was astonishing. I felt like I had a fever afterwards, in the best possible sense.

“Being able to build something complete in a compact form is difficult and challenging and exciting and a lot of fun.”

NC: Do you have a favorite story in your collection?

DMO: I think my favorite story in the book might be “Fear Not: An Incident Log.” I kind of wish I could just do a collection of Bible stories like that.

NC: I loved that one. The part where the narrator said they all take turns being the Satan made me laugh for some reason.

DMO: Right, and you know, in the Book of Job, the Satan is like a job description—the Adversary—not the personification of all evil, but the one whose job it is to advocate against mankind. I loved that idea, like “hey man, it’s nothing personal, I just work here.” And the way we can be so cruel when we try to justify ourselves—that felt important to get through in that story.

NC: Your narrators were all very smart and funny and no-nonsense, with these great flashes of fun for the reader.

DMO: Each narrator had a specific voice, and that was so exciting to get to find. What does this person find funny? What absurd situations do they get into? What happens when someone finds humor in their agony? I loved getting to sink into those voices; that was one of my favorite things. While the book is full of horror, it is not relentlessly grim. I love finding humor, and I love writing humorous dialogue. It’s really important to me to not shoo out the clowns.

NC: Have you always liked taking known and beloved stories and twisting them around, telling them in a way that’s new?

DMO: Absolutely. I remember in high school my friends and I would rewrite Shakespeare plays to make more jokes. I’ve always been kind of a reteller. Redoing upsetting stories to be more upsetting; remixing stuff has always been my jam.

NC: I adore the fairy tale form, and they’re already so horrifying—there’s cruelty, brutal poverty, violence against women and children, kidnapping, murder. A lot of your stories kind of subvert some of these themes and give some measure of power back, even if that happens through more horror.

DMO: One thing I was very aware of is that I am a writer and a feminist, so that was going to be present, but—transition stuff aside—I did not have an interest in writing a book where the position was: The world used to be sexist and bad, and now we are enlightened and smart, so I am rewriting bad fairy tales to make women take over everything, and that’s the only relationship we can have with the past.

There were moments when I did want to flip certain structures; when I wanted to show people abusing power via family dynamics, but with different gender roles, or when someone abused power over a same-sex partner or a friend.

But it was also difficult for me at times. The first story I wrote was “The Six Boy-Coffins.” I love that story. It has a lot to do with female silence, with building community, with men who don’t want to kill you. After I wrote that and realized, “oh, fuck, I think I’m trans; I don’t think I’m gonna be a woman by the time I finish this book,” there was part of me that felt this real sense of guilt—almost like I was betraying something. I don’t think it was coming from a place of reality, but at the time it was still painful.

NC: When you reread this book now, from a place of certainty—knowing that yes, you are trans; yes, you are transitioning—how do you feel? I hope you feel proud.

DMO: I do. I love to reread this book now. I think it’s sharp and I think it’s funny and I think it’s lovely.

And it is the product of a bad year. Not an unproductive year, not an un-useful year; everything about that year was ultimately good and important. But there were so many painful things going on that I could not name or acknowledge—not just transition-related things, but other aspects of my life I hadn’t changed. This is the book I started writing before I could name what those things were. When I read it now and remember where I was when I wrote these stories, I’m extremely grateful to not be there now.

You know, I was on that 90-day trial run of low-dose testosterone, and then I paused for about three weeks, and it felt very clear to me: I can’t do this, I can’t not be on this hormone treatment, I need to transition, I’m excited to transition. I’ve been so anxious about this, and have wanted to talk around it and avoid it for so long. This is the first interview where I’ve said out loud: I am transgender, I am transitioning, ultimately I will change my name to Danny and go by male pronouns although that day is not yet. [Ed. note: Since this conversation took place, Daniel has debuted his name and male pronouns in an interview with Extra Crispy].

And to be on the phone with you, who I have known and loved for years, the day I just got my first shot of testosterone—to finally say, “Yeah, I’m doing this”—is powerful and exciting beyond words. There was a time when I thought, I’m going to go on this book tour and try to look as much like I used to as possible, and I’m so glad I’m not trying to do that. That would have been agonizing. And frankly, at this point, impossible.

“When I read it now and remember where I was when I wrote these stories, I’m extremely grateful to not be there now.”

NC: It would have worn you down in every way during what is supposed to be a celebratory book tour. I love you, too, and I’m honored to know you and to have read your book and to be having this conversation with you. I am so glad for you and hope your tour is everything you deserve.

You just sold a book of essays, which I’m also very excited about. Will it be all or mostly new essays, or a mix? Does it have a particular focus or theme?

DMO: It’s going to be new: a combination of cultural topics I have tackled in The Shatner Chatner, but at greater length and with more autobiographical details, including more about transition. It’s not a transition memoir, or a memoir at all, but it will have more personal elements in it, and I’m really excited to find out why I’ve always been obsessed with Captain Kirk. One of my friends who’s also trans said to me, “Remember when you used to write all those pieces about how [The O.C.’s] Ryan Atwood was a lesbian? The vibe I got was that what you were saying is that you were a trans guy.” And I was like, “fuck me, I did not realize that at the time, that would have been good to know.”

I really want to avoid the temptation to write a very on-the-nose trans memoir—“my journey from Mallory to Danny”—although I joke with friends that the title would be Son of a Preacher Man. That’s really not something I want to write. I think there’s going to be a lot of commentary and humor and thoughts and ideas about characters, books, movies, etc.—it’s not gonna be “now the jokes stop and you finally get to meet the real me!” But I do want to disclose what’s happening a little less coyly, and I’m excited and nervous to do that. Much like writing The Merry Spinster was so different from writing my first book, I really have no idea how I’m going to write this next book, but it’s going to be exciting.