Daniel Mallory Ortberg is one of the Internet’s more beloved voices. Ortberg began publishing at Gawker and The Hairpin, two now-defunct outlets known for championing writers new to the business of writing, then founded The Toast, also now defunct, known for an idiosyncratic mix of humor and seriousness.
Ortberg has published so many hilarious pieces that choosing one to quote here is impossible. In 2014, they published Texts from Jane Eyre, an affectionate parody familiar to any of The Toast’s loyal readers. Since 2015, Ortberg has been Slate’s “Dear Prudence” advice columnist.
Tomorrow, Ortberg will publish The Merry Spinster: Tales of Everyday Horror, a collection of short stories. Ortberg’s fans will recognize the stories’ wry, bemused voice, as well as their command over the texts of Western civilization, which the author gleefully remixes into fairy tales that resonate in the current moment, as fairy tales are meant to.
“This book is really different from my first,” they told me. “It’s not necessarily the follow-up you would expect, and it wasn’t exactly difficult to convince my agents or my editors, in part because the first book sold well. I earned back my advance, and then some.”
Ortberg’s candor about the business of writing—money is something few writers discuss publicly—is unsurprising. They are candid about essentially everything, and our conversation was marked by the honesty and intelligence I’ve always considered key to actual humor. We talked for an hour; I laughed much of the time.
The Rumpus: Are you a writer? Are you a humorist? Are you both?
Daniel Mallory Ortberg: I definitely have almost always gone with writer. I don’t understand what people mean when they say humorist. They’re clearly trying to do something fancy with the word, and I do not know what it is.
Rumpus: I feel that humorist is meant to describe people like P.J. O’Rourke.
Ortberg: I don’t know who that is.
Rumpus: He is the least funny person in the world. Did you study to write?
Ortberg: I went to an evangelical Christian college in suburban Los Angeles, which was not a great choice for me. They were very wonderful people, but I thought—it’s somebody else’s fault that I decided to go here, and am taking no steps to change my situation. I’m going to be kind of shitty, and hope that somebody eventually figures out that this is not my problem to solve. Which did not result in robust self-acceptance or a sense that I got the most out of my college career.
Rumpus: Part of the territory you’ve claimed as a writer is things that are rarified, like art history or literature. Are you self-taught?
Ortberg: I have read a lot. Both my folks are pastors and they’re big readers, and I think if you have a more religious upbringing, there’s still that slightly old school Western education that’s prioritized. I grew up reading Bulfinch’s Mythology and the Bible and Chaucer—which lots of people do; it’s not unique to Midwestern pastors’ kids, but it was a huge part of conversation with my parents. “Oh, that wacky Bulfinch, at it again with his things about Apollo and Daphne.”
Rumpus: When you talked about art history on The Toast, for example, part of what was funny was that it was very astute.
Ortberg: W. Somerset Maugham used to call himself the first of the second raters. It’s such a great way to duck out of getting critiqued, which I am so here for.
Rumpus: I think underneath the project is a respect for the material.
Ortberg: There’s a difference between humor that comes from a place of contempt and humor that comes from a place of familiarity and affection. I don’t think they’re total opposites, in the sense that you can be familiar and affectionate towards something that you do have some contempt for. Not that all humor has to be totally defanged and mutually supportive and loving, but you know—you’ve got to save your contempt for something that has really earned it.
Rumpus: Are you conscious of thinking about the craft of your writing?
Ortberg: I think I’ve learned the most about writing through the times that I had to write the most. There was a short stint I did at Gawker, and then at The Toast, in addition to all the reading I did. Just doing it over and over and over again, and figuring out what worked and what didn’t, that was absolutely the most helpful thing.
Rumpus: You can develop expertise by going to school. Then, there’s the approach you’re describing, which is more like practice makes perfect. They’re not quite at odds, but they are different philosophies about how you do something.
Ortberg: I’m just not an expert. I’ve never gotten an MFA, I’ve never done that sort of work, I don’t know.
Rumpus: So is The Merry Spinster a book of humor, or is it a book of short stories?
Ortberg: It’s a book of short stories. I think there are lots of funny moments in it, but it’s not a funny book, exactly. I would say it’s my knee-jerk response to the stories that I grew up with, and the ways that I feel about my life now, which is not to say that I’m in it at all. There’s a lot: What does abuse look like outside of a romantic context, and how hard can it be to recognize? What does it mean when someone tells you something is love, and yet it is not love? What does it mean when you inherit something violent? What does it mean when you perpetuate that violence, and you don’t want to acknowledge that to yourself? What does it mean when you’re not honest about what you’re doing?
Rumpus: It’s interesting to hear you talk about it thematically, because the text presents itself as a postmodern remix project—
Ortberg: I just want to stress right now, I don’t know what the word “postmodern” means, so we’re super clear.
Rumpus: I’m using a lazy word to describe a strategy that feels playful. Especially because you have a page of source materials—that seems to be saying, Yes, this is still the Mallory you remember having fun with the canon of Western art, and here they are talking about texts.
Ortberg: I was terrified that somebody would think I was plagiarizing Thomas Aquinas. If I’m directly quoting a Bible verse and putting quotes around it, the reader will get that this is not a thought original to me. If a character has a monologue where they’re interpreting Thomas Aquinas’s thoughts—what if someone thinks, “Is Mallory trying to fucking pass off Thomas Aquinas’s thoughts as original? Because if so, that’s fucked up.” I want to make sure no one yells at me, which is all I ever want, to never be yelled at.
Rumpus: I think it gives context for understanding those individual stories. Because ironically, however much you like to talk about yourself as not being smart, you have a deeper foundational education in the canon than a lot of readers.
Ortberg: Well, let’s be clear I genuinely mean that, and part of it is not just self-protection, but its own form of brag. When Maugham said he was the first of the second raters, essentially he was saying, I am amazing, and don’t critique me.
Rumpus: You talk about yourself as a person with some security in the world, but the worlds depicted in this book do not feel that way. Why was the fairy tale was of interest to you personally?
Ortberg: I’m safe and I’m secure and I’m doing well, but I’m also a human person who’s lived in the world. It’s not like every day I wake up on a bed of money, and then go enjoy my security for a couple of hours. There’s a grand tradition of rewriting fairy tales. G.K. Chesterton wrote this fabulous book called Orthodoxy. He has this whole chapter about the morality of fairyland, and there are very specific rules there that are never tapped into any sort of predictability. You never understand why it is that way, you just know if you open this door, you’re going to lose your husband, or if you eat from this table, you’re never going to be able to leave. It’s a very unstable, unsafe, emotionally fraught world—
Rumpus: I’m also curious about the fairy tale as a subject is a gendered subject—
Ortberg: Fairy tales are labeled by the nature of the protagonist. There will be entire subsets of fairy tales that are about the seventh son, or the third daughter, or whatever. There’s so many ways in which not just your gender but your relationship to your family, like whether you’re a daughter, whether you’re a son, whether you’re the oldest, whether you’re the third, whether you’re the seventh, some other significant number, shapes you. It shapes your role in a story, and it’s almost a job. The ways in which being a father in a fairy tale sets you up for one of several paths that you can be in, or being a stepmother, or being a mother, or being an older, envious sister.
Gender feels like a job that you can sort of apply for, and you could just as easily not get that job. It didn’t interest me to write about a world where gender was better, so much as —what if it was not tethered to the same things that we tether it to, what would be ways in which it would still be a trap and a fiction and a prison? Which is not to say that that is the only thing that gender is, but in the terms of things you can explore in a short story, that’s some serious grist for the mill. I was just trying to think of an imaginative way somebody else might be trapped by gender, in a world where they were not trapped in the same way that we are?
Rumpus: It’s a mistake to read too much into the fiction, but are you conscious of yourself on these pages?
Ortberg: I think there is rightly a sense that authors get asked too often, How does this track to your autobiography? The pushback against that can sometimes sort of make it sound like, “Look, I just work here at this factory…” As I was writing the book, I ended up having lots of thoughts and feelings about my own gender identity. Again, it’s not that you need to know this autobiographical information in order to appreciate the book, but that absolutely came up while I was writing it. I feel like I woke up one morning and I lost some of the ability to have gender that I always had had before. That was unsettling and destabilizing and frightening. It was exciting, but yeah.
Rumpus: Many people feel so comfortable inside their understanding of themselves that to hear someone articulate frustration with that, with their own understanding of themselves, is truly destabilizing.
Ortberg: I think just about everybody, regardless of their gender identity, has moments throughout their life where they bristle against gender roles or the expectations placed on them, or the assumptions made about them based on how their body is read.
Rumpus: Are you still a religious person, personally?
Ortberg: Not still in the sense that it has been lifelong or consistent or legible or that it makes a lot of sense, but yeah, religious is the word. Not spiritual, religious, in the sense that I like saying words that were already written down, but not religious in the sense that I’m good at it, or have a really strong sense of what reality is, or that everybody else ought to be interested in the same things that I’m interested in. It feels more to me like this is my inheritance, and I can have any relationship to it that I want, including total rejection.
Rumpus: There’s a trickster spirit inherent in the fairy tale. That particular register does not have as much to do with a contemporary or conventional understanding of morality.
Ortberg: If you look at the Christian Bible—again, that’s the story that I come from—you look at the Book of Job, and there’s this fascinating, open-ended question of what is the Satan? Because that’s literally the name of the character in the book. It’s called the Satan, not like the devil or Lucifer, Satan, like that’s his name. It’s just the Satan, and it means that he has a job. It’s your job. You bring evidence against humanity, and you are in God’s employ, and obviously we lost some of that over time. You remember the cartoons of the sheepdog and the wolf who would fight all day, and then they would end by swiping their punch cards? That’s been lost, and there’s just the sense of—it is this actual demonic, supernatural entity that lives somewhere in the ether and is out to get me. I think if you look at those stories, they are incredibly destabilized and all over the place, and that’s fantastic.
Rumpus: In these fairy tales is a universe that is random and tricky. You write with a real confidence, yet a lot of what you’re getting at in this book is the ways in which no one knows anything.
Ortberg: The confidence is in saying, This work is worth doing, not, I know what the work is, or Here’s how we all get it done.
Rumpus: How do you feel going into publication for this book?
Ortberg: I have been incredibly excited for a long time, and I would say really anxious. This is the first time I’ve done a lot of public appearances since I started really questioning my gender, or considering or starting hormone therapy. I’m just very self-conscious about my appearance. I’m anxious at the thought of being seen. I’m anxious with the thought of people saying, “You look different.” I’m anxious at the thought of people saying nothing. I feel both afraid to go on and afraid to go back, and I think it’s going to be fascinating and amazing to talk about all this, and have to leave my house and show up and put my name and my face to all this stuff. That’s because of the work that I’ve chosen to do. I’m not J.D. Salinger. I can’t write a book and hang out in Maine or wherever the fuck he lived.
Rumpus: The book feels very different to me than what people think of from you.
Ortberg: I’m not anxious in the sense that I’m worried that people will speak wrongly of me. That’s not it at all. I feel comfortable at this point saying, like, “This last year, I’ve been in gender therapy. I go to a transgender support group, and I have done a test drive of hormone therapy.” It’s certainly not a transgender experience, but beyond that, I don’t have requests to make of people. That’s real, that’s genuine, and it’s not because I want people to be confused and bewildered. It’s because I genuinely don’t have any requests to make yet. I think the anxiety is just the problem of being known. It’s not that I’m anxious people are going to say something wrong or hurtful. I believe I will be met by my peers and readers with the same love and affection and respect that I’m trying to show them.
Rumpus: The work kind of shows that you exist with some comfort in a state of uncertainty, or you’re comfortable articulating that we all kind of live in that state.
Ortberg: It took a while. It took a pretty rough year to get to this point. I could not have done this three months ago, or six months ago, but I think I’m here now and I’m really grateful.
Rumpus: The human brain is a crazy fucking thing, right?
Ortberg: Yeah, it’s wonderful.