Daniel Mallory Ortberg Talks The Merry Spinster, The Toast, and "Dear Prudence" in the Era of Trump and #MeToo

There's no mincing words: Daniel Mallory Ortberg is a legend. Whether you're talking about his role as cofounder of one of the greatest websites of all time — The Toast — or his ongoing role as Slate's legendary advice columnist, "Dear Prudence," or even his satirical bestseller Texts From Jane Eyre, it's hard to find a single aspect of modern culture in the last decade that Ortberg hasn't had a hand in shaping. And for his latest foray, The Merry Spinster: Tales of Everyday Horror — which hit bookshelves on March 13 — Ortberg tackles a whole new genre: fairy tales.

POPSUGAR caught up with Ortberg by phone, and the conversation — which encompasses not just The Merry Spinster but also The Toast's future prospects and what it's like being Prudie in the era of #MeToo and Trump — appears in full below.

POPSUGAR: I was taken by this quote on the back cover of the book. It says you have a "keen sense of feminist mischief," which I'm totally in agreement with. What role do you think that kind of approach to the world takes in 2018?

Daniel Mallory Ortberg: I love feminism, and I love mischief, so those two things definitely feel super appropriate. Yeah, mischief feels important to me. Change feels important to me. Oddness feels important to me. Distress feels important to me. Yeah, I'm never as good at explaining what went into the thought process of doing something or why I might have done something as I am at doing it. So I always feel like it's this cliché — like asking a really wonderful athlete afterwards how they did something. It's just like, "I did it. I tried really hard, and I did it." Now I'm comparing myself to a professional athlete [laughter]. Sure, let's do that. It's just this sense of, "Yes, this is what I do, this is the work that I'm interested in, and these are the stories I am interested in telling." And I think, ultimately, that both feminism and mischief are still pretty glorious.

PS: What was the inspiration behind The Merry Spinster?

DMO: So, I was thinking about what I wanted to do for my second book for a while and had a sense that I wanted to do something that was different and challenging — my first book sold well, so I knew there was a really good chance that I would be able to at least sell a proposal for a second book based on whatever I wanted to do next. That doesn't always happen; if a first book does well, a second book might not . . . so I felt like this was my one chance to really go for it, to do something a little different. I really wanted to write fiction but didn't want to write a novel, and I knew I wanted to do something that was weird, a little religious, and a little upsetting.

PS: Based on that, I gotta ask: Were you thinking of doing something similar to "Children's Stories Made Horrific"? Or is the book completely separate from your work in The Toast?

DMO: It's similar in the sense that there are a handful of stories that originated in that series, but certainly they're not all children's stories, and it's not all just making something as bleak as possible. It's not the subtitle or the official series, and this isn't the book version of the series, though they're obviously inspired a lot by that. It's not all horror . . . I mean, there's horror, obviously, but it's not all horror.

PS: So what would you say your biggest influences were when you were writing the book?

DMO: So there's some obvious influences, especially in "The Wedding Party." Shirley Jackson, I think, comes through loud and clear on the page. Obviously, the fact that I read The Pilgrim's Progress and the Bible a lot as a child, that leads to there being a lot of religious language in there, a lot of biblical language — and even just biblical manners of speech, in certain sections. I think there's a lot of Nancy Mitford in this, especially in the dialogue in "The Wedding Party" and in "The Merry Spinster."

And certainly — especially in the sort of self-pitying or melancholy bits — there's a little bit of Hans Christian Andersen. Like, what if a candle was sad? I love that guy. He was such a big, gay bummer — and I think that's so wonderful, and I love the fact that he basically invented Pixar 100 years before Toy Story. But he was way sadder, and it was way more than just toys.

What if literally every inanimate object and tree you've ever come in contact with was alive and full of despair and full of unrequited longing for a fire iron that it could never get close to? Wouldn't that be a lot? And it's like, "Yes. It would. It would be a lot, Hans Christian Andersen."

PS: He was certainly a prophet — in oh so many ways. Speaking of a lot, what is it like giving advice [as "Dear Prudence"] in the era of #MeToo and Trump with all of this turmoil?

DMO: A lot of that certainly comes up, both in the column and in the podcast, and I think it's important and necessary. Sometimes it's a lot to go through, hearing a lot of traumatizing and painful stories. But I feel grateful for a chance to get to be helpful and talk about things that feel important. It's also deeply moving (and, of course, painful) to hear from so many different people who are trying to figure out how to make sense of their own lives in the wake of this enormous pain — and the pain derived from the response of others who are normalizing or dismissing what's happening. How do you figure out how to speak clearly and truthfully if you're in an environment where no one has responded appropriately to the truth before? That's really hard to do.

PS: Do you think as a whole you're looking at everything a little bit differently now? And are the questions that you're getting more specific and pointed? And do you think the tone of the column has changed?

DMO: I think there's been a lot of this going on for a long time. I don't know that I would say it feels like there's been a huge shift in the tenor of the questions that I get, but it's certainly there. I was getting questions about stuff like this before and dealing with it in much the same way, but certainly there does seem to be a shift. Even just with people writing in and kind of re-evaluating things that either they have experienced or that they have done or said in the past. I think one of the hardest positions to be in is half-realizing something — that sort of dim, dawning awareness of, "Oh, maybe that was not right." And just getting to be part of it and trying to push and encourage in those moments, saying, "Yes, that's the beginning. But there's more."

I'm sure from the inside I'm not as good at detecting change as somebody else on the outside might be, but I'm certainly in a very different position than when I started the job. I have in some ways developed a little bit more comfort with the ways in which I inhabit the "Dear Prudence" role. I'm sure there have been some changes, a little bit less of a sense of, "All right, it's my first day on the job. Got to prove myself," and more of a, "Oh yes, I'm a seasoned, old Navy veteran friend who walks atop the mizzenmast." I don't know what a mizzenmast is, but I think you can walk atop it.

PS: As we walk along the mizzenmast, let's take the plunge: do you miss The Toast?

DMO: Hell, yes.

PS: Would you ever consider doing something along those lines ever again?

DMO: If we could afford to hire five more people and I was not in charge of the day-to-day operations, yes, absolutely. But at that point it's very different from The Toast. So, yeah. I don't know if there will be anything like that again in my future. There are still a lot of other types of writing that I'm really interested in trying to get to do, but yeah. If there's still an internet in five years and I'm still alive and there's still people to look at things and somebody wanted to give us five amazing employees and the money . . . I feel like I could try to talk Nicole into getting the band back together. But it's like the Eagles. She's going to be hard to win over.

PS: Finally, if you could give one piece of advice — nah, let's call it a recommendation — if you could give one recommendation to POPSUGAR readers (as Daniel and not as Prudie), what would it be?

DMO: I think everybody should put their phone in the trunk of their car when they get in their car. I think that's the kind of advice I kind of want to give to myself. We should all be better about not checking our phones while we're driving, even at stoplights. I need to do that. I want to do that. And we should all drive more safely. Which feels very ridiculous and like a cop-out. But I am genuinely like, "I should remember that I'm piloting a very giant steel machine." Even though it's something that I do every day and have since I was 16. Because it's a giant steel machine. I don't know if you knew this, but it is very dangerous this thing that I do all the time. Only while driving, by the way — not suggesting that I shouldn't run around the house watching YouTube tutorials on my phone. But yeah, everybody should throw their phone in the trunk of their car when they get in.