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Dear Mallory

“It was like being asked if I wanted to be Santa Claus, or happiness.” The new Prudence tells all.

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

If you’re younger than 35 and you spend a lot of time on the clever parts of the Internet, you already know Mallory Ortberg. She’s a founder and editor of the Toast, a brilliant, hard-to-describe site that mixes humor, feminism, and a willingness to pursue oddball interests. She wrote the best-selling Texts From Jane Eyre, which imagines smartphone conversations between literary figures. And she’s a constant and hilarious presence on Twitter. She’s 28, she lives in Oakland, California, with her dog, and this week she’s taking over Slate’s Dear Prudence column. She answered some questions for us by email.

Gabriel Roth: What did you say when Slate asked you to consider becoming Dear Prudence? 

Mallory Ortberg: I think I asked Julia [Turner, Slate’s editor in chief,] if she was my friend Nicole messing with me, and that if she was, I was never going to forgive her. It was like being asked if I wanted to be Santa Claus, or happiness, or Calliope, the muse of poetry. I was astonished and so thrilled. It wasn’t even something I had thought to want, and then the moment it was suggested to me, I was consumed by the wanting of it. I’m so glad to be here. 

Is Prudie a character you’ll be inhabiting? If so, what’s she like? How does she differ from you? 

I think Prudie is a bit more like Doctor Who than James Bond—each regeneration has unique characteristics, but there’s a common thread of Prudence-ness that binds us all. I can’t imagine I’ll be quite as freewheeling and whimsical as Prudence as I am on the Toast. Let’s say she’s 30 percent less theatrical and 15 percent more open-minded than my standard setting. If I were to compare my various online personae to the wives of Henry VIII, my self-as-Prudence would be Anne of Cleves: sensible, practical, pragmatic. She’s not flashy like Catherine Howard, doesn’t know any French like Anne Boleyn, but she knows how to see things through, and would never have an affair with Thomas Culpeper. She is also a homeowner, which is nothing to sneeze at.

Or, if she were to have an affair with Thomas Culpeper, she certainly wouldn’t leave a paper trail. See what I mean? Practical. 

Do you give a lot of advice in your personal life? Do people come to you for advice?

I think advice-asking and the subsequent advice-giving is a very particular kind of dance. Sometimes someone already knows what they’re planning on doing and all they want from you is the chance to talk it out. Sometimes someone needs—and wants!—a swift kick in the spine to get going. (I do not advocate spine-kicking. I speak in metaphor.) You have to gauge what kind of answer someone’s angling for, especially if you are friends in real life and they do not actually want you to tell them you think they’ve made a mess of things. The best wisdom is, I think, knowing just how much truth someone wants to hear, and adjusting their dosage accordingly. 

I don’t think I’m asked for advice much in my personal life, although I do get a fair amount of professional requests from younger people looking to start their own businesses or become writers themselves. 

What’s the best piece of advice you’ve ever given? The worst?

The best advice I have ever given was telling people to read Walter Miller’s A Canticle for Leibowitz. It is criminally under-read and everyone who has read it at my request has been made happier for it. It is the only advice I have ever given to be met with universal approval, the only advice I am confident will work for everyone. If you read it and regret it, please address your complaints to me directly, and I will spend my life trying to make amends to you and your children.

The worst advice—or, let’s say, not the worst but the most misguidedI’ve ever received came from a very important man in his office in Connecticut. (I did not take it.)

Do you have any favorite questions from Emily Yoffe’s tenure as Prudie? Can you think of anywhere you’d give a very different answer from Emily’s?

Oh, there’s so many to choose from! Who can forget the sandwich-waggler? The gay twin brother-lovers? The woman who was being slowly poisoned by her mother-in-law and wanted to know if she should say something about it? [Part onepart two] I cannot choose. Do not ask me. They are all precious jewels that have brightened many a dark lunch hour of mine.

As for the second part, I think that Emily’s answers stand on their own! It’s no fair trying to revisit old scenarios and play armchair advice columnist. I’ll have my own questions to answer soon enough.

What would you say to a longtime Prudie fan who is terrified of change? 

Oh, change is the worst, especially when you don’t see it coming. I wouldn’t blame someone in the least for hating the woman who has slightly altered their Thursday morning ritual. If you find something to like in my tenure, so much the better; if you don’t, I will not be Prudence forever and perhaps you will like my successor. 

Also, Emily is joining the staff of the Atlantic, so she is not leaving you forever!

Also also, if you object on moral grounds to reading advice from a 28-year-old blogger (and what right-thinking person wouldn’t), consider joining the Elder Wisdom Circle, which is a very charming nonprofit that connects advice-seekers with “volunteer grandparents” aged 60 to 105, who “share their knowledge, insight and wisdom … [in] a free and personalized e-mail response.” Alternately, wait for time to exact its relentless tithe on me. I will grow old and die like everyone else. 

What would you say to a longtime Mallory fan who thought you were sort of kidding about how much you love Dear Prudence?

I wasn’t kidding! Who doesn’t like to read about other people’s problems? And the only thing more fun than agreeing with an advice columnist’s answer is disagreeing with it loudly and often. “You won’t believe what Dear Prudence said to this guy” is one of the most pleasant sentences I can think of. 

What does the advice column, as a form, have going for it? What made you want to work in that form? 

It distracts one from one’s own problems! There’s nothing like it. You get to feel superior, horrified, titillated, prurient, sensible, and sympathetic all without leaving your desk. It’s fascinating! And, I think, it can be genuinely helpful to both writer and readers—seeing people ask different variations on How do I tell someone I love something I think will hurt them or Should I speak up for myself or Have I been an absolute ass, because I’m afraid that I might have been an ass has made me, at least, reconsider how I set boundaries with people both at work and in my private life, how to handle criticism without dismissing it out of hand or letting it overwhelm me, and keeping my cat indoors. 

I read my wife’s email and found out she can only orgasm with me when we’re on vacation. (NB: This is a hypothetical—I would never read my wife’s email.) What should I do?

Oh, I entirely see what you did there, Gabe. You should end things with your racist sugar daddy before your stepmother finds out and insists on wearing her old wedding dress to the ceremony when you get married.