Mallory Ortberg: Q&A

This article appears in our 2017 Spring issue, Family Values. Subscribe today!

Since becoming the latest arbiter of life decisions at Slate’s Dear Prudence column about a year ago, hilarious writer, founder of the beloved and now-defunct feminist humor website The Toast, and unbelievably empathetic human Mallory Ortberg has been providing sensible, compassionate, and amusing feminist advice to the masses. In short form and with several installations a week, each Dear Prudence column is infused with Ortberg’s characteristic humor and warmth, and she’s breathed new life into one of today’s most widely-read advice columns with a podcast and a distinctive style. Crucially (and refreshingly), Ortberg’s answers are always written with an awareness of the power dynamics in our families, our personal relationships, and our daily lives. A few days before Christmas, I caught up with her about setting boundaries with family, why it’s hard for her to answer questions about weddings, and striking the right balance between entertainment and meaningful advice.

How did it come about that you took over the Dear Prudence column?

Gosh, that was a little over a year ago now. I got an email totally out of the blue from Julia Turner, who’s the editor-in-chief [at Slate], which was super surreal. I had not been in any way trying to build a career as an advice columnist. It was like being asked to be Santa Claus, basically, or if you wanted to audition for Santa Claus.

So what kind of stuff did you do to prepare for it?

What they had us all do was just write a couple sample columns, so they gave me a set of ten questions from a long-ago column, and because I was so obsessed with the column, I already knew them all. So it was really exciting to be like, “Yes! I know the answer!”—but having to come up with something totally different, trying to find the right balance between making jokes and trying to be useful and finding a good voice for it.

So it sounds like you were a big fan of the column before taking it over, and you were really familiar with it.

Yeah. I mean, I love all advice columns. I wish there just like an IV drip I could hook myself up to, to read advice columns. And the one weird, sad part about being Dear Prudence is now, I’m kind of like one of the only people in the world who cannot read Dear Prudence. Because I know what’s happening.

Since you’ve been a fan of Dear Prudence for a while, do you see your tenure in the column as being part of the same style of advice column, or were there certain things that you wanted to be different now that you’re running the column? Or different priorities that you think you have in any way?

Well, there’s been now at least four, possibly five—if I’m not mistaken—incarnations of Dear Prudence. The column itself goes way back to the late ’90s. I’m inclined to think of it more as like a Doctor Who situation where there’s just a new incarnation every couple of years. I tend to think each person who takes up the Dear Prudence mantle is a totally different person with wildly different life experiences, different goals, different ways in which they’re situated in life. And I think that’s part of the fun of letting each new person add stuff to the column.

It feels to me like recently there’s been kind of a renewed interest in the advice column. It seems like there are a lot more of them popping up at various publications or people kind of experimenting with the genre in different ways.

Yeah, yeah! I mean, it’s been what? Only the last five years that Dear Sugar publicly identified herself, and that was huge. And there’s Ask Polly over at The Cut, and that’s fantastic. I think there’s been interest in advice columns for a really long time, but I think it’s fabulous there’s more. Saeed Jones is doing one over at BuzzFeed now, which is fabulous. It’s cool to see more men, more queer people and people of color getting into the advice game too. The stereotype, historically, has been sort of like a prim white lady, and it’s kind of cool to see that changing.

Yeah, and also interestingly, it seems like a lot of the older advice columns were actually prim white men posing as prim white ladies giving advice.

If you go back far enough, it’s kind of remarkable. It’s sort of like the flip side of how lady novelists used to write under male pseudonyms. I actually kind of love that back in the 1700s, you had all these guys writing advice columns under female pseudonyms and all these women writing novels under male pseudonyms. That’s kind of fabulous.

So what kind of role do you feel like the advice column is playing for people at this moment?

I think people love rubbernecking, and they love arguing over the right thing for someone else to do. It’s a wonderful way to work out common problems, as well as experience the relief of, “Oh, at least that’s not happening to me.” It’s like social grooming. It’s like picking lice off of each other, and that’s sort of a wonderful human tradition. And I think it’s just easier [now] because of the Internet. You can publish them more often; you can get more questions; it’s just ease of access.

Are there any particular things that you feel like you want readers to be taking away from your column or a certain philosophy that you have for approaching their questions?

You know, I think certainly something that comes up often is this question of, “How do I get what I want without asking for it?” And I think if there’s nothing else, I hope that everyone takes away from this column that you can’t get what you want without asking for it. You have to have the conversation. If you can’t bring yourself to ask for it, I don’t know what to tell you. And also that you can handle an uncomfortable conversation. Often, there’s this sense of, “If I have to have this conversation with my partner or a parent, and it’s kind of uncomfortable, or there’s a stilted silence, or they don’t say yes right away, that will be the end.” And it’s like, no, that’s the first conversation you will have of many.

And then there’s other people, kind of on the opposite spectrum, who have really stunning tales of people who have just treated them horribly—often family members, often parents—and there’s sort of this question of, “Do I owe them continued contact for the rest of my life even though they continue to say and do horrible and abusive and deeply cruel things to me?” No. No. If you feel like you would prefer not to be in contact with someone who is repeatedly abusive to you, that’s okay. You can do that. You don’t owe someone a relationship if they can’t meet the basic criteria of respect and kindness, politeness even.

Yeah, a lot of people write in, and they say, “I’m thinking about cutting off contact with this person.” And a lot of the time, it’s like, “Should I do that?” And then, other times it’s like, “I want to. Can I do that? Am I allowed to?” And it seems like the advice you give is usually like, “You have every right to do that, but I really don’t recommend it unless it’s sort of the last resort, really cutting off a relationship with people.” So I was wondering where you think that line is drawn.

You know, I’m really inclined to give permission freely but to not make a ruling one way or the other. I know a lot of people in my own life and through the column who have really complicated relationships with family of origin. If the idea of cutting off your parent feels terrible, distressing, isolating, and like it would bring you great pain, you don’t have to do it. You’re allowed to figure out the boundaries that you need to keep up so that you maybe have limited contact but still some. I would not, I think, tell someone—unless their life was in danger—”You have to cut off your parent,” if they’ve decided it’s worth having some limited contact.

I try to figure out what the letter-writer needs, what they want, what would be a best-case scenario, what would be a worst-case scenario, how could they interact with the parent or the person in question in a way that would maybe minimize the pain. I always wanna be careful because I have not had to cut contact with a family member. So I don’t wanna tell someone that really casually, like, “Hey! They sound awful. You should just cut them out of your life.” I want to listen to what it is that they want.

I think a lot of those questions and answers seem to have really big feminist implications. ‘Cause you’re helping people to figure out negotiating boundaries, or what do I owe other people, or when am I allowed to say “no.” And I think a lot of those questions have been, and still are, big issues for women in negotiating their relationships.

Absolutely, and also for queer people and for trans people. Trying to distinguish between conflict and abuse can be a really thorny and complicated question, especially if you or the other person has experienced abuse in the past. Trying to figure out where’s the distinction: What’s harming me versus what’s just uncomfortable? It’s just a lifelong, difficult question. I think it’s really important for a lot of people to remember that there is a basic standard of decency that you can expect from other people, and if they can’t meet that—even if they are related to you; even if they gave birth to you—you have the right to ask yourself, “Do I want this person to be in regular contact with me?”

Do you feel like people are often asking for permission rather than actually asking for advice?

I’ll occasionally get a letter from a person who is beginning to realize that they are causing harm. And there’s layers of harm that don’t meet the criteria of abuse, right? A lot of the questions I get are not about abusive situations so much as they are about painful situations where two people see a situation really differently, and it’s sort of an ongoing disagreement.

How many letters do you get in a week, usually?

I would say on any given week, the inbox gets between 50 and 100, and the live chat probably gets about the same. So probably between 200 and 300, but that’s a total guess. More than I could ever answer, certainly.

Are you answering questions just from that week, or do you kind of add them to a pool and then pick depending on what feels interesting that week?

Generally, it’s from that week. Every once in a while, if I have a question that sort of sits with me for a while, I’ll pull it back out of the mailbag, and I’ll try to take a whack at it.

How do you choose which questions to answer?

I look for stuff that has a clear thing I can do to be helpful. Is this both something that I think a lot of readers would relate to and something different? I don’t just wanna answer the same five questions every week. Do I feel like I have something useful to say? And then just also, did I enjoy reading it? Did I find it interesting, thought-provoking, whatever? Those are sort of the criteria I’m looking for.

I have a hard time answering questions about wedding etiquette just because my first inclination is always just, “I think you should care less about this,” which is not necessarily the most helpful attitude. So I’ll either have to figure out a way to find a more meaningful issue underneath it or just say I’m not gonna answer this one.

I loved the recent question about the bridesmaids’ sleeves. So many people in the chat were like, “No, you’re wrong. It’s her right to decide, and she’s paying for the dresses. So they should just wear whatever she picks.” But your answer was like, “Right, but if they’re gonna be unhappy, isn’t that more important? Do you really care that much about the sleeves at the expense of the enjoyment of all your friends at your wedding?”

Yeah, we got a lot of responses to that. To begin with, I think it’s sort of ridiculous that there’s a day where you pick what your friends wear. You know what I mean? You’re not the military. They’re not in dress uniform. I think it’s kind of bananas that there’s even this expectation that when a person gets married, if there’s a bride involved, the bride gets to choose what six other women wear to the ceremony. That’s weird to me! It should just be like, “Wear something nice that you like.”

But it’s a tradition, and there’s also this idea that if you have money you can control things. And I think that’s kind of an illusion. I think money does not actually allow you to control as much as you want it to. If you’re paying for their bridesmaids’ dresses, and you’re asking for sleeves, you’re hardly asking them to wear something really outrageous. Sleeves aren’t that bad. But the question is, “How much of your life do you wanna spend fighting about the sleeves?”

I don’t wanna make it sound like I think that weddings are stupid or that people who have conflict around weddings are all wasting their time. I get it. It involves money, it involves romance and your personal relationship, it involves your relationship with your family, expectations, what do you owe other people, what do they owe you, who’s paying for it, how’s your financial situation? It’s a real cluster of a lot of different issues, and there’s this real question of like, is the best thing to get my way? Does the person who’s spending the most money have the right to dictate other people’s choices? How much compromise is acceptable? What do I owe the people around me versus what do I owe myself? What traditions are meaningful to me, and which ones feel constricting? It brings up a lot.

I’ve seen people mention fake questions. Do you feel like you know? Do a lot of people try to send you fake questions; is that something you can pick out?

Every once in a while—it’s kind of funny—people would send in works of classic literature disguised as questions, and it was always really fun to try to spot “Brideshead Revisited” or something. I’m not especially worried. If a fake letter occasionally slips in, it’s probably because something about it seems real to me, like this is a position a person could find themselves in. So even if the letter writer is not a real person, it’s not a waste of time.

I’m remembering the one letter that someone wrote in that was like, “My friend is having a wedding where we’re all required to go topless at the reception.”

Yes! It was awesome!

And you answered the question, and you were like, “I really don’t believe this question is real, but let’s go through it.” And then there were some comments that were like, “I can’t believe you answered this. This is an insult to all the people who try really hard to write good fake questions every week.” And I loved that comment because it sort of hinted at this whole world of Dear Prudence fandom that could just be simmering under the surface.

Yes, like “You can do better than this. Just because you saw the phrase ‘topless bridesmaids,’ I can’t believe you’d fall for something so cheap.” I love that, actually. That’s beautiful. And I wanna apologize to all the subtly-crafted fake letters out there that maybe got missed that week. You gotta go big or go home, man. If you wanna try to get your fake letter in, cut somebody’s head off, get a topless wedding, really swing for the fences.

Since taking this over, do you feel like it takes any kind of emotional toll on you?

Nope. No, it’s funny. I do get asked this question occasionally. And I always have a super clear answer to it, which is, absolutely not. I get paid to do this. I spend as much time as I need to. And when I’m working, I’m fully engaged, I’m fully present, I’m trying to make sure that I’m answering the person as best I can and giving them the full weight of my emotional and mental attention. And then when I’m done for the day, I don’t worry about it. I know everyone who writes in is an adult who’s capable of making their own decisions. I’m not responsible for their choices. I have a really clearly articulated sense of boundaries when it comes to this job. I get paid really well for it. So the emotional labor question does not come into play.

And is it a full-time job? How many hours a week do you spend?

Mondays are given over to the live chat and prepping for the podcast recording. I usually record the podcast once a week. And then Tuesdays, we’ll talk about possible future guests and going over ad work. Wednesdays, I’m usually doing edits on the column. Generally that leaves Thursday and Friday free for my other work. I’m finishing my book right now, and I also occasionally write freelance. There are always questions that come in. There’s always going back and forth with my editor about how to handle a particular question. I’m always looking for new guests to be on the show and trying to figure out what the schedule looks like going forward. There’s a lot of people who would like some Prudence.

What is your new book about? When is it due out?

It’s a collection of short stories in the vein of the Children’s Stories Made Horrific series that I used to do on The Toast. Sort of in the vein of Shirley Jackson, Flannery O’Connor, creepy, unsettling, that sort of thing. I’m supposed to be done in March. So it’s probably gonna be out in late fall of 2017.

As we’re talking now, Christmas is in a couple days, and I’ve noticed you’ve been answering a lot of questions from people who are writing in and saying like, “Christmas and the holidays are really miserable with my family. Am I allowed to skip it?” And you’ve been very confidently telling them that they absolutely are welcome to skip the holidays any time they want.

First of all, shout out to everybody who doesn’t celebrate Christmas and yet has to listen to a lot of questions about how anxious other people feel about Christmas every year. But yeah, there’s often a lot of talk of, “If you don’t come, you’re gonna ruin the holidays.” Whenever somebody says this is gonna ruin Christmas, unless you’re talking about an actual meteor striking the Earth, it’s not. If you spend one Christmas without your family, they’re not gonna die. I think if everybody buys into this idea that it’s unacceptable to miss Christmas, that it’s better to be miserable if we’re fighting and not getting along than it would be to just go do something you enjoy, like taking yourself out to a movie and hanging out with friends, I just think it’s silly.

I’ve noticed that you often recommend therapy in your answers to people. Could you talk a little bit about how you feel like that fits in with the advice column?

I try not to just say it to everybody, although I do think in general, most of us could benefit from some form of therapy at some point in our lives. I think it’s useful. I think if we thought of it as like, “Hey, it’s nice to sometimes go to the gym or take a walk so that your body can experience use.” It’s the same thing for your mind and your psyche. Oftentimes, if someone is going through a point of crisis, I think it can be really helpful, especially for someone who’s a little reluctant to go to therapy, to go with a specific point of time in mind. Like, if you’re thinking about redefining the parameters of your relationship with your mother, for example, go to therapy for six months and see. And I think that can be sometimes better than just feeling like, “I’m really messed up. I need to go to therapy for an indefinite period of time until I guess I feel better.”

I was wondering how your own personal experiences or relationships with family inform the advice you give. Basically, I’m wondering how you got to be so wise about all of these things that you advise people about.

I have a really good relationship with my family of origin. I’ve actually had most of them on the show at this point, which has been really fun. But we’ve also experienced plenty of conflict. I was a real butthead when I was a teenager and in a lot of my twenties. Generally, I think I got to see my parents model a really healthy partnership. They made it really clear that conflict is not a thing to be avoided, but it’s often the best route to intimacy. There was not a real sense that certain topics were off-limits, or that it’s not OK for someone to experience certain feelings. When I came out, they were really wonderful, so that was meaningful for us. I owe a lot of the good stuff [in the approach that I take to the column] to my family, my parents especially. I’m pretty grateful to them for it.

What do you feel like are some of the things that you’ve learned from doing the column or since taking it over?

The challenge for me in the column is always to find the balance between usefulness and entertainment, finding ways to find humor that doesn’t necessarily come at the expense of the letter writer. I do think that there are times when a particular letter writer could use some light joshing in order to be sort of shown, “Hey, your position isn’t actually so serious as you think it is. It’s OK to laugh about this.” I was primarily a comedy writer before Dear Prudence. I’m not doing Dear Prudence as a comedian. The goal of this is not just to mock. I’ve really learned a lot trying to strike that balance as Dear Prudence, and that’s very different from a lot of my other writing.

If you could give just three pieces of general advice, what do you think are some of the most important lessons that you would want to give someone?

I would say one pretty big thing is you don’t get what you want unless you ask for it. And that sometimes it feels like, if someone really knows us, they will be able to anticipate our needs. I don’t think that that’s true. I think that even if someone knows you really well, they can’t anticipate your needs unless you state them.

The other would be there’s almost no conversation that is unacceptable to have as long as you go into it with the awareness that you can ask for something, and you might not get it. You can state a feeling, and someone else might disagree. But there’s not a lot of conversations that are impossible. You don’t have to pretend not to want something that you do because you feel like it would not be okay to have that conversation.

And then another one is just to think really carefully about anger and power. I think a lot of the letters that I get come from a misuse of anger and power dynamics. And often, that’s with kids, like an adult who has an anger problem. That also happens in terms of other power differentials, whether that’s social, financial, gender-based, sexuality-based, racial. The difference, I think, between anger and rage and abuse is really significant. It’s OK to say, “I’m really mad. I’m not quite sure how to express this.” Instead of, “You’re a terrible person. You made me do this. You’re always like this.” If someone feels like they can’t get angry unless they are murder-level angry, they will wait and say really terrible things, and that’s not helpful.