Advice is so much more enjoyable to give than it is to receive that its long flourishing as a genre—from the conduct books and periodicals of the seventeenth and eighteenth centuries to the current plethora of columns, livechats, and podcasts—could seem mysterious. Of course, watching other people being told what to do might be the most fun of all, which surely helps account for the enduring appeal of the advice column, and explains why living online seems only to enhance that appeal. Yet the genre is also unusual in the opportunities it offers a writer, in its combination of surprise and repetition, of intimate address and public service, of sincerity and entertainment—and in its total reliance on the voice and character of the advice-giver. That's why, despite the apparent simplicity of the task, and despite the democratizing drive of the Internet, there are still only a few true artists of the form, and they tend to draw an ardent following.

Heather Havrilesky, whose Ask Polly columns (for New York magazine and The Awl) have been collected in a new book, How to Be a Person in the World, regularly puts her own life on the page in the service of her detailed, exacting counsel. She answers her readers with enough gusto and compassion to outdo the ladies' journal that once promised questions would be "weekly answered with all the zeal and softness becoming to the Sex." Dan Savage has enthusiastically consoled and chastised the lovelorn and the sexually confused for decades via Savage Love, his column in The Stranger, and its audio successor, the Savage Lovecast. Mallory Ortberg recently took over Slate's Dear Prudie slot, where she braves a flood of requests to adjudicate awkward conflicts of taste, manners, and ethics. And Kristin Dombek, who has just published her first book, The Selfishness of Others, braves readers' existential dilemmas in occasional, exceptionally thoughtful columns for n+1.

Recently, the four of them got together on a 1990s-style conference call to discuss the advice-column form, the value of lying, and how to avoid becoming a role model.

Kristin Dombek: How do you choose the letters you answer?

Mallory Ortberg: There are only so many themes of human pain. There's a ton of "my friend's wedding is coming up and I'm mad at her." I try to look for what's unusual; or something that is universal enough that it's okay that it's like others. Something that a lot of people could relate to, or something that everyone would be like, "Ah! How could you let this happen!"

Heather Havrilesky: Bad behavior letters are kind of the "Dear Prudence" signature in a lot of ways. Bad behavior dilemmas. It's kind of the new "Dear Abby" in that way.

MO: Yes.

HH: It's got a little Real Housewives in the DNA.

Lidija Haas: Do you think an advice column has the role of social cop, or do you think it's supposed to be more creative than that?

MO: People associate "Dear Prudence" with non-sexual relationship boundaries: My coworker—or my in-law, my sister, my mother, my neighbor—is doing this thing that I consider super-outrageous. Am I allowed to be a jerk to them?

HH: That would scare me. If I had to answer questions about where do I draw the boundary, what are healthy boundaries . . . I would really flounder. That's not my specialty, people asking me, "Dare I encroach?" It depends on my mood, but I'm usually tempted to encroach too much. The questions I get are more, "Hey, I'm really trying to figure out what sort of life to lead, and what sort of career to have, and I feel generally empty."

Dan Savage: Every sex act and every sex toy and every position has a Wiki page now. All that's left for sex-advice columnists is situational ethics.

HH: I've gotten questions that said, "I sent this to Dan Savage too, but I don't know if he's gonna answer it." I want to say, "Keep waiting for him because he's the one, you need him."

DS: He's the one with the pile of permission slips. "Yes, you can have a three-way."

KD: When I started reading "Savage Love," there weren't Wiki pages on everything. I was coming out of a very conservative evangelical Christianity, and I read your column to find the opposite of a policeman. It made me realize all the things that might be OK.

DS: I've been writing "Savage Love" for twenty-five years—before Google and after Google. Before Google, people needed to know where the swinger club was, how to get a fist in their ass, what a butt plug was, and how a cock ring worked, and those were easy columns to write, so I could drink a lot more then. And now the questions are all really hard. I'm very resentful of Google and Wiki.

MO: I've gotten so many more questions than I thought I would about whether or not it's OK to kill your neighbor's dog. Including some that have just straight up been "I killed my neighbor's dog, do I have to tell them?"

DS: Wow.

MO: My one goal was to never talk about dogs in an advice column. As soon as you say anything about dogs, you'll get a thousand letters. "If you don't personally give birth to your own dog, and feed it out of your mouth, you're Hitler."

LH: Do you think that people send existential questions to columnists who are known first as writers rather than as an authority on something?

HH: The kinds of letters you already answer are the kinds of letters you tend to get. If you write about a dog you're going to get a lot of letters about dogs. The second I write about someone cheating on their wife, I get fifteen thousand more letters saying, "I really should cheat on my wife, right?" I used to read Dan's stuff when I was in my 20s. I never had any ambition to become an advice columnist, but the writing itself was so inspiring. I would read his column and think, Jesus, you can really do whatever the fuck you want, with writing. You can use your own voice, you can say exactly what you want to say, and you can make jokes about things that other people don't make jokes about. That's the shadow lesson of advice columns in some ways. The subject matter is everything under the sun, and you can do with it whatever you want, and half the people who read them are people who are also looking for permission not just to kill their neighbor's dog, but for permission—whether it's to write or to express themselves in another way. To show the full force of their personality, in their day-to-day lives.

DS: To have a threeway with the neighbor's dog.

HH: That too.

LH: I suspect that a lot of people who read advice just desperately want to have their own advice column. Do you get a huge amount of mail from people asking, "How do I become you?"

DS: Absolutely! Weekly. How did you get an advice column? What qualifications do you need? I have to patiently explain to them that it's always an accident, and you don't need any qualifications.

MO: Nobody asks me that! It sounds like a tough question.

DS: Give it time. It will come.

LH: Heather, do you think you get different questions now that you've moved from The Awl to New York?

HH: The Awl had its own strange little audience. New York is a wider swath of humanity. Reading the letters Kristin gets, I feel a little bit nostalgic for The Awl because they're more like the letters that I got at The Awl. Existential treatises. When I wrote advice on my blog, people wrote me long, weird letters about all kinds of shit. You almost want to write your own insane letter and publish it so that people will start sending you really crazy stuff. The letter can be half the fun of the whole thing. If you have a great letter to launch off of, it's inspiring. Kristin, do you feel like you encourage weirdness in your letter writers?

KD: I actually wish I got more practical letters, because the weird ones take me forever to respond to. I'll spend a month or two working on a response. When I first started the column, the email that we sent out invited long stories. And the early people who wrote in were writers. They created a model question.

DS: You would take a couple of months to reply? How are they not dead or problem-solved by the time they get their response?

KD: They're not any of them solvable problems.

DS: Oh.

KD: I would love to get more of those. For some reason, the readers of n+1 don't write in with solvable problems.

MO: The majority of the questions that I get are not from hyper-ambitious, bitter strivers in New York. I get questions from people who do not spend a lot of time online. For better, and also for worse. I get fewer questions of the "how can I be a person, how do I deal with the concept of bitterness" sort, and more like: "This bitch did this thing to me. What do I do?" But am I the only one who inherited their column? All of yours started with you guys, right?

DS, HH, KD: Yeah

MO: "Dear Prudence" has been around for a really long time. There is a house style. Prudence is never going to be like "Dear Sugar," with an answer that's a long essay. It is straightforward advice about a particular situation. Answer the basic question, move on. It's more about volume, and that kind of works for me. And I'm done talking.

DS: People write in, "We're at this impasse and what do we do?" Ninety percent of those impasses are not passable. I call them the "unscrew the pooch" questions, when people have so thoroughly screwed the pooch, and they just want you to unscrew that fucking pooch for them, and there's no unscrewing the pooch, no un-shitting the bed, and you just have to cut your losses, which is not usually what people want to hear. In most cases, you are just the bearer of bad news, like, "Wow you really are a terrible person."

HH: I got a letter from a woman who put off breaking up with her boyfriend for a long time, and then cheated on him, and then he got cancer. She had wanted to break up with him, all along. She kept telling me, "I wanted to break up with him, I really was about to break up with him, and then he found out he had a year to live." Not only did you screw the pooch, but now you're saying, "Can I just bail on this?" Now?

DS: I've gotten that exact question. "My partner's dying, but I wanted to divorce them, and I don't think I can hack the next six months." You can hack the next six months of anything, and then you get to be the star of the funeral, and you get brownie points in heaven. I got a question once from a guy whose girlfriend was dying of cancer and she wanted to get married and he didn't. She had six or seven months, maybe a year to live, and he wanted me to back him up. It's not like he wanted out. He wanted to stay with her but he'd always been opposed to marriage, and it was her dying wish to marry. Jesus Christ, marry her.

HH: What if there's a miracle drug and she lives forever?

MO: Then you can divorce her. I've had similar letters, where there's one person who's saying, "I'm sort of generally opposed to the idea of something" and the other party is saying, "Here's my hugely significant reason for why this is deeply important to me." A lot of times, it seems like the person who says, "Uh, this is just a vague stance for me," digs in their heels. But if it's not that important to you, and it's deeply important to someone else, give way. A couple weeks ago one woman was like, "I've been with my fiancÚ for five years. I have two twins whose biological father is not in their lives. They've only ever known my partner as their father and they want to call him 'Dad.' These little five year olds try to call him 'Dad' and he won't let them. He objects to the term 'Dad.'"

HH: So what did you say? "Dump that guy"?

MO: I didn't say dump him. It sounded like in other ways he's a good enough guy. Hopefully they don't wake up every morning like, "Please may we call you daddy today," and he's like "No! Get out!" I said something along the lines of, "Obviously what he's saying and what he's doing are really at odds so you basically need to lay it out for him. 'Look, it's very important to my toddler-aged children that they call their dad their dad. Can you explain to me why it's so important that they call you 'Trevor'?"

DS: It's obvious what his problem with it is. He made a commitment to her that he can extract himself from just by breaking up with her, but the emotional commitment of allowing children to call you "Dad"—it isn't boyfriend or husband. "Dad" is supposed to be forever, and maybe he has a problem with that kind of commitment. Not the commitment he's made to her, but the commitment that would symbolize for those kids.

MO: If they're trying to call you "Dad," you've already unsuccessfully avoided this problem. They want to call you "dad," so you've already, like, screwed this pooch, right?

DS: Can we talk about the advice to dump him? Or her. I find that if I'm not careful, every column is "dump the motherfucker, already." Over and over again. People writing, "I love him, or I love her, and it's a wonderful relationship, but, you know, he punches my mother." They throw out something so disqualifying that if you're not careful, the advice column is just the same advice every time.

MO: Yesterday, a friend of mine told me, "I love reading your column because of how often your response is just, 'Dump him.'" But I've been trying so hard to scale back that. Fifty percent of the time, I'm telling people to dump him. Or her, occasionally. There are some pretty lousy girlfriends in these columns too. But I'll ask myself whether there's even a small chance that they could make this work, and think, Fine, all right, you could try this, but you're probably going to have to leave him right after it doesn't work.

DS: When you find that small chance, and game out how he or she might be able to make this work, the comments are all, "Why didn't you just tell that person to dump them, for fuck's sake, why are you trying to fix this?" Sometimes the obvious advice is "dump them," but then you're reading the letter and they're in a situation where they ought to leave, and the advice should be to leave, but it would be irresponsible to advise this person to leave because of extenuating circumstances. Those get really depressing.

MO: That's where the idea of harm reduction is helpful. For the column this week, I have a letter from a woman who writes, "My daughter's an active addict, I feel like I have to cut her out of my life, but I don't want to," which isn't quite the same thing as, "My husband's abusive." My advice is, "You do not have to cut her out of your life. If you don't feel you're in danger, if she's not trying to borrow money, if you can set appropriate boundaries, then no, there's no rule that says you have to cut someone out of your life just because they're an addict. It's not a guarantee that she'll get sober faster. Go ahead, see your daughter once a month, have coffee with her, send her an email—you don't have to throw her to the curb."

HH: People think, "Either I have to love this person and be in group therapy with them, and everybody's gotta own all their shit, or I have to cut them out and never speak to them again." People don't think, "I have a wildly dysfunctional friend or partner, and for whatever reason, maybe some dysfunctional reason, I really care about them." Who doesn't have some crazy, shitty, bad reasons for being with someone? We all have some of that. There's a tendency or desire to believe that nothing is ever so messy, or if it is, you're fucked: you're an emotional vampire and so are they.

MO: Cutting someone off is an option, of course, but it's not a cure-all. It's not: "I can either be in a relationship with someone and co-sign all their nonsense or I can cut them out and be totally free." There is the option of staying in connection with them, but also saying pretty clearly what you will and won't accept. That's difficult because it requires active confrontation and conversation, and for some people, conflict is something to avoid at all costs.

HH: Aren't there relationships where you bullshit the person a little bit and that's part of the structure of the relationship? There's no such thing as the perfectly clean, perfectly healthy relationship.

DS: Is there a relationship out there where there isn't some bullshitting going on on both sides at all times? I lie to my husband every day, and I assume he does me the favor of lying to me every day, about something or other. You want an artful bullshitter, sure—a considerate bullshitter—and you don't want somebody bullshitting you about whether or not they have a secret second family. But there's going to be bullshit around the edges. I get annoyed with people who get annoyed that their partner has kept the smallest thing from them. They had lunch with an ex and didn't get advance permission, just because they knew it would be a thing, and they lied about who they were at lunch with, and the person has this meltdown. "Oh my God, they lied to me!" Of course they lied to you, they're your husband. It's one of his responsibilities.

MO: I had a woman write in to me because she had looked through her boyfriend's phone and found out that he sometimes texted an ex-girlfriend of his. There was nothing in the conversation that suggested that they were seeing each other, but he didn't mention his girlfriend in the text conversations, and she was asking, "What do I do? Can I call him out about this?" If you want go to your boyfriend and say, "Hey, I went through your phone and I found out that sometimes you talk to other people and you don't bring me up," go ahead. Good luck with that fight. I don't think you're likely to win it.

LH: Everyone is a liar, right? Yet the person asking the question is the hero of the story. Do you feel like you're being pushed into a narrative in which your advice assumes everybody else is a secondary character?

DS: That's a hazard of the genre. You have one person's version and you're that person's confidant. Sometimes I've gotten follow up emails from the other party, with the rest of the story. But you have to go with what you've got because you can't subpoena everybody.

HH: "This person is serving a terrible role in your life but that doesn't mean this person is bad," is something I'll write, or even, "If I were giving your boyfriend advice, I might tell him something different."

DS: I once got a letter from this woman who was very upset because her boyfriend, Stanley, didn't want to invite her to go with him to his sister's wedding. She insisted that she had to be invited or he couldn't go. She caused this big scene in advance, and then at the wedding she felt that she was being snubbed by his family, so she got really drunk and went up to her room and then came down and got into fistfight with her boyfriend and flipped over a table. "But what he doesn't understand is that his family drove me to this." It never occurred to her that she was the common denominator in all of the insanity. I had to break the news to her that I wouldn't invite her to my wedding, either.

MO: I had a woman write to me, "My son is in high school, and he told me that last summer, he had a relationship with a girl from school when they were at summer camp. I recently found out that he got pulled into the principal's office because he's been sending her texts and voicemails upwards of fifty times a day, and she claims they never dated and he's been stalking her, and I'm really worried about how to advocate for my son because this girl's family is rich." The best way to advocate for your son is to get him some mental health treatment, because your son is stalking a girl. She could be as rich as all five of the gods and it wouldn't matter, your son's not a victim here. It was distressing.

LH: You're all literary critics, essentially. You're reading partly for what is behind the story but all that you have to go on is the text. They're revealing themselves in what they write and the way they've written it.

HH: It's harder to respond to a badly written letter. You get distracted by the fact that the person isn't expressing himself very clearly. I try to start with the assumption that I'm going to stay on the letter writer's side. My job is to empathize with the letter writer—you're addressing one person, your job is to understand and advocate for this one person.

KD: How often do you guys respond to a letter because you feel a broader responsibility? Or an opportunity to address the ethics of a situation on behalf of people other than the letter writer?

DS: It's a privilege to be able to point out something in the world that offends or appalls you. I seize that opportunity when it comes along, without much hesitation.

HH: On days when you feel like a mess yourself, or days when it just seems like hordes of people with the same problems over and over again, how do you handle that?

DS: I have two things that help me: marijuana and I drove a nail into my head in fourth grade. It punctured my brain and I have memory problems. I get the same letters frequently but they're always kind of a surprise to me. When Emily Yoffe stopped doing "Prudence," she said in her farewell, "I've been doing this for almost ten years and I have nothing left to say about X, Y, and Z." I've been doing this for twenty five years and I can't stop popping off about X, Y, and Z. My editors will have to pry my column from my cold, dead hands and pop my wig off and throw me into the crematorium. I get letters from people saying, "I read this ten years ago in your column or five years ago in your column and suddenly now here I am." The advice pops back into their head. To me that's the beauty and utility of the advice—the way the advice can impact people down the road who are filing this stuff away.

HH: I think it's important not to fall into the trap of feeling like a beacon. "I must live the ultimate life, and if my life is feeling difficult then it means I have nothing to say to anyone." Dan, do you get treated like a beacon? Has anyone ever said to you, over the years, "Oh, you're not a beacon, you're not enough of a beacon!"

DS: Somebody started an advice column in Seattle and her first column was all about how no one should take sex or relationship advice from me because I'd been with the same guy for more than a decade, so what did I know about dating? What did I know about heartbreak? Because I kept not breaking up with my husband, because my relationship was too stable, I wasn't out there in the dating and sex and romance world, I wasn't on Tinder or whatever, therefore I didn't know what people were facing today, and everyone should stop listening to me, because I'm too good at this relationship stuff. Apparently. I let her kill her own advice column slowly. I watched it happen. That was the best revenge.

LH: Do you feel like the form of the advice column has taught you something as writers?

DS: Nothing makes you into a writer more than writing. I had to shit this column out every week. My voice was un-self-conscious because I wasn't trying to affect a writerly tone. I didn't have any attachment to the idea that I wished to be a writer and writing is what I want to do, and how will I be received as a writer, as I crap out twelve hundred words of jokes about butt plugs. I started writing the column as a joke. But writing it made me into a writer.

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