I’m a lifelong advice column devotee. As a kid I’d “steal” the life section of the newspaper while my dad was reading the sports page, and I’d read two things: the Nancy cartoon, and Dear Abby. As a seven year old, it’s not like I had a ton of my own wisdom to dispense, and my seven year old problems could mostly be solved by “sometimes we gotta do things we don’t wanna do (like homework)” and “sometimes people are dicks but telling them directly to knock it off is usually worth a try.” But over the years, advice columns were an early testing ground; on letters about cheating spouses, ungrateful children, relentless parents, and infuriating coworkers, my baby self could imagine my way into and out of various scrapes. I learned to navigate the space between “what I would tell this person to do” and “what I myself would have done in their shoes” and I tried to close the gap between my own advice and actions.

There are a lot of thoughtful, challenging, and generous advice columns out there that I’ve found myself returning to over and over: Dear Sugar, Captain Awkward, Ask a Manager, Ask Polly, Ask Bear, Ask a Fuck-Up, You Need Help. But among excellent options, the advice column closest to my heart has undoubtedly been Danny Lavery’s tenure at Slate as Dear Prudence (both as columnist and podcast host) and his current podcast project, Big Mood Little Mood. Lavery’s approach is ethically rigorous in a way that gives an outlet to righteous indignation while also finding unexpected and generous depths to problems that might have received superficial answers in less capable hands. I’ve found a lot of wisdom, and a lot of joy, in his approach to conflict, comedy, and compassion, and now, to celebrate the publication of Lavery’s Dear Prudence highlights, Danny and I got to talk shop! In our conversation last week, we talked about stepping into and out of character, the expectations and hopes we bring to advice columns, the questions that advice columns send back over the net to readers, the relationship between perspective and pattern-finding as he reflects on his run as Prudie, and more.

Yashwina: Well, I want to kick things off just by saying that I’m a huge fan. Your work at The Toast, the work with the column, your newsletter The Chatner… You’ve nurtured a charming and wonderful part of the internet, so I really appreciate the community that you’ve built. One of my very best friends, Naomi, and I actually got close because we used to read the letters to each other every week! It was a sacred part of our week!

Danny: Oh my gosh. Would you read them out loud before you’d read the answers?

Yashwina: We would read all the letters out loud. We’d be sitting on the floor of each other’s apartments and reading them out loud to each other, and then we’d thoroughly discuss your advice and our own advice and what we’d do in the letter writer’s situation. There were a lot of hot takes. It was a sporting event for us! Advice is a contact sport!

Danny: Wow. That is delightful!

Yashwina: All this is to say, Naomi gave me this idea for our opening question and she gets all the credit. Are the high camp names like Prudence and Sugar, and the “agony aunt” in general, a kind of queerness encoded in advice columns? What do you think draws queer readers to advice columns specifically?

Danny: Gosh. I can only speak for myself as such a reader, but I would imagine a lot of the same things draw to advice columns that draw everyone, which is just that same impulse to run outside if somebody says there’s a fight. Just the sheer delight in spectacle and other people’s problems, which is not just nosiness or looky-looism, but just, if something’s happening, people want to look at it. And especially if someone says, “Can you help me figure this out?”, people love to come over and try to figure it out, even if they have no idea what to do. I do love that idea of maybe there’s something especially dramatic and campy about pseudonyms. And I think especially, yeah, obviously it’s not in the same category as the Scarlet Pimpernel or Zorro. But anything that involves putting on a little Venetian mask or using a stage name is certainly in the right category to attract a certain type of queer person. So, there’s definitely that element.

I know almost everybody who talks about advice columns usually talks about Nathanael West’s Miss Lonelyhearts. But it certainly, I think that one, it goes back a way, just this incredibly frustrated guy taking on this role of helpful, slightly religious spinster while also trying to navigate his own personal life that has a sort of beautiful madcap Fred Flintstone air to it. I don’t know if that answers the question, but it certainly explains a lot of why I’ve always been interested in them.

Yashwina: I love the idea of a Prudie to Zorro pipeline. And I do think that if any advice column-based vigilante justice starts happening, I will be happy to provide you with an alibi.

Danny: I appreciate that immensely, but I am so unqualified for any kind of vigilantism, and that could only end a disaster. I’m glad I confined myself to a few years of suggesting things that strangers might do, but any more than that and I would not feel prepared to take responsibility.

Yashwina: There were a few core tidbits of Prudence. I have so many times thought of the line, “Reconsider the orientation of your heart.” which is a Hall of Fame mic drop. There were so many wonderful little Prudie-isms. I’m just thinking about the kind of things that we go to advice columns for, and what we want out of that exchange. We go to advice columns to ask questions, obviously, and now here I am to ask you questions about those questions.

Danny: Yeah, and I think that bit about that line is really apt. There’s often some sort of desire for pithiness in the advice column, and especially in the figure of Prudence, which was a long-running identity and had been written by both men and women before me. But the idea of Prudence, I think, evokes a sort of slightly no-nonsense maiden aunt. A little bit antiquated, a little bit folksy, not too folksy. And I think every advice columnist has to decide for themselves how folksy they’re willing to get. But yeah, somewhere in between all pith and no-nonsense.

Yashwina: “All pith and no-nonsense” is such a good tagline.

Danny: I wish I had thought of it five and a half years ago, but unfortunately I thought of it now.

Yashwina: But yes, there’s two layers of questions, and I’m actually here in both capacities. Full disclosure, you answered a letter from me on the podcast a few years ago!

Danny: Oh my gosh!

Yashwina: Yes, you were very helpful when my visiting friend stole my vibrator! (TL;DR: A friend from overseas came to visit me in my new city and was already expressing some jealousy in a way that made me feel like she was trying to take over my life, and when I came home from work one day I discovered that she’d gone through my stuff and helped herself to my vibrator, which she tried to hide in the couch cushions right in front of me. I wrote to Danny because I felt pretty thoroughly invaded and had no idea how to address what had happened with my friend, or how to tell her that I no longer felt comfortable hosting her when she asked to visit me again.)

Danny: Oh, wow, I remember that one!

Yashwina: It was the kind of thing where when you’re alone with your own problem, it’s so easy to just keep chewing and spiraling on it until it’s like you’ve said a word so many times that it doesn’t have meaning anymore. That’s why I felt very reassured by your advice, and by the sense not only of guidance, but also there was just a level of justice. It felt nice to be able to turn to someone whose judgment I trust and be like, “That was crazy, right? You saw that? That was weird, right?”

Danny: Yes, and that’s part of that element too, of running out to see if there’s a fight. Running out and being willing not necessarily to help but being on standby if somebody says, “That shouldn’t have happened,” that you can say, “You’re right! It shouldn’t have!”

Yashwina: Absolutely! The whole thing made me think about how we bring all of these questions and all of these hopes to advice columns. But I was wondering: What questions do you think that advice columns pose to us as readers?

Danny: I think that’s useful. I don’t know if I’m the best person to answer it, just because I had such a specific role in my tenure there that thinking outside of that immediate scope was sometimes kind of difficult. But certainly I think it can be useful to readers who are thinking about more general ideas about how they want to conduct themselves or how they want to handle conflict. Or whether or not they think of themselves as being similar to a lot of the letter writers, or different from a lot of the letter writers.

Yashwina: Talking about advice and justice, it brings me back to your remark about the role of being a witness. When you’re answering these questions, how do you balance and move between the roles of witness, counsel, and judge?

Danny: I think that can depend upon the question. You do eventually develop a sense for if someone primarily just wants to know that somebody else has read about or listened to their problem; if they’re really, really totally at sea with absolutely no idea what they’re going to do; or if they seem pretty determined on a particular course of action and they just want somebody else to confirm that that’s an option. But I think it also depends. Sometimes someone’s just reflecting on a lifelong relationship. I think the more longstanding the relationship or the bigger the issue, the less I felt like I might be giving someone advice that will seriously change the trajectory of their life, which actually may or may not be true.

But my sense was if somebody’s asking me about their sibling or a parent or someone that they’ve known all their lives, they’re probably a little bit more likely to do something that they feel capable of and prepared to do, rather than something a stranger told them to do. And if it’s more about somebody they encounter on their commute a few times a month or a brand new acquaintance, they may be a little bit more likely to take my advice because it’s lower stakes. So, sometimes I would feel paradoxically a little bit more responsibility over the new relationships or the smaller scale stuff, because I thought that’s the type of person who’s probably likeliest to carry out whatever I suggest.

Yashwina: Well, I was someone who carried out what you suggested, and I can confirm it worked! I survived initiating conflict, and I survived having a difficult/awkward conversation, and no one has stolen any of my sex toys since. I’d love to talk more about those quirky, weird problems that arise, whether it’s someone who’s annoying on the commute or the houseguest who has decided to be bizarre or the deep family conflict. You organized the book by broad themes and categories you noticed from the letters. But I was also really, really interested when you mentioned observing these unexpected trends like jewels and poisoning!

Danny: Yeah, I was surprised by that one too, but it kind of made sense. When I thought back on the history of the column, I remembered before I was the Dear Prudence reading occasionally about somebody who suspected an in-law of unintentionally or intentionally poisoning their food. And I thought, “Yeah, that happens not infrequently.” Not necessarily that in-laws do it, but that people suspect it. And I suppose it makes sense. They’re the people who are most likely to serve you food, and they’re also the people who are probably most likely to have an ax to grind against you! So they’ve got motive and opportunity! But I had never previously thought that this was something that happened outside of the history of the Borgias.

Yashwina: I found that observation so fascinating, because it made me realize that occupying the Prudie throne gives you this kind of bird’s eye view over people’s problems. When you are looking down from such great heights, like that Postal Service song, what are some of the other patterns that struck you? Were there any other weird themes?

Danny: Gosh, I love the idea of looking down from a great height. I can tell you that’s definitely not what it felt like, checking the inbox on a regular basis, but I appreciate the mental image immensely. Often, it felt less like I was collecting patterns or looking for data and more just a sort of panicked sense of being on a treadmill. “I need to wade through all of the spam and all of the just general opinions or feedback to find the actual problems that people have. And then I need to also be able to read through possibly a 10-paragraph email to figure out what question is nested somewhere within a lot of backstory!” So, I would often not feel a sense of noticing any patterns week-to-week, but occasionally, it was a little bit like the four-minute mile. Once somebody broke that barrier, all of a sudden people were running four-minute miles left and right.

And sometimes if I would answer a question about a brand new problem, I’d start to get questions about that particular type of issue or type of relationship, whereas previously I hadn’t gotten very many. Certainly, once I started transitioning, I got more questions from trans people and about transition more generally. That was probably the most obvious and straightforward pattern. As well as once I became estranged from my own family, I got more questions about family estrangement. But that’s a little bit different because I was already getting quite a lot of those to begin with. So it was simply an increase rather than a brand new trend on that front.

Yashwina: As soon as you mentioned the inbox, I can see how that would really feel like a treadmill or really being in the thick of it. Email inboxes do feel very much like dark, scary fairytale forests sometimes. You weren’t just drawing connections between letters there though; one thing that I found really interesting in the book was the connective tissue that you wrote between the letters you’d gathered to build upon their conclusions and add a layer of behind-the-scenes commentary on your advice-giving process. What was it like to be in conversation with yourself in that way?

Danny: This was something I knew that I wanted to do, since most of the book is anthology and a lot of it is answers that people would have either read in the column or heard on the podcast previously. I didn’t want to just repackage a bunch of little columns and be done. But then there was also a question of “how much do I want to spend time trying to reassess everything versus drawing connections?” And I thought about some of the older advice column anthologies that I had read when I was younger. I always really loved Since You Ask Me, which is an Ann Landers book from the sixties that involved slightly pithy summations, parables, or drawing-together of certain trends that she noticed.

It wasn’t this encyclopedia, and it wasn’t this grand vision of the advice column. But it was just a nice, readable, thoughtful series of problems that she noticed patterns in. And so that was something that I took a lot of my cues from. “What did I notice that I didn’t get a chance to say at the time?” What does it look like to think about these from the vantage point of being done?” That was something that I also really enjoyed getting to do.

Yashwina: It’s really interesting to hear about the other books that you were drawing inspiration from! What other columns did you read or draw inspiration from, and were there any particular responses or letters that you remember that really shaped your approach or stuck with you?

Danny: I do think Since You Ask Me, which I found in a used bookstore when I was in high school, was a big one, as well as the Dear Abby and Ann Landers TV movie from 1999 starring Wendie Malick, which I just loved and should try to rewatch at some point. There’s certainly elements, too, of Marjorie Hillis who wrote a couple of very modern proto-self-help books in the late 1930s. The first was called Live Alone and Like It. It was republished back in 2008, and it’s enjoyed a sort of resurgence in popularity.

Those books were very practical: “Take care of yourself and be as cheerful as possible within reason. And look for the things that you can change to make your life more interesting and enjoyable rather than waiting or complaining about your circumstances.” It’s very bracing and light and effervescent. I loved her style, and I’m always looking for some of her other out-of-print books.

Yashwina: Marjorie Hillis! I remember when those books were republished, and I remember there was a recent biography of her that I enjoyed. I wish they’d bring back the rest of her books! I think there is a really interesting early and mid-20th century sensibility to the advice column.

Danny: So much of it was just really fun, too, because she would tell so much of the book in parable. It would just be like, “Now, Miss C. is a secretary who brings home $30 a week and she has a one-bedroom apartment and she enjoys flower arranging. And here’s something she’s doing wrong.” And I could just eat that stuff up all day! It’s like reading popcorn.

Yashwina: That playfulness also helps alleviate some of the urgency or anxiety that a letter writer’s initial question might have, that sense of  “Oh my gosh, this problem. I am the only person who has ever had this problem in the whole world.”

Danny: I do wonder sometimes if there’s a particular type of person who’s more likely than another to write to an advice columnist. I don’t feel prepared to make any sort of sweeping generalizations on that front. But I do think, at least during my tenure of Prudence, I did notice a common thread of often hearing from people who did not have a history of difficult or painful conversations with people they really cared about. They had avoided that for a variety of reasons, and tended to avoid conflict if they thought that they could.

And again, that wasn’t everybody all the time, but it did pop up quite a lot. So maybe someone who’s inclined to write to an advice column is somebody who is realizing for the first time, in order to maintain a relationship, they’re going to need to choose to have a fight or an argument. And they’re going to have to be the one to bring it up, and they’re not sure what that looks like since it’s new to them. So I think that that’s also a pretty interesting pattern as well.

And there’s also a chapter in the book that is something like, going from being all the way right to only 50% right. One of the more difficult versions of that particular problem is somebody who has mostly avoided conflict for a long time and then eventually got to a breaking point and really, really overreacted. Maybe they had a totally justifiable grievance or complaint, but they went way over the line in how they brought it up or what they said or what they did.

And now they write in the sense of, “I let this go on for a really long time. Then I blew up and said something that I really shouldn’t have. And now I’m in this awful position of having to apologize to somebody I’ve been mad at for seven years.” I want to help people avoid that situation wherever possible, because I think it’s truly one of the most unpleasant emotional scenarios! “I have to apologize to someone who I think has been more wrong than me for a longer time, but now because I did something that was wrong in and of itself, I’ve got to start.” And it’s just unpleasant.

Yashwina: That section in particular was such a difficult needle to thread, where you’re trying to display a lot of sympathy for the backstory, but the backstory has to be kept separate in some ways from what has immediately happened.

Danny: Right. Because you cannot meaningfully apologize for something that you’ve done wrong if you also then try to bring up, “But I’ve been mad about this other thing that you’ve been doing.” It just takes all the spine out of the apology. No one’s ever received an apology that ends with, “But you’ve been doing X, Y, Z!” and felt, “Oh, good. This is a good apology. I feel I really can accept it.” That just gets everyone on the defensive.

Yashwina: So, I’m wondering now, after having been Prudence for a while, how was moving out of that character? Has inhabiting this character role changed the way that you approach advice-giving, just as Danny to your friends?

Danny: Probably like most advice columnists, I don’t have a lot of close friends coming to me asking for my advice because of my work as Dear Prudence. Every once in a while, somebody will lightly ask for input, but in the way that almost anybody would ask a friend for their thoughts, not like, “Hey, you decide what I’m going to do next with my life.” So I don’t think it actually changed all that much. Every once in a while, a newer acquaintance might be slightly likelier to ask for my thoughts on a situation, but again, it’s fairly rare.

I definitely worked hard to cultivate a particular persona that I felt worked for me in that column, and it was a really interesting process. But ending it was pretty easy. I stopped doing it, and I didn’t feel myself waking up in the middle of the night thinking, “I’ve got to advise eight people in the next hour or I’ll lose it!” So it was a very cool and interesting job to get to do, but being done with it was as easy as being done with any other job. It didn’t leave a ghost sort of hanging around.

Yashwina: The idea of being haunted by the spirit of Prudence…

Danny: Yeah, like the end of A River Runs Through It. “I’m haunted by waters.” It was just not really the case!

Yashwina: It’s good to hear that there’s no Prudie poltergeist lingering! Has it changed the way that you seek advice or relate to your own instincts? Do you ever call upon your own Prudieness?

Danny: I do think so! Every once in a while, I find it useful to think of a problem of my own through a Prudence perspective, and that usually proves pretty useful and insightful. I’m afraid I can’t recall a really specific example off the top of my head, but that’s been a useful addition to my mind palace.

Yashwina: It’s nice to be able to access it when you need it! Like Prudie is there to call upon in an advice emergency.

Danny: The Scarlet Pimpernel will always be there when you need him!

Yashwina: My last question as I wrap up an interview is always “What do you recommend I read next after finishing your book?” What should we have for dessert after Dear Prudence?

Danny: I definitely recommend Marjorie Hillis! And, if you enjoy her books, I would recommend trying to get your hands on a copy of New York, Fair or No Fair, which is her 1939 guide to tourists coming to New York City for the World’s Fair. It looks like a lot of fun. I found a copy of it at a library near me, and I’ve put in a request. So hopefully in the next week or two, I’m going to be able to go and give it a read myself.

If you haven’t read Nathanael West’s Miss Lonelyhearts, I do think that it’s very much worth a read as well. It’s short, so even if you hate it, it’ll be over fairly quickly! But he’s a really compelling writer, and it’s a lot of dour fun, if that makes sense.

Yashwina: I love the idea of following Dear Prudence with some of Prudie’s forebears, and the predecessors of the genre that brought Prudie to where it is today. What a good black hole of reading to fall down!

Danny: My last recommendation, if you just want a general book that makes you think more thoughtfully and carefully about how to live, is always Middlemarch.

Yashwina: Can’t argue with Middlemarch. It’s a banger!

Dear Prudence: Liberating Lessons from Slate.Com’s Beloved Advice Column by Daniel M. Lavery is out now.

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