The Rise of the Messy Advice Column

Why has advice become a safe bet in an otherwise precarious media landscape?

by | December 8, 2020

We are living in an era of unprecedented saturation of online content, such that I marvel at my peers who seem to read every single article — where do they find the time? I have mostly given up on the task of reading everything, but every time I see that a new advice column has been published, no matter the source, I am inclined to click. The format triggers a Pavlovian response: I’m anticipating the satisfaction of either experiencing someone’s fragile self-delusion being eloquently, satisfyingly dismantled; a banal human problem being taken seriously (it does matter that you’re lonely, or chronically dissatisfied, or mired in self-loathing); or, if nothing else, reading some truly bonkers shit that will serve as a much-needed escape from the present. 

I am not alone in viewing advice columns as an exception to a wider content exhaustion. And publications have noticed: It seems that there is now an advice column for just about everything and everyone. Ask a Manager tackles workplace concerns; the New York Times has one lighthearted advice column focusing on social situations, one for work etiquette, and a more serious-minded one addressing ethical quandaries. In 2018, writer and Twitter personality Brandy Jensen launched her advice column Ask A Fuck-Up at The Outline; when The Outline folded earlier this year, Jezebel snatched up the column almost immediately. The hilarious John Paul Brammer began his queer advice column ¡Hola Papi! at INTO in 2017 before moving to Out and eventually landed at Substack — it even garnered a book deal from Simon & Schuster. Canonical columns like the Chicago Sun-TimesDear Abby — whose pseudonymous writer now has a star on the Hollywood Walk of Fame — and The Cut’s Ask Polly by Heather Havrilesky (which originated at The Awl) are still going strong. Cheryl Strayed’s legendary Dear Sugar was recently rebooted as — what else? — a newsletter. 

The consistently high demand for these columns indicates that they are fulfilling some dire need both on the part of both letter writers and readers. There are masses of people longing to be heard, to be taken seriously, and to be the focus of another person’s earnest efforts at solving their problems — even when that person presents themself not as a moral authority, but as relatable and fallible. When I asked Ask Polly’s Havrilesky how she viewed her role as an advice columnist, she described herself as more “archaeologist” than therapist, and more of a “weird philosopher and cultural critic,” she said, than moral authority. “I examine this one short document [the letter] and I look for clues about what the person who wrote it wants and needs,” she said. 

“What’s sad is that just acknowledging that you have needs and asking for what you need can be incredibly difficult for a lot of people, particularly women,” she added. “We’re trained to behave like appliances, conveniently serving up whatever everyone else wants from us. It takes a lot of reprogramming to turn an appliance into something that’s happier and less convenient and noisier and more satisfied.” 

In other words, the people writing to Polly are not looking just for answers, or for a diagnosis. They want the columnist to transform how they see themselves and their place in the world. 

There was a time before giving advice was a form of self-expression. To read through the archives of Dear Abby — the widely syndicated advice column founded in 1956 — is to step through a time portal, when advice-giving was a largely practical matter, concerned with solving the expressly solvable and telling a person exactly what they should and should not do. Columns from 20 years ago make me wonder if moral quandaries were simpler back then, and I am struck by the brevity and often brusqueness of Abby’s answers. 

A husband resents his wife’s extravagant spending while visiting her wealthier sister. Abby responds in a few sentences: “If your wife’s visits to her sister make her feel deprived to the point where she routinely busts the budget, you are overdue for a frank talk about it. Tell her how hurt you feel — and give her this message from me: If you don’t appreciate what you’ve got, you’ll lose it.” Complicated matters are addressed with a jarring snappiness. A man writes in, having learned that the child he had been raising for a decade is not his biological son, that the mother had lied to him, then abandoned both him and the child, leaving him bitter about lost time and resentful of his responsibilities as a single parent. “Quitting is not an option,” writes Abby, who advises him to set aside some time for himself or seek out a support group. No time is wasted empathizing with the letter writer; that is simply not in the columnist’s job description. 

Abby — the creation of founder Pauline Phillips and co-edited by her daughter, Jeanne Phillips, beginning in 1987— was authoritative, firm, and no-nonsense. But the Phillips duo had humor and personality, however antiquated it reads today. Upon Pauline’s death in 2013, the New York Times described the voice of her Abby as “if Damon Runyon and Groucho Marx had gone jointly into the advice business.” The obituary also credited her “comic and flinty yet fundamentally sympathetic voice” with carrying the genre “from its weepy Victorian past into a hard-nosed 20th-century present.” 

By the 21st century, the column’s brusqueness began to look more like callousness. In 2016, when a teenage girl who had been sexually assaulted wrote in asking for advice, Abby blamed the incident on a “breakdown in communication” and chastised the letter writer for going to a secluded location with her assailant. In 2018, she was accused of xenophobia when she advised a couple against giving their children “difficult” Indian names. Aside from giving alarmingly bad advice, both columns feel so out of touch it’s hard to believe they were published within the last five years, that they made it through any kind of editorial process, and that they appeared in a column purported to have 110 million readers.

The trajectory of Abby’s rise as a household name dispensing benevolent guidance to her demise as an out-of-touch rich white lady writing cringey columns illustrates the profound shifts in what we, as readers, want from an advice-giver. Abby’s tone may have been genial and joking at times — even the shortening of the columnist’s pseudonym from Abigail to Abby suggests a kind of familiarity — but she drew her power from a public perception of authoritativeness. The photo of Jeanne still in use, intended to represent the all-knowing Abby, projects an old-fashioned refinement, with perfectly applied lipstick and coiffed blonde hair. I remember seeing her photo when I was younger and doubting that she was even a real person. I assumed that the column was using a stock photo. I couldn’t imagine writing to this person for advice; I didn’t believe that this smiling woman in her red jacket and understated gold jewelry could understand my life at all.

In the history of the modern advice column genre that superseded Dear Abby, there are two distinct eras: Before Dear Sugar and After Dear Sugar. In 2010, Cheryl Strayed — writing anonymously at the time — became the new author of the advice column at digital literary magazine The Rumpus, and it is to her that we owe the current reign of messy advice columnists like Polly, Jensen’s Fuck-Up, and Brammer’s Papi (Brammer describes ¡Hola Papi! as “the preeminent deranged advice column” from “a Twitter-addled gay Mexican with anxiety.”) Strayed’s Sugar was vulnerable and humble, down in the dirt with her beleaguered advice-seekers, in contrast to Abby’s tendency to sound like a sage in a tower, dispensing advice from on high. 

Sugar’s letter writers were not seeking an arbiter for specific situational dilemmas as much as they were seeking guidance on how to live with themselves. They wanted to know how to forgive themselves for past misdeeds, how to ask for love and affection, or how to overcome profound guilt and grief after suffering a miscarriage. Sugar’s responses were long, sweeping, cathartic — they were quoted, enthused over, ranked in “Best Of” lists. Strayed’s most famous Dear Sugar column answers a letter asking what advice she would give her twenty-something self. Strayed’s response is moving in its specificity but illuminating in its universality; one piece of advice involves regret over not being sufficiently grateful to her now-departed mother for the gift of a winter coat. 

The column’s subtitle — Tiny Beautiful Things — became the title of a compilation book that was rapturously reviewed, and which is now just as significant a part of Strayed’s legacy as her memoir Wild. Strayed provided a blueprint for a different kind of advice column: she confirmed that there are people writing to columnists because they want to feel held and affirmed, not simply told what is right and wrong.

In the last decade, advice columns of both the Abby and Sugar schools have proliferated at nearly every type of media outlet. In this crowded field, Slate stands out as something of an advice column powerhouse. It has been publishing Dear Prudence, now authored by beloved The Toast alum Daniel Lavery, in some iteration since 1997, and has more recently launched Care and Feeding, an advice column about parenting and families hosted by a number of writers, including former The Toast managing editor Nicole Chung and essayist Emily Gould; and How To Do It, an advice column about sex. It also produces a stable of advice podcasts, including one accompanying Dear Prudence that is hosted by Lavery. 

In short, there is an immense supply of advice to meet an immense demand for guidance. And this demand, it seems, makes betting on advice columns a safe business decision at a time when many media companies are laying off staff. “They’re just perfect for audience development,” said Bill Carey, Slate’s head of strategy and audience development, who noted that Slate had seen interest in its advice columns grow since mid-2016, when he first took on the position. “We think of our advice columns as something that really helps us to expand and retain our really loyal readership…There’s such a feedback loop you get just from the structure. You start with someone writing in, then one of our columnists responds, our readers read them, they comment on them, they discuss and debate the answers.”

Carey stressed that the decision at Slate to put out a flurry of advice columns is not strictly business. These are ultimately editorial calls, and Slate sees these columns as complementary to the rest of its content, not as a separate enterprise. Advice columns help people understand the world through their own lives and the lives of others, he said, just as news and political analysis help readers understand the world through power and events of national significance. 

In fact, Carey told me that a predictor of a column’s success is often its reader’s ability to see themselves in the questions. “When we write the headlines and think about how we’re positioning the columns, relatability is one key part of it,” said Carey. “Some of the really successful columns are ones that are based on a question that feels very familiar…you feel like you have a direct connection to what’s going on there.”

That’s one type of successful advice column, and anyone native to Twitter will be familiar with the other. One Dear Prudence question from 2017 stands out in my memory as an example: a letter writer whose daughter is getting married tells Prudie they want to cut their daughter’s best friend from the bridal party because she walks with an “unsightly” limp. Prudence eviscerates the writer — “I encourage you to reread it and to ask yourself that time-honored question, ‘Do I sound like a villain in a Reese Witherspoon movie?’” — and advises them to “profoundly reconsider the orientation of your heart.” 

Slate knows we relish the schadenfreude of the bonkers advice column. On Election Day this year, they compiled the “best, weirdest Dear Prudence letters of the decade” to serve as a welcome distraction, a list that included a woman who suspects her mother-in-law is poisoning her food, a college student who was bitten by a bat and then hired an escort who turned out to be an undercover cop, and incestuous twins debating whether to reveal their relationship to the family. Carey puts those into the category of “escapism.” Those are, he said, “ones that are the exact opposite of relatability — they are on the extreme end of some other spectrum where the details just sound really wild.”

The editor of Dear Prudence, Megan Weigand, cited escapism as a key component in the advice column boom. “It’s a way to peer into somebody else’s life for a few minutes and forget about everything else that’s happened,” she said. “My hunch is, especially seeing the growth over the last couple years, it’s a way to take a break from the relentless news cycle.”

I asked Weigand about the people earnestly seeking advice — what is driving them to write to a stranger on the internet? She theorized that the desire for an external perspective combined with a dearth of options for a listening ear could be contributing factors. “They’re looking for an outsider who doesn’t have anything in the fight,” she said, and linked the genre’s popularity to living in “a time when therapy is really expensive and really hard to access.” 

“I’m absolutely not saying advice columns are a replacement for therapy, because all of our columns recommend therapy on a regular basis,” she added. “But I do think it’s hard to find a neutral referee, and [advice columns are] one way to try to get at that.”

While Slate’s podcasts tend more pragmatic, Heather Havrilesky’s Ask Polly is, in many ways, the spiritual successor of Cheryl Strayed’s Dear Sugar. Polly will toil over a problem with an advice-seeker, in a manner that suggests that we are all kind of figuring this out together, and that’s ok. In one letter from this past summer, the writer confesses that they “feel ashamed of almost everything” — their skin, their apathy towards their job, their dating life, their familial relationships. (It’s a quintessential Polly letter because there is no specific, solvable quandary — everything is wrong.) “I know I tend to write ‘Oh, I was just like you at your age!’ way too often, but with every new line of your letter I thought I could’ve written this,” Havrilesky writes in response. 

When I asked Havrilesky why she thinks people write to advice columns, she suggested that the format offers more than practical solutions to specific problems. At least in Polly’s case, she’s there to acknowledge the existential elephant in the room, a perspective that might get lost in everyday guidance. “If you ask a friend for advice, they tend to say things like, ‘Don’t text that guy anymore, he’s bad for you,’ or ‘Maybe you should look for a different job,’” Havrilesky said. “It’s hard to take concrete advice at face value without understanding some dimension of the wider picture: Why am I chasing an unavailable man again? Why do I feel so stuck? Why is it so hard for me to change my life?”

“Most of the people who write to me start off by saying they’ve read my column for years. So there’s a very specific flavor of big-picture perspective that Ask Polly advice seekers are looking for,” she added. “They don’t just want short, concrete directives. They want to have their view of their lives shaken up dramatically.”

As for the advice column boom, Havrilesky feels there were a few contributing factors. “Advice columns are popular right now because people feel pretty lost, and they’re not turning to more traditional or old-fashioned sources of wisdom for answers as much,” she said. She also points out that advice columns, in their current iteration, are a distinctly internet-native form of self-help — people also seek advice via online forums like Reddit’s Am I the Asshole? or r/Relationships (also sources of bizarre situational drama ripe for voyeurism and Twitter virality)  — and the format’s popularity has grown as we live more of our lives online. “At a time when your world is mostly curated by the internet, going in person to a priest or asking your mother who watches the news on TV to give you guidance about online dating doesn’t feel quite right,” Havrilesky said.

The advent of COVID also seems to have accelerated this need for guidance. Havrilesky said that since the start of the pandemic, the volume of letters she receives hasn’t changed, but “the desperation level found there is much higher.” Vogue recently launched a new advice column geared specifically towards COVID advice. In the column, called Asking For a Friend, writer Emma Specter brings her quandaries to experts who can help settle uncertainties around mundane questions, like how to date in the time of COVID. “I feel like suddenly everyone’s a fucking ethicist, or epidemiologist,” Specter said. “Everyone has an opinion, and I think most of us aren’t sure how to handle this.” 

Culture writer Kelsey Lawrence (who, full disclosure, is a friend), considers herself something of an advice column superfan and finds the medium performs a unique role in her life, distinct from any IRL source of input or consolation. Kelsey reads advice columns every day; she marks eras in her life by different advice columnists she has especially loved through the years (Dear Sugar, she tells me, helped her through her first unhealthy relationship); she became a Slate Plus member in order to gain full access to the Dear Prudence archives. She speaks of Havrilesky with something approaching reverence. “This sounds so corny, but it really has changed my life,” she said.

Even when the advice isn’t directly applicable to her life, there is something cathartic about the way advice columnists tackle problems that are not clearly solvable, she noted. She tends to gravitate towards them when she feels anxious. “It’s like watching a soap opera. It serves a similar purpose in terms of working through a storyline,” she says. “You’re seeing someone introduce their problem, lay it out, and then the advice columnist work through it like they’re combing through a hair knot.”

I wondered whether the attraction of advice columns was more about this — the attraction of watching someone deftly resolve someone else’s knotty problem — than actually changing the way we live our lives. When I spoke to Specter, also an advice column fan, she was blunt in her assessment: “I never take the advice,” she said. “I always do the thing.” Havrilesky noted the same dynamic in her column: “Some people want the truth and some people really don’t,” she said. “I try to proceed with a lot of compassion and also leave giant decisions up to the letter writer, generally speaking.” 

She didn’t always take this approach, but now she sees the humility it requires as integral to her job. “I used to wade right in and say, ‘You’re wrong, you need to change!’ But life has humbled me, just like it humbles everyone! And I think that humbling process has made me better at my job,” she said. This philosophy reflects the overall trend in advice-giving: We don’t want a sage in a tower. We want a real person who wears their frailties on their sleeve to tell us that they understand how we feel because they’ve felt the same way. In a world that feels senseless, cruel, confusing, and lonely, we want a concentration of empathy.

Subscribe to Study Hall for Opportunity, knowledge, and community

$532.50 is the average payment via the Study Hall marketplace, where freelance opportunities from top publications are posted. Members also get access to a media digest newsletter, community networking spaces, paywalled content about the media industry from a worker's perspective, and a database of 1000 commissioning editor contacts at publications around the world. Click here to learn more.