The advice column ought to be a relic. It belongs to a time when local newspapers were a community’s main window on the world: before widespread therapy, and before Google was around to autocomplete our anxieties. Yet the advice column in the online era remains wildly popular, evolving in form and audience: from traditional Q&As to live chats and podcasts, there are now innumerable ways to share our dilemmas with the world or eavesdrop on other peoples’.
These forums let us examine and judge one another, but they also expand our understanding of the world. Advice columns intensify the compact of trust between journalists and readers and rest on a mutual assumption of good faith. They only work if the problems are real and the advice genuinely given. In an online world of grifters, scammers, and trolls, it’s appealing to seek the input of someone who is who they say they are and to trust them with our knottiest questions about love and life.
In the past, advice columnists were overwhelmingly white women, often disguised behind a pseudonym, and they operated on the understanding that a white perspective was universal. Modern columnists, especially online, are breaking with that tradition to make identity and personal experience more central. “When we take it for granted that ‘white’ or ‘straight’ automatically means ‘universal,’ we do a major disservice to queer people and people of color,” says John Paul Brammer, who writes the ¡Hola Papi! advice column at Condé Nast’s online LGBTQ site Them. “We also cede ground to this notion that people can’t step outside themselves for a moment to see someone else and recognize their humanity.”
“Given the American history of black women being forced into a position of caregiving, is it weird that I have voluntarily put myself in a caretaking position by doing this column?”
As a rare Latino advice columnist, Brammer is filling a gap left by Gustavo Arellano, whose OC Weekly column (turned radio show turned book), ¡Ask a Mexican!, was marked by an exuberant sense of humor that poked fun at stereotypes. In late 2017, when Arellano left his position as editor in chief at the paper, his departure highlighted the woefully low numbers of Latinx journalists in American newsrooms. “There is lopsided representation of straight white voices in media,” Brammer says, “and if I can provide even a sliver of refuge in this landscape, then I want to do just that.”
Heather Havrilesky, who writes the Ask Polly column at New York Magazine’s The Cut, describes herself jokingly as “just some fucked-up white lady with delusions of grandeur” and resists the idea that advice can’t cross categories of identity. She cites a recent example of a reader challenging her ability to give good advice to single people because she’s married. “Not only did I spend decades struggling like crazy as a single person,” she says, “but the whole idea that married people and single people belong in utterly separate and completely different categories feeds into this bullshit perception we place on single people that they’re somehow the ones who haven’t figured out coupling yet.”
Havrilesky’s intensely personal, empathetic, and lengthy replies to readers show the influence of the quintessential modern advice columnist, the originally anonymous Dear Sugar, who gained something of a cult following in her (or was it his?) mid-aughts heyday. When Sugar was revealed as the author Cheryl Strayed, on the eve of the publication of her memoir, Wild, she told the New Yorker, “Being anonymous felt to me like a form of literary performance art,” a temporary pose that was both liberating and limiting. Unmasked, Strayed’s cult following quickly turned into genuine, bestselling, Oprah- and Hollywood-endorsed literary fame. But it was the freedom offered by an online literary magazine, The Rumpus, that allowed Strayed to push the boundaries of the advice form. (She has reprised her advice-giving role in a podcast co-hosted with Steve Almond, her predecessor as “Sugar.”)
Dear Sugar was the rare advice column that leaned into the secrecy of its author, but most pseudonyms today are a matter of convention rather than concealment. Daniel Mallory Ortberg took over the mantle of Slate’s Dear Prudence column in 2015, bringing to the role an already high profile as the beloved founder of The Toast. The column has always had the writer’s name and face clearly attached, but for Ortberg, those details were not fixed: Shortly before publishing a second book this spring, the writer came out as a trans man. In an interview with Heather Havrilesky, he admitted that the thought of changing the byline and picture over the column was “terrifying.” Yet the role of the columnist provides a kind of mask. “I’m probably about 30 percent more thoughtful and careful in Dear Prudence mode than I am in other forms of writing,” Ortberg says. He agrees that readers likely “self-select” when they write to an advice columnist but suggests that has less to do with a shared identity than simple familiarity with their voice and likely opinions. We welcome advice from those we know and trust.
The most successful columnists today make clear who they are and where they’re coming from, and they acknowledge the pressures of living in an ideologically divided world.
Ashley Nicole Black, a comedian and writer for Full Frontal with Samantha Bee who writes the new Sip on This column at the online feminist site Dame, concurs that it’s helpful for readers know something about where a writer is coming from. She celebrates those who are “honest about how their life experiences inform their work.” Yet as one of the very few women of color to helm an advice column, Black sees a distinct irony in the work she’s doing. “Given the American history of black women being forced into a position of caregiving, is it weird that I have voluntarily put myself in a caretaking position by doing this column?” she asks rhetorically. “I don’t know!”
It’s possible that a columnist’s identity and background take on a particular urgency today, in a political moment when marginalized identities are under threat. For Black and Brammer, whose columns both debuted during the Trump era, the pressures of the current administration inform everything. “Every question we’ve gotten so far has an undercurrent of ‘the world is burning and that is making my life extra stressful,’” Black says. Meanwhile, Brammer faces regular questions from readers about whether to cut off family members who voted for Trump. Even when the question is less direct but deals with “bullying or marginalization,” the connection seems obvious to him. “There is a rash of malice against queer people right now,” Brammer says. “If we advice columnists take our jobs seriously, then we recognize our capacity to help provide a balm for it, even if it’s just in a small way.”
At the same time, advice columns have to be entertaining, and Black often uses humor to get her message across — a tactic that comes naturally to her. “I’m that friend who tries to comfort you by cracking a joke when you are crying.” Brammer uses humor in his replies but says he’s careful to resist the temptation to “pummel” people who make thoughtless or homophobic claims in their letters. Amusing the broader readership has to be balanced with empathy, which can be a rare quality online. “One challenge the advice column faces in an era of callouts and absolutism on social media is figuring out what kindness means,” Brammer says. He strives to offer patience and the benefit of the doubt; to strike a balance between understanding and advising without “coddling” his readers.
The most successful columnists today make clear who they are and where they’re coming from, and they acknowledge the pressures of living in a hyperconnected but ideologically divided world. For Ortberg, it’s never been “either possible or desirable” to separate our personal lives from politics or to pretend that our private dilemmas aren’t affected by the world at large. The dispassionate authority that readers may once have sought in an advice column — a voice of moral certainty and clear dos and don’ts — is being pushed aside in favor of authenticity. Columnists are increasingly open to revealing their own flaws and doubts in the quest to make advice-giving an inclusive genre.
“Everyone who reads my column regularly knows that I’m a very emotional, sloppy, bossy, impatient wild card of a human being,” Havrilesky says. “If you want a smooth, gorgeous, admiration-worthy, one-size-fits-all guru lady to give you advice, you’ve got to find a different source.”