CULTURE & ARTS
11/10/2015 01:29 pm ET

The New Generation Of Agony Aunts Transforming The Advice Column

These new advice columnists aren’t regular aunts. They’re cool aunts!
Kansas City Star via Getty Images

Slate has a mobile app that has graced my iPhone for years. It ensures I have at least a little fresh reading when I’m stuck in a waiting room or on the subway, and besides, I love Slate’s contrarian takes. But three times a week -- Monday, Tuesday and Thursday -- there’s just one column I’m refreshing the app feed over and over again hoping to see: Dear Prudence.

I didn't always agree with Prudie's advice, dispensed by writer Emily Yoffe. Sometimes Yoffe actually drove me (and many other readers) batty with her quickness to suggest frequent tipplers may be abusing alcohol, or with her skepticism toward readers who reported being sexually assaulted while under the influence. Her tips were often on the money, though, and I loved her letter selection and her no-nonsense tone. 

On Monday, Slate's editor-in-chief Julia Turner announced that Yoffe was stepping down as Prudie, and would be replaced by Mallory Ortberg, cofounder of The Toast and minor Internet celebrity. It's a bold move for a fairly traditional advice column at a mainstream web magazine: Ortberg has a youthful, distinctive voice and has mastered the Internet version of sardonic deadpan, which she employed to hilarious effect in her book Texts from Jane Eyre, imagining what famous literary couples would text to each other. 

Yoffe herself, in her time as Prudie, has played with the conventional boundaries of advice columns. She would drop significant revelations about her personal life, when relevant -- every devoted reader knows the story of her husband’s first wife, who died young -- and didn’t hesitate to sometimes take strong, seemingly contrarian positions in her advice. She wrote for Slate outside of her column, sometimes on controversial topics like rape in college. But her free-wheeling replacement still promises to be a big step away from convention.

"I think there will be some continuity, because of Mallory’s deep regard for Emily’s work in the role," Turner wrote in an email on Monday. "She is a close reader of the column ... so it seemed natural to reach out to her." Still, Ortberg’s own website, The Toast, exemplifies a willingness to experiment with media conventions that suggest a far bigger shift for the column. She writes about narrative tropes in classic literature through hysterically funny listicles, or critiques a TV show by spinning out increasingly insane episode premises. She has a whole series of art history posts in which she imagines subtitled conversations between the subjects. When her new position was announced Monday, her Twitter reaction was exuberantly unpunctuated.

One thing's certain: It's hard to imagine such a fresh, identifiable young voice would have been handed the keys to an established advice column in years past. How did we get here?

In 1991, Dan Savage gave a bit of casual advice to Tim Keck, cofounder of The Onion, who was about to launch the alt-weekly The Stranger in Seattle: “Make sure your paper has an advice column -- everybody claims to hate 'em, but everybody seems to read 'em.” The massive success of the column he ended up writing for The Stranger, Savage Love, lends support to this truism.

I’m just one anecdotal example of this: I know advice columns are typically lowbrow, gossipy features with a less-than-intellectual image. As a member of the media, I didn’t feel proud admitting that I looked forward to my Dear Prudence interludes. But I voted with my page views, as do so many readers, which is why advice columns continue to proliferate and mutate to fit the zeitgeist.

This proliferation has gone on, now, for centuries. The publication believed to have invented the modern advice column, The Athenian Mercury, may be just a bit before your time: It was published in the 1690s. But by the 20th century, syndicated columns in newspapers and features in ladies' magazines dominated the genre, dispensing succinct, practical solutions to social and personal problems across the U.S. 

In England, these columnists became known as "agony aunts," and the cozy, cookie-cutter image of a motherly, upper-middle-class white lady was typically used to emphasize this unthreatening image -- the nurturing woman you'd take your problems to for proper but sympathetic guidance. (There have been male columnists, and non-white ones, but they've generally been confined to niches; most men in the genre, for example, give advice on specific topics, like ethics, rather than more tender personal matters.)  

Ann Landers and Dear Abby, written by sisters Eppie Lederer and Pauline Phillips (née Friedman), perfected this approach. The pair doled out dueling advice, both drawn from a traditional, family-minded set of values, and delivered with incisive brevity.

"Don't make any hasty decisions," Lederer told a recent divorcée who'd met a new man. "The best way to deal with it is to say nothing," Phillips wrote to a woman too embarrassed to face her boyfriend's father after he walked in on a private moment.

Most answers were dispensed in a couple blunt sentences, with naught more than a corny joke to sweeten the pill. 

Author and 'Dear Abby' columnist Abigail Van Buren, circa 1958.
Hulton Archive via Getty Images
Author and 'Dear Abby' columnist Abigail Van Buren, circa 1958.

Readers continued to avidly devour these columns, even when it was the same bland PB&J they'd been fed for years. But when Dan Savage kicked off Savage Love in 1991 -- a column he originally pitched as Dear Faggot, which he did in fact use as a salutation to advice-seekers for years -- it was far more than a Dear Abby for the indie media crowd, or a Miss Manners with an LGBT focus. It was creative, brash, sometimes offensive, but always thought-provoking.

Savage himself was an avid fan of advice columns, but before him, the genre was stuck in a fairly consistent rut for generations. Columns were generally reassigned to new writers or ghostwriters when the original writers died or retired, instead of being given a new image and voice. Savage Love broke new ground, taking a new irreverent tone and opening the field to all sorts of new subject areas. Readers could ask about the finer points of exchanging oral sex, or complain that they were no longer attracted to a spouse who’d gained weight, without being castigated or dismissed. He and his readers coined terms like “pegging” and “santorum” (Google it). He brought the rather fusty tradition of advice dispensation to a world of free-wheeling sexuality and queer relationships, which had long been ignored or handled awkwardly by agony aunts.

Savage Love heralded a new generation of agony aunts -- the cool aunts. Savage was really less like an aunt and more like your popular, funny older cousin who gave you his full attention every now and then. And as web media blossomed, so did other cool aunts. 

Probably the most influential modern agony aunt, aside from Savage, is none other than Cheryl Strayed, who wrote a column called Dear Sugar for The Rumpus starting in 2010. Ruth Franklin of The New Republic deemed her "the ultimate advice columnist for the Internet age," arguing that Strayed -- then writing the column anonymously -- was "remaking the genre."

In a Reddit AMA, Ask Polly's Heather Havrilesky credited Strayed with "populariz[ing] the extremely thoughtful, beautifully written advice column/personal essay format," of which Havrilesky is now, perhaps, the reigning practitioner. Strayed wasn't afraid to tell a reader, "You are a fucking amazing person," after sharing a painful memory from her own past. "I think she showed a lot of us what was possible with Dear Sugar," Havrilesky wrote. 

Within the past decade, these columns have multiplied. There's Captain Awkward, which dispenses nerdy, feminist-friendly advice from an eponymous website. Havrilesky’s Ask Polly launched on The Awl in 2012, but it wasn’t her first venture into the field; she wrote an advice column for Suck.com in 2001 and answered questions at her own website for years. Andrew W.K., in addition to his rock career, writes an advice column for The Village Voice (after having written one for a Japanese magazine for nearly a decade). Gawker Media offered Pot Psychology, which launched in 2007, an advice video series in which the two advisors, Tracie Egan Morrissey and Rich Juzwiak, got stoned together before answering queries.

Dimitri Otis via Getty Images

For those of us who’d grown up on syndicated newspaper fare (I’d been a devoted reader of Ann Landers, whose column appeared in my local paper in Indiana), these new columns were fascinating -- all the human interest, but without the adherence to conventionalities and brief word counts. These were agony aunts willing to unpack your quarter-life crisis with you, or to direct you how to tell your new fling about your sexual fantasies, or to flout the accepted wisdom of hoary etiquette and social expectations. Each column had its own flavor, its own personality.

Havrilesky’s Ask Polly, which now appears on NYMag’s The Cut, is both a particularly idiosyncratic and a particularly successful example of the cool agony aunt. She answers just one question a week, in long, capslock-studded, instinctual prose, pouring in doses of empathy, comparisons to her own misguided youth, paeans to her husband, and real talk about her familial dysfunctions.

Though there are hints of Dear Sugar in Polly's unrestrained verbosity and enthusiasm, it's the individual personality that defines the column. “I’m very influenced by other writers in my other work,” Havrilesky said in an email Monday. “But when it comes to writing advice, I really follow my own instincts. I’m not trying to create something that’s perfect or stylistically awe-inspiring. I’m just trying to find a vivid way to unlock some kind of answer or epiphany for the reader. I want every single column to make the reader say HELL YES, I CAN DO THIS.”

In a field that was long so rigid as advice-dispensing -- Ann Landers, Dear Abby, Miss Manners, Emily Post et al generally followed fairly unvaried formats and lines of response -- this honest, personal approach blasts open what the genre can do, and shifts our understanding of what it can be.

"People in the beginning really complained about how long-winded [Havrilesky] was," Stella Bugbee, editor of The Cut, said over the phone. As a reader, I also noticed comments taking issue with her frequent comparisons of readers' problems to her own life experiences. "My feeling was Heather and Polly were basically perfect, and I wasn’t going to trim any of it." Now, with Ask Polly firmly ensconced at The Cut, Bugbee said, "I think people have caught on to her unique cadence." The column is, she pointed out, one of their most consistently popular features.

Havrilesky's open, raw approach also capitalizes on the clearly insatiable hunger readers possess for personal essays, without subjecting writers to the same emotional and professional wringer that can follow with standalone pieces offering up the minutiae of their lives. Instead, we get the scandalous details of anonymous readers, then a response, tinged with personal anecdotes and the casual tone of a close friend, which weds the TMI appeal with the appeal of familiarity.

The semi-confessional nature of these responses also allows room for more nuanced, self-care-focused advice, in which your struggle with getting over an ex isn't reduced to "just move on" but acknowledged for the thorny, complicated emotional quagmire it is. It's more like unpacking a break-up with your snarky but caring BFF, while traditional columns can sometimes feel more like listening to your grandma sniffing over inappropriate seating arrangements at your cousin's wedding. 

This human note is essential, said Bugbee, who'd experimented with various advice columns, including one called "Ask Google," at The Cut before bringing Ask Polly on board. "What I learned through that process was that people just want really good advice," she said. "They don’t want a gimmick."

Turner agreed that while the essential content of advice columns -- sincere insight about common real-world problems -- won't change, writers need to offer something unique to keep the form exciting. “The best advice columns are made by the quality of their prose -- it takes skill to keep all those misbehaving in-laws, pets and bosses fresh and fascinating week after week,” she said. How Ortberg will change the Prudie game remains to be seen, though her body of work suggests her column will be unlike any we've seen before.

Havrilesky, for her part, thinks the revolution is just beginning. “Advice columns are the new TV recaps,” she said. “Soon, everyone will be writing them! ... And as with recaps, some will be amazing and smart and funny and others will be bland and dull and worthless.” Though she doesn't read many advice columns, she's eager to see what Ortberg will do at Slate. 

Does she have any advice for a first-time advice-giver? “My only advice to Mallory is this: Don’t take anyone else’s advice. Do this your way, period the end,” Havrilesky emphasized. “THEY DON’T KNOW, MALLORY. YOU’RE THE ONE WHO KNOWS.” To clarify, she added, “That’s not my advice to any other advice columnist, mind you. That’s just my advice to Mallory. But see, Mallory already knows all of that.”

In other words, kids, don't try to write an advice column at home. But more importantly, Havrilesky's words show how far the advice media has evolved. These days, knowing and fighting for your own voice, in all its crazy and quirky glory, might be the best and most important qualification to be an advice columnist to begin with.

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