Heather Havrilesky made me cry, but it’s (probably) not what you’re thinking


The doorway to Heather Havrilesky’s living room is festooned with silver streamers, like the beaded curtain at a fortune teller’s. I am immediately disarmed, and like the countless people who write into her online advice column at New York Magazine every week, privately hopeful that she is about to divine some truth about me that will Finally Change Everything.

This is not a professional parallel that I’m certain Havrilesky would relish. Her column, the inspiration for the book “How to Be a Person in the World: Ask Polly’s Guide Through the Paradoxes of Modern Life” coming from Doubleday in July, does not fit comfortably into rote self-help discourse. Under her Ask Polly moniker, Havrilesky dishes radically honest, no-nonsense advice tempered with self-deprecating humor, gleeful profanity and an unfettered voice.

“It’s not like I’m some amazing earth-mother type,” she says, although her hair is wet from the shower and we are sipping cups of honeyed tea. “I don’t walk out into the world and feel loving to all creatures at all times.”


The streamers, it turns out, are a remnant of her daughter’s “Star Wars”-themed birthday. There is a movie poster on the wall for a party game on which you can pin-the-tail-on-the-dark-side.

It is clear from Havrilesky’s impassioned Ask Polly responses that she cares deeply about the struggles of the anonymous letter writers — and also that she is incapable of not telling it like it is.

Havrilesky weaves tales of her own foibles into her column, and for a certain demographic of unmarried, thirtysomething women (*raises hand*) her hilarious and sometimes-humiliating disclosures are uncanny. An aside from one entry about delivering a speech to a disinterested partner that “was just like a TEDx talk, except with swearing and weeping and snotty tissues where the wireless microphones and pointless anecdotes and life lessons should go,” feels eerily familiar. (Just me?) And yet imperatives like this one — “You can admit that you haven’t figured it all out yet. You will revisit this feeling over and over in your life” — are, if not exactly comforting, something close. It doesn’t feel like schadenfreude to read Ask Polly because she meets her reader’s vulnerability with her own.

Havrilesky and I are sitting on either end of her couch, and as the conversation progresses, we tuck our legs up beside us. The intimacy of one-on-one conversation, as in her column, seems to energize Havrilesky; she is both hyper-focused and willing to go wide-range. “You can be lost or feel like your circumstances are humiliating, and you can still be on fire,” Havrilesky tells me. “You can be a beacon to other people even in the midst of that mess.” She references her own wet hair as an example. “You’re in the shower and the interviewer’s here. Nice one!” She laughs.

“How to Be a Person in the World” is a collection of mostly never-before-seen Ask Polly columns; now that she’s done working on it, Havrilesky is exploring an Ask Polly podcast. She is unsure about how to structure the episodes, which will include not only advice but also music and humor. “I wanted to be Terry Gross,” she says, “but it turns out I’m Crusty the Clown.”

Havrilesky established herself writing brilliant snark for Suck, the Internet’s irreverently named first daily, after which she served as Salon’s TV critic for seven years. The progression from critic to advice columnist did not strike me as an obvious jump, and I asked how her work as a critic informs the work she is pursuing now.


“The psychological aspects of any show were always at the forefront of my mind when I analyzed TV. I wrote a lot about ‘Six Feet Under,’ ‘The Sopranos’ … shows that were so completely obsessed with psychology and our emotional lives and how impoverished they are generally.” Havrilesky, unsurprisingly, holds a psychology degree from Duke. “The advice column feels like my most natural skill set. … It’s almost like I’d been finding ways to write about these things, and now I have a direct route to write about the things I want.”

Havrilesky, who has also published a memoir, reveals almost as much about herself as she does the people she’s advising; her empathy closes the gap.

Her particular brand of advice, however, has been characterized as “tough love.” I asked Havrilesky what she thinks of the label. “It can sound obnoxious to just state the truth,” she says. “When you say, ‘you’re a total wreck right now — I’ve been there, I get it — but you have to stop this and do that instead. …’ My feeling is that people take that as invasive.” In other words, she gets into people’s heads.

Certainly, I disclosed all manner of things to Havrilesky, which she appeared to relish. “I don’t think I’ve ever said to anyone, you’re giving me too many details about the little folds of your personality,” she says, and that what she hopes to remind people with her column is “how much there is to appreciate in the texture of mundane, flawed, day-to-day life.” I found myself incapable of leaving without asking for advice — I had Ask Polly captive after all — and so I ventured: How do I balance my ambitions while still enjoying the ride? During the warm, invested, near-hourlong conversation that followed, she was in her element. Havrilesky gave me permission to aim for the pinnacle, but with the challenging caveat that when alone, “you have to be that person for yourself.”

I left Havrilesky’s feeling like a million bucks, but by the time I arrived at a concert that night, I was overcome. When the lights dimmed I burst into such explosive tears that a stranger offered me a suspect-looking tissue from a tiny sandwich baggie. How do any of us manage to walk onto the stages our lives? How do we become, as Havrilesky advises in her column, our “own rickety-ass invention, and every day … find (our) swagger all over again”? How, finally, to be a person in the world?

I don’t have any of the answers, but I know someone who does.

Ask Polly.

French is a writer in Los Angeles.


Havrilesky will appear at the Los Angeles Times Festival of Books on Sunday.