Monday, July 11, 7 p.m., free
Motorco Music Hall, Durham

Heather Havrilesky made her name with her critiques of books and TV, but she’s found a new level of success critiquing people’s lives. The former Durhamite comes home on Monday, July 11, for a live version of Ask Polly, the popular advice column she writes for New York magazine, at Motorco Music Hall. Hosted by The Monti’s Carter Kersh, the Regulator-sponsored event is part of a tour for Havrilesky’s new collection of Ask Polly columns, How to Be a Person in the World.

Havrilesky first became known to many as the TV critic for Salon, a position she occupied for seven years, and as author of the cartoon Filler on Suck.com. She’s moved on to outlets like The New Yorker, All Things Considered, The Baffler, and, most recently, Bookforum‘s The Bestseller List column. She also wrote the 2011 memoir Disaster Preparedness, which chronicles her family life growing up in Durham in the 1970s and ’80s.

“I always felt like I had a voice as a writera grouchy voice, but a voice,” Havrilesky says of her eclectic output. “Becoming a more flexible writer is like learning to play different instruments, different types of music. There’s more tools at your disposal. So it’s true that my voice used to speak in a lot of two-syllable words and short sentences, and now it’s got more flourishes, and is a lot more whimsical and fun.”

The weekly doses of advice Havrilesky dispenses in Ask Polly are longer, deeper, and more self-lacerating than what readers of Dear Abby or Ann Landers might recall. Her average response to readers’ qualms runs a few thousand words, with Havrilesky bluntly recapping her own experiences and failures. It feels more like sitting down with a friend for a pep talk than being lectured by a know-it-all.

“I try to go back to the basic premise of, ‘What is the issue here?’ Not so much how to solve the problem immediately, but how to figure out what the central issue is for this person, where the slippage is in their existence,” Havrilesky says. “The other question is, ‘Does the response immediately grab you by the throat?’ There’s no reason to believe I should be giving anyone adviceall I have are words on a page. If you don’t want to read beyond the first paragraph, then I’ve failed.”

How to Be a Person in the World organizes many of these columns by theme. The topics range from “Am I Too Weird?” and “I’m Thirty-Eight and Everything Is Awful” to “I Feel Haunted by My Affair.” Whether Havrilesky’s advice works is purely subjective, but it always feels like the result of sincere personal introspection.

“The experience of reading the book feels like a whole different experience from reading the column online,” she says. “The first column is about a woman who doesn’t want her sister to bring her gorgeous boyfriend to the woman’s wedding because she feels like he’ll upstage the bride, and the last one is about mourning someone who’s died. It kind of starts micro and gets bigger and bigger.”

How to Be a Person in the World is more than just reprints; Havrilesky wrote many new columns for the book. In “crazy binge-writing sessions,” she says, “I learned to embrace the terrible void as a writer much more than I did before.” (Don’t worry, she laughs as she says it.)

“I was answering two advice letters a day and sending them to my editor to pick the best ones,” she continues. “It was like OD-ing on advice-giving and other people’s problems, which was pretty hardcore intense. But it was also really great. Doing so much of it gave me confidence in the sustainability of the column. It helped me move to another level of believing in what I was doing, and enjoying it more than I ever had before.”

Havrilesky admits she might not go back to her TV-critic roots for a while, as she feels burned out and behind on TV. But trying different kinds of writing is still her best advice to herself.

“I feel like every different genre I try to write in is good for my writing overall,” she says. “By straining to write good essays about good books, I can turn to my advice writing and find that this crazy, florid prose flies out of me, as applied to someone’s bad boyfriend.”

This article appeared in print with the headline “Polly Explains It All”