Ask Polly

Advice from Heather Havrilesky, author of Ask Polly, formerly of New York Magazine


I’m Heather Havrilesky and I created the Ask Polly advice column in 2012 for The Awl. My initial plans for Ask Polly weren’t ambitious at all: I just wanted to have some fun and foist some of the unwanted advice I’d been rudely pushing on friends and family for decades onto a new set of unsuspecting strangers. Much to my surprise, given my poor track record, Ask Polly became one of The Awl’s most popular features, and in 2014, Stella Bugbee brought the column to New York’s The Cut (this move was enabled by Awl co-founder Choire Sicha, who generously granted me all rights to the column and supported my move to the Cut). My advice book How to Be a Person in the World was published by Doubleday in 2016.

In April of 2021, Ask Polly moved to Substack where it publishes twice a week (on Mondays and Wednesdays) for subscribers only. Along with advice columns on subjects like how to embrace your secret creative dreams, how to make a lifelong commitment, and how to navigate difficult friendships, I also write features with faintly suspicious titles like How to Be Exuberant and How to Handle Regrets.

I love writing this column. It’s been the biggest surprise of my writing career how much I love it. I’ve written essays (New York Times Magazine), criticism (Salon, Bookforum), cartoons (Suck), moody prose (Ask Molly, written by Polly’s evil twin), and four books, the latest of which, Foreverland: On The Divine Tedium of Marriage, is a memoir of my marriage that will be published by Ecco in February of 2022. (You can pre-order it here.) But nothing brings me more satisfaction than diving into a stranger’s problem and rediscovering some basic truth that makes our (frankly terrifying) world feel less harrowing and impossible.

What I discover over and over again is that you can’t think your way through life like it’s a difficult puzzle that needs to be solved. You can’t expect yourself to improve constantly. Your happiness doesn’t depend on unlocking a new levels of success, status, wealth, fame, beauty, and adventure. We weren’t built to chase empty goals through infinite mazes, satisfaction always eluding us. We’re here to savor the conflicted, melancholy pleasures of each day. Our joy depends on embracing our imperfect selves as we are, treasuring the impermanent wonders of this moment, and fighting to make the world a more just and habitable place for everyone.

I’ve learned so much from Ask Polly readers over the years, and that wisdom has grown exponentially over the past few months, thanks to the fact that Substack’s format enables much more vibrant reader discussions. Week after week, we remind each other of what’s important (kindness, patience, anime, really good cheeses) and what’s not (obsessions, stinging insects, extremely online idiots). When you subscribe, you get two new columns a week, you can comment on any column or discussion thread, and you can read everything in the archives. Thank you for reading and supporting Ask Polly!

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