Ask Polly’s Heather Havrilesky: ‘I feel connected to the people who write to me’

The advice columnist brings her wisdom off the web and into the bound pages of a collection of almost entirely new letters, How To Be A Person In the World

Heather Havrilesky is the advice columnist for people encountering doubt about the magic dwelling inside them. If this sounds corny and sentimental at first, that is because it is. While much of the modern advice material dispensing wisdom to readers takes the form of small and practical steps toward self-improvement, Havrilesky is an unapologetic evangelist for sentimentality and believing in our own enormous potential. She speaks in the language of the epic, the supernatural, and the celestial.

Since 2012, her weekly advice column, New York magazines Ask Polly, has broadcast these beliefs in human potential through letters tackling modernitys most pressing existential crises for a growing and devoted following. The column has provided reassurance to readers, but also instilled in them a sense of responsibility, to themselves and others, to use their potential wisely.

This week, Havrilesky brings Pollys wisdom off the web and into the bound pages of a collection of almost entirely new letters, How To Be A Person In the World: Ask Pollys Guide Through the Paradoxes of Modern Life.

Havrilesky is not the most likely advice columnist, by her own admission. She is hardly a stoic observer, she does not consider herself to be much of an expert on how to feel. I find my own emotions very bewildering. I always have. I am a very moody person and have a very uneven experience of the world, she tells me over the phone from her home in Los Angeles, where she lives with her husband and daughters. (As we talk, our conversation is occasionally punctuated by interruptions of her dispatching her husband to a parenting task and making sure that her dog had not gotten into something poisonous.) I will never become a person who is not floored by her emotional experience.

But for the millennial women who make up the bulk of her audience, it is precisely those emotional experiences that have made her into something of a wise and occasionally profane aunt, in whom we find wisdom and hope for our own futures. Havrilesky, 46, regularly discloses her own encounters with her readers issues. Sometimes it comes as heart-wrenching recollections of events like the loss of her own father to a grieving letter-writer (I wanted him to be alive, to eat a great meal, to read something funny for HIS sake) and sometimes light-hearted admissions that she too has struggled with obsessing over boys, a habit she compares to weaving a rich tapestry and then using it as a dog bed. (I was a mind weaver of rich fucking tapestries, too, back in the day, with some demure yet straight-talkin, slightly slimmer, slightly more hygienic version of my actual self ). Regardless of the issue, Havrilesky makes clear that she too, has skin in the game.

Empathizing so deeply with the feelings of others, fairly miraculously, does not diminish the joy that Havrilesky gets from engaging the despair and complexity of her readers problems. Its very easy to pick good letters because there are so many good ones. It really is an embarrassment of riches, she says a somewhat baffling declaration that being bombarded with messy, often heartbreaking stories is an enviable position.

My nature is to be fascinated and curious and engaged and to feel connected to the people who write to me. I like hearing peoples problems. I love complicated problems. I love long-winded, difficult letters. I dont think everyone alive is like that, she says.

While most of the letters are new, the terrain covered in How To Be A Person In The World will be familiar to much of her readership and she repeats similar themes throughout the book: your feelings are valid but misguided in a very particular way, your lack of romantic fulfillment is not a result of some inherent flaw of yours, all of your hurt is real, and all of your hurt can be healed. These are affirmations worth repeating and so they are, but the prose in which Havrilesky plants them is plainspoken while still appealing to the grandness of the celestial and the gravity of the scriptural.

In the book, Havrilesky speaks frankly of evil and malice when responding to a woman grappling with her friends welcoming of the social return of a man whose sexual advances profoundly violated her boundaries, noting lines from a song called Devil Town by Daniel Johnston that reads: Oh lord, it really brings me down about the devil town.

But the proverbial profane aunt has some fun, too. To a woman who is convinced she has a fundamental flaw she cant pinpoint that is driving romantic prospects away, Havrilesky points out in earnest, Every night you pray to the gods of rejection. Your prayer ritual involves replaying the past, loading one reel after another, footage of men who broke your heart, only to become comically exasperated when she later declares, YOU ARE CURRENTLY PRAYING AT THE ALTAR OF THE MOST TEDIOUS RELIGION IN THE UNIVERSE.

To a woman who distracts herself with fantasies about men rather than focusing on her own challenges, Havrilesky tells her what she plans to tell her own daughters when they start to place all of the magic outside of themselves and become similarly preoccupied: The world has told you lies about how small you are. You will look back on this time and say, I had it all, but I didnt even know it. I was at the center, I could breathe in happiness, I could swim to the moon. I had everything I needed.

I read this section aloud to Havrilesky in our call but make it only to the end of the first sentence before bursting into tears. It was a mixture of sudden relief that my nagging suspicions that I am more than the world has allowed me to be were true after all combined with the grief over time lost living in the smallness of the lie. Havrilesky then began to cry herself, a moment that might have been awkward for someone less tolerant of a fate that floors them with their emotions. Most people alive are not like that.

This sentiment more than any other is what echoes throughout the book, the untelling of the lies about our smallness. She declares life is full of twinkles and twinges, even amid poverty and ageing and death late in the book, sincere and corny as when she began. This mean, mean planet still rewards those who can see the depth and beauty of what they carry around inside themselves, she reassures a letter-writer who yearns for a big, exciting love amid lukewarm interest from men in an appeal for more brazen self-love modeled on Kanye Wests. It is these small reflections that Havrilesky sees us for what we are: not tiny specks of light in a dark sky but enormous sources of light and energy in a brilliant universe. We have each other. We have worlds within us, me and you, she continues, unflinching as she delivers the message that every person carries their own peculiar magic whether they can see the enormousness of it or not.

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