The Messy Woman

Heather Havrilesky’s advice column urges readers to revel in their own hot mess-ness.

Sonny Liew

“Imperfect things are the most beautiful things of all,” writes Heather Havrilesky in How to Be a Person in the World, a compendium of her unruly, swaggering “Ask Polly” advice columns. Polly, billed as an “existential advice columnist,” came to life on the Awl, channeling that site’s chatty self-deprecation and expansiveness, and migrated to New York in 2014. She’s not the orderly, reasonable voice we’ve come to expect from Dear Prudence and Carolyn Hax, her sisters in the flourishing advice column genre, or from Gretchen Rubin and Oprah, in the related juggernaut field of self-help. Dan Savage, Jolie Kerr, Amy Dickinson, even Carrie Fisher: They all promise to help us clean up our messes. But Havrilesky leans into the mess until it swallows her, its embrace resembling something like light. Think of Havrilesky as a unique hybrid of the conventional advice giver and the messy woman.

Who is the messy woman? In Havrilesky’s words, she is a “blaring siren,” a quirked-up soulful neurotic. She’s “smart, unpredictable, sensitive, unique,” and she has an “overactive imagination.” She’s gained prominence in movies like Trainwreck and Obvious Child, shows like My Crazy Ex-Girlfriend, books like Jenny Offill’s Dept. of Speculation and Sheila Heti’s How Should a Person Be, and albums like Beyoncé’s Lemonade. A variation on the wounded woman, she seems attractively damaged, except powerful, not mute. The messy woman does not wait for you to notice her but demands your attention. Her exuberant passion and reactivity, instead of holding her back, are inseparable from her sway and incandescence. She evokes a “hot mess” in its most humblebraggy sense: the creatively “confessional overthinker,” Taylor Swift’s “nightmare dressed like a daydream.” Havrilesky herself finds the perfect metaphor in her dichotomy of “mountain people” (stable, serene, poised folks) and “volcano people” (those whose issues and complications give off a beautiful glow, even though they might burn you).

Like fellow messy advice giver Cheryl Strayed (“Dear Sugar”), Havrilesky lets her answers run long. At the end of one, she reassures a letter writer who fears she is too anxious to find love:

Volcanoes are breathtaking and spectacular. You will have more love than you know what to do with. You will have more passionate feelings, more colorful notions, more amazing epiphanies, more heartbreaking realizations, more shivers of recognition and inventive ideas and breakthroughs and grateful tears than you can possibly deal with. Be exactly what you are. Be thankful for what you are. Let it flow.

An outpouring of language miming the spilling forth of emotion, tons of anaphora, lyrical catalogues bookended by short, percussive statements that are meant to hold the weight of revelation: This is Peak Polly (no pun intended). In the “passionate feelings” sentence, she uses and to accelerate into her overarching motto: “Be exactly what you are.” Havrilesky flips the letter writer’s fear on its head: Rather than driving others away, perceived neurosis will draw in the world—“you will have more love than you know what to do with.” Hers is an artist’s creed: Always err on the side of expressivity. Let it flow. 

Heather Havrilesky.

Willy Somma

If you’re a delicate, volatile sort who doesn’t want to be a volcano, maybe you’d prefer to identify as a zesty root vegetable. “I was a radish tossed into a sack of potatoes,” Havrilesky tells one letter writer, the one who wonders why the guys she dates are so boring. (Often Havrilesky refers to herself in her answers: her past, or how she feels in the moment of response.) Elsewhere in the book, she compares her personality to an anchovy—“oily, salty,” or in human terms “emotional, thoughtful, moody, obnoxious, demanding”—rather than a “sweeter, snackier” Little Debbie.

If these categories are meant to represent neutral types, they fail. Isn’t it self-evidently better to be a radish than a potato? Who wants to be a potato? The opposite of the messy woman is not the together woman; it’s the dullsville boyfriend or the substance-less sorority girl. “Let’s breathe fire and magic together,” Polly urges a letter writer, the one who wants to figure out what she’s doing wrong with men. “Let’s never live under that mountain again.”

I cherish nourishing potato people and stable mountain people, and sometimes I worry Polly doesn’t give them enough credit. One might also question whether creative brilliance has to go hand in hand with messiness—aren’t there plenty of calm, focused artists and disheveled, shallow normals out there? (I often suspect that I am an anxious normal; even if Polly might atomize that qualm with the glistening affirmation that my anxiety is a byproduct of my awesomeness, I’m not convinced she’d believe it.) But I’m also making Havrilesky sound more insufferable than she is. She’s not a first-person essayist reframing her weirdo habits and painful fallibilities as empowering virtues. She’s an alluringly wry cheerleader, an enthusiastic volunteer offering sports drinks as we struggle past during the half-marathon of life.

For curious things begin to happen when the messy woman becomes an advice columnist. To start, she is officially anointed as an aspirational figure, someone qualified to instruct others. (This is very weird! We should be taking life advice from Mount Vesuvius? But Havrilesky’s book makes a strong case.) No longer the object of concerned attention, she gains authority and loses urgency. You can put her in a box: “I definitely do not want to be one more human being on the planet … to slowly and surely become a consistent and sustainable and lucrative brand,” Havrilesky tells one LW. Well! You may be thinking. Good luck writing a weekly advice column! The reliable, steadfast personalities of our oracles are part of what keeps us returning to the cave. They’re the static ones, the relatively flattened deus ex machinas with consistent axioms and catchphrases.

The conventional advice column is about gawking at car crashes, delighting in the contrast between the sensible advice giver and the insanities endured or perpetrated by the LW. But in the mythology of the wounded or messy woman, having the answers—being fundamentally OK—makes you less interesting. And in a typical Ann Landers scenario, the figure who compels all the drama and tension is not the columnist but the seeker—the character in flux, awaiting transformation in a time of crisis.

Maybe that’s why Polly writes to one LW:

So here’s the main thing I want to say to you: There is no peak. You are where I am. We both have magic, but we both have to dig for it.

Note the magic metaphor, and the informal emphatic signposting (“here’s the main thing…”) meant to drench what comes next in special meaning. Most importantly, Havrilesky levels the playing field, dismantling the traditional dynamic between advice giver and advice seeker. “You are where I am,” she insists. But if that’s so, what’s the point of writing in? Don’t agony aunts traditionally use their position of authority to clean up your life or inspire you toward self-improvement, not empower you to “do you” in all your chaotic glory?

In an era that is wholly fixated on identity—as definitional and as a form of knowledge—Polly peddles the fantasy that all you need to do to succeed is simply be the most you. “Beyoncé,” she pep-talks one LW, “doesn’t tap into a higher quality of magic than you.” Putting aside the indisputable fact that Beyoncé has 1,000 times the magic of any mere mortal, such a sentence is the result of appointing the messy woman, with her ethos of perfect imperfection, the custodian of personal worth. It’s a tautology: If you’re dissatisfied enough to write to an advice columnist, you must be emotionally complicated and searching and sensitive, which means you are already magical. Should the complacent potatoes be worried? I bet Havrilesky would say they contain magic too. (The spud magic BILLOWS OFF YOU! she would write. BREATHE FIRE, MAGIC POTATOES!) Yet in championing hot mess-ness as a superpower, Polly comes across as less democratic than she seems to want to be.

Havrilesky is often grouped with Melissa Broder, the So Sad Today essayist and poet, an association both women have encouraged by doing an interview together. But while they share a “don’t pretend to shiny fakey happiness” mindset, they also mark the two ends of the reactivity spectrum. Broder’s aesthetic is affected numbness—she can’t even bring herself to punctuate questions or capitalize first letters. (“how many licks does it take to get to the center of my core underlying issues,” murmurs one representative tweet.) Havrilesky, on the other hand, is all fortissimo, flinging majuscules and exclamation points, telling LWs to weep and rage like Shakespearean heroes. She’s an emotions maximalist. “Once you start accepting yourself in your self-talk, you may find yourself feeling overcome, literally bursting into tears,” she writes to the woman who “doesn’t know” her own heart. “THAT IS A BEAUTIFUL FUCKING THING!” In the foreword to How to Be a Person in the World, Havrilesky recalls replying to the editor who approached her about moving Ask Polly from the Awl to New York: “You know my column is three thousand words long every week, and half of those words are fuck, right?”

But they have to be. Superlong, profanity-laced columns are, for Havrilesky, enactments of giving a shit. She wants you to care because when you care about things, you put in effort, and when you put in effort, you come alive: We both have magic, but we have to dig for it. To the LW who dreams of quitting her job and pursuing stand-up comedy, Polly advises: “What matters is the feeling that you’re doing it, every day. What matters is the work—diving in, feeling your way in the dark, finding the words, trusting yourself, embracing your weird voice, celebrating your quirks on the page, believing in all of it.”

I am not sure I believe in all of it. I think what passes for magic in Polly’s world might be illusion and stagecraft rather than pure lava-bright enchantment, because sometimes your messy self, instead of liberating you, flings you against a wall. Still, there’s something irresistible about Havrilesky’s conviction to the contrary. We do want to believe that if we could only truly embody who we are, we could exhale flame and sorcery, and find out that nothing (besides superficial lifestyle flourishes) really separates us from Beyoncé. The conventional advice column is a hospital emergency room, where fools and victims rush in, mangled by life and their own mistakes, and conscientious professionals use agreed-upon standards to put them back together. Advice as practiced by the messy woman, though, more closely resembles therapy: a deep working through of vulnerabilities one yearns to see as universal, a sense that while the columnist appears to be addressing somebody else, she is really, magically, speaking directly to you.

How to Be a Person in the World: Ask Polly’s Guide Through the Paradoxes of Modern Life by Heather Havrilesky. Doubleday.

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