Polly Asks: New York Magazine Wants Me to Write Ask Polly For Them. Should I Tell Them to Piss Off?


Dear Readers,

I need to tell you a story. That means this will be just like every other Ask Polly column, except this story is a little longer than usual, and at first, when you read it, you’ll ask, “Where’s the tepid dude of the week?” Just bear with me.

In September of 2012, after reading and admiring The Awl for years, and writing a few short humor pieces for them, I sent Choire Sicha an email.

Subject: Existential advice column
That’s what I should be writing for The Awl.

Come on, pay me a tiny bit and it’s yours! Just enough $ so my husband doesn’t roll his eyes and spit whenever he hears the word “Awl.”

Choire’s one-word reply was:


Two days later, I sent in my first column and The Awl published it, and thus began one of the best gigs of my career. My first editor, Carrie Frye, let the term “pious fuckwinder’ run in my second column. My second editor, Choire, was even more tolerant of dubious strings of adjectives. (He also once forgot to pay me for five months, but when I responded with a three-thousand-word screed on the madness of freelance writing, he sent me a check and published my screed and paid me for that, too.) My third editor, Matt Buchanan, let the term “dickweasel” run. In a world full of pious fuckwinders and dickweasels, in other words, The Awl is an island of sanity, and originality, and humility. I had hoped to never leave.

Then three weeks ago, Stella Bugbee, the editorial director from New York Magazine’s The Cut, called me. She told me that they’ve been in the market for an advice columnist, but haven’t been able to find the right person. Apparently people want real advice, not gimmicks, she said. People want good advice from a writer with a really strong voice, she said. People want guidance from someone who’s wise and thoughtful and fair.

“Why are you talking to me, then?” I asked.

“We want you to come to The Cut,” Stella said, whose voice seemed to indicate that she dresses really well. “We’re prepared to double what you’re making.” I snorted audibly. Then I multiplied my current rate by two and wrote it down on a nearby piece of paper. Hmm, not exciting enough. So I multiplied my current rate by three and wrote that down. Then I multiplied it by four, then five, then ten…

“Hello?” Stella said.

“I don’t know,” I said, staring at the largest number on the page and imagining myself on a beach in Belize, surrounded by bronzed towel boys serving fruity drinks in hollowed-out coconuts. I pictured other bronzed towel boys arriving with huge platters of aged cheeses and soft cheeses and fresh breads and cured meats. “Eduardo, I said Cambozola, not Gorgonzola.” “I’m so sorry, Miss Heather.”

“Are you still there?” Stella asked.

“I love The Awl so much,” I said. This came out quite naturally, because I wasn’t lying like I usually am when people ask me how I like my current employer.

Stella proceeded to tell me more about The Cut, how they don’t just write about breastfeeding and sixteen super-sexy summer styles. They cover a wide range of topics, and it’s very writer-driven, just like the rest of New York Magazine’s empire. She said some other stuff, but by that point I was so deep in a Belizian towel boy fantasy I sort of lost the thread. “So what’s it going to take?” she asked.

“I like aged cheeses a lot,” I said. “And they’re pretty expensive. But I don’t want to change the column, You know what Ask Polly is: It’s four thousand words, half of which are variations on ‘fuck’ and ‘motherfucker.’”

Stella sighed. Her lips sounded so glossy.

“You would retain full creative control.” Creative control, yes, I thought. The bronzed towel boys came back to mind.

So I got off the phone to talk to my husband, who looked disappointingly unbronzed and wasn’t carrying a towel or an array of soft cheeses.

“People will think I’m a sell out!” I told him. “That’ll be refreshing, for people to imagine me doing something that someone actually pays me for.”

“What’s a sell out?” my husband asked. (I guess people don’t use that term anymore.) “Does that mean you’ll make some fucking money for a change? Because that would be fucking awesome,” he said.

“But it’s a fashion and beauty website. People will think I dress better than I actually do!” I said. “That’ll be cool, for people to imagine that I’m not just some dipshit who bumbles around the house in soft pants all day. I wonder if they’ll imagine me in white linen…”

“White linen? Like Don Johnson used to wear on ‘Miami Vice’?” my husband said, who would never sass back to me like that if I made more money.

So I emailed Choire. I thought he might be really angry or BEREFT at the thought of losing Ask Polly, but instead he was very nice and said it would be crazy for me not to seize a great opportunity, and that The Awl is all about nurturing young writers with cool ideas and letting them fly and be free when they move on to bigger things.

“I’m not actually young,” I replied. “I’m older than you.”

“Lol,” he wrote back. (Did he think I was joking?)

“I really am older than you,” I wrote back.

“OMG, I hate olds! Lol!” he replied.

Anyway. As someone who, generally speaking, hates change, I know this might not sound like great news to some of you who read the column every week. But I think it’s a great opportunity for Ask Polly to reach more people, and a great opportunity for me to give the column more of my attention instead of squeezing it in between other gigs. (No, I didn’t get Belizian towel-boy money; this is still an online magazine we’re talking about, and not the Sultanate of Brunei.) New York Magazine is run by smart people and employs some of my favorite writers. I’ve been assured that they don’t want to change Ask Polly at all, and they intend to nurture and support the column for the long haul.

Writing this column has been much more rewarding than I’d ever dreamed it would be when I first pitched the idea to Choire on a whim. I’ve gone from getting one or two letters each week to getting ten to twenty letters every single week, without fail. I love writing the column. I don’t want to stop doing this anytime soon.

I’m not a big believer in gushing about your love for your readers. But Ask Polly readers are pretty fucking special, let’s face it. We have a few things in common, maybe. A certain kind of stubbornness that’s often misinterpreted as a bad attitude. A certain kind of skepticism that’s often misinterpreted as contempt. We are unique snowflakes who sometimes feel uniquely fucked, even when we can recognize, intellectually, that our experiences might just be universal. We are sensitive flowers who act tough anyway. We are damaged goods who remain optimistic — in spite of having spent a little more time in the half-priced bin than was good for our tattered egos.

I’ll publish my last Ask Polly column on The Awl next week at the usual time, which is also the same day that my first column will appear on The Cut. I hope you’ll join me over there, among the glossy-lipped and the snappily dressed. The habitat might look a little shinier, and you might be simultaneously repulsed and turned on by headlines that say things like “Yoga For Swoll Hunks.” But I’ll still be offering up the same digressive opinions and pious fuckwindery you’ve come to expect from me.

Whatever happens next, though, please keep on telling the truth and sticking your necks out. Good things come to those who are brave enough to show the world exactly who they are, without shame. And look, soon enough, you can be sure that someone will give this owning-of-your-flaws an embarrassing name, in the hopes that we’ll all get shamed back into the closet and go back to believing that every misstep and mistake should be airbrushed out or masked behind a smile and a high five.

Let’s not let them shame us, though, ok? Let’s keep on fumbling along, imperfectly, with pride, with grace, with humility, with an open heart. Let’s be messy and courageous, you and me and all of us. Let’s not be afraid to ask for exactly what we want, and to celebrate exactly who we are, and to eat lots of aged cheeses if possible. But most of all, let’s stick together and celebrate our messiness, and our courage.


Heather Havrilesky (aka Polly Esther) was The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses.

Photo by itchys