meet ​the internet’s most existential agony aunt

As part of Mental Health Week to talk to Ask Polly’s Heather Havrilesky about shame, Kanye West and the problems that have stuck with her most.

by i-D Staff and Jack Sunnucks
19 May 2016, 10:49pm

In the age of perpetual singledom and eternal best friendship, agony aunt columns are supposed to be redundant - brunch with the girls should solve any issue. The reality is however, that we all contain deep, dark questions no amount of mimosas is ever going to solve - enter Ask Polly, a weekly column on The Cut. From 'can I dump my dying boyfriend' to the more commonplace 'how do I start believing in my worth', there's no question Heather Havrilesky won't answer (at length - most columns are around 4,000 words). Heather's column is much read, loved, and debated in the comments section, and so it's not much of a surprise that she has a book out soon, called How To Be a Person in the World, out on 12 July. I talked to Heather about how she became a person, or more your favourite, sweary internet online aunt.

How did you become Ask Polly? It's so modern but Agony Aunt columns are...
So what you're trying to say is: Agony Aunts are kind of an old thing, but Ask Polly's sort of weird and irreverent, and how did it start?

I had a job in my 20s writing for this magazine, Suck. During the dotcom crash, the first content crash if you will, an omen of things to come these days, I had a job there and wrote all kinds of irreverent stuff. And then I didn't have a job anymore! So I needed to do something, and someone said, 'Start a blog, blogs are all the new rage.' This is like 2001. So I started a blog, but I didn't want it to be a journal. I wanted it to be obnoxious and interesting. And I needed a structure. So I started answering advice letters on my blog. Mostly it was aggressive, nasty stuff that I wrote.

And then slowly as I got older, the blog evolved into this weird, real advice giving thing, where I would go on and on about the psychological reasons for people feeling the way they feel. If you read it, it's like bad, rambling Ask Polly answers. So it was like a practice ground. It was something just to get me to write. I was pretty much unemployed and needed ways of writing. But I kept answering advice letters. In 2003 I got a job as a TV critic on, and I worked there for seven years but kept answering letters.

I was mostly doing cultural criticism in 2010, but I didn't have enough regular work and was starting to pitch TV columns to The Awl. But they didn't really want to run a TV column - I mean, weird, they didn't want to run what everyone else was running [cracks up]! Mostly what I craved was a weekly deadline, because throughout my writing career since 1996 I'd worked from home but I'd had a deadline so I had structure to my life. As long as I was fulfilling that one deadline everything was fine, I was a productive human being. So I wrote to Choire Sicha, I pitched him saying "I should write an existential advice column for you guys." And he said yes, great, do it.

So I just started doing it. And because I was writing for The Awl: the publication that you write for determines your tone to a huge extent. And if the place you write for is pretty open tone wise, or appreciates swearing and strangeness… These days, that's how people write online. But back then, 2012, it was a little different. Certainly in 1996 there was no online tone, it was all over the map. Then it got more conservative, and now there is a tone, but the tone is irreverent..

The Awl didn't edit much and were happy with what I was doing and I was allowed to create the column exactly how I wanted it to be. So it came naturally, it evolved naturally into something that suited my taste as a reader and as a writer. I definitely wanted the freedom to be aggressive, in the early days I wanted to be as obnoxious and funny as possible. And it evolved into something heavier. But that's how it started! This will be fun I'll be really mean to people [laughs].

I'm not that mean to people anymore.

How many letters do you get a week?
It depends on the week. If I answer a letter that addresses a problem a lot of people have, I get loads of letters. I would say the average is probably 20 letters a week. It's a certain kind of reader… you don't just send a letter that says, I have a concrete problem that I need you to solve. Most readers start out with, 'I've been reading your column for a long time', then it goes on to 'I have a complicated problem.'

And if it's about a girlfriend or a boyfriend, it'll start with 'Here's why my girlfriend or boyfriend is perfect in every way,' and then the next paragraph is 'Here's the totally wretched thing that my boyfriend or girlfriend just did.'

How do you choose which letter to answer?
I'm very moody, so I base it completely on my mood. There are days when I don't want to answer anything about dating. There are days when I don't want to answer anything that's too heavy. There are days when they have this concrete problem that opens up into a very familiar trap.

I just got a great letter from a woman whose mother told her that her feelings didn't matter over and over again. So she's angry at the world. And says 'I want to win arguments with people.' It's like she's doing this emotional Rubix cube in her head 24 hours a day. And those kind of letters I definitely revisit a lot because I think there are a million different ways to approach that particular problem. Any kind of problem that feels like it lays the groundwork for a million other problems, from being attracted to bad relationships to addiction to neglecting yourself to blocking yourself from doing what you're really meant to do with your life. I mean I've had all those problems [laughs]. So I know the texture of how it feels to be in that space. And I also have good ideas about how to break through.

Do you get feedback from people once the column's out?
Yeah I do. People who have a lot of anger in their letters will write to me and say 'At first your letter made me really angry." [laughs] But then they'll say "But then I thought about it and a lot of what you say is true." I sometimes get something two years later. I got a great response, recently, from a woman who said "I get blind drunk every night but that's fine, right, I'm not hurting anyone." I wrote back and said "You're not going to take my advice whatever I tell you but you're fucking yourself up right now." And she wrote back two years later, and she doesn't drink anymore, she's a firefighter - a lot of interesting things were going on in her life. I've sort of been dabbling with starting a podcast, and I ended up talking to her on the phone on the podcast and had a great conversation with her.

Do you carry the heavier ones around with you?
Sometimes I hear other advice columnists talking about the fact they sit down and write people back immediately. I don't know everyone is different. I think you have to manage your own experience. My thing is like, sometimes I open a bunch of different letters and I think, these are all hard. I'm either not in the mood to answer one of them, or I don't have what it takes to get into the humour of another one or the knots of another one. And then I land on the hardest one of all and that's the one I take on.

If I'm feeling hopeless, sometimes I write the best response to the most hopeless letters. It's an interesting thing.

The great thing is it's different every day. So you don't really know. I think I could do it three or four times a week, I love writing the column I love it. But I only do it once a week. Sometimes I'll answer two or three a week just because I love it so much and I don't have 15 other things to do. It's like my fun day when I get to write the column.

How did you start collecting the ones that make the book?
I knew that I needed a range of things, but for a while I just started answering a ton of letters. Our approach was very unscientific at first, it was just do a lot of extra work. There was a while where I was definitely doing too much and I was like, Jesus, all these responses sound the same. I wasn't going into it with enough inspiration. [My editor] had so many letters at one point… I feel like he had 45.

I started by writing a ton of shit and then I went back and cut out the bad stuff.

Is there a column that's your favourite?
I wrote one about the band Yes that I really like. I try not to do just insane pop cultural metaphors every week, but I love it when columns like that come about, because I'm good at writing that kind of stuff! When it blends in, and seems the perfect vehicle for addressing all kinds of abstract things that appear in the letter… it's a little decadent, indulgent, writerly pleasure.

I had one that I wrote that's in the book about Kanye, that's one of my favourites of all time. Kanye's such a good example of a million different things, I love his music. And then there are some weird ones where - there's one in the book where I write about my tenth grade English teacher screaming at me, because I misinterpreted a poem in class. There's one about a girl who is bitter about all her ex boyfriends which I really like.

The book definitely has some of my favourites. The first chapter of the book is about a bride who doesn't want to invite her gorgeous, fabulous sister's gorgeous fabulous boyfriend [to her wedding], this perfect European boyfriend. She doesn't want him to come to her wedding. She wants her sister to come, but she told her sister she can't bring her brand new perfect sophisticated boyfriend because it's her big day. That's one of my favourites of all time too.

I get great letters because people don't just describe a problem, they describe very honestly how they're haunted and they feel guilty about their really negative reactions to these things. Which is good for everybody everyone to read the background. You can relate to so much of it. Some of my favourite letters are those where someone feels really envious or is obsessed. You know it's just such a relatable feeling. That it's nice to see it written down. You feel like when you're going through it, you feel like you're the worse kind of rat in the universe.

There's one in the book and one I just answered, fantasising about people who are unavailable. And specifically this woman is fantasising about her flatmate. Who's in a perfect wonderful relationship with the perfect girl and they're madly in love, you know. And she listens to them having sex all the time. But she wants the guy for herself. And it's so, for me it's like crawling into that mindset I had 10 or 15 years ago when I was single and obsessive and depressive. Anxious and all those things. And travelling back into that and remembering how it feels... it's humbling. It reminds you of how low you've fallen and how far you've come from that point. Temporarily at least, you've crawled out of the gutter for now! You want to be like, "And now I live on the mountain, I will never go back into the gutter again!"

Does how you're feeling change how much a letter speaks to you?
The ones I want to answer depend on what I'm going through that week. Luckily I'm usually going through something! I find a have week of the month where I don't relate at all, I'm just Teflon Polly. I was going to say Teflon Heather then I realised no one knows who Heather is. Then I have a week where I'm in the gutter.

Then there's a week where I'm obsessed with a concept, like shame. I had a week where I was like, 'Wow, shame, shame is a thing that molds me, all the time!' And in some ways just having that obsession broke me out of certain things. By suddenly being aware of how ashamed I was of myself, I shook half of it off. So it feels like this passage. And to be able to put that into words and give it to people, it's great.

How to be a Person in the World is out 12 July.


Text Jack Sunnucks

mental health week
agony aunt
ask polly
heather havrilesky
how to be a person in the world