Talking about friendship with Heather Havrilesky

a new interview series!!!

Helen Frankenthaler, Nepenthe, 1972

To say that I’m a fan of Ask Polly would be a huge understatement. Before I discovered yoga, meditation, or psychedelics, I was soothing myself with Heather’s writing. At the time Ask Polly ran in New York magazine and I would go back through the archives until I’d read every single answer. Then I would go to The Awl, where Ask Polly ran from 2012-2014, and read each of those. I was (still am!) trying to answer all these Big Questions for myself: why am I so anxious in my relationship with my boyfriend? How can I be a writer when I have so many insecurities about my writing? How do I deal with my overwhelming fear of rejection?

No one is better at answering those big, messy questions than Heather. Take this iconic column in which the Question Asker is too obsessed with her boyfriend. Or this one about sharp knives who need champion listeners. Or this one about hot baths and boundaries. Or this one about praying to a closed door. I think about these answers all the time!!! Heather has helped me Become A Person, and she’s also a huge inspiration for my Substack—I think of her writing as everything that self-help can be at its best. Firm but deeply generous, imaginative and passionate, with a deep conviction in everyone’s ability to do better. And she also writes these amazing books.

I’m starting a new interview series where I talk to cool people I admire about their work and their friendships, and I’m so thrilled that Heather is the first person I got to ask. You could say that it’s been a long-time dream of mine to get to ask her a question. And of course if you have not yet read everything she’s ever written you can start with Ask Polly, Ask Molly, and her wonderful memoir about marriage.

I know you’ve been writing an advice column since 2001, and this particular column since 2012. What’s it like having a job where you’re constantly trying to answer the question of “how should a person be” and what about it continues to give you joy?

My first advice column was pretty casual and was mostly an excuse to write whatever I wanted. I received hilarious letters, and then it grew more earnest over the years, but I mostly considered it a writing exercise that complemented my work as a TV and book critic. Ask Polly started in 2012, but it’s changed as I’ve changed. In the beginning, I loved the chance to write adamantly about aspects of modern life that drove me nuts and felt completely illogical, stupid, destructive, and inhumane. Okay, actually, I still love writing about those things, but I was much more focused on the perils of bad romance and broken friendships back then, and now I’m more concerned with the big picture of how to feel satisfied and fully alive, which goes hand in hand with these practical building blocks of joy that I feel like I’ve been studying and questioning and rearranging every day for the past five years.

Around 2019, my focus shifted from asking “who’s fucking with me?” to asking “how do I continue to fuck with myself?” Once you finally break away from seeing other people your most important puzzle to solve, then I think you can move on to more interesting puzzles, and eventually you put the puzzles on a high shelf, breathe in the air, and savor your existence as a wild, curious, brilliant animal in a terrifying and beautiful world.

That sharp turn away from blaming others happens once you finally address your shame. Shame is something everyone has, thanks to our shame-ruled, shame-dispensing culture, but some people obviously have it worse than others. I’ve always been massively ashamed and self-hating, and for a long time, even in Ask Polly, I described shame as a thing you have to work around and accept. But in the past few years I’ve really seen my shame drop off, which – whew! The world is suddenly enormous and full of promise when that happens.

So I really believe in the path I’ve followed, and I love writing about it. Even though it’s so easy to start to subconsciously rebel against any career that actually helps you pay the bills (hilarious and stupid but true!), what I love the most about asking how a person should be is that I keep discovering new winding, adventurous routes to the same truths.

The truths are basic, of course, because humankind has been searching for them since they started walking upright and high-fiving each other. But the route to those truths can be endlessly enjoyable and challenging. And I don’t want to come up with one simple idea and then stand on a stage with a headset on and repeat that one idea over and over. I want to invent new paths forward every day. And I want to make people feel their way to the truth. I want to rearrange their hearts using my words. I want to redesign their minds -- artfully and thoughtfully and inventively. When I give that gift to someone else, I receive it, too. It’s the absolute best. It’s not easy but it never gets old.

How do you balance writing your two Substacks, Ask Polly and Ask Molly, with working on your books/other writing?

I find that having a few different projects that I’m fully engaged with works very well, because if I’m stalling on one thing it can feel like a relaxing break to work on something else. While I was writing Foreverland, for example, I experienced writing Ask Polly as a kind of vacation. Writing a book about my marriage was hard enough, but I also wanted the book to be funny and weird and never boring, so that exerted a certain kind of pressure on me, particularly when I wasn’t in the mood to write humor.

Likewise, I created Ask Molly in order to provide some relief from the earnest optimism of Ask Polly. I needed to write in the voice of Polly’s evil twin in order to explore different dimensions of my personality and play with new emotions and ideas.

But everything can feel like pure drudgery on the wrong day. For me, switching it up is a way of reminding myself that I have lots of options, I can create lots of different things. Sometimes I feel strongly that I should be making puppet shows and putting them online, the way I did in the early 2000s for Salon.com. And other times I just want to write poetry. I’m not claiming that any of this shit is brilliant, believe me. But giving yourself the right to dabble and explore is a big part of staying interested in the hard, daily work that makes up a creative life.

It's strange to call it “hard” after talking about poetry and puppets and advice and other fun things. But as long as you’re inventing everything from scratch, you’re always coming up against the limits of what your body and mind want to do. A lot of the time, my body wants to eat cheese and my mind wants to think about nothing at all. So reminding yourself that what you love the most is crucial. And Ask Polly lives at the center of my life for that reason: it forces me to revisit the question of what I love the most, over and over again.

Exercise is also mandatory for me, because I’m not that ambitious or motivated about writing without it. Getting a treadmill desk in 2016 was a huge breakthrough, because I stopped feeling tired and in pain from trying to write all day slouched in a chair. Standing desks made my hips hurt but walking feels great, keeps your brain alert, and it makes writing easier once you get used to it. (I wrote about it here if anyone wants to know more.)

Could you tell me about one friendship that’s been really meaningful for you in the past few years?

Three years ago, I moved from LA to Durham, North Carolina, which is my hometown. I had to make a bunch of new friends, which was pretty daunting. Somehow I ended up with two very close friends, both of whom are extremely sensitive, emotional, intense, creative, grounded, and absolutely uninterested in our culture’s notions about how a person should be – to return to that theme!

I think I’ve historically been attracted to slightly more guarded, avoidant people at times. I probably admired that control, and I feared emotional people who might get anxious and needy, which was just a side effect of my shame and self-hatred, honestly, because I can be anxious and needy myself. But I can’t gush enough about how rewarding it’s been to love people who are as intense as I am. I guess I’d say they’re also very principled, each in their own way, which I didn’t understand was very important to me until recently.

Intimate friendships require work and a lot of patience. Finding two people who are absolutely all in has been such a gift. You know, shit comes up. Things get weird when you’re both really invested. You get emotional over random stuff, and shame and fear show up. That’s emotional engagement. It’s always messy and vulnerable. I love understanding that and not feeling as terrified of it. I mean, look, I tried to befriend people who were a lot like me when I was younger. It was very challenging for me. So it’s great to be able to do that again, but with much less fear and shame in the mix.

Based on your newsletter, I’d guess that you struggle a little less with friendships and also shame, because you always sound so smart and balanced and open-hearted when it comes to your close relationships! I’m just arriving in that secure territory, but my god, it’s great here!

What’s one way that friendships (or one particular friendship) has challenged you? Whether it’s through conflict, friendship breakups, or relating to people in a new way.

I have a lifelong friendship that’s always been challenging to me but it feels much less difficult lately, possibly because my newer friendships have instructed me on the ways I tend to fuck things up, or possibly because we’re both so much less defensive and self-protective than we were years ago. Our trust has slowly grown over the years, and it continues to grow every day.

We both had pretty dysfunctional upbringings and we both had bad boundaries when we first met and for years after that. We were hard on ourselves so we blamed each other for everything, projected like crazy, and proclaimed each other nuts repeatedly. Think “Girls” season 1: “No, you’re the wound!” That was us.

But it was impossible to break up. We knew each other so well, talked about everything, wanted the same kind of life, loved the same people, were angry about the same things over and over again. And beyond that, my lifelong friend is truly brilliant and magical. I like to think of her as a fairy, as ridiculous as that sounds, because she has so much positive energy that she’s dying to share at all times, and it comes out in ways that can be confusing or hard to interpret if you don’t know that she’s a fairy at heart. She grows every day in ways that are so impressive. I feel so proud of her and I owe her a lot.

How has writing Ask Polly affected the relationships in your life?

Well, I’m still flawed and I can be as chippy as the next person. But writing Ask Polly has made me into a much more compassionate and patient person in ways that are hard to express. When you keep returning to other people’s problems repeatedly, they inevitably end up feeling like one shared problem. The questions in every intimate relationship and close friendship are the same: Can you see this person clearly? Will you let them see you clearly? Are you too afraid? Are you too ashamed? Can you feel your feelings? Can you dare to let someone into your heart and trust them? Can this person let you in, or are they secretly terrified?

That’s not to imply that everyone alive is easy to love, or that love conquers every ill. Obviously there are users and power-hungry freaks and serial killers out there, along with the big-hearted strangers. But fear and shame disguise big-hearted people so they’re harder to see. And once you notice that, you start to notice that you’ve disguised your own big heart, too.

People get tired of hearing this from me, but intimacy with others necessarily includes facing yourself, reckoning with what you truly desire, humbling yourself, noticing your bad habits, and observing your defense mechanisms. You have to be able to admit the many, many ways you fuck up and blame others and distance yourself every day in order to be a good friend to another flawed human being. You have to take responsibility for the fact that you are a fallible animal, ruled by huge emotions, and you’re never going to get it exactly right – never, ever, ever.

When you surrender to that simple fact, it’s very romantic. And when two people surrender to it, watch out! Fireworks, shivers, lust, loyalty, optimism, joy, communion. Deep connections are everything, yet we walk around pretending we don’t need each other. It boggles the mind how warped our culture is! But noticing just how bent and ashamed and angry this world is just as important as noticing your own flaws and taking responsibility for the self you drag through the world.

Understanding your own fear and shame feels so demoralizing and humiliating at first, but it really is the start of a new life that feels entirely different. I think if I didn’t write Ask Polly, I never would’ve known this. So now I feel like it’s my job – and I take it very seriously! – to share this understanding with others.

I want to give other people the gift of allowing themselves to be sad and confused and fearful, like all animals are. It’s a massive disservice to humanity that we all pretend we’re not afraid and bewildered a lot of the time, no matter how old we are. You would be amazed at the layers and layers of shame and fear that are acting on everyone you know, including the wisest, calmest humans among them. Smart people struggle with neuroticism a lot, I want to add. And it takes a lot of very good habits and a lot of compassion for yourself and others to step back from that puzzle. You can’t turn everything you feel into a twisted knot of ideas and problems to solve. You can’t intellectualize your heart all day long.

Overachievers struggle with this the most. It’s so important to resist the urge to control, to become more perfect, to gain status and power, to fix everything. At the center of living without shame and fear is a spirit of surrender. You surrender to the moment, you surrender to the day. You put away every puzzle and you step outside to soak in the springtime air and give your love generously.