Deez Interviews: Heather Havrilesky on darkness, joy, and all that lies ahead

Happy Friday, Deezers! This week’s interview is with — and I CANNOT BELIEVE I AM TYPING THESE WORDS — Heather Havrilesky: the writer / author / therapist to the internet behind The Cut’s existential advice column, “Ask Polly.”

Last year, she launched her newsletter “Ask Molly,” which reads like something between journal entries from your most terrifying yet hilarious friend and the manifesto of a luminous cult you really want to join. So we talked about her newsletter/alter-ego, but also more general things like if the therapizing ever gets old and if we’re generally doomed. Enjoy.

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You've been writing “Ask Polly” since 2012, but you launched “Ask Molly” last year as Polly's evil twin. What inspired you to, so to speak, let Molly out?

I’ve toyed with starting a newsletter or a podcast many times, but I knew that whatever I made couldn’t be based on the presumption that people wanted to know more about me or found me inherently interesting. 

For a while, I tried out a podcast but I got sick of hearing my own voice. I briefly entertained the idea of creating a musical version of “Ask Polly,” where each letter is a song and each reply is another song.But that’s not exactly something you can do well week after week, and I didn’t want it to be shitty. 

A few years ago on Twitter, I joked that I was going to start a shadow advice column called “Ask Molly” that featured a lot of nastiness and insults. When I started the newsletter, I wasn’t sure what I wanted it to be, but the name “Ask Molly” seemed like a good way to link the newsletter to what I’m known for without serving up more Polly. And then, of course, evil Molly herself took over and drove the whole project straight off a cliff. I’m not so sure we should all let our Mollys out, but I’m definitely enjoying mine. 

Does it ever get old? Both the advice column writing part but also the general writing/living/writing-about-living part?

I’m pretty obsessed with how to live and how to feel less alone, honestly. I’ve been this way since I was very young. My journals are filled with questions about what I truly want and need. And I’ve always analyzed the people around me and also intuited things about people before they said a word about themselves. 

That makes you a creepy party guest and a completely obnoxious friend, but it does work in the context of an advice column. So it’s nice that I have somewhere to put this creepiness. And no, I never get remotely tired of it. I get tired of reading sad letters some days, but I never get tired of answering them. 

I also enjoy writing about my own life, but it gets old quickly. I’m writing a memoir right now, and I’m stuck right in the middle of my small-children years and it’s fucking drag. I’m bored with myself. That’s a very natural stage in the writing of a memoir, and I don’t actually think I’m boring. But it’s hard to write well when you’re tired of your past self and you’d rather spend more time with your far more interesting current self. In that way, “Ask Molly” is almost like a form of procrastination. 

It’s also a place to experiment with my style, in the hopes that it will elevate what I’m doing with the memoir beyond the realm of “HEY LOOK AT MY LIFE, WEIRD, HUH?” I’m allergic to explanation at the moment. I want to write vivid haikus about how it feels to be inside my skin instead. 

What does it feel like for people to equate your writing with public therapy? Do you feel a deeper affinity with your readers when your writing gets so personal? 

Yes, when people understand and appreciate and even change their lives based on my words, I tend to encounter them as friends. I assume a kind of mutual understanding. I automatically like anyone who is excited by what I do, honestly. I feel grateful that people like that exist and that they enjoy diving into 3,000 words on, say, obsession. I love writing those words and I can’t imagine not doing it. But there are times when my life feels a little crowded. I have kids and dogs and the most excellent husband in the world, and I also have all of these people saying, “I need your help!” in my inbox.

Right now I’m personally a little obsessed with people who live lives that are entirely different from mine. I love the idea of walking around in some busy media or tv production office, trafficking in concretes. I’m fascinated by tv showrunners and media managers, specifically. I harass my boss, Stella Bugbee, around the clock. I love that she’s too busy for me. The woman flies to Milan to schmooze, what in the fuck is that like? 

I sort of wish I were some kind of international jet setting show-off at the moment. Or at the very least I’d like to pack up this circus and move to New York. It’s all pretty foolish. I might have to settle for creating something deeply wretched and depraved and then horrifying as many people as I can with it right here in Los Angeles. 

Given the state of, well geopolitics, and the industry, and everything in between: Are we doomed?

I have no idea. My energy right now is very “Let’s not stick it out. Let’s burn it to the ground instead.” 

But the more I allow this feeling some room to breathe, the easier I find it to view what’s happening through a dispassionate lens. You have to get a little healthy distance from almost everything in order to make rational decisions about how to proceed. 

I don’t think I could hurl myself back into this election without stepping back and quieting my dread first, then pretending I’m a man while I read the news. View this puzzle through the deadened eyes of mankind, Heather. I also feel like a man in general, lately? Not in any abiding way, just in an “I can have anything I fucking want” sort of way. 

And also “If I can have everything I want, then I want everything.” It’s all pretty nihilistic but I’m rolling with it for now because it’s giving me life and making it possible to write 3k words a day, which I pretty much have to do every single day in order to stay on top of my current workload.

Finally, what lies ahead?

Well, I’m writing a book, “Ask Molly,” and “Ask Polly.” I’m also writing songs on my guitar, and I have an idea for a musical TV show that I’m figuring out. And I will pretty much do anything under the sun that requires me to travel, stand on a stage, show off, stay in nice hotels, and drink overpriced cocktails. 

I just don’t want to talk about nurturing your soul. I’d rather talk about, you know, living it up as the world burns down. I need to find some way to help save the planet, but I also need to live it up. I won’t help anyone if I can’t embrace my own joy — and my darkness. “Ask Molly” is an attempt at modeling that duality and enjoying it instead of letting it drag you under.

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Don’t forget to follow Heather Havrilesky @hhavrilesky on Twitter, and subscribe to Ask Molly here!! Now, go consider your duality this weekend.