How Heather Havrilesky Became the Advice Guru Behind “Ask Polly”

The L.A.-based columnist has made a living of answering the missives of the lost and lonely
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As told to Marielle Wakim.


I’ve always given unsolicited advice. I’d meet people at parties and start telling them about themselves. And people do not love that. It’s very nice to get paid for it and not be creeping people out left and right.

I did a strange little advice column for an online magazine called Suck when I was 25. My pen name was Polly Esther. At the beginning I was in San Francisco, but then I moved to L.A. in ’97 and wrote it from here. After Suck went under in 2001, I wrote advice for my blog till 2010 or 2011. It was very aggressive and rambling. I read Dear Sugar a handful of times, and I was amazed at how good Cheryl Strayed was at writing advice that made you cry. I thought, “That’s such a powerful thing, to be able to make people cry.” So I pitched an advice column to The Awl, and I would find myself teasing someone, and then it would shift into, “But I know how you feel because I’ve been there.” By the end of the column I would be crying, which was unexpected. In the fall of 2014, New York magazine called me to do “Ask Polly.”

Trusting that you can find what you need here is half the battle. In L.A., you can be openly weird and kind of a freak and be too honest, and people accept you for who you are.

No one sorts through my letters for me. They all come flooding into my phone and on to my computer, and most of the time I find them fascinating and amazing and interesting. I get something like 20 a week, but I wrote this thing about shame a few weeks ago, and Yahoo picked it up, and I got, like, 20 wild letters in a day. Like, “My husband is in jail, and his girlfriend keeps calling me.” Crazy shit. One question that comes up in Los Angeles is “How do you find the right people?” Trusting that you can find what you need here is half the battle. In L.A., you can be openly weird and kind of a freak and be too honest, and people accept you for who you are. You can’t be self-conscious about your weirdness because people here are allergic to insecurity. If you stay the course and keep your eyes open, you will find people who are serious about their lives.

Every now and then I get a letter and I’m like, “It’s too much. I can’t handle it.” A lot of people have big problems that I cannot address in the column. There are times when I have something great to offer, and there are other times when I realize, by writing, that I don’t have enough to offer. Generally speaking, I like the heavy stuff because I feel like there’s more of a chance to inspire people. But it stresses me out. Sometimes I feel, like, “I’m not an expert. I don’t know.” I’m not doing therapy. I’m doing performative direction-giving. A therapist’s role is to guide you very gently and expensively toward answers. What I’m trying to give with the column is something a bit more artistic and creative that makes a lot of room for flaws and ugliness and self-doubt. I love it, and I’m proud of it.


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