Heather Havrilesky
Credit: Doubleday

When Tavi Gevinson posted a picture of her current reads to Instagram last month, one of them called out to me like a cheese sandwich at midnight: How To Be A Person In The World by Heather Havrilesky.

Gevinson’s caption read, “Reading Heather Havrilesky’s column makes me feel better 100% of the time, even when I don’t relate to the situation she’s advising on. I am happier and healthier for Ask Polly and for this book’s existence!” And oh, how true that is.

Havrilesky is the writer behind the “Ask Polly” column, in which she answers those daunting, big life questions every week, magically distilling universal themes into perfect answers that you want to write out and stick on your bedroom wall so that you’ll see them every day. I spoke to Heather on the phone last week about her new book, a collection of mostly new readers’ letters and her own answers. I was pinching myself for the next hour as she spoke on everything from navigating the world as an opinionated woman, to seeking therapy, to getting a dog, and not feeling like a loser in your 20’s.

Hello Giggles (HG): Now that you’ve been doing the column for four years, how did you know it was the right time to put the book together?

Heather Havrilesky (HH): I was writing a column a week, but I felt like I wanted to write more than that. I knew that I wanted to write a book of either essays, or guidance, or something — but I wasn’t sure what form it should take. My idea was that I would answer letters — do the same things I was doing with the column, but have the letters organized in a way that… felt like one letter was building on the last letter, until the end when you feel like all the different advice coalesces into one fabulous, perfect message. I don’t know if I hit that high mark exactly, but I do feel like the letters in the book do build on each other… When you land on the end it does feel satisfying, as if you’ve been on this weird twisted journey with someone else — dare I say the word journey.

The next book I write, I kind of want it to be just the answers with no letters. …I don’t know if I can pull that off, but I’d like to try and organize… the answers in a creative, artistic way. I’m not sure how it’s gonna happen, but that’s my next impossible challenge.

HG: Are you getting feedback from readers of different generations?

HH: Yeah, some of my mom’s friends have read it and love it. They’re in their 70’s. I know a few men who read it and really like it. There are a lot of letters from men in the book — it’s not just one woman with relationship problems after another. There’s a pretty wide swathe of humanity represented in it.

HG: The way you write allows a reader to take something from your answers for herself, even if it’s not about a problem that affects her life. Is that something you think about when writing answers?

HH: Yeah, I do. I think a lot about trying to give the best possible answer to the person who is writing the letter. But then, there are times when I question myself and think, “Is this really the person’s problem? Am I making certain assumptions about this problem?” …Then I have to ask myself, suppose I am off track, does this digression serve the greater good?

I do think a lot about trying to write in a way [so] that anyone could pick [the book] up and feel like their needs are being served as well. I mostly do that organically by following my own whims …I think I am served well by following my own impatience… which is not to say that I don’t digress in ways that I shouldn’t at times, but I think I’m… a little better at getting to the heart of the problem but also shedding light on problems in the same neighborhood.

Good writers know how to follow their whims to interesting places.

Heather Havrilesky
Credit: Doubleday


Do you ever hear from people again after you’ve answered their questions?

HH: Every now and then someone sends a follow up. One of my favorites, which must be from a few years ago (as I can’t quite imagine giving the same advice today), was from a woman who wrote, “You were so right, you told me to get a dog — here’s a picture of my dog!” [Laughs]. I think she had put something in the letter about being lonely, and had said she really wanted a pet but her apartment didn’t allow it. So I wrote, move to a place where you can get a dog, and get a dog.

It’s funny, people always ask me, “What kind of advice have you taken from other people?” But I never take advice from other people — I’m just that a**hole. But this friend, the advice she gave me at the time when I was… in this relationship [and] didn’t know if I was ever gonna marry this guy… She said, “Just get a house and a dog and you won’t give a sh*t whether he marries you or not.” [Laughs]. And it was really true! I dumped him a year later, because I had my house and my dog and I was like, what’s this guy doing here? I don’t need this guy who doesn’t think I’m good enough to marry in my house. This is my house, get the f*ck out! It’s prohibitively expensive in many places… [but] if there’s any way you can do it.

HG: Does your own inner circle come to you for advice?

HH: I would say about half my friends call me and ask, “What should I do?” But they don’t think of me as “advice lady.” With old friends, you just listen. The other thing is, you get to an age where very few people are saying to you, tell me how to live. I’m obnoxious, my friends know what I think. They’re like, “Oh God, you’re the last person I’d ask.”

By the same token, it’s much easier to ask a stranger for advice… What you need is this blank slate person who is just focusing on you in a vacuum without knowing every single thing about you.

Sometimes it’s a matter of, let’s teach you how to trust your own instincts a little bit more. Because if you’re writing to me, maybe you don’t trust your own instincts. Maybe you feel like you keep making the same mistakes. Let’s talk about how to get to a place where you can trust your own instincts.

HG: So…where does this fountain of knowledge come from? Does it take from your energy to share all of this advice?

HH: No, not at all. I have been talking at length about human problems since I was really young. I thought I was annoying, and obnoxious… and no one wanted to hear these things. And then, I met some really smart women who also loved to talk endlessly, and that really helped! Until you meet the people who really understand what you’re made of, and what you have to offer, it can be really difficult. I think that a lot of people, when they’re really young, they take all of the mismatched energy in their lives, like [problems in relationships], …and they turn it in on themselves thinking, “I’m the only one who doesn’t fit.”

The good thing about accepting your flaws, accepting who you really are, accepting the emotions that drive you… and being led by these things, is that it leads you to the people who DO love someone who has the qualities and affinities and flaws that you have.

Sometimes your flaws hold the key to what makes you the most brilliant of all. If you’re fighting those flaws that are attached to your brilliance, you’re actually fighting your own brilliance. You’re stomping on your talent, just by trying to be more like the people around you.

I think that’s something a lot of women, in particular, need to hear. In this culture, women are told we talk too much, we perceive too much, we can see too clearly and it’s annoying… The truth is, these are our strengths, these are good things.

Credit: Doubleday

HG: Do you think it’s especially hard for women to accept their flaws if they’re outspoken?

HH: Women and men are put off by assertive women, often, and it’s bullsh*t. But also, something you have to notice is, are you yourself as an assertive, opinionated woman… tolerant of other assertive, opinionated women?

The other side of it is, if you never feel like you can run free and say too much… it’s very hard to notice how much you want to say to anyone.

You’re always either saying too much… or saying too little. It’s hard to leave some room for other people if you just don’t feel like anyone has ever really heard and understood you.

That’s a need and desire that women have, and people have, that they’re not willing to acknowledge for a long time. When you can accept it and say to yourself, “I’m going to need to be understood by someone. I need someone to be patient with me,” you realize, who am I being patient with?… If the answer is no one, then you have to start by trying to be that kind of friend to another person, first.


: Do you have any advice for young women heading out into the world, who might be starting new jobs, leaving home, finishing school?

It’s just a long slog to the beginning of a good life. The only things I’d say concretely: don’t get drunk a lot, and don’t sleep with people until you feel comfortable with them.

These are things that I did — I got drunk all the time, I slept around, I felt terrible about myself. I did make really passionate friendships at the time, and I was very social, and those things were good.

But if I could go back, I’d be more self-protective and I’d be more patient with myself. My mom said this to me over and over again: You don’t have to decide what you’re going to do with the rest of your life immediately. You can try something, and it can turn out to be terrible, and then you can try something else.

Accept that it’s going to be a rough road for a while… You’re gonna look at your life and say, this isn’t what I want, how long does it have to be this way? It’s just what it’s like to be in your twenties.

I think patience, and self-acceptance is really crucial. You have to do that for the rest of your life. You have to keep saying, the world will not be this way forever, I’m just trying new things, I’m just here now, it’s OK to feel the way I feel, I’m not a terrible loser because I’m in this situation.

I think not defining yourself as a loser in your twenties is one of the most obvious challenges of your twenties.

How To Be A Person In The World: Ask Polly’s Guide Through the Paradoxes of Modern Life by Heather Havrilesky is out now on Doubleday.