Asking Polly: Heather Havrilesky's best advice for our modern age

The Cut's lovingly acerbic advice columnist on agony aunts, feeling your feelings and making good choices.

Heather Havrilesky is Ask Polly

Photo, Kristin Rogers.

Being a human is hard. Should you have kids? Should you take that job overseas? Almond or coconut milk? (See? So hard!) But here’s an illuminating truth: No one has a clue what they’re doing — not your parents, not your buttoned-down boss, not even your ex-boyfriend’s new girlfriend with the perfect beachy waves. For centuries, we’ve asked faceless oracles from Dear Abby to Dear Sugar to airlift our hopeless species out of its perpetual fog. But modern questions — Career or baby? Desk job or artist’s life? — demand a modern voice. Enter Heather Havrilesky, a California-based writer, whose expletive-packed “Ask Polly” columns for New York Magazine‘s style site, The Cut, are feverishly shared each week. In her new book, How to Be a Person in the World: Ask Polly’s Guide through the Paradoxes of Modern Life, Havrilesky sets her alter ego’s sometimes acerbic, always affectionate gaze on such evergreen issues as loneliness, pathological people-pleasing and herpes anxiety. Here, Havrilesky discusses exactly how to be a person in the world.

What’s the best advice you’ve ever received?

My mom was always encouraging me not to get hung up on guys. She would say, over and over again, “You’re not going to care about this guy in a few years.” I just took it as a sign that she wasn’t in touch with my emotional life, and I’d say, “You don’t understand! I love him so much!”

Which was probably true at the time . . . 

People tend to say things like “Never move for a man” or “Don’t put too much stock in what other people think of you.” And it’s like, “Okay! I’ll just stop doing that!” But good advice is never one line long. The whole point of this book is to go into more depth. If you say, “Here’s what happens when you put too much stock in what other people think of you,” it’s more of a road map.

Why do we feel compelled to give advice when no one really takes it?

One of the great joys of writing an advice column is that people are taking my advice for the first time in my life. Your friends call you on the phone and they ask for your advice, but they don’t want it; what they really want is to tell you how they feel. And since most of us had parents who didn’t have the time or energy to truly get us, we’re kind of looking for that experience over and over again. Giving and pretending we want advice is the loose structure by which we seek to understand and be understood.

Related: Cheryl Strayed talks fidelity and regret

Polly’s voice is pretty different from, say, the neat and tidy aphorisms of Ann Landers. I’m referencing your liberal use of shit and f—-s. Do you think that tone is better suited to the modern age?

I don’t know. It’s just my voice. When you’re talking about all the heavy things you have to swim through in your 20s and 30s — shitty boyfriends, bad choices, go-nowhere careers — it’s natural to be appalled and outraged. The language for that is pretty angry and bewildered. When I first started writing my column, I was angry at so many things and could finally let them out, so I would use f–k five times in a single sentence. What feels authentic now is saying it three or four times per column.

That’s slightly more moderate.

It’s not so much the word, either, but what it signals: It [conveys] the kind of intimacy you’d have with a good friend talking with you about what you’re going through.

Between you, Cheryl Strayed’s Dear Sugar and Dear Prudence at Slate, it seems like we’re seeing a resurgence in agony aunts.

I hate that term.

Yeah, it has a kind of old-crone-y vibe. Regardless, what does our renewed interest in advice columnists tell you about how existentially screwed humanity is these days?

Even though there’s more understanding and acceptance of mental health issues, there’s also the sheer difficulty of moving your way through a world that is less traditional. Making choices used to be easier: the marriage, the job you’d have for 20 years, the retirement with full pension. Suddenly, we have a universe of choices, and, thanks to social media, there’s a feeling that everyone can see which choices you’re making, on video and with sound, which is a deeply self-consciousness-inducing thing.

Our current culture is so comparative — and we’ve always been like that, but it’s now on a much, much larger scale.

You know those times when you’re like, “My God, some people have infinite money and infinite beauty in their lives”? And then you turn back to your life, and there’s a stain on the carpet right next to your foot? The sense that you’re living the wrong way is ever-present. We need constant reminders to do the best with what we have and enjoy it — to create what we really want in our little corner, and not always feel like the centre of the world is located somewhere else, somewhere far from us.

We’ve also moved away from the mindset that only those who’ve lived perfect, sanitized lives are qualified to weigh in on other people’s business.

I’m not some clean, perfect human being who doesn’t f–k up. I do constantly. I have a lot of built-in trouble on board. But I’ve been paying neurotic attention to a lot of crazy things for a long time, so while I’m not the paragon of how people should be living by any stretch of the imagination, I do know what the f–k they should be doing.

You inject your own experiences into the advice you give — problematic drinking, the early death of your dad, your taste for flinchy guys. Do you think it improves your advice to say, “Hey, I’ve suffered too”? Or does it take away from it?

I can’t necessarily find the centre of a problem until I travel back and say, “This is something that I went through that feels similar.” Just saying “Here’s what you have to do” doesn’t acknowledge where the human being is, or that you care deeply about what that person thinks.

Related: Here’s the advice a sex worker gives new moms

What are some other tenets of giving good advice?

Sometimes, when I read a letter, the person’s values are different than mine, and even though I can’t relate to those things, I try to honour their priorities. One thing many of us have lived through is having lazy parents who don’t validate our choices — they just want our choices to look like theirs. So saying to someone, “Look, you need to honour what you give a shit about, and not mould your desires around what someone else thinks,” is a very essential part of good advice. Another part is the reminder that you’re not on a journey that will land you in a glorious, exalted spot, which is a message our culture gives us over and over again: Get better, work harder and eventually you’ll be in a golden castle on a hill! Or that the only people who are really alive look like Kim Kardashian.

Ah, yes, the chosen one.

The power of [that messaging] is so great. I’m 45 years old, I have three dogs, two kids, and I live in a nice place. But I can look at a picture online and get the sensation that I am a maggot underneath someone’s shoe.

Still, a lot of people see “self-love” as clichéd, probably because it’s so different from the usual North American MO, which is striving.

You can have all of the trappings of happiness and still struggle like hell. The best thing you can teach yourself — no matter what you’ve been through — is to appreciate and enjoy the shitty, half-formed picture that you’re in. At 28, I moved to L.A. and had started therapy in the middle of a very sad phase. And I remember putting on this Alanis Morissette album—

Supposed Former Infatuation Junkie?

Yeah, the one with “Thank U.” She sang about how she would be fine if she gained a lot of weight, and she would be good even if no one loved her. The notion that you don’t have to earn your right to feel okay was completely new to me. I was like, “What is this?”

We could have therapy up the wazoo, off-load all of our childhood garbage, have a kind, loving partner and a gangbusters career and still not figure out how to be a person in the world. Can we ever know?

People live like their brains are in a tank, you know? It’s so easy to become someone who’s calcified, someone who’s been saying the same shit they’ve said for 20 years. But the idea is to be aware of how incredible it is to be alive as much as you can during every day. The thing that makes it possible to be adventurous, to go into different environments without fear — and to not take every single thing personally — is just deciding that it’s okay to be a cobbled-together, broken human being who is flying by the seat of her pants. Everyone is doing that.

Many people won’t like you saying they have to feel their feelings.

A lot of people have just a ton of emotional stuff inside of them that needs to find something to connect to and to come out. But the more I feel good and bad, the happier I feel. So when things come up that make you feel things, feel them instead of saying, “Stop! Stop! Stop!”

I just need to watch one of those online videos about animal friendships, like dogs and elephants playing, and the feelings kick in.

I listen to heartbreaking music or I answer my column. I used to want to be a rock star; I wanted my feelings to come out in carefully curated ways. But my career is built around total openness. The thing you realize as you get older is that you might think you’re tricking everybody, but no one is fooled. At some point, you have to say, “Everyone can see me. I might as well tell the truth about myself all the time.”

It’s like how dogs need a pack leader: People need to know how to think about you, and you need to be the one to direct them. Otherwise they get nervous.

Absolutely. My friends accept my inconsistencies, but generally, the masses want a pack leader. They do not want a conflicted, inconsistent human in their lives.

Well, too bad for them, I guess. 

Yeah,  f–k them.

The mid-career drift: Women step off the corporate ladder
Mothers and daughters on pride, regret and the things they’ve never said
There’s no guide to queer motherhood in a straight world