11 times Ask Polly knew exactly what you needed to hear

Some of the smartest writing on the internet right now is happening in advice columns. Slate’s Dear Prudence column gives readers the singular, unhinged genius of Mallory Ortberg. Captain Awkward hands out life scripts with kindness and empathy, and Ask a Manager explains professional life with all the wisdom you wish your school’s career counselor had.

And then there is Ask Polly, the existentialist advice column born on The Awl and currently on New York Magazine’s The Cut.

As Polly, Heather Havrilesky responds to problems that would stop other advice columnists in their tracks. People reach out to Polly because life just seems … empty, somehow. Or because the letter-writer is dissatisfied, but not sure exactly why. Or because they’re wondering if they’ll ever find love, or a fulfilling job, or make peace with their parents.

Havrilesky responds with thousands of words of profanity-laced, empathetic wisdom. The specifics might vary, but the core of the advice is the same: You will be okay. What you’re feeling is messy and unpleasant and hard to control, and that is okay. Lean into the messiness, accept your unpleasantness, and refuse to settle for less than you want from life.

And now, her advice has been collected into book form in How to Be a Person in the World.

It’s not a book that benefits from being read straight through. Havrilesky returns to the same core messages again and again throughout the book, and “You should be with someone who loves your particular kind of messiness,” lovely and affirming as it is to hear, gets a little wearing if you’re reading it for the third time in 20 minutes. But as a resource to turn to, something to dip into whenever life seems just a little bit empty, How to Be a Person in the World is invaluable.

As a sampling, here are some of the best words of wisdom in the book:

If you are sick of wasting your time with tepid people:

You need to tell tepid to fuck right off, Kanye-style. If you vow right now that the second you see tepid, you’re going to back up and say, “No fucking thanks,” and move on without looking back, then your self-esteem will immediately bounce back from years of abuse. That means retiring the soliloquy about how great you are. That means no more badgering. Replace the badgering with a rap. Write it down, file it away, move the fuck on. (Fuck you AND your futon. I’ll fuck your best friend, Sean. I’ll fuck him till the dawn. I’ll make your man my pawn. Fuck having late-night drinks. Fuck playing tiddlywinks. Fuck all your tepid kinks. Your half-assed shit still stinks.)

If you told a grabby asshole to fuck off, and now you feel guilty:

What you’re describing is not a bit of drunken, idiotic grabbiness or unfortunate cluelessness. It’s malignant and purposefully demeaning. I suspect that most women reading this know exactly what that energy feels like. We’ve been there. It’s different. …

And now you’re the bad guy because you exploded! And even you believe that! Your mistake was that you tried to push your emotions aside and accept a situation that is un-fucking-acceptable. Trust me, I’m all for pushing emotions aside and dealing when life requires it. But you can’t forgive and forget, because it turns out you’re still angry.

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If you can’t figure out how to be angry, because you’re pretty sure you’re always supposed to be nice:

This is what I want you to accept, first and foremost: You are a nice person, and you’re also full of anger. You’re a walking tangle of contradictions. That’s okay. Most of us are like that. Women, most of all. How could we not be? People want us to be sexy warriors who roll over and play dead on command. They want us to be flirty burlesque dancers in burkas, aggressive conquistadors with cookies in the oven, Dorothy Parker meets Dorothy Gale, Sandra Bernhard meets Sandra Dee, Kristen Stewart meets Martha Stewart.

Experiments in asking for exactly what you want will go badly. Do it anyway. Do it and expect people to react badly. Because you’re sensitive, you won’t like this. Think about how they feel, and try to empathize. Watch how other people do it. I know it sounds like a management technique, but good communicators usually start with something positive, then move to the negative gently: “I love this about you, but I have to draw the line here.” “I know you’re trying your best, but this is what I need from you.” “I care about you so much and you’re such an important friend to me, but I don’t think I can do this one thing.”

If your family won’t stop telling you you’re fat:

So, look, the reasons for your anger and frustration couldn’t be more clear, and they’re completely justified. I think you need to express them. I don’t think you’ll be happy until you do.

It’s a complicated problem, but it has a simple solution: Draw boundaries and stick to them. Express the emotional side of it with care; go into detail if you want. But then shift gears and tell your family precisely what you expect from them: “No more talk about weight, food, or how I look. None.” Don’t apologize for it. Don’t second-guess yourself. Don’t get mad if you can help it. Just say, “Hey, this is what I need.”

If you keep finding yourself hooking up with guys in relationships:

When a guy gives you attention, you feel like you’re “winning” somehow. We all grow up believing that only one of us can win — one beautiful princess at the ball, among all the goofy sidekicks and maiden aunts. So every time we’re at a party, or a dinner, or a club, we organize the scene based on the same notion: Either we are the one who sparkles and thrills, or we’re some dog in the corner. We’re either the girl in the kitchen alcove, giggling and flirting, or the sad ignored girlfriend in the blurry background. We’re either the white-hot sexy girl making out in the car or the sniffling loser girlfriend waiting around at home for her boyfriend to come back.

This isn’t really winning. It’s hurting yourself and hurting other women in one blow. It’s serving your ass on a platter not to a prince but to a predator. It’s feeding into everything sick and wrong about the blindest, least soulful dimensions of our culture. When you soak up the attentions of some smarmy creep, you’re throwing away your compassion and your power and you’re empowering that creep to pick a “winner.” He’s the one who determines which girl is superior and which girl is a sucker and which girl isn’t worthy of his predatory gaze.

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If you think you want to be an artist but that sounds so pretentious:

There is the artist, and then there’s this pragmatic person within you who bails you out when you’re drowning. Don’t let the artist fuck with what the pragmatist is trying to do. But do let the artist take up a lot of space. Let the artist call herself an artist, even to her parents’ skeptical friends. Practice saying it out loud to exactly the people who are the most likely to think you’re a fucking joke.

You’re an artist if you create art, period. You’re a writer if you write. First, you have to claim the title. You can’t work hard until you claim the right. (For women, I think, that’s particularly true.)

Artists, pretentious or not, blustery and swaggery or self-abnegating, need to find their faith in their work all over again, every morning of their lives. You need to devote yourself to your religion, Lost Artist.

If you want to quit your crappy day job and make art but you’re scared to death:

Spend the next six months in a state of total obsession. Get up two hours earlier than usual and write before you go to work. Come home and exercise (not optional, sorry), then write for another hour. Read or watch the kind of comedy you love before bed. Don’t waste all your time socializing. Do a little socializing on weekends, but focus. Focus! …

Of course you will still question what you’re doing every stupid day, maybe for the next two decades. Even after you write a hundred funny things, you’ll believe that you’re all tapped out. I’m always convinced that every essay I write will be my last. I’m always wrong. And I can tell you from experience that if you get up early, drink your caffeine, and fill yourself with the sense that you are going to TURN THIS MOTHER OUT, SOMEHOW, SOMEWAY, you will find the inspiration and the tenacity you’re looking for.

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If you want to quit your crappy day job but you don’t know what to do instead:

You already know for a fact that you don’t want a job in corporate banking. That’s never going to change. I would make a plan to quit within the next year. I would make a plan to save money and scale back your spending. I would commit to exercising once a day, to keep your spirits up and tackle your anxious nature. I would put your ideas about your new career on paper. I would talk to people who do what you want to do for a living. I would take action, and yes, maybe dedicate nights and weekends to figuring it out.

If your friend’s in trouble and you don’t know how to be a good friend to them:

Never use an “I told you so” attitude to let yourself off the hook from showing up for someone you love. And don’t use the “I don’t know what to say” excuse, either, or the “I’m afraid I’ll say something wrong” excuse. You probably will say something wrong. That’s okay. JUST SHOW UP. Show up and say, “God, this sucks. I’m so sorry.” Just keep saying that, and keep showing up.

If you’re not satisfied with what you’re getting from life:

Stop being grateful for scraps. Everything good in my life has surged forth from one crucial moment or another when I said, “I am not settling for these scraps anymore. I want more than this for myself.”

And finally and most importantly, if you feel unlovable:

It’s time to forget about being lovable. And in fact, it’s time to forsake someone else’s idea of what gives you a spark or no spark. Block the “other” from this picture. No more audience. You are the cherished and the cherisher. You are the eminently lovable and the lover. You are a million brilliant sparks, flashing against a midnight sky. Stop making room for someone else to sit down. Fuck “good” partners. Fuck waiting to be let in. You are already in. You are in. Cherish yourself.

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