Ask Polly: Am I Pretty?

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Dear Polly,

I’ve always been an insecure, neurotic, shy introvert. The best of all worlds. Even now, at the age of nearly 42, I am still these things. I am married with two children, but still trying to figure out who I am. And I find a lot of that comes back to the ridiculously vain and immature question of: Am I pretty? It’s as though I have been constantly evaluating the evidence of my prettiness over the course of my entire life (e.g., in ninth grade someone said I was one of the five prettiest girls in the freshman class [1 point for pretty], but my best friend then said, “But none of them are really all that” [-2 points for not being pretty and having a lame best friend]. Why are people looking at me in the grocery store? Because I look nice or because I’m such a mess? Why is no one commenting how beautiful I am on my Instagram photos [never selfies, for the record, but mom/kid photos] like pretty much any other woman’s Instagram photos?), and assessing my sole value to humanity in terms of how pretty I am.

I know this is ridiculous. I also understand how growing up in America in the 1980s/’90s could set me up to feel this way. But why can’t I get over it? More important, how do I make sure my 5-year-old daughter doesn’t grow up with this unhealthy focus?

I am vastly aware of the many larger problems our country is currently facing, and how shallow and self-centered this concern is. I am doing my part to support the resistance. But this matter haunts me on a near-daily basis.

So tell me, Polly. Am I pretty? Does it matter?


Dear Pretty?,

What if someone walked up to you and said, “You are so pretty. People don’t tell you this all the time? Well, they must be intimidated.” You ask around, and everyone agrees. Soon it’s clear that the people in the grocery store are admiring your beauty. You are pretty. There’s no doubt about it.

So what has changed for you? Does your future seem brighter? Do you have more choices? I’m not mocking you; I’m asking you to think carefully about what you think you’d deserve if you’re pretty that you wouldn’t deserve if you’re not. Can you do more daring things, have more adventures, feel less self-conscious and neurotic, because those are the benefits of looking great? Will Instagram be more relaxing? Will you think, “These friends look happy, but they probably see my pictures and know that I’m pretty great, too.” Will you feel less shy and second-guess yourself less?

And what if someone walked up to you and said, “Everyone thought you were so hot in high school, but you weren’t hot at all.” (A high-school classmate of mine once said this of me, to someone else! HAHAHAAha
heh eh.) What if you pressed a friend about it and she said, “You’re fine! You’re just like … you can look really nice when you put an effort in, but it’s not like you’re stopping traffic or anything.” Are your possibilities limited now? Do you want to crawl into a hole and hide for the rest of your life? Is it embarrassing to exist? Does the future look grim? Is Instagram an exercise in shame, where everyone else is beautiful and special and you’re just a bucket-headed ho, as Kendrick Lamar might say?

Tempting as it might be to fall down a “What Is Beauty, Anyway?” rabbit hole, let’s get concrete. First, I think you’re trying to reach some kind of peaceful place about your looks. I don’t necessarily believe that place has to do with figuring out how objectively hot you are, even though that’s how it’s presenting itself to you. I think you’re conflicted about looks in general: what it means to care or not care about looks, what it means to make an effort or make no effort at all. In your letter, you guess that people at the grocery store either think you look nice or you’re a mess — as if those are the only two options. Maybe you’ve been a pretty mess for a few years because you have a young daughter, and now she’s old enough that you can stop being a mess, but you’re ambivalent about it. You feel like making an effort (on top of harboring a secret obsession with looks) would mean that you’re inexcusably vain.

Our culture demands that women make an effort to look good, and then it demeans us for doing so. We’re either slobs or we’re high-maintenance girly girls. We are letting it all go as we age or we’re sad cougars chasing our youth. But there are a million and one good reasons to try and not to try, and none of them are simple. If you’ve never really felt comfortable with the slob route OR the polished route — and I’m going to guess that tons of women fall into this category — it makes sense to examine what you really want, and to separate your prejudices about what it means to be “vain” from the picture, and to interrogate your worldview about why “pretty” magically makes you worthy and full of promise while “not pretty” somehow makes you worthless and doomed.

Nell Zink describes having been allergic to “dressing up” and then having an epiphany about it in her recent essay for n+1:

It (getting dressed up) suddenly appeared a privilege, rather than a form of half-shameful submission. On this day, the mirror did not say to me, “Dude, you’re in drag,” and I did not say to the mirror, “May I help you?” (For decades, my impression of my well-groomed, pulled-together self was of a friendly stranger who hoped to sell me something.) I felt relaxed and cheerful in my becoming new outfit. I had a lovely day.

God, do I relate to that. I didn’t feel comfortable trying to look presentable and professional until just last year, when I became extremely anxious about doing a book tour while still looking like your average bucketheaded 40-something. I decided I had to stop wearing the same bad dresses that made me feel like a frumpy middle-aged loser and putting on the same half-assed makeup that made me feel like a sad old woman who still doesn’t know how to clean up nicely. I hate shopping, but I did find one excellent shirt and I immediately bought five of them. I asked a friend who seemed to know about the new, modern world of makeup for concrete suggestions. I threw out my shitty author photos, in which my expression might best be described as “Please forgive me for inflicting my Not Young Enough and Not Hot Enough self onto the world!” I hired a good photographer who hired a makeup person and made styling choices, so I didn’t have to fuck it all up with my own bad choices. And when the photos came back, I picked a few of them and used them and resolved not to beat myself up over the fact that they were a tiny bit professional looking, which is obviously unbecoming of a serious writer. And when people published these photos of me, it was so refreshing to see my face forming an expression other than UGH I KNOW. I’M THE WORST. Instead, my expression says YES THIS IS ME, SO FUCKING WHAT?

And now, before I go out to an event or party, instead of putting on shitty 3-year-old foundation while berating myself for looking even shittier in makeup than without it, I use primer (like clear gesso for your face) and tinted moisturizer (the new name for foundation that doesn’t look shitty). I use lip pencils, which is just lipstick for idiots. I literally haven’t worn lipstick since 1998, and now I wear it whenever I’m in a YEAH THAT’S RIGHT, LIPSTICK FOR NO REASON, YOU GOT A PROBLEM WITH THAT? kind of a mood.

If all of this sounds defensive, that’s because it is. I spent my whole life feeling sure that the second I paid the tiniest bit of attention to my looks, I was an unforgivable asshole. But somehow I also felt that I had to look great or I was worthless. So I walked around trying to ignore my looks, mostly by rarely purchasing clothes or showering regularly. Spending money on anything looks-related was stupid, I said. I would rather buy really good cheese, I said. I didn’t want to be noticed anyway, I said. And as a young woman, sure, it was easy to feel TOO visible in public places. I wanted to skulk around without drawing attention to myself. That was fine when I was young, but a little less fine once I gained 20 pounds after my second kid and my hair turned to white crinkly straw and my face got wrinkles but still broke out all the time. I felt like a lumpy old dork. Eventually I had to stop lying to myself and admit that it bugged me.

I would rather be someone who isn’t bothered by such stupid things. But you know what? I’m not. I care about how I look and I always have. I was that kid. I was that teenager. And my parents told me it made me shallow. I knew that I was shallow. I tried to be less shallow. It didn’t work.

You know the only thing that worked, the only thing that made me less shallow? Deciding to be a tiny bit vain for a change. Once I gave myself permission to be a little vain, I could find the ONE FUCKING SHIRT I like and treat my previously untreated rosacea. I could take a photo of my face saying “YEP” instead of “DON’T HIT ME!” And I could leave the house without feeling like a dumb piece of shit who was trying too hard. By paying a tiny bit of focused, calm, non-stressful attention to my looks, I freed myself from thinking about my looks so much.

Once I could do that, I didn’t magically become hotter. I still exist squarely in the realm of Almost Hot but Almost Kind of Ugly, Too. I’ve always lived there. But that was never really the problem. I don’t care about some objective “Am I hot or not?” numerical rating. People think I’m just average? I’ve heard that all my life. Maybe I have the personality of someone who thinks she’s hot and therefore needs to be taken down a notch. But that was never a big deal for me. The big problem, for me, was that I was very tired of broadcasting SORRY FOR BEING HERE, I’M AN IDIOT! everywhere I went. (And yes, you can have a lot of swagger and also do this UGH I’M GROSS thing other times — a common conflicted-woman thing, in fact!) I was tired of that routine, which I developed as a response to being a clueless slob who felt out of place everywhere I went, which I developed as a response to not putting in any effort whatsoever, which I developed as a response to being called shallow and vain by my parents when I did put in an effort.

Here’s the moral: Sometimes the things you hate the most are also the things you care about the most, underneath all of your defensiveness and self-hatred. And some difficult areas of your life really do require careful, thorough unpacking. I needed to notice that I was carrying around a lot of shame, and that shame was there whether I looked fantastic or shitty. The problem was the shame, not how I looked. And I needed to notice that I thought anything I did for me and me alone was a clear sign that I was a terrible, selfish person.

So ultimately, I needed to learn how it might feel to please myself first. I guess that’s why I hate it when people give women a hard time for caring about whatever the fuck they happen to care about, or politicize stupid shit like bikini waxes. There’s so much built-in shame that comes with just being a woman with a body who has to put clothes on that body and leave the house. We all know it. I get that all choices are political choices. But we can’t all be pure and rise up like glorious gray-haired saints of pure, true feminism, armed with only the big issues and the radical feminist texts, and with none of the goddamn lip pencils and slogan T-shirts and strong cocktails and other signifiers of the high-capitalist urban sellout. We have to operate within the confines of our poisonous culture, and make choices that challenge the status quo but also feel right to us personally. Condemning yourself for every impure choice is just another way of reinforcing the anti-woman shame you already have onboard. You’re still living in a culture that fucking hates women, hates black people, hates Muslims. Maybe you can cut yourself some fucking slack and honor your desires and do what you do, knowing that it will free you up to give much more to the people and the world around you, knowing that telling the truth to yourself and to others is a radical act for a woman, one that creates more room for women to speak their own NECESSARILY complicated, conflicted truths out loud (to loosely paraphrase Adrienne Rich, that glorious saint of pure, true feminism, to be read and reread until the end of time).

Like I said, I’m defensive. I’d prefer to be someone who doesn’t use the word “lipstick” in her fucking advice column. That’s deeply ingrained self-hatred. That’s what I want you to look for, as you examine this question of what Pretty or Not Pretty means to you: Look for the things that embarrass you the most. Ask yourself why. And ask yourself: What if I were to engage in the radical act of choosing for myself what I like and don’t like, what I want and don’t want, without taking a poll of other people’s opinions first?

I don’t think you need some Pretty or Not Pretty answer. Maybe some women get told they’re beautiful on Instagram constantly and some don’t, based on some “You go, girl!” calculus we haven’t studied closely enough to understand. I think you need to find some peace with how you present yourself instead. This might, paradoxically, require some extra effort. Or maybe you want to put in less effort! In order to stop wondering why people look at you, you need to examine your choices more closely. Because it’s not about how good you look. It’s about how good you feel about your personal choices. Right now, you’re angry at yourself all the time. That’s not going to disappear quickly, whether you’re proclaimed Gorgeous or Ugly. That anger and insecurity will still be there.

You have to figure out how you want to be. This is less about asking more and more questions (since you already define yourself as someone who doesn’t know anything about herself and hasn’t “arrived” anywhere real yet), and more about reaffirming the answers you already know in your heart. It’s clear from your letter: You want to be someone who seems confident, who can speak up when she needs to, who isn’t always trapped in a prison of her own circling thoughts. I think you call this kind of person “Pretty.” You want to move through the world like someone who knows what she thinks and what she wants and who she is. “Pretty” is a false flag for something much bigger and deeper.

So how would that confident, calm person dress? How would she act? How would she spend her time? Do those things. It really is that simple. And that’s not faking it or pretending. That’s being who you already are; it just doesn’t show because you won’t let it show, because you’re ashamed. You are a question mark instead of a statement because you’re actively choosing to remain a question mark. Maybe you’re putting off something important to you by remaining undecided, and by polling the outside world in search of direction (and, just as important, rejection). You look to the outside world to define you. You look and you ask, “Am I good enough? Is there a problem? What do you think?” You read faces and you study Instagram. “Have I arrived? Am I impressive in any way? Was I ever good enough? Am I better now?”

The best way to feel “pretty” (confident, calm, sure of who you are) is by resisting the urge to ask questions. Turn yourself into a statement: “I am good enough. I am worthy. I have a right to take up space.” Instead of reading faces and looking for proof that you’re good enough, ask yourself what would help you feel good. What small things could you do to feel more confident, less tormented? Personally, along with finding my one fucking shirt (ha!), I also remind myself, “You don’t have to please anyone. You don’t have to fix anything. You can just exist.”

Human beings are strange animals. They spend a lot of their time torturing themselves. So many of us look for rejection wherever we can find it. I’ve noticed that this is my default mode in unsettling social situations and in broken friendships: Who disapproves? Whose mind can I change? What can I do to be “good” again?

Stop returning to this prison of Pretty or Not Pretty. Be the person you already are. Stop asking questions and be a statement. Be a statement that remains the same whether the people around you are cringing or smiling.

When you are a statement and not a question, your kids are statements, too. You don’t have to instruct them on how to be that way. You simply make your own choices, interrogate your desires, celebrate your true self and enjoy yourself as much as possible without trying to hide or improve or seem better than you really are. You simply allow other people to make their own choices and be who they are, and you don’t stigmatize or reject them every time their tastes and desires don’t match your own. When you live that way, you don’t stand around neurotically worrying about whether your kid is dressed the right way, or whether she ate enough or too little, or whether or not she’s looks “right.” You don’t put your fears about looks into her. You give her room to decide for herself.

Pretty is often just about trying to stand out, trying to win something that will magically make you feel less ashamed, trying to prove that you have something that other people don’t have. Instead, say this to yourself, and to your daughter: You don’t have to be better than anyone else. You can just be who you are, and let everyone around you be who they are. That is the most beautiful thing in the world.


Order the new Ask Polly book, How to Be a Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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Ask Polly: Am I Pretty?