When I was a little girl, I asked my mother, “Am I pretty?”

I clearly remember her recoil, her curled lip as she snarled, “Self-pity is disgusting!”

I don’t remember what prompted the question, maybe my older sister telling me I was ugly.  “You have to have blonde hair to be pretty,” she said, “like me! Haven’t you noticed – all the main character girls are blonde?”

The kids at school picked on me, and the most common refrain was “you’re ugly!”

I asked my dad, half-afraid, hopeful. He was always the kindest to me. “Am I pretty?”

He’d frowned and said, “It’s more important to be smart.”

I took that as a no.

So it was unanimous – I was ugly.

Charles Horton Cooley came up with the concept of the “Looking Glass Self” in 1902.  Basically, he found that people formed their opinion of themselves from what they saw reflected in society and their peers.  It didn’t matter what the actual looking glass showed me, I saw myself reflected back as an ugly creature.

When I was 18, a sweet fellow-freshman held a mirror in front of me and said, “Look at yourself! You are pretty!”  I don’t remember the self-deprecating thing I’d said to prompt her. I remember her brush-stroke eyebrows, her eyes as wide as she could make them, our fellow-friends sharing this moment of girly camaraderie on a dorm bed.  I remember being a little puzzled that, in fact, I didn’t look bad in the mirror.

I have always had the advantages of conventional good-looks. My features are regular and symmetric and unblemished, but I would have sworn before a jury that I was hideous up until that college freshman dorm room.  Even then, it took a few years for it to sink in. In some ways it still hasn’t.

Within a year, my bitterness at being born ugly morphed into bitterness at having been lied to. I had wasted all my best years not being pretty! I was almost twenty! Practically a spinster! I could have dated!!

I started Dressing Nice. I started combing my hair regularly and showering regularly because now, you see, I had a reason to.  Being attractive was no longer something I could never achieve, it was within my grasp. I just needed to keep myself neat and clean and smiling.

The project took on a sense of frenzy. The clock was ticking!  Twenty wasted years!

I panicked over my first wrinkle at 21.  Once you start noticing the tiny flaws, they fill the mirror.  The real mirror was no longer kind, even as the society-mirror was infinitely nicer to me.

Why do I care so much? Why do I have to make myself pretty, when I’ve already wooed and won my life-partner? I’m 43. There is nothing wrong with looking middle-aged when you are, in fact, middle-aged. Yet I feel like there is. Like no one will like me anymore if I start to look more like the Old Battleax than the Ingenue.

Like life is nothing but an audition for central casting.

Recently, I’ve tried to make a Real Effort at learning how to use makeup.

And now, I have a tween girl under my wing, and I’m seeing her ask all the same questions. Am I pretty? Am I pretty ENOUGH?

And I’m… a little horrified. I want to say what my dad said, because now I understand it wasn’t meant to hurt me, it was meant to encourage me not to be an ornament. But also I remember the pain of un-prettiness, that Dad’s advice hadn’t encouraged me.  Society demands prettiness of girls and to fail at this is painful. It’s unfair, but true.  I say, “You’re pretty. You’re beautiful. You are amazing.” Because that is all true, too.

And “Pretty” never meant “pretty.” It was an easy stand-in word for “socially acceptable” “conventional” “normal.”  “Pretty” is classist. “Pretty” is racist.  “Pretty” is HELLA ablest.  “Pretty” is a death by stoning by pebbles. It’s a constant rain of rejection, pushing down those who don’t exactly fit.

I want my niece to feel pretty. I want to feel pretty.  I want everyone to feel pretty. If my older sister had been confident of her own prettiness as a child, would she have any reason to assure me of my ugliness?

I want to steal the word and democratize it so no child will ever feel ugly again.  I know that’s not possible, but some days, when it’s sunny and a stranger smiles at me, I feel my fingertips almost catch it.

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