Not Pretty, Not Ugly

What happened when I stopped tying my self-worth to being seen.

It was fifth-grade science class. I was sitting at my desk, doing whatever assignment the teacher had given us, when the boy sitting across from me started talking about me.

“She’s not pretty, but she’s not ugly.”

He was looking at me like a scientist observing a specimen, genuinely curious about how someone could be both “not pretty” and “not ugly.”

The boy beside him told him to stop, but he kept repeating it: “Not pretty, but not ugly”.

Twenty-something years later, I still remember that moment clearly.

I didn’t say anything back. To be honest, I think I took it as a compliment - that at least he considered me “not ugly.”

That day might have been the beginning of something: the beginning of my awareness that others had opinions about how I looked. Maybe it was the first time I started caring.

Throughout primary school, one of the things I did at night, lying in bed trying to fall asleep, was count all the boys who’d had crushes on me.

I’d start with Jake from kindergarten, then Michael from first grade, and go on, counting on my fingers.

Why did I keep track of this? Why did it fill me with pride?

My mom was friends with many of the other moms at school, and she’d often tell me when she heard that a boy liked me.

“Collin’s mom said he goes home every day and just gushes about how smart you are,” she’d say, smiling down at me.

Was she proud? Was this what success felt like? Had I achieved something?

I learned to equate external validation with achievement. If I was pretty, then I was valued. If boys liked me, then I was worthy.

And while I was proud of the attention I got, I wasn’t learning to be proud of who I was. I was learning to be proud of how I was seen.

The older I got, the more appearance became a kind of currency.

When I started middle school, one of my best friends, who lived down the street, stopped talking to me. Apparently, I wasn’t popular enough.

I don’t remember being particularly heartbroken. I think I had enough friends that it didn’t sting as much. But the message stuck: if I wasn’t pretty, or popular, then I didn’t matter.

It wasn’t until I was 13, when I hit puberty, that I really started caring about my image.

The shorts got shorter. The tops became cropped. A dark smudge of eyeliner rimmed my eyes. I still wasn’t that interested in boys, but I was interested in their attention. Attention became part of my identity.

Despite my best efforts, no one blatantly hit on me until high school.

I was at Barnes & Noble browsing the young adult section, when I noticed a kid, maybe ten years old, following me.

He came up and pointed toward a boy my age browsing books nearby.

“That’s my brother. He’s very lonely. Will you talk to him?”

I stood frozen and speechless as his brother quickly walked over.

“Sorry, is my brother bothering you?” He asked. Then, “Hi, I’m O’Neil.”

I think we shook hands. My legs were shaking. I told him my name. He asked for my number. I was so nervous - I said no, but gave him my Facebook.

I left the store stunned. Did that really just happen?

I told my sister and my friends, and the more I told the story, the prouder I felt. Like I had finally reached a new level of maturity - being hit on in public.

In my freshman year of high school, a friend roped me into drama club. He was in charge of the sound board and needed someone to train before he graduated.

I didn’t really like doing sound, but I loved being in the club. Mostly because of the attention I got from the boys (and sometimes girls) who were part of it.

At the end of each production, they handed out paper plate awards, and after my first show, I got “Cutest Girl.”

Forget the honor roll and academic awards - that paper plate made my heart explode.

I don’t know when I started tying my self-worth to my appearance, but it happened.

Throughout my teenage years, I rarely felt good when I was alone. I only felt good when I was out. When I was getting attention. When I had a boyfriend.

I craved attention like it was proof I existed.

When I entered a long-term, serious relationship, seeking male attention suddenly felt wrong. But that didn’t mean I stopped wanting to be seen as pretty.

The desire just found new forms: trying to be as fashionable as possible. Compliments from girls on my outfits validated me just as much as being hit on.

I started shopping at all the trendy stores, making it a point to be overdressed wherever I went.

In my early twenties, I moved to one of the fashion capitals of the world - a place where women dressed like models just to go grocery shopping.

I used to joke that living there made me feel like a sack of potatoes. But honestly, it did. I tried my best to fit in, to look “European,” but it never felt right.

Eventually, I decided I didn’t want to fit in. I wanted to stand out. I started wearing long, patterned dresses. They got attention. They got compliments.

But at 27, when I began my healing journey, I started to ask myself: was I wearing them because I liked them, or because of how people reacted?

So at the start of this year, I decided to try something different. I committed to wearing only jeans and a white top every day. In March, I stopped wearing makeup too.

In a way, it’s been liberating, wearing the same thing every day. But I also miss feeling “pretty.” Not that I don’t think I look pretty without the dresses. I just miss the feeling of putting in effort. Of being seen.

But now, there’s a war in my mind. When I think about putting on makeup, I just… can’t. I don’t know what my reason is. Am I doing it for me, or for someone else?

I feel like a pendulum, swinging from one extreme to the other. I just want to find the version of me that doesn’t care what anyone thinks. Who just is.

Still, I’m proud of where I am now. Proud that I’m even aware of how deeply I’ve tied my self-worth to my appearance. Proud that I’m no longer chasing easy validation.

But I know I’m not done. I still have a journey ahead of me.

Maybe the point isn’t whether or not I wear makeup.
Maybe the point is learning to exist without asking for permission to be seen.

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