The Trouble With Pretty — 'It's A Trap Dressed Up As A Compliment'

Written on Dec 24, 2025

beautiful woman with a conflicted thoughtful expression, illustrating the hidden complications and quiet costs that often come with being seen as ‘pretty’ Yaroslav Shuraev | Pexels
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As a child, I longed to be pretty. Girls are taught that this is something to long for. My younger sister was the looker in our family, somehow inheriting a Mediterranean complexion from our pale-skinned parents. 

My skin, meanwhile, bordered on translucent. In the fluorescent light of dressing rooms, my veins draped like blue lace across my thighs. During summer months, despite my avid use of sunscreen, scarlet splotches inevitably graced my knees, and darkening freckles threatened to consume my face.

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My eyes were small and squinty, and my closely cropped hair did me no favors in the cuteness department. Oh, and did I mention my buck teeth? Yep, my two front teeth protruded from my gums at an impressive angle. The gap between them was so cavernous that many people assumed the space was on account of a missing tooth.

The trouble with pretty

woman who has trouble with being pretty Spectral-Design / Shutterstock

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RELATED: The Heartbreaking Truth Behind Every Pretty Face You See

My Gerber baby sister blossomed into a round-faced child with a button nose and straight, thick shoulder-length hair that shone when you brushed it. Adults told my parents, in front of me, that she should pursue a modeling career. Boys in my elementary school class asked me why I wasn’t as pretty as my sister.

When I finally grew out my hair, that helped, but I had no idea how to tame it. My parents thought it was wildly funny to ask me if I’d brushed it with an eggbeater.

In middle school, I discovered LA Looks Megahold hair gel, and things got a little better. But I was suddenly short. My friends were all growing around me, both in their height and bosoms. I failed to grow in either department. My doctor suggested bloodwork to make sure I didn’t have a growth disease.

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I had no disease; I was just a late bloomer. 

But being a late bloomer felt like a disease in my book. I nodded along as friends complained about periods and the sensitivity of their swelling breasts. As a high schooler, I was all elbows and knees — skinny, scrappy, and still short. 

Thankfully, I no longer had buck teeth, but the struggle to confine them to a proper angle raged on. I decorated my braces with purple rubber bands, which did little to enhance the visual aesthetic.

One of my best friends from childhood, who struggled with her weight in middle and high school, told me recently that in retrospect, she’s grateful that she didn’t get consumed by the quest for male attention at a younger age. She just counted herself out and focused on other things.

I can relate. While I very much wanted male attention, and while I did occasionally get some, I was decisively not fawned over, nor was I consistently pursued. My late-arriving period was one of those blessings in disguise — a source of deep insecurity at the time, but also something that motivated me to build my sense of self-worth in other ways, like through school and sports.

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Thirty years later, as society begins its insidious work of rendering my middle-aged face irrelevant, I can still run, and I can still use my brain.

I asked a college friend once if he thought a female classmate was pretty. He said, “Sometimes,” and it kind of blew my mind. I thought men either deemed women pretty or not pretty.  It had never occurred to me that you could be pretty “sometimes.”

Sometimes, pretty was, in fact, the exact kind of pretty I was growing into. Even though I still spent plenty of time lamenting all my physical flaws, sometimes being pretty was also a relief. I could turn it off when I wanted to, retreat into baggy sweatshirts, pull back my hair, forego eyeliner and mascara. If I were in the mood for attention, I could also look hot.

In hindsight, my early 20s were an ideal time to become sometimes pretty. I had the emotional maturity to understand what men were after, whether sinister or well-intentioned, and I also understood how to use my secret, pretty superpower to my advantage, whether for bartending tips or for donations to the nonprofit I’d co-founded.

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I could exercise the pretty privilege when it suited me, but I only occasionally had to contend with its ugly underbelly — the constant attention, unwanted advances, and persistent pressure to appease the male gaze.

Much to my surprise, my daughter bloomed early; she became acquainted with beauty’s ugly underbelly while still in elementary school. 

From a young age, she has received consistent external validation for her beauty, which has gotten all tangled up in her sense of self-worth. Unlike me, her beauty didn’t develop at the same pace as her brain. And unlike me, she doesn’t have the luxury of retreating from it. 

She has the large eyes and symmetrical face that our culture swoons over, and her nut brown skin is flattered by most any light. When adults aren’t telling her she looks like Zendaya, they’re asking if she’s thought about modeling, or they’re remarking to me, in front of her, that I have a very beautiful daughter.

If I’m being honest, my gut reaction to these comments is pride ,  as though birthing and raising a beautiful daughter is an accomplishment in its own right. If the comment is directed at me, I sometimes say, “Thank you,” because I am used to thanking people when they pay me a compliment.

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RELATED: Therapist Explains The ‘Higher Risks’ People With ‘Pretty Privilege’ Have To Deal With Daily — ‘People Are Anxiously Waiting To See You Fail’

Then I feel disgusted with myself and disgusted with a society in which the value of female beauty is so deeply ingrained that even feminists, like me, still experience a Pavlovian reaction of pride when someone tells them that their daughter is beautiful.

My daughter, I can’t help but notice, also takes pride in being “beautiful.” And who can blame her? Throughout her life, adults have made it quite clear that female beauty is cultural currency, that beautiful females are valued, praised, and adored. Who doesn’t want to be valued, praised, and adored?

The one thing she hates, with a passion, is her tightly coiled hair, which grows out, not down, and which she can’t flip over her shoulder. She spent most of this past Saturday in tears because her attempts to straighten it didn’t result in the silky, flippable hair that would make her “look pretty.”

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I am left torn between reassuring her of her beauty and telling her that pretty can go screw itself. 

I see the pressure she feels to live up to her own beauty, mostly in the form of products that line her desk from end to end.  I see it in her tearful quest for flippable hair — Zendaya has it, why can’t she? 

I see it in every skincare product, every haircare product, every eyelash extension, every hair dryer attachment — each one a representation of a flaw that needs to be corrected. A problem that a profit-hungry society invented, then offered to solve for only $19.99.

I’d like to say that the beauty industrial complex has nothing on me. As a 45-year-old feminist, I’ve overcome my insecurities and made peace with my so-called flaws. That I no longer feel the need to lean into sometimes pretty. That I couldn’t care less about the male gaze.

I’d like to say all that, but it would be disingenuous. I still like feeling pretty from time to time, and my definition of pretty is still largely dictated by patriarchal norms.

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Luckily for me, I’m rarely motivated to invest too much time and money into my physical appearance. But when I do, I’m reminded just how much time and money it’s possible to spend. 

In preparation for a presentation I made last month, knowing that I would be up in front of a roomful of 100+ strangers, I decided to treat myself. I had some rainy-day money from a story I’d written that made its rounds, so I started scheduling appointments. A facial, a manicure, highlights, and a lash lift. A whopping total of six hours and $500, all for beauty rituals that women are advised to get every 4-6 weeks.

I am always contending with a vague sense of guilt when it comes to beauty rituals, with attempts at justification that don’t really hold water. I could say I just wanted to get pampered, which is true, but it doesn’t explain why I added sugaring to my facial, which isn’t exactly pleasant.

Likewise, I could insist that I shave my legs because I enjoy the silky feel, which is true, but it doesn’t explain why I shave them far more often in the summer. I could insist that I wear bras because the support is comfortable, which is also true, but it doesn’t explain why I sometimes opt for a push-up bra.

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I have been known to brag about my simple skincare routine — face wash, sunscreen, night cream — but I leave out that two of those products have retinol in them. I’ve told my kids that I mostly wear foundation and mineral powder because they offer two extra layers of SPF, but would I bother if they didn’t also even out the reddish undertones of the too-pale skin that I still lament under fluorescent lights?

The patriarchy continues its quest to tie up my sense of self-worth in my appearance. 

At the same time, capitalism stalks me across the Internet with anti-aging products and procedures. Neither quest can be pronounced a resounding success; neither is it an abject failure. I’m not as terrified of aging as I’m “supposed” to be, but I still want to “look good for my age.” Whatever that means.

While I lament all the time and money it’s possible to sink into the superficial work of improving one’s appearance, I also remind myself that beauty rituals can be fun. Humans have practiced different forms of these rituals for thousands and thousands of years, long before capitalism snatched them up in its greedy, grubby hands.

RELATED: People Judge Me Just Because I'm Really Pretty

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I remember braiding my friends’ hair during story time in elementary school, applying face masks at slumber parties in middle school, convening with friends in high school and college before proms and parties to do each other’s makeup. Usually, the time I spent “getting ready” to go out was far more enjoyable than actually going out.

Now, when I spend 10 hours box braiding my daughter’s hair, it’s 10 hours I get to spend with a teenager who would otherwise never willingly spend 10 consecutive hours with me. We listen to true crime podcasts and eat chicken wings. 

While it hurts my heart that she so deeply scorns her hair’s natural texture, she is also taking advantage of it, applying her creative talents to dozens of different hairstyles and braiding patterns that would never work with my thin hair. Each one is a work of art in its own right.

I have male friends and coworkers who have discovered how much fun it is to paint their fingernails, to experiment with different colors and designs. In my hometown of Portland, Oregon, people of all genders pierce various body parts and adorn their skin with tattoos. 

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And while I can hem and haw over my motivations for shaving my legs, I adore the ritual I make of it — the slow descent into a fragrant, frothing bath; the foaming cream and the careful gliding of the razor; the slow, sensual application of coconut oil over my newly smooth skin.

How can women lean into the fun of beauty without getting consumed by the insecurities and desires that society is intent on instilling in us?

I stumbled across one answer quite by accident. I never got around to hanging a mirror in my bedroom, and the two mirrors in my bathroom are both strategically positioned in low-light areas at flattering angles. 

Actually, there is nothing strategic about it. There are only two possible spaces for mirrors in my bathroom, and when the specialty bulbs in the lights above our medicine cabinet mirror burned out, I couldn’t find viable replacements.

I tend to look great in these mirrors. As such, I don’t spend a lot of time gazing into them. I do a quick check before leaving the house, making sure I don’t have food in my teeth or a flyaway hair.

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It’s not a permanent solution. It’s unsettling, really, how forcefully all my old insecurities resurface, and how many new insecurities surface, when I catch sight of myself in a mirror that refuses to flatter me. 

During a work trip last month, I became a bit obsessed with my ever-loosening neck wattle and discovered a deep wrinkle etched into my forehead that I’d never noticed before. One Airbnb bathroom had so many mirrors that I could see each sagging portion of my body reflected into infinity. It was terrifying. Mirrors like these have even sent me spiraling down Google rabbit-holes, researching creams and chemicals and noninvasive surgery options.

Then I am seized by shame because here I am, playing into it all. This stupid, pointless, expensive, time-consuming war against inevitable bodily changes, this fear of becoming invisible and irrelevant, this refusal to let go of being pretty, and the social validation that comes with it.

Oh, how I wish we could all hold onto the blasé self-assurance embodied in India Aire’s Video song:

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Sometimes I shave my legs, and sometimes I don’t
Sometimes I comb my hai,r and sometimes I won’t
Depend on how the wind blows I might even paint my toes
It really just depends on whatever feels good in my soul

Unfortunately, a lifetime of patriarchal conditioning and capitalist exploitation makes it hard for most of us to know what really feels good in our souls. In a culture that flagrantly promotes unhealthy beauty standards for women, particularly women who have the audacity to age, is it any surprise that even the most confident among us will gaze into a too-bright, too-big, ill-positioned mirror and not feel enthusiastic about every angle of ourselves?

My cats, I’ve noticed, have no use for mirrors. By the way they preen and parade around, I can only deduce that they always think they look like hot stuff — and nothing, or no one, ever challenges them. Lucky jerks.

As for myself, I can only try my best to distinguish what I’m doing for fun from what I’m doing out of fear or insecurity. And I can also give myself some grace for my insecurities. 

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I don’t want to become consumed by them, but the fact that I have them doesn’t mean I’m a “bad feminist.” It simply means that I’m not a feline. That, for better or for worse, I’m a human who exists in a social context and carries the baggage that comes with it.

RELATED: All I Care About Is Being Pretty

Kerala Goodkin is an award-winning writer and co-owner of a worker-owned marketing agency. Her weekly stories are dedicated to interrupting notions of what it means to be a mother, woman, worker, and wife. She writes on Medium and has recently launched a Substack publication, Mom, Interrupted.

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