Bad With Men: Am I Pretty Enough?

Dana Norris is the founder of Story Club and she once went on 71 internet dates.

I go on two dates in two weeks. I meet both men via Both have vaguely amusing profiles and are smiling in their pictures, which is harder to find than you’d think. I meet them both at the Bad Dog Tavern, a restaurant near where I live. In both cases they’re already sitting when I arrive. I approach, they stand, I smile warmly, and they hug me hello, but their faces register nothing but cool detachment. Why don’t they smile?

I sit, we start talking and I work to find something that we have in common. Eventually the conversation gets easier—they laugh at my jokes, I laugh at their jokes, we agree to forge ahead through drinks and order dinner. At the end of the evening they hug me goodbye. I’m willing to go out with them again, but they do not email. They do not call. They do not want to see me again. 

I try not to take it personally. People have lots of reasons for not wanting to go out with other people. I tell myself I can never know what they’re thinking. But part of me thinks I know for sure why they don’t want to see me again. Part of me thinks it’s because I’m not pretty enough.

This pervasive, destructive thought occurs to every single woman. The voice that speaks this thought is thin and shrill and it tells us that men are superficial and only care about whether or not we present a perfect package at first glance. The voice tells us that pretty women have easy lives and since our lives are a little bit difficult we must not be pretty enough. And this voice is not alone. It’s echoed by the constant, quiet chant of TV commercials, reality shows, women’s magazines, and morning radio DJs, all of whom seem to agree that we all definitely need to work at being prettier. So we wonder: Should I whiten my teeth? Stop eating carbs? Wear lip gloss? 

Dating makes me feel like I’m 15 years old again, living every day with the fearful hope that someone somewhere will notice me and step out of the crowd and tell me, finally, that I am pretty, I have value, it’s all going to be OK. But that keeps on not happening. Instead I receive indifference, which I turn on myself. No one is picking me so I must not be pretty enough.   

But: No. This can’t be the way the world actually works. The idea that men will only like you if you’re the prettiest is the opinion of an adolescent mind, frantically trying to make sense of the chaos of the world. And this theory breaks down before logic because empirical prettiness does not exist.

Take the most beautiful woman you can think of—for me, Megan Fox—and show her picture to 10 people and at least one person will be like, “Nah.” There is no such thing as being attractive to everyone. We like to pretend that dating is a meritocracy and if you’re “pretty” or “smart” or “good” enough every man that you go out with will fall to his knees and immediately beg you to change your relationship status on Facebook. But that’s not how it works for anyone.

Even more, this fantasy is insulting to both women and men. It pretends that men are only looking for female decoration and women are only looking to be the best decoration they can be. But no one is awarded love based on how closely they hew to the image of an Abercrombie & Fitch model. Besides, half of those models are single and there are several hundreds of thousands people currently in happy relationships who would never find catalog work. 

We pretend that attraction is determined solely by our outward physical appearances: We pretend that it’s extrinsic, obvious, when really it’s intrinsic, mysterious. It’s the way your stomach feels when you accidentally make eye contact, the smell they leave on your skin after you touch, the way the dopamine splashes over your receptors when they smile at you. It’s subtle and chemical and so much deeper than a single, evaluatory glance. 

So why do I still worry that I’m not pretty enough?

Because it’s a seductively simple answer to an incredibly complex question. If the answer to “why don’t they call me?” is “you’re not pretty enough” then I can do something about it, the situation is within my control. A little severe calorie restriction here, some light cosmetic surgery there and *poof* I’ll be happy forever. But, like most easy answers, this one is false. I am single because I am and I need to work on becoming comfortable with that. I need to stop hoping that each date will be the one that rescues me from my singleness. I need to find a way to feel comfortable even while strange men decide whether or not they want to see me again.

And I’m working on it. 

Dana Norris is the founder and host of Story Club, a monthly show for stories in Chicago. She has been published in Tampa Review, McSweeney’s Internet Tendency, and The Rumpus. She is currently pursuing her MFA in Creative Nonfiction from Northwestern University. She performs around Chicago you may find a list of upcoming shows at

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