Jennifer Tress was inspired to write her new book You're Not Pretty Enough after being told just that by her ex-husband. If it sounds like the stuff that rom-coms are made of, the movie hasn't been optioned just yet, but it's only a matter of time her message is turned into a story of an ugly duckling who is saved from thinking she's hideous by her trusty cat and her beautiful new boyfriend, with a heavy dose of makeover squeezed somewhere in there.

Tress told Marie Claire that she started a website before her book, called You're Not Pretty Enough, based off of this exchange with that former partner:

He had been really distant, so I asked him, "Why are you treating me this way?" And he said, "Jen, sometimes i think you're not pretty enough for me." Eventually, I found out he was having an affair with an intern at his office, this blonde, big-breasted California girl. It made me think for the first time, Wait, was I pretty enough? Even if you have strong self-esteem—which I do—when your spouse says that to you, it's a heart-piercing sort of thing.

At first, the site was just supposed to be for her stories, kind of a joke, but as time went on, she evolved it into a place where women could feel empowered about their looks and share their experiences:

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I realized that so many people — thousands every month — were reaching my site after Googling phrases such as "Am I pretty enough?" It was startling. At first I thought, Why are you asking the Internet? It's like asking a Magic 8 Ball! But that sparked something in me. I wanted to take action.

This is a particularly topical issue, Tress noticed, among young women, and so she's touring college campuses with her book to talk to women about how they feel about how they look. So far, Tress's most captivating argument comes from those somewhat anecdotal conversations she's had with about young college-age women in Washington D.C.; in 2012, she talked to 450 women and found most of them wondered about whether they were pretty enough every day.

The problem that people who grapple with these issues on a daily basis have to confront is that there's no way to define these user-generated terms, because they're based on a vague set of value judgments. What is pretty "enough" or what is good "enough"? The only way to get a good visual, so to speak, is to compare and contrast. Even the Washington Post article about Tress mentions that she's conventionally attractive:

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The book has a retro-looking photograph of her 13-year-old self on the cover, sporting alarmingly bushy eyebrows and a frizzy mullet.

Now 42, Tress regularly has her eyebrows waxed. She has thick, frizz-free brown hair that flows over her shoulders, clear skin and a pleasant smile. She’s, well, pretty.

“I have been 20, even 40 pounds heavier than this. I like to eat. I like to drink,” she offers while setting up for one of her salons last month at George Mason University in Arlington. “When people hear what I’m doing, they say, ‘I don’t know, Jen, you are pretty, so should you do this?’ ” She relates this anecdote with the breezy confidence of a woman who once had a bad spell, has come out of it and is using her newfound confidence to inspire others.

The cover of the book is worth mentioning; the book cover itself appears to be an attempt by Tress to push her readers to look at her when she wasn't considered pretty (or at least when she didn't consider herself that way) and hopefully confront the fact that they're making that judgment at all. As human animals, our first conclusion about a person before they speak is always going to be what they look like. It's when those conclusions are made without consideration or awareness that they're happening that we get into trouble, like looking at art without realizing why we like or think it's beautiful or think it's "enough". Even more to the point, "enough" is such a funny word; one person's enough is another person's nothing, so to consider an aesthetic without considering how alone you might be in having an opinion on it is also living your life in an uneducated manner. The more a person can be educated about what they consider beautiful and why, the more they're able to realize they're making an aesthetic value judgment, and better the chances are that they'll grow out of the idea that someone's face has to be enough of anything.

Pretty Is As Pretty Does [Marie Claire]

‘You’re not pretty enough’: Dealing with ugly self-doubt [WaPo]

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Images via You're Not Pretty Enough