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From 9 to 5, Jennifer Tress is a strategic planning consultant for the federal government in Washington, D.C. in her off-hours, she's a competitive storyteller who has gained a following for her wry, self-deprecating wit. A book of her stories, You're Not Pretty Enough (Createspace), is being published this month. But Tress never dreamed her most famous tale—the one that inspired the book's title—would go viral, kick-starting a campaign that's changing how women see themselves.

Marie Claire: So tell us where "You're not pretty enough" came from.
Jennifer Tress: It was something my ex-husband said to me during a fight. 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.

MC: How did you take back that hurtful comment?
JT: In 2010, 13 years after my divorce, I started getting into the live storytelling scene in D.C. I thought about the stories I wanted to tell, the defining moments in my life, and that was a big one. This is a story people really connected with. They would see me and say, "You're the 'not pretty enough' girl, right?" Then when I went to create a website to publish my stories, I chose yourenotprettyenough.com, thinking it would be a funny joke for people who knew that story.

MC: And what happened once you launched your website?
JT: Because I had set up analytics, I could see how people found me online. And 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.

MC: What did you do?
JT: I decided to turn the site into a support and discussion group for women on self-esteem issues. I wanted it to be a conversation about empowerment: Let's talk about how to get out of that space where you start questioning whether you're pretty enough. I conducted surveys and videotaped women's responses. I asked questions such as, "When was the last time you didn't feel pretty enough?" Most came back saying, "Literally 30 seconds ago, or at least today." And I asked people, "Specifically, what do you do to get out of feeling that way?" One of my favorite stories came from a woman who talked about how she always used to untag herself in Facebook photos because she thought she looked overweight. She said, "I had to ask myself: Do I look different in person than I do on Facebook? No, I don't. People know what I look like and they like me anyway." I think it's especially important to spread messages like that to young women. This fall, I head off on a tour of college campuses that will continue through spring 2014.

MC: What has this experience taught you about women and self-esteem? Is the problem getting better or worse?
JT: I think it's getting better. And the more we see a variety of people represented and accepted in pop culture—think Lena Dunham—and in our daily lives, and the more we talk about what that means and how we feel about it, that's when change happens. @jdtress

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