'You're Not Pretty Enough': Heartbreak to a Movement

By Maggie Freleng

When Jennifer Tress' husband told her he had an affair because she “wasn’t pretty enough,” the Washington D.C.-based consultant had no idea this heartbreaking insult would become the pillar of a movement.

After writing a humorous (David Sedaris-inspired) book for about five years, Tress started telling her collection of stories publicly. What she discovered from sharing the 15 stories was a universal theme that spoke to other people--the dissolution of a first marriage.

“People really resonated with the ‘you’re not pretty enough emotion,’” she tells VITAMIN W.

So when the time came to pick a website URL, “You’re Not Pretty Enough” stuck. However, what stuck more was what she discovered people were searching when they stumbled on her website, including things such as “how to be pretty when you’re not” and “am I pretty enough.” Tress says these “heartfelt searches” coupled with YouTube videos of girls asking viewers the same questions really spurred her into action.

“People are finding my site because there is a need,” she says. “I thought I could fill that space.”

From there her website turned into an “action center.”

The Movement

Tress traveled the D.C. area working with universities, gender and women’s studies departments, and women’s centers administering hundreds of surveys to find out why so many women and girls think they’re not pretty enough.

“The answers were very surprising and interesting,” she recalls. When she asked the question “when was the last time you felt not pretty enough,” answers ranged anywhere from five minutes to an hour ago.

“The fact that it is on our minds so much was what really surprised me,” she says. “I wanted to start a conversation around this in a meaningful way with the motto ‘it gets better.’”

In honor of this, Tress started a web-series, now a big part of her website, featuring different people talking about their experiences not feeling adequate.

The videos highlight women and men, from different walks of life. Tress is really proud of the fact that her site reaches everyone.

One of her favorite videos is by Lindsey on hating online photos.

“I thought she did a great job examining what was really driving that feeling and coming out on the other side of it.”

Another favorite was by Niyati on how growing up a second-generation of non-white parents can affect how you feel about your self image.

One video she is particularly proud of is “Building a Sisterhood at GMU” where young African American women at George Mason University highlighted how high school girls are affected by stereotypes. They expose these stereotypes and counter them with reality, leaving it for the generation behind them to see.

On her website she encourages everyone to share their stories.

Learning Experiences

After each presentation Tress always makes time for discussion, which she said is crucial to community-building.

“Because [viewers] share their personal stories, they leave there with a different feeling about something,” she says. “There is a real community spirit that builds in the room.”

When Tress speaks she loves seeing the “aha” moment people have, when everything she is saying clicks. Sometimes men or boys in the room come up to her and say they think they have perpetuated some of these body image issues, and they never even considered it until then.

People also frequently ask what to say to a friend who is always self-loathing, seeking a good response that will support the person in need. Tress suggests asking that person what they want you to say.

“Force them to stop and realize what they are doing,” she says.

Even Tress has learned some new things along the way.

“The biggest thing I’ve learned from this is that pretty is the...easiest and laziest way we assess ourselves and others.”

“Some people have learned how to manage that properly, but for others it morphs into ‘im ugly therefore im not worth anything, therefore I’m unlovable.’”

Tress believes we need to stop and learn how to manage these thoughts before they get carried away. For some of us they will never fully go away but we have to learn how to get control.

Some examples she listed are to remind ourselves about the things we do really like about ourselves instead of focusing on the negative. Put on an outfit that makes us feel great, or even some makeup if we want.

But sometimes it may be deeper than a bad hair day.

Others, “have to really work hard to train your brain differently and not evaluate yourself based on your physical self."

“You have to dig deeper and say, ‘who am I really? what are the other characteristics that make me me? I am smart, I am funny, I am passionate, I am a great worker.’ It’s those kinds of things you have to remind yourself of to distract yourself.”

Tress lists these strategies on her website plus many more including “language to use” when we ask ourselves “am I pretty enough?”