“Jen, sometimes I think you’re not pretty enough for me,” were words Jennifer Tress’ ex-husband actually said to her during a fight.  That’s partly why he is now an “ex.”  The words are pretty shocking, not to mention the last thing you would expect your husband to say.

Tress, who is a strategic planning consultant in Washington D.C. during the day, is a competitive storyteller by night.  This, unfortunately, is not fiction.  It turned out her husband was having an affair with an intern at his office.  To be totally cliché, she was blonde and had large, let’s say, bosoms.  This was a typical, yet devastating, turn of events.

Pretty woman looking in mirror

Not pretty enough? Too many women ask that question every day.
Image: Shutterstock

It made Tress stop and ask herself if maybe she really wasn’t pretty enough.  She had never thought of herself as someone with low self-esteem.  Yet, the words cut her to her core.  It became a defining moment in her life.

Later on, when she would meet people at the storytelling events she attends, they would say, “You’re the ‘not pretty enough’ girl, right?”  Now, let’s be clear.  Jennifer Tress is drop-dead gorgeous.  She has large brown eyes and shiny, ebony hair.  Her smile could be an advertisement for a dentist’s office it’s so perfect.  Nothing about her makes you stop and think she’s anything less than beautiful.

So, why do those kinds of words still hurt so much? She decided to start a group for women to talk about self-esteem issues.  She had found a lot of women Googling the phrase, “Am I pretty enough?”  There were literally thousands every month.

Tress wondered why these women were asking the online community.  “At first I thought, why are you asking the internet? It’s like asking a Magic 8 Ball! But that sparked something in me,” she said.

She wanted women to get out of that space where that was the question they were asking themselves.  What about your intelligence, skills, talent, enthusiasm, passion or creativity?  Weren’t those more important than looks?

One of Tress’s favorite stories came from a girl who would always un-tag herself in pictures because she thought she looked fat.  However, eventually she asked herself if she looked any different on Facebook than in person.  Of course, the answer was no.  She said, “People know what I look like and they like me anyway.”  She stopped un-tagging herself.

Tress is now on a tour of college campuses talking to groups of people about the issue.  In an interview with Marie Claire, Tress said, “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.”