You're Not Pretty Enough

The thing about You're Not Pretty Enough, storyteller Jennifer Tress's alternately hilarious and searing memoir, is that it's not really about being pretty. In fact, save for the argument with her then-husband that the book's title comes from—uttered unbelievably (except totally believably) in the midst of discussions about his inattentiveness and infidelity—prettiness doesn't make much of a star turn at all. Yet that's exactly why I found it valuable, because the thing about not feeling pretty enough is's not really about being pretty either. It's about being enough

When Tress launched her website, she'd titled it You're Not Pretty Enough because of that stinging exchange with her then-husband. She soon noticed that search terms that landed people at her site were those of people looking for comfort in the midst of feeling...well, not pretty enough. And so in addition to compiling her personal tales, which showcase the best of what storytelling has to offer, she conceived a mission: Get women talking in a more thoughtful manner about appearance. (Lo and behold, that's exactly the mission I've got here! You see why I'm pleased to feature Tress.) I asked her to expand more on the "enough" part of "you're not pretty enough," and this is what she had to say:

"'Enough' is such a weird qualifier, isn’t it? But it’s one that we use a lot when describing our dissatisfaction with ourselves or with others. Whether it be good enough, smart enough, or pretty enough—it’s all about feeling 'enough.' That we’re whole, we’re valuable. It reminds me of that old skit from Saturday Night Live with (now Senator!) Al Franken as Stuart Smalley: I’m good enough, I’m smart enough, and doggone it…people like me!

Based on the work I’ve done through the You're Not Pretty Enough website, I’ve found that not feeling 'pretty enough' is often the entrée into self-esteem issues because it’s the easiest/laziest way we assess ourselves and others (which is reinforced by media and other cultural standards that we compare ourselves to). On the positive side, I also believe that beauty matters very little to most people, and to some, beauty doesn’t matter one bit. The key is for beauty to matter very little to ourselves. I want to share with you a message someone posted on the Facebook page that demonstrates this point. She says:

One statement you said has changed me. You said, "...It's the easiest and laziest way we assess ourselves." I had never thought about it this way before. I got up every morning to scrutinize my physical self. My state of mind would depend on how good I felt I looked. I'd obsess about it all day. And ultimately felt I didn't measure up, therefore I was unlovable. I was getting sick of myself. I started to walk by the mirror without looking. Then I watched the ABC story online. [Jennifer appeared on Good Morning America to talk about the "not enough" syndrome.] Never for a minute had I stopped to think to assess the things that make me, me. It does take time and effort to assess myself for other qualities and to become a better person. It's so simple. I wasn't ready, I guess. Or I was just being lazy. The next day after this mind-blowing revelation, I looked in the mirror. I saw me and I actually loved what I saw. I had been faking it for so long. I was brought to tears. Yesterday, the quality I reminded myself of is that I'm kind. Today, it's that I'm smart. In time and with some effort, from now on I will always love what I see in the mirror.

Coming back to my own experience, I don’t think my ex was saying I wasn’t pretty, he was saying I wasn’t pretty enough. And the problem with that is I took that word 'enough' and ran with it: enough for who? For him? For society? It was the first time I really considered whether I was pretty “enough” and luckily—by simply focusing on things I like (reading, connecting with people who cared about me, doing a good job at the things I invested my time in like work, etc.)—I was able come out the other side and know: I’m more than enough.
Below is an excerpt from You're Not Pretty Enough (also available on Kindle and other outlets), and Tress is offering a signed copy to two readers. To enter, answer the same question I asked Jennifer in the comments by September 25 at 11:59 p.m.  EST, and we'll select two winners: What does the phrase "not pretty enough"—as opposed to "not pretty"—mean to you?

*     *     *     *     *

The background: When I was 16, I fell head over heels in love with Jon Bon Jovi based on seeing the “Shot Through The Heart” video. I didn’t know who this guy was, but I needed to find him and meet him because I was sure once we were face to face he’d feel the same way about me. As luck would have it, a huge radio station out of Cleveland, Ohio moved its broadcast operations to my small hometown and on a dare I went there one night to meet the DJ on hand and plant some serious seeds to get me closer to Jon. It worked. One day the DJ contacted me and offered to take me to the concert in a limo (with some contest winners) to meet the band back stage. I had 8 weeks to prepare…

Operation “Make Jon fall in love with me” included the following steps:


  • Lose seven pounds to get to 125
  • Find the perfect outfit
  • Identify all the different scenarios that could occur
  • Determine and practice a response to all scenarios identified


Step one would be easy: skip the cafeteria pizza and do some of my mom’s Jane Fonda tapes. Step two required an inventory of my closet. Nothing outfit-wise struck me as just right, but I did have a white leather jacket that fit me perfectly and a pair of low, but sexy white pumps. I just needed a dress. A trip to the mall would fix that, and I found a light pink sleeveless number that went down to my knees and hugged my curves. Done.

For the last two steps, I would need to imagine all the possible ways Jon would act. For instance, if he was cocky, I imagined myself saying, “Think of all the fans who support you. You would be nothing without us. NOTHING!”  I couldn’t really imagine him being anything but lovely, but one had to prepare. I practiced my responses in the mirror until I felt I was ready.

And then the day came.

I got dressed, teased my long, permed, and frosted hair to the sky, and stepped out to enter the limo as an eighties goddess. The contest winners were two female friends in their twenties who were as psyched as I was, and we were accompanied by Cat and another DJ, Rick Michaels. The mood was giddy as we jammed out to music on the thirty-minute ride to the Richfield Coliseum on a warm May day.

Several groupies were gathered around the area where the band buses and VIP guests pulled up. Suddenly, everyone in the limo took notice that from the waist up I looked exactly like Jon, especially with hair, leather jacket, and shades. Cat suggested that I pop out of the moon roof and give the groupies a show.

“You think it’ll work?”

“Try it.”  The girls in the limo egged me on.

“OK…”  I jumped up on the seat so that my top half was showing and raised my hand with my three middle fingers folded down and waved my pinky and thumb in the classic “Rock on!” sign. The groupies went crazy. When the limo parked and I got out—obviously no longer a man, they started shouting, “FUCK YOU!”

Heh, I thought. I’m about to meet my soul mate, so fuck YOU!

We made our way through the melee near backstage—sound guys and wires were crisscrossing us—until we arrived in a large holding room with about fifty other radio station representatives and various guests. I could hardly deal. My skin was crackling with excitement, and I sat with my hands underneath my thighs to keep from biting my nails.

We waited. For over an hour, we waited. I barely spoke to anyone because I was there for me, and I wanted to be inside my head preparing.

Cat, noticing my tension, said, “You know, I don’t want you to be disappointed if it’s just Tico who comes out.”  Now, I loved Bon Jovi for the sum of its parts, and one of those parts was the drummer, Tico Torres. But I had not come this far to just see TICO. No fucking way. As this thought bounced around my head, I became more anxious. But then I looked down the long hallway that led to the holding room, and there was Jon walking toward us. I grabbed my camera.

It sounds cliché, but it really felt like everyone disappeared, and it was just me and him, separated only by a hundred yards. No one had noticed him yet, and I watched him walk toward the room, as if in slow motion, dressed in tight leather pants and a cut-off shirt. He was smaller than I expected—maybe five-eight and thin—and he looked tired. I could feel tears well up, and I pinched myself on the thigh to get it together.

When he entered the room, several handlers marshaled him over to us. Apparently, as the concert sponsors, our group got first dibs. Cat and the others stood up, but I remained seated, frozen, and he stopped right at the base of my chair, shaking their hands, looking down at me, and smiling. He started to tell a funny story that I can no longer remember, and I sat there, mute. All that practice down the drain! Cat, noticing my catatonic state, decided he should step in.

“This is my friend Jen.”

“Hey, Jen,” he said, smiling warmly and extending his hand to the one that was holding the camera. Instead of simply moving the camera from one hand to the other, I dropped it and shook his outstretched hand with my mouth wide open. I didn’t even say hi. He looked at me with an expression that read Am I crazy or does she look like me? and then one of the handlers told us it was time for Jon to move to the other groups, but not before pictures were taken.

“Anyone want me to take a photo with their camera?” asked the female handler, and I momentarily regained my consciousness to hand her mine.

We stood up in a group—the concert winners to his right and me to his left—and I felt him put his arm around my shoulder. I managed to wrap my arm around his waist and willed my molecules to remember his shape so I could replay it later.

The handler took some photos with other peoples’ cameras, and when she got to mine, she said “Honey, it’s not working.”


“Your camera. It’s not working.”

“No, did, um, did you try…”

“Honey, I can’t make it work, sorry,” and then she gave it back and began to corral Jon to move to the next group. I looked at him, trying to think of something brilliant to say to make him stop and realize I was not just his female, mute doppelganger.


Who is who?

“Don’t worry,” he said over his shoulder as he walked away. “The station can get you a picture.”  And then he winked at me and walked on. I sat down on the chair again and watched the other groups as they showed off their gregariousness. Stupid talkers! Stupid me!

Cat patted me on the shoulder in a way that said, “Buck up, kid,” and joined the other DJs. I slumped. When Jon made his way out, that was our cue to leave. Cat escorted me to the place I needed to go to get to my seat, and I turned to hug him. We stayed in touch for about a year, and even though I never got that photo, I’ll always think fondly of him.

When I got to my seat, the opening band was playing—I can’t remember if it was Cinderella or Tesla—and my mom and Margie were there. My mom’s face lit up immediately and then toned down slightly when she saw my face.

“How was it?”

“It’s over. I met him and he didn’t fall in love me!” I howled.

“Oh, honey. Why don’t you just…you know…try and enjoy the show?”

I sat in my seat, disgusted with myself, and cried and cried and cried. I didn’t cry at school, but I cried at home. After a couple weeks, I had to move on.

*   *   *

In the early 2000s, some friends convinced me to go to a Bon Jovi concert for nostalgia’s sake. I demurred at first, but they told me to get over myself and come with them. Just before the band came on at the sold out area, I wondered, What am I doing here? I still like him. He seems like he’s a serious man. He does a lot for charity and is married with kids to his high school sweetheart. He’s hardly ever in the tabloids and has been able to maintain popularity and relevance over the span of nearly thirty years. In fact, I admire him. But really, What am I doing here?

And then the lights went down, a guitar started playing, and he walked out on stage flashing a perfect smile on that beautiful mug.

And I was sixteen again.