Jennifer Tress On Men, Memoirs, and One Editor’s Sage Advice

Editor's Note: Jennifer Tress is the author of You’re Not Pretty Enough: Extraordinary Stories from an (Un)ordinary Life, a recollection of enduring -- then ditching -- the man she thought she loved. She realized in a flash that she could do better. Much better. Jennifer joins us to discuss writing her first memoir, and how her editor's armchair psychoanalysis, while first triggering a defensive response, brought about some powerful revelations that helped propel her story forward. 

Publishing a memoir about your life is not for the faint of heart. Especially if you’re not famous, because then who really cares about your life besides your friends and loved ones? That’s good for what, approximately 100 sales and twenty are from your mom? Bring on the mansion!

I had to face this realization when I started writing my essay in memoir collection You’re Not Pretty Enough over five years ago (the book was published back in August). Because the general public didn't have an inherent interest in me, I had to create an interest via the stories I told and how I marketed them. They needed to be compelling and real and honest, and they needed to say something different and fresh.

That takes a lot of writing and rewriting. Determining which stories to tell and how to tell them evolved throughout the process, which included input from others. I got a lot of formal feedback from many sources: writing groups and workshops, live storytelling, hired editors, and eventually, agents and publishers. Ultimately the stories that ended up in the book were those that represented the defining moments of my life so far -- stories that were funny and engaging but also highly relatable, encouraging the reader to reflect.

Reflection could be a theme of the memoir genre, and I had to do a lot of it while writing about my life. I thought it would be easier. Nobody was more an expert on the subject of me than me, right? But it took me a while to untangle myself from the revisionist narrative I had long held, the one that comfortably explained why I was the way I was. It took me a while to own the truth, let alone write about it.

I had some help getting there. Friends and family members who were involved in the stories (even the DJ who helped me meet Jon Bon Jovi) shared their memories, read drafts, and provided comments. That helped ensure the stories were told with as much honesty as collective memory provides.

The most cathartic moment for me came when an outside editor made a comment that Blew. My. Mind. and made me consider things in a way that I never had before. It was regarding a chapter/essay in which I was a 26-year-old who had just gotten a divorce. My ex-husband had an affair and blamed me "not being pretty enough" as the reason. Upon learning the truth about each other, the other woman and I met up, discovered we liked one another and then confronted my ex together one night. A few months later, we were divorced (without ever really talking about how our marriage had gotten to that point), but that’s…another story.

The point is I was angry and seeking validation and working a stressful job with a deep and enveloping drinking culture. A married man I worked with frequently ("Ray") became obsessive and we developed a real dominant/ submissive dynamic (I was the dom). Though our interactions were barely physical, they were wildly inappropriate. In earlier drafts, that plotline stayed in the background to make room for what I felt was the "bigger" story, one about the workplace itself. My editor’s feedback over the phone was blunt:

"Yeah, I’m not really interested in how an advertising agency works," she said. "I watch Mad Men. What I’m interested in, is the relationship you had with that married guy…"

My stomach clenched. Never, ever in all my thinking about that period had I ever considered it a "relationship." I felt shame when I thought about it, but calling it a relationship meant I was an active participant versus a victim of circumstances -- something I had thought for 12 years.

"It wasn't a relationship," I said flatly.

"Oh honey!" she laughed a little. "Yes it was." We remained on the line in silence for several seconds.

"Holy shit," I said, finally. It was so obvious. I felt a little sick about this revelation, but dammit if some puzzle pieces didn't start to come together.

Publishing this book took a lot out of me, but it also gave me a lot. People ask me if I’ll do a follow up memoir and aside from having to live more, I also need that time to reflect. Some of the stories I wanted to include in You’re Not Pretty Enough didn’t make the cut because my parents put the kibosh on them. "You can tell those stories when we’re dead," they say.

I’m hoping I have several more years before that’s true.