Pleasing Your Parents as a Transgender Woman


Photo from the Jessie Hart

Growing up it was extremely difficult to please my WWII era/Great Depression generation parents. It seemed to me whatever I did well, they always thought I could do it better. I am fond of saying they were long on being great providers but extremely short on providing any sort of emotional support.  As you can guess, or possibly went through, the whole parental process was complicated by gender issues. Especially when a well meaning adult would ask me what I wanted to be when I grew up. Even back then, I knew the true answer and I also knew I couldn't tell anyone. The main thing I wanted to do was to grow into a woman. With the complete lack of outside interaction with anyone who may have felt the same, I felt completely alone in the world. My gender closet was very dark and lonely.

In the meantime, life went on and my parents made it very clear what they expected of me as I grew up.  Short term they expected me to attend some sort of at least a mid level prestigious university and/or college. In no way did they ever let on they knew anything at all about my desire to change my gender. I always thought my Mom just had to know I was exploring with her clothes and makeup but never said anything. Until I finally came out to her after I was honorably discharged from the Army, we never discussed me being a transvestite (as it was called then) and I found I shouldn't have discussed  my needs then.  She only volunteered drastic psychological interference in my life. We never discussed my primary issue again.

As my life progressed, I did my best to seek the approval from my parents as a faux man. I worked hard at my two careers, had a child and even completed my military duty. In the meantime I tried to duplicate my Dad's success in building his own house by restoring an 1860's era house of my own. Through it all, two things sadly happened. The first of which was I never heard the words they were proud of me and secondly my desire to be a woman never went away. In fact, the desire just became stronger the older I became. To make matters worse, the more successful I thought I had become in my parents eyes made my desire to transition to a full time transgender woman  even more complex. I had a successful job and a loving marriage at stake if I attempted any radical changes to my life. The whole process caused me to push many people away from me which resulted in having fewer and fewer close friends.

I seriously doubt if I pleased my parents. I was just stubborn enough or selfish enough in some eyes to please myself.  My parents passed on without ever having an impact on my gender issues, so they became a non factor. I was fortunate in that my most important immediate family accepted the true me and the rest who didn't just didn't matter. Plus I was able to locate a whole new set of friends who again accepted the new me without ever knowing my old male self. 

A part of me wants to think all my parents really wanted for me was to have a happy life. Which is what I hope for my daughter and grandchildren. Perhaps being a part of their so called "greatest generation" precluded me ever achieving my goal of pleasing them. Just like being transgender, the deck of life was stacked against me.  I just had to overcome it.