My Last Date...as A Man

 

Long Dark Haired Wig Look
From the Jessie Hart 
Archives.

In many ways this was the final straw in my attempt to live in a male world. Approximately two years following the passing of my wife, I had the opportunity to date the Mother of one of my servers. She was smart, single ( near my age ) and very attractive. If I was a "real" man, she was the ideal woman I had ever wanted. As always, I realized nothing had really changed with my gender issues when it came to dating other women. Still I went ahead and tried and succeeded on setting up a few dates.

Along the way, we went on dates to places such as the Frank Lloyd Wright designed home in Springfield, Ohio all the way to a company sponsored suite at a Cincinnati Reds professional baseball game. Seemingly we were moving along at an reasonable rate until she sprung the question on me which probably ended it all. She asked me what my deceased wife would say about the situation I was in life without her.  I fired off the answer I drove her to an early grave without thinking of the consequences. Even though essentially I told the truth, I didn't immediately realize my future days with her were numbered. Obviously I decided not to mention any of my gender issues as probably added to the extreme stress of my wife's life.  

Through it all, my daughter had monitored my return to the dating field with some interest and at that time I hadn't come out to her as a transgender woman yet. As a gift she gave me two tickets to the late Joe Cocker who was performing at a nearby outdoor venue. I immediately took the opportunity to invite my new friend to join me. Initially she said yes and I thought all was good. Then about three or four days later she abruptly called me and said she wanted to end all dealings with me. I was shocked and said goodbye forever. Then I had to decide who I would invite to go with me to the concert.. Fairly quickly i decided I only knew one other woman well enough to invite and that was me. It was a great opportunity to judge how well I could present in a totally different situation. 

First I had to come up with a proper wardrobe choice which would blend in with a probable slightly upscale audience. For the evening I chose my black slinky wide legged slacks along with a black sleeveless top. The outfit was one of the benefits of having nearly hairless arms. By this time, I had arrived at a point where I didn't have to worry anymore what people may think of me for having hairless arms when I was still presenting as a man. For the evening I selected my long black straight haired wig to go with comfortable flats and sensible makeup to fit in. 

To my knowledge, all went well during the concert. Nobody gave me an extra glance and I was able to enjoy a cocktail as well as the concert. I ended up being one of the better dates I had ever had. A fitting end to my often discouraging history of my dating as a man. Something it turned out I never wanted to do anyway.  

When I transitioned to a transgender woman and was dating women such as my future wife Liz, I relaxed and was finally able to enjoy a new and wonderful life. The entire process was similar to everything else I had discovered about myself. Living a gender lie was never easy or successful, My last date as a man just proved it again.