Looking for Love


My "Sad Eyes" Photo
from the Jessie
Hart Archives

Perhaps I should say looking for love in all the wrong places. Maybe you remember the country song from the "Urban Cowboy" movie. Sadly due to extreme loneliness many transgender women and trans men experience, we sometimes look for love in all the wrong places. Back a decade or so ago, on line dating was just becoming a thing and due to my extreme loneliness I thought I would give it a try. Due to a lack of finances and overall knowledge I attempted to find dates on three of the free dating sights.  My biggest success turned out to be a real bonanza. 

On one of the sights I had a response when I was on a "woman seeking woman" page. To be clear, I was always up front about being a trans woman which wiped out much if not all of my responses.  Ironically, I had a response from my current wife Liz eleven years ago when she said I had sad eyes in my profile picture. Since she only lived a manageable distance from where I did, we decided to correspond in writing. The "writing" phase of our relationship started eleven years ago and we are still going strong. It took awhile though for me to feel secure enough with my voice to talk to her on the phone but when I survived the test I decided to gather the courage to ask her out on a date. She was a Wiccan lesbian and sad eyes or not I was fascinated,  The first date was a drag show and all went well, even when I followed her into the women's room on our way to the gay bar which was putting on the show. She didn't flinch much and our first date was fun and successful. 

At the same time, I was still frequenting the big sports and social venues where I had become a regular as a single transgender woman. The only problem with all of that was, the usual stigma attached to a single woman drinking by herself in a bar. For the longest time I was unsuccessful in locating any companionship in any way. Outside of a few dates I had with men who actually bothered to show up as they had promised. The brief encounters I had with men were strangely exciting but not to the point I could ever feel comfortable. Especially with the men who seemingly wanted to just wear my panties. As close as I came to really ever getting around to knowing a man I met was the one I ended up meeting briefly at a TGIF Fridays Grille and Bar I was a regular. He was a big sweet heart who drove a classic motorcycle and had just gone through a very messy and brief marriage with a part time exotic dancer he had just met. I was able to lend a sympathetic ear and in a short time we became friendly but not to the point I ever got the chance to ride on his bike before he was transferred out of town for a new job.  As I bid him farewell, little did I know he would be the last man I would be interested in and women were to be my future as I was looking for love or at the least, companionship. 

By pure accident I was able to meet two other women who happened to be lesbians. One was the Mother of a bartender I knew The other indirectly introduced herself one night to me in venue where I was drinking. Together, the three of us formed a bond and we had good times partying.  Topped off by the experience of going to lesbian mixers and being introduced to the culture. It seemed destiny was paying me back for all the recent hard times I had suffered by providing me with a group of friends who provided fun and companionship including one other transgender woman who sometimes joined in and partied with us.

Call it luck or not but somehow I was able to sort through the junk and locate quality friends who helped fill my void of not having any friends. It took awhile and effort but I did find love by looking in all the wrong places. I found good people and to this day I am still married to one of them. 


  1. Sometimes we can be fortunate but also be distracted by searching in desperation and settle just not to be alone. I find at this stage of life that by being authentic we may be alone but at least lead an honest life which possibly attracts the person who loves us for simply bring us.

  2. That should have read "being" us :)


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