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  • Rebeckah Loveday

Dating as a Transgender Woman

Updated: Jul 22, 2019

Dating can be a difficult, challenging and exhausting experience for anyone at the best of times. With dating apps at our fingertips and in the palm of our hands, communication and connecting with potential partners or lovers is easier than ever, right?


We all want to meet that special someone who will love us passionately and unconditionally and accept us just as we are (flaws and all). We want and need to share ourselves with others but for some there is always an extra level of acceptance that is required from a partner and more importantly deserved when sharing who we are with someone special.


For a lot of transgender people, dating can be a nightmare. Especially for those that are attracted to cisgender and heterosexual, predominately male counterparts. For a lot of transgender women that are attracted to heterosexual men and wanting to be romantically connected with these men, dating can be an intimidating, confronting and at times a deadly experience.


When I first went through my transition and started to feel comfortable as the woman that I am, I gained a lot of attention from men. Some of these men I was attracted to in turn, but at this stage of my life (despite being tall, blonde and feminine), being a pre-operative transgender woman and dating or being romantically connected to a red-blooded straight man was a potentially dangerous game. I would often flirt, occasionally swap numbers or even share a kiss but I knew deep down that these encounters would go no further, mostly out of fear for my own safety.


It took one encounter, with a stranger on a plane followed by a rendezvous in Alice Springs that confirmed my decision to undergo gender affirming surgery. In my mind, this was my only choice if I was to be accepted as a “Woman” by the men I was attracted to and wanting in my life. Young and naïve, I chased this dream which lead to having gender affirming surgery at age 24.


Post-surgery, I thought to myself “great! now I don’t have to tell anyone that I am transgender, and I can convince the men I date as well as myself that I am just like every other woman”. End of! I lived this way for many years and often questioned why the relationships I endeavoured never prevailed.


After many failed dating attempts and relationships, reality set in. When I met someone I really liked, I would often internally ask myself and then my friends “when should I tell him? What should I tell him? Do I have to tell him?”. A lot of the times I would just break up with the guy to save myself from the inevitable unacceptance and heartbreak I knew would be on the horizon once I outed myself. This was an incredibly sad, self-damaging and exhausting way to live.


I battled a lot of internalised transphobia towards myself throughout these year's which lead to getting myself into promiscuous, risky and dangerous situations. Internally and for a moment in time, I felt as though the encounters I had with these men, were validating me as the woman I thought I wanted to be. I found my way of validating myself as a woman, was to place myself into sexual situations with men that I knew didn’t care about me and were only using me for my body.


Throughout theses early years, I met a handful of openminded men who I felt comfortable enough to sporadically share my story with and were willing to continue dating me despite knowing I was transgender. Each of these situations had their own risk and reward and it was often at my expense. Whether that be dating a drug dealer, sex addict or someone that was unfaithful. There was the occasional good egg but unfortunately in these cases the chemistry or attraction just wasn’t there. Other’s I told did not react as acceptingly, leaving me with a fat lip and bruised self-esteem.


As the years went on and I matured, I became more comfortable in my skin. I set myself some dating rules. If there was a guy I wanted to date, I would get to know him and if I liked him and felt that he liked me, I would share my story with him prior to intimacy. This method worked at times but occasionally after a few dates and a few glasses of wine, I would break my own rules and be back at square one.


The reason I tried my best to use this method of dating as a transgender woman was for three reasons;


1) For my own safety – physically, mentally and emotionally


2) Out of respect for the men I was dating to allow them to make an informed choice if they wanted to continue dating me without feeling as though they had been “cheated” or “tricked”into bed


3) Knowing that if I met someone I liked they still needed to earn my trust and respect in order for me to want to share my truth with them


The third and most important point is what stuck with me in many of my approaches with relationships over the past several years. This is not only with romantic relationships but friendships and professional relationships as well.


As a transgender person you only need to share as much of your story as you feel comfortable sharing and with whom you feel most comfortable sharing that information with. You do not owe anyone anything unless they earn your trust and respect first. Only then should you feel any need to want to share this part of yourself with another person and always know that your own self-respect is worth so much more than a free meal and a date with someone who doesn’t care about you.


When it comes to sexual relationships and one-night stands, the rules can be a little different. If you are quite open about your gender identity and want to share this information about yourself upon initial contact with people, then be proud to do so ensuring your inviolability first. But for those just wanting to have some fun with someone that you are attracted to and they are attracted to you, then you are free to do so without feeling guilted into laying all your cards on the table at the expense of your own personal safety and well-being.


These rules of thumb would differ based off personal circumstances of course but the one rule that works in any case of dating or relationships for anyone is that you don’t need to feel obligated to share any part of yourself (physically or otherwise) with anyone else unless they earn your time, trust and respect.


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