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TRANSITIONS: The Dating Life of a Trans Woman Experience

Hello everyone and welcome back to another chapter of Transitions: Enlightened Conversations with our Trans Community. On this chapter we will dive into the exciting dating life as trans.

Needless to say, this is based on my own experience.

Dating as a straight cisgender person is difficult as it is, you add being trans and lesbian, and makes it even harder. When a Cisgender person dates, there are different things that can either make it easier or more difficult to meet people interested in you. Usually you need some sort of catch when you are presenting as a cisgender straight male. I had the looks, a career at the iconic Fontainebleau Miami Beach and I presented myself as a cocky, arrogant male, which for some people was magnetic. They were drawn to me. However, because of how I felt internally, meeting women’s expectations was sometimes difficult. I knew I was in the wrong body and that made it a real challenge. Nevertheless, I continued with my representation and still dated women while trying to convince myself that I had overcome my identity, until finally I accepted my own reality and started my transition.

Everything changed - my appearance was a radical shift into a more feminine form and while it was jarring for some, made me feel at home in my skin for the first time.

Since then, dating became exponentially harder than when I presented as male. First, going through transition, you question your attraction and you try to define it. As my body was more in line with my mind, I was hesitant about whether I was straight, lesbian, bisexual or pansexual, and as the opportunities presented themselves, it became more difficult to figure this out. While I lived in Maine, I quickly realized that men saw me as a taboo and an “opportunity” to experiment. The amount of times I got the “I think you are hot, I’m not gay, but I have always been curious” comment is truly shocking! Beyond unwelcome fetishizing, encounters like that can also turn sinister quite quickly with suffering attacks by those who freak out after being intimate and end up reacting aggressively. That’s when I realized most of their focus towards me was on sex and fulfilling the “curiosity” behind being with a trans woman. Definitely not what I wanted.

Then I attempted dating a trans person but the connection was not there. Then, I met this amazing woman who asked me about my attraction and I expressed that I had not decided yet. She was such an amazing teacher and led the way into being intimate with me and opened my eyes towards being a lesbian, which was a magical experience. She helped me realize what I was looking for.

From that point on, I moved to Miami, and I thought living here would make my dating life easier, I was wrong.

Even though I identified as lesbian, I was still open to dating anyone because I realized the importance of a strong connection regardless of the person’s assigned sex at birth, identity, gender, gender expression, etc. especially after having my Gender Confirming Surgery and knowing that I was in this new life a virgin again. Unfortunately, this just opened the doors for some people to attempt to reach out to me but only asking questions about my genitalia and not really interested in getting to know me. I was lucky to go out on one date with a guy that seemed to be focused on getting to know me. It was a lovely time, however, his idea of a second date needed to include coming to my place and sleeping over. Since I said no, that was quickly the end of that. Never heard from him again.

Even more surprising, I experienced issues attempting to date as a lesbian because unfortunately, some of them literally said to me that they didn’t see me as a woman, which was definitely a push back I was not prepared to experience, but luckily, I met an amazing person with an incredible heart. The experience of dating this person was so unique and special due to the amazing connection we shared and the ability to make me feel how I always wanted to feel in my whole life. This person elevated my standards of dating and made me realized what I wanted and why I’m proud to consider myself a lesbian. We did not last a long time, but it was definitely meaningful to me and something I will always cherish.

I’m currently at a point in which, even though dating hasn’t gotten any easier, I know what I want and what I’m looking for and it’s time to be picky and not settle for just anyone. Yes, dating is hard, but life is amazing, and we only have one so it’s important to live it to the fullest while pushing for what we want in life.

Don’t let yourself get down if things do not seem to be working out, always put your safety, self love and self esteem first, as you are beautiful and deserve to be happy with the right person and rest assure, that person will come. I believe it, and I will continue to be here waiting, after all, our happiness is worth it!

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Disclaimer: Views and opinions expressed in this article are those of the authors and do not necessarily reflect the opinions, beliefs, and policies of the Miami Beach Pride Organization. Content provided by writers and bloggers on this site are not meant to malign, offend or insult any religion, ethnic group, club, organization, company, anyone or anything.


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