Searching for mister right – Dating cis men as a trans woman

By Alejandra Ortiz

Couple weeks ago I spent a weekend in a picturesque fishing village right outside Amsterdam. I went there invited by Bas, a 40/something year old Dutch guy whom I met via a dating app. I’ve been talking to him for about six months now and in between lockdowns we met for lunch in the city. I went to see him for the New Year and now this time again. Bas has been inviting me to come since we met; yet, it wasn’t till December when I felt I could trust him enough to be more intimate with him. I mean, I am no prude but fast hook-ups aint my thing. I want love and a long lasting romance with someone I can also connect on an intellectual level. Bas is certainly a match, he turned out to be not just an amazing host and a wonderful cook but also a caring lover seeking to provide me with as much pleasure as I could get. Ever since our first and second encounter I have not been able to get the memories of him off my mind. We‘ve been messaging back and forth but it seems that while he enjoyed our time together, he doesn’t see himself in a relationship right now. Well, he may not be ready to be someone’s steady lover, but I am.

Thinking of this Bas experience got me to reflect on my dating history. As a 38 year old trans woman, who is attracted to cis males, and who has been through many phases of identity (pre and post hormones, pre-op, post-op, stealth, you name it), I have plenty to tell about dating. Meeting men has been an up and down of the happiest, most exciting and, at times, the most challenging I can recall.

When I came to The Netherlands in 2015 I started meeting men right away. First it was Danny, a really cute German student 10 years younger. I met him while looking at old paintings in the Rijksmuseum. Although short lived, our two-week affair was full of passion and love for adventure. It was he who first introduced me to Amsterdam, while taking me on the back of his bike around the canals. Then there was Altin, a guy from Albania who talked and walked like Tony Montana from Scarface and who made me feel the most special girl in the world with his love and affection. Lastly, I dated a horny Iraqi man who had left me a bad case of PTSD, he should remain nameless. I really thought and hoped he was the one but after two years together things ended up the worst way possible. After him I was so broken, I decided to forfeit men altogether.

But being the optimist woman I am, I decided to give love yet another chance. Thus, last year I made up my mind to start dating again in the hopes that my mister right would come along. Thus, I opened profiles on several dating sites such as Tinder, OkCupid and Badoo, with mixed results. From getting ignored once I disclosed my trans status, to the usual dick pics, to men only interested if I had a dick, or if I was open to secret meetings, to going out to the movies, meeting at a cafe or going on a boat tour in the canals. As a -dare to say- cis passable trans woman, dating has not been a major issue for me. Finding a reliable man who is also looking for a long-term relationship, that has been the problem. But if you ask me why this is, well, I wish I knew the answer.

On my search for the optimal site in which to find my mister right, I stumbled upon MyTransgenderCupid. Although the title seems to aim at those looking for a transgender woman as a dating partner and not the other way around, the site does offer a platform for transgender women who are on the (heterosexual) love path. For trans women subscription to the site is free…. Men have to pay. This may come across as courteous to trans women but at the same time it underlines inequality between the two parties. 

I’ve been on it for the past week and so far I haven’t had any luck. Several guys liked my profile but they either live in the USA, Northern Europe or Asia. When I use the search tool to look for men in The Netherlands very few options appear and in a quarter of the profiles there are no visible pictures. Which in turn gives me a bad déjà vu of men seeking to keep things secret. Then there are all those questions about my body, height and even about the status of my genitalia. Honestly, I feel it’s very intrusive to ask that, because in dating sites for cis people you never see questions about the status of ones vagina or penis. I will continue keeping my profile open for a bit but I am skeptical about how feasible it will be for me to meet a guy to connect with in real life.

In my quest to know more about this site, I contacted MyTransgenderCupid founder Stefan de Jong, and asked him the following questions:

Why was this site founded?

The story behind MyTransgenderCupid has kind of a sad touch attached to it. It was on my trip to The Philippines back in 2014 where I noticed a lot of transgender women and the difficulties they face in society. There is general tolerance for trans women in some countries, but they are not wholly accepted. And still today, a majority of the people still hold intolerant views toward transgender persons. This is also reflected in the dating sites that exist for transgender people. There are plenty of dating sites for trans people, but sites that are genuine and portray trans people in a respectable way and not as objects are unfortunately very scarce. So the idea was born to create a decent dating site for trans women that is strictly focused on creating a long term relationship and promote them in a decent manner.

It started with MyLadyboyCupid that opened its doors back in 2014. While the term ‘ladyboy’ as reference to trans women is very common and widely accepted in the Asian world (mainly in Thailand and the Philippines), in the western world it is often associated with sex and porn. That is why in 2015 we opened the doors of MyTransgenderCupid.com.

How are trans women involved in this project?

At the start there were no trans people involved, but during the progress and growth of the website we are now working with a team of three persons, a trans woman from The Philippines who helps us to maintain the website, doing social media promotion and handles our customer support, A trans woman from Thailand we hire regularly to write articles for our blogs and for website translations.

What makes this site different?

We stand out in the crowd as being a dating site that has as main goal to help trans women find a real relationship and create a website where they are accepted and appreciated. When creating the site, we did not want to create yet another website for sexual fantasies or the so called ‘tranny chasers’ who fetishize trans persons. We believe that we created the best decent dating experience for transgender women and trans oriented men.

How successful is dating through this site?

We don’t have hard numbers of success stories, in general there are not a lot of people who shares them. But we did receive a fair amount of success stories, on our website myladyboycupid we have enlisted a few of them.

Are only cis men allowed to register as dating partners for trans women or are trans men also welcome?

In the nearest future we have plans to expand our gender selection, but as it is for now we mainly focus on trans woman <-> man dating. But of course, trans men are also more than welcome!

Now that my questions have been answered, I am still not convinced that I will find my mister right here. Still on my quest to find the right dating site for me, I cannot help but think and feel that perhaps the ideal dating site for trans women like me is yet to be created.

I am curious to know how similar or different the experiences for other trans women reading this have been. What have been the ups and downs of dating as trans women? Are you on this site? If yes, what has been your experience so far? Do you think these kinds of sites are helpful for trans persons? What about those who are more open to or have experiences outside the binaries? I am curious to read your stories. Please leave a comment below or contact us via info@transmagazine.nl.

Disclaimer, this is the opinion of a hetero post-op trans woman of colour, with many intersections behind me and who only dates cis men. I by no means want to say that my experience is or represents the general voice of the trans community. All names have been changed to protect the identities of the subjects.

Author Alejandra Ortiz is one of our freelance writers. She applies the experiences she gained as a trans woman of Mexican origin on a daily basis, when standing up for bicultural trans-migrants and refugees in The Netherlands.