The Real Struggle Behind Trans Dating

Couple toasting with wine in cafe
Couple toasting with wine in cafe

Dating can be fun for everyone. But we all know it's not easy. The possibility of rejection or lack of chemistry is enough to make anyone reconsider going on date period. If you're a transwoman, things can become a little more complicated.

Not only are you faced with the same possibility of sexual objectification from men through dating that cisgender women face, but there is this extra layer of garbage you have to get past. 

I think one of the first "layers" if you will, is weeding out the men who are what I call "closeted chasers." Pretty self explanatory.

They are men who only use trans women for sex and keep it a secret from their friends and family. They are the men who always ask to go to your place, and if they do invite you over its usually late at night and they want you in and out like you were never there. Completely dehumanizing.

Cisgender women typically don't have to worry about being hidden unless they are having a relationship with a married man.

But those closeted chasers are a lot different from the typical chaser. Most chasers I've known are pretty open with their friends and family about being transamorous.

"Cisgender women typically don't have to worry about being hidden unless they are having a relationship with a married man."

One man who I knew was a tv editor and was open about his interests not only with his friends and family, but also everyone at his place of employment! 

I found this to be especially strange. While I'm all about being open and honest, your place of employment really doesn't seem like the appropriate setting to share your sex life. Then again, this is Los Angeles and he did work in television.

He and I had our first (and last) meetup at a local coffee shop to get caffeinated and talk. Starting off, everything was going well. He told me how he's only dated transwomen his entire life and within the last 10 years became very open about his love for them. I immediately became interested once learning his attraction was exclusively to transwomen. 

He was "painting the picture" really well. He then went on to say his longest relationship with a transwoman was a year -- off and on. He's 40 years old. That was the first red flag. 

The second (and most offensive) red flag was waived in my face shortly after I ordered my second double shot of espresso (sweetened) and sat down at the table, when he decided to take the liberty to ask me about surgeries. Hmm... 40  years old, his longest relationship wasn't even a solid year, and he's asking me personal questions pertaining to my physical appearance? I was done.

I'd crossed paths with a chaser who was trying to paint a different picture about who he was and he didn't do a very good job of it. But this goes back to these layers I keep referring to.

This guy was open and comfortable enough with who he is as a man to have me around his friends and colleagues, BUT he was also going to objectify me if given the chance. You get one you lose one.

I now make a habit of asking every guy that sends me a message questions, like "So how long have you been dating transwomen?" or "Are you open about the fact you like to date transwomen? or is this something you keep to yourself?" so that I find out sooner than later who these guys are and don't waste my time meeting the type of men I'm not looking for.

"I now make a habit of asking every guy that sends me a message questions, like 'So how long have you been dating transwomen?' or 'Are you open about the fact you like to date transwomen?'"

I had one guy reply to my question once saying something along the lines of, "Well, some people know and some don't. I don't openly talk about it because it just never really comes up in conversation." 

And it was this response which revealed to me he was living the "don't ask don't tell" life of dating transwomen. Even our own military repealed that way of thinking! I had to cut him off. Fast.

In addition to having to do all this digging, there are additional hoops to jump through. There's the question of whether you as a transwoman are "passable" or not. In my opinion, there is no such thing as passing. It's just how people see you on that particular day.

Despite all the technology and surgeries available these days, I can always tell a transwoman from a cisgender woman. So I know there are many others that can identify trans from cis as well. When I walk out the door I always assume people know I'm trans.

It's not so much about passing as it is being sexy or attractive. Because passable or not, sexiness is something that always sits very well with men. Especially men who may be potential dating material.

"It's not so much about passing as it is being sexy or attractive.'"

I'm not saying that a transwoman has to be sexy to find a decent guy, but it definitely makes it a lot easier and a lot more difficult all at the same time.

There is so much emphasis placed on our appearance by ourselves, and by others. And all of these physical factors are taken into consideration by men we are dating too. It's just the way it is.

The moment men can become more comfortable with their attraction to transwomen will be the time when dating becomes easier for us.

I think many men would openly date a transwoman if they had more courage, or if our society was different.

Some men probably feel that sex is the closest they can get to a transwoman without enduring too much judgement, because he can always disown his actions by saying it was "experimental" or " a mistake". Even some celebrities have used these same justifications.

But to openly be in a committed relationship with a transwoman requires a conscious effort and much more accountability, making it more difficult to create excuses. And that's not something men, or our society is comfortable with yet.


This post is part of HuffPost's Journey Beyond the Binary blog series, an editorial effort to bring diverse trans and gender non-conforming voices to the HuffPost Blog during and after Pride month. As the LGBTQIA community celebrates great strides forward this June, it's important to acknowledge the struggles still pertinent to trans and gender variant members of the community. Please email any pitches to