Dating as a Trans Man - Real Talk

Last Updated 26.11.2022
12 min read

Reggie is a fully transitioned trans guy. This has been a long process because his hormone treatment and eventual surgery were not covered by health insurance - he was on his own to save and borrow for what he knew was the right thing for him.

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"For a long time, I just told people I was asexual. It was easier, and no one questioned why I didn't pursue dating. Once I was fully male with my own identity, I was ready to date - straight women, trans women, and even bisexual women. You could say I'm an equal opportunity dater, as long as the genitals are female."

"But dating has opened a whole set of new issues for me. I'm not an experienced dater and getting into that world is really hard. I am shy and can't bring myself to ask a woman for a date. I did one time. But my first time with transgender status as fully transitioned was a disaster. Friends tell me it will get easier once I am 'out there' in social situations. In the meantime, I have joined and am getting much more comfortable at least chatting with women online. Hopefully, this will carry over into the real world for me and I'll have my second in-person date soon."

Reggie is Not Alone

Meet Jules! "Being born female was a big mistake. I knew early on I should have been born male. And then I grew up around only cis people. My parents were clearly in denial and thought that they could "make" me female by insisting that I live a completely feminine life - dresses, Barbie dolls, ballet dancing, recitals, etc. I hated every minute of my childhood. And when boys asked me out on dates, my parents insisted I go.

"Once I could get out of there I did, and I announced to family and friends that I was a trans man. The backlash was pretty bad, but I was determined. I've started hormone therapy and am close to having enough money for surgery. Meanwhile, the rejection and condemnation from my family and many former friends are painful. I have found a great online support group that helps. As for dating? I have been dating trans women who understand my current situation and we have even found ways to have some sexual enjoyment. And I have certainly enjoyed a romp or two with a lesbian or a female bi. But I know that eventually I will be fully transitioned and, as a trans guy, I worry about how and when I reveal my history to partners I am seriously dating. How will a straight woman respond to dating me? I'm going to have to figure out some strategies to test their feelings about these things before I come out to them."

And Here's Sam

"Oh my gosh, where do I begin? I hated being in a woman's body as soon as I reached puberty. I wanted to be a man, began to dress as one, and endured the teasing and wrath of my schoolmates (not to mention the whispers of teachers). Glad I had such support at home and from a few friends. Because of them, I felt no shame going into adulthood. I was lucky. So, I am a confident transgender man entering the dating world. But I am still in a woman's body. How do I date and who will want to date a man without the right genitals? Certainly, no straight women. Maybe a lesbian or a bi? Shit. Parents are helping with the cost of HRT and eventual surgery. Someday, this trans person will have a normal dating life, but I'm impatient as hell right now."

Let's Back UP a Bit

Lottie L'Amour, UK blogger, has an important reminder for us all. "Gender is who you are. Sexual identity is who you do." For everyone in the LGBTQ+ and straight communities, this is the way we must think.

But for trans people, it can sometimes be difficult. They are used to having grown up in the opposite gender identity, coupled with what is often called "genital dysphoria"- a hatred of their own bodies coupled with the knowledge that they really are the opposite gender. And what's more, a large chunk of cis people, many of them in positions to make laws and policies, don't accept non-straight orientations as real and, in fact, humiliate and demonize trans and non-binary people.

Even within the LGBTQ+ itself, there are those who shy away from even being remotely interested in relationships with trans people unless they are "fully transitioned" with a body they define as passable. So, given the stories above and the experiences of other trans men, let's take a look at some of the dating challenges a transgender man may face and some solid strategies to overcome them.

Challenge #1 When to Reveal

The dating pool may be pretty limited if you decide to reveal that you are a transgender man when you first meet someone you want to date. Transphobia is still alive and well in all corners of our society, even though many profess "not them." They may not ever "condemn" a trans person as long as they are not involved with one personally. Revealing on a first date can be disastrous, but it might be a good idea to weed out anyone who is interested in disrespecting you.

Even if you date only online right now, are you revealing that you are a trans male in your profile? Why? The answers every reader has will vary, so do what you are comfortable with.

Meeting this challenge will be an individual thing for transgender men, but the best strategy is to let that date get to know you as a person first. You certainly don't have to have sex on the first date. Take it slow and begin to subtly explore their feelings about trans people while you allow them to get to know you and vice versa. A healthy relationship builds over time. Making it all about sex and your body is not a healthy relationship. That's just a hookup, fully sexual relationships are okay if that is all you want.

Even when you do decide to reveal that you are trans, you need to make a clear distinction between your gender and your sexual identity. Your gender is male and your sexuality is however you identify. Might you experience rejection? Yes, but the idea is you avoid those who will make you feel ashamed of your body, sexuality, and sexual orientation.

Alex, the founder of also has this advice about that all-important reveal: "Timing is a pretty important factor in terms of how this 'I’m trans' piece of information is received. I already talk about this in my previous article, but in addition to that, I would highly suggest NOT telling them when you’re in the middle of making out. Do it in a park or over dinner, ideally with no alcohol involved. But not while you’re horizontal on a sofa, because you’re feeling pressure to take things further."

Challenge #2 Defining and Explaining Yourself and Fielding Questions

Sometimes when you do the reveal, especially with a straight woman who doesn't know much about transgender men and may not even have known a trans person before, you may be met with a look like "deer in the headlights." At this point, you may be peppered with lots of questions that require you to define exactly what being trans means, when you became trans, how you fit into the culture of transgender people, what your genitals look like, how you perform sexually, and on, and on, and on.

Meeting this challenge depends totally on how much detail you are comfortable revealing about your life, your history, where you are in a transition process if at all, how you define what sex is to you, etc. And this may vary with each date, depending on their response to your reveal. You may want to anticipate the questions you might get and how you will respond to them if you decide to. This way, you won't be caught off guard and stumble through your answers. Pretend that any date you have will have little-to-no knowledge of transgender people and formulate your responses based on that.

Above all, NEVER feel that you must answer any questions or give any explanation that you don't feel comfortable with. You have a right to as much privacy as you want. And you deserve as much respect as any other human being.

Challenge #3 Dealing with Misconceptions

This ties in with the challenge above. For example, you might hear something like, "Well, you're just a lesbian, right?" this is usually in response to a reveal that you have not undergone transition, neither HRT nor surgery and still have female genitals. Or, if you have had the surgery and now have male genitals, your date may say, "So, are you gay?" While you find all of this laughable, it isn't to for them to define.

Meeting this challenge will depend on how much time you want to spend providing education to someone you are dating. If you really like the woman, man, or person and are hoping that the relationship will continue, you very well may want to spend time with being trans in general and the validity of this gender. You may also want to tell your personal story so that they understand the challenges you have faced during your life. Add to this an explanation of transition and surgery and the implications of that (e.g., you cannot have children), and other unique genital traits. Explain the difference between a cisgender man and a trans male. you might also want to provide some online resource material if you believe they are really sincere in their quest to understand. It will also be important to explain some of the challenges they might face dating a trans person, so they are prepared to make decisions too.

Challenge #4 Being Defined Primarily by Your Gender Identity

Cis men are never just defined as hetero males. They all have individual personalities, interests, goals, and so forth. So do you. For so many people, your gender status is the key defining character trait, and your personhood takes a back seat to that. Any date who has this type of tunnel vision is not worth your time.

Meeting this challenge should involve not doing a gender reveal early on. You need to take the time to date someone, show interest in their career, their interests, their goals, and such. Don't forget to discuss yours as well. Compatibility at these levels is not just important but it gives them the opportunity to truly know you as a person. Then when your gender is revealed, they will know you as far more than that. If at that point, they can't handle it, then you will both move on. Is the rejection painful? Yes, if you have developed real feelings for them. But the problem is theirs, not yours. You have your dignity intact.

Challenge #5 Being Confined to Your Own Culture

While this is related to challenge #4, it is a bit different. For so much of society, and that even includes many within the LGBTQ+ community, trans are in a separate "world" like no other. For one thing, a transgender man does not have a biological penis as a heterosexual male does. They may also be at various points in their transition. Some may not transition at all and use a strap-on for sex. They may or may not have top surgery. If they have bottom surgery, there are various types, some of which do not provide a penis large enough for sex and some of which keep the internal female reproductive organs intact. All of these things separate trans guys from cisgender men. And all of this variety in looks and performance impacts how others may respond in a dating situation.

Meeting this challenge of dating in this environment will take some thought and preparation. Obviously, you won't explain all of this on your first date, maybe not even on your fifth. But what you can discuss once you do reveal your identity to someone, is the misconception that you are somehow not a "real" guy with male sexuality. You are not confined to any small isolated cultural group. You are a man and a part of that culture. Have that talk. Anyone you date must accept this, or you have no future together.

Challenge #6 - Safety

Anyone in the LGBTQ+ community must consider their safety when dating. Even if your partner accepts you, there may be others within their circle who are not so accepting. In particular, men who engage in toxic masculinity. It is the attitude of a straight man that he must behave in a very masculine way that usually involves aggression, domination (usually of women), and homophobia. He will certainly exhibit aggression toward trans people, and that would include you.

Meeting this challenge will involve, more than anything else, being very aware of your surroundings when you are in social situations. If a straight man begins to speak or act aggressively to you, then you must take precautions so that he does not catch you alone. And explain to your dating partner that you are not comfortable being around this person ever again.

These Six...

Are these the only challenges you may face in dating? Probably not. But they are the major ones. Review them again. Look at how you can meet these issues and take the steps that will make your dating life more successful. Above all, remember this: You are worthy of a great dating, sex, and love life.

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