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  • Writer's pictureHarley Preston

Do’s and Don’ts for Dating Trans Women

A guide to dating a trans woman (according to Harley)

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Since writing “Trans Women and the Cishet Men Who Love Us,” I’ve received many messages from trans-attracted cisgender heterosexual (cishet) men expressing how they have a genuine interest and desire to date a trans woman but simply lack the know-how. I’m not referring to the guys who simply look at us as a fetish but rather those men who truly have a desire to date us romantically. They exist! A lot of the messages I received express how, when they begin a conversation with a trans woman, they feel as though they are vilified and given the title of a “chaser.” I got a sense that they feel as though they are damned if they do and damned if they don’t. Which seemed pretty ironic to me since I had been on the other side of their romantic pursuits in the past. The feeling I was often left with from dating was frustration, until I met my current partner a year ago (who is a cishet man).

There is nothing more that I want to see than fulfilling and genuine relationships for my fellow trans woman, so I thought it wouldn’t hurt to put together some thoughts to help bridge the gap between cishet men and their desired trans partners. Frankly, from my past experience in the dating world, and conversations with my trans sisters, as well as my partner and other trans-attracted cishet men, I couldn’t help but feel like there are a few fundamental missteps that men tend to make when in pursuit of a transgender partner.

First, I should note that no two trans women are the same. Our lives and experiences with gender and sexuality are very nuanced and unique to each. However, I do feel as though there are some general do’s and don'ts that (to me) seem obvious. While I would love to sit here and say it is as simple as “treating her as you would any other woman,” I know first hand that that isn’t the case. Trans women have lived experiences that cisgender women will never have, nevermind being at the intersection of daily prejudice and discrimination. These subtle (and not so subtle) differences lead to very different life experiences that should be respected and acknowledged when pursuing a transgender partner.

Have a genuine interest

The first rule of thumb is the most important in my opinion. When a cishet man “slides into our DMs” if you will, you have to understand that our first objective is discerning whether you like us for us, or simply have some sort of sexual fetish you seek to explore. I’ll also mention that there is no shortage of men in pursuit of us and most of which are coming from a sexual/fetishized place. A cishet man needs to remain respectful if he is to stand out amongst the “chasers.”

Now the difference between being trans-attracted and a chaser is paramount. A chaser is someone who solely seeks trans women for sexual reasons. They are fixated on our anatomy and usually are pretty easy to discern. They’ll typically get through all of two messages before they ask you something about your genitalia. If a conversation becomes sexual too quickly, you’ll immediately be categorized as a chaser and we’ll move on to the next DM. Don’t be that guy, it’s giving creep and I haven’t met a single trans woman that’s into it.

To stand out from these guys, you need to have an interest in us as people. Now I’m not saying “pretend” to have an interest, I mean genuinely have an interest. Instead of asking us about our genitalia, why don’t you strike up a conversation instead. It’s not rocket science and it can be as simple as “what’s your favorite color?” or “what do you do for work?” Or you can quite literally say that you are interested in getting to know us as a person. Have genuine curiosity and you might be surprised at the type of connection that develops because I haven’t met one trans woman that isn’t completely interesting or incredibly self aware.

Do not fixate on our anatomy or our surgeries

Ultimately, the relationship a trans woman has with her body is unique. Like I mentioned previously, no two of us are the same and all of us experience gender dysphoria to varying degrees and for various reasons. What causes dysphoria for us is not universal. For example, some of us have certain words to refer to our anatomy and others prefer certain parts of their body to not be touched or even acknowledged. When it’s appropriate, it’s important to have conversations with your partner before referring to or engaging with us physically. The key words here are “when it’s appropriate.”

Surgeries are another thing. The occasional “did you cut it off” question is not uncommon. Yes, outrageous but true. The reality is, it is never appropriate to ask a trans person about the surgeries they’ve done or will do. Surgeries are incredibly personal and if your basis for being with a trans woman is contingent on them having or not having sexual reassignment surgery, you should really reconsider if you are the right type of guy for us. I’ll tell you right now, you probably aren’t. Ask yourself; would you ask a cisgender woman if her vagina was functional or if she got her boobs done upon meeting her? I don’t think so.

As I write this, I think about how my partner handles my relationship with surgeries and I have to say he does it perfectly. For example, and to be frank, I have not had sexual reassignment surgery and I have no shame in talking about that. At this moment, it isn’t something I’m necessarily interested in but that said, my partner knows and has expressed that if that is something that I ultimately decide to do in the future, I have the right to do that. At the end of the day, we have bodily autonomy and the right to make these decisions or change our minds. While I can’t say I would never do it, the decision to do a surgery is not contingent on my partner's acceptance.

To drive the point even further, my partner has expressed that if I were to ever stop hormone replacement therapy and “detransition,” that would not impact his commitment to our relationship. Not that I necessarily would detransition, but it is so nice to know his feelings for me are based on a genuine interest in me as a person. In doing this, my partner has allowed me to continue to explore myself without the anxiety of how that might impact my relationship. Amazing, right? Take notes. Giving a trans woman the space to expand and grow in her relationship with her gender and body is the greatest gift you can give us as a partner.

Reflect on your own gender and sexuality

This is a big one. You’d be surprised how many times we receive messages from men asking if their attraction for us makes them gay, and while I can understand that many questions around sexuality arise for a trans-attracted man, the truth is we’re not your therapist. The reality is that some of the men who pursue us are gay and simply haven’t brought themselves to accept it and others are straight (another thing that trans women often need to discern). The point is, no one can tell you if you are straight or gay. Trans women are the personification of strength and a lot of men feel comfortable unloading their questions and anxieties around their sexuality onto us. As trans women you have to acknowledge that we, as individuals, have done a lot of work towards accepting our own sexuality and gender and that you are not exempt from doing that same work yourself. Don’t cheat the process, have a solid understanding of your own identity before pursuing us, and do the work in reflecting on your own experiences and desires.

Do not keep us a secret

If you can’t introduce us to your friends or family because we are trans, you should not pursue us. Period. There is nothing more unattractive than the cowardice that comes with dating a trans woman in secret. Yes, social pressure is tough. Being afraid of what people might think, what people might say– trust me, I get it. But you have to understand that trans women display an immense amount of strength everyday by simply just being ourselves. Every single day that we wake up we go against what society expects or perpetuates as “normal.” So you can imagine how much of a turn-off it is when the man pursuing us only does so behind closed doors because he succumbs to society's prejudices.

On the reverse, there is nothing sexier than a man who is proud of his trans partner and does so out loud. My partner thinks I am the coolest thing since sliced bread, and he couldn’t be prouder of who I am and what I had to overcome to get here. His willingness to claim every part of me literally makes my heart skip a beat, it is that hot. You will not find a trans woman who doesn’t agree with this. At the same time, it is important to remember that disclosing your partner’s transness should only be done with consent. Meaning, while we don’t aspire to be dated in secret, it isn’t anyone else’s business or right to share such a personal part of our identities. Some trans women would prefer to exist in stealth, others find their transness to be a vital part of their identity and existence. This distinction, and how to move forward in moments of disclosure is another thing that should be discussed with your partner prior.

Have insight to the challenges of the trans experience

We wake up every day to a different news cycle, often transphobic, with headlines that probe at our realness or question our sanity, especially in our current political climate. Nevermind the general, everyday harassment or discrimination that we can experience at any given moment. I’m not saying that you need to be abreast of every single thing happening to the trans community but you should be aware of what is happening to the community at large to some degree. If you aspire to be a partner to a trans person, you need to be prepared to help carry the burden that unfortunately often comes with existing as a trans person in today’s world. As a cishet man you innately possess more privilege in society than a trans woman, and that needs to be acknowledged and respected if you are to make for a good partner. And the ways that you show up are fairly simple but will require cishet men to step up. Whether it is happening to a trans person or a conversation with friends or family, one way you can do this is simply by speaking up when you see or hear something transphobic. It is also important to listen to your trans partner on days where things are feeling especially difficult. Whether it is dealing with harassment, a bad spout of gender dysphoria, or a series of transphobic news headlines, all we want is to feel like we have someone on our side.

While each trans woman is unique and there is no universal “rule” to dating us, I believe these five fundamental things are important to consider and practice when pursuing a relationship. Trans women, at the end of the day and for the most part, are not much different than cisgender women. However, the nuances of our existence do make for unique challenges that I believe most cishet trans-attracted men just aren’t aware of. Respecting the nuances while being aware and sensitive to them will make for more fulfilling and genuine relationships for us all. It is my dream to see more cishet men step up and grow comfortable in their attraction for us and to ultimately love us out loud and proudly, because to be a part of a trans woman’s journey is truly such a unique gift that many will never have the luxury of experiencing.


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