Five Reasons Why I WOULD Date A Transgender Woman


The older I get, the more I realize just how much work, energy, and even flat out luck goes into finding a romantic partner. It’s not just from my own personal experience, either. I see it play out in my friends and family as they find lovers, some of which work out and some of which don’t.

At the moment, I am single and my efforts to find love have been difficult, to say the least. I’ve tried online dating. I’ve tried putting myself out there. I’ve even tried flirting a bit. It hasn’t really amounted to much, thus far, but I remain hopeful that I’ll find that special someone one day.

Recently, though, someone asked me an interesting question. Over the course of a conversation about our respective struggles in finding love, he asked if I would ever consider dating a transgender woman. That’s the first time someone asked me that question seriously and I needed a moment to think about it.

As I’ve said before, my knowledge of transgenderism is fairly limited. However, writing about the issue has given me opportunities to interact with a few transgender individuals. I can say without hesitation that much of my interactions with transgender people have been positive. Nearly everyone I’ve met, thus far, has been decent and sincere.

With those experiences in mind, I thought long and hard about this issue. I’m not the first one, either. According to a poll done by, which isn’t exactly scientific, about 65 percent of adults say they would not date a transgender individual. There are any number of reasons why that might be, but I don’t want to speculate so I’ll just give my answer.

Yes, I WOULD date a transgender woman.

Now, I’m not saying that to virtue signal. I’ve already made my feelings on that fairly clear. I came to this conclusion after thinking about what I want in a lover, what kind of person I would want to be for them, and how I would go about pursuing a relationship. After considering all that, the answer became fairly clear.

I would, indeed, be open to dating a transgender woman. I don’t deny that it would be somewhat different than dating a cis-gendered woman, but every individual has their quirks. I don’t see why being transgender should be a deal-breaker in a relationship, at least for me.

I even came up with a few reasons as to why I would be open to such a relationship. Please note that these reasons are coming from someone whose experience with transgender people is limited. I have had issues in the past where my discussions on the issue have inadvertently offended certain people. I will make an effort to avoid that here, but please bear with me if I slip up.

Reason #1: A Transgender Woman Has A More Balanced Understanding Of Gender

This is probably my top reason and the first that came to mind when I contemplated this issue. A transgender person who often has to approach gender in a radically different way from what the social and cultural norms dictate. Their world is one where it just doesn’t work to put clear, defined lines between men and women.

This is kind of a big deal for me because there have been times in my life where I’ve been insecure about what’s expected of me as a man. I love romance. I love passion. I like to explore emotions and walk the fine lines of certain cultural expectations. Some of these things will earn awkward looks from other men and even other women. That was why I often hid my love of romance as a teenager and even a young adult.

I think a transgender woman would understand that feeling better than most, not conforming to certain expectations of their gender and trying to navigate those issues that the Ben Shapiros of the world say don’t exist. I think I would find a lot of common sentiments with a transgender woman, more so than a cis-woman in some cases.

Reason #2: A Transgender Woman Has Greater Insight Into Male AND Female Anatomy 

This was probably the second thing that popped into my mind. I admit, it’s fairly crude. It’s probably the same idea an immature teenage boy might give if asked about the benefits of dating a transgender woman. I have a feeling a number of transgender individuals would roll their eye at that, but I also think there’s something to be said about someone’s experience with the diversity of human anatomy.

In my conversations with transgender women in the past, that experience often involves a disconnect between the mind and the body. The mind says they’re a woman. The body says they’re a man. The struggle is trying to get the body and mind on the same page.

Gender reassignment surgery is just part of that experience and one that’s too big to cover in one post. As it stands, the process has advanced to a point where a transgender woman can have a fairly comprehensive understanding of what it’s like to have both a penis and a vagina.

I think that understanding would help with the intimacy of a relationship. I’ve been with girls who think a penis is basically a faulty light switch, which has made for some awkward moments. Regardless of your gender, it helps to have a better understanding of how genitals actually work.

Reason #3: A Transgender Woman Has A Firmer Grasp On Her Identity

This is a more introspective reason. It’s a reason that also reflects on issues of identity, as a whole. I’ve met men and women throughout my life present themselves in one way, but it’s obvious they’re forcing it. They don’t always know who they are, but try desperately to be what everyone around them expects.

Transgender individuals probably have greater self-awareness than any cis-gendered person ever will. It takes a lot of personal insight to understand that your mind says you’re one thing, but your body says another. It’s difficult for most cis-gendered people, like myself, to comprehend. That’s why it’s so easy to take self-awareness for granted.

For me, dating a transgender woman who is secure in her identity means dating someone who understands who she is and what she wants to be. That’s a rare and under-valued quality in a partner. If one or both people in a relationship lack that, then there will be problems. I imagine a transgender woman would teach me a thing or two about my own identity that I might not have realized.

Reason #4: A Transgender Woman Better Understands The Importance Of Personal Growth

There are a lot of things that go into a successful relationship. One trait my parents often emphasized is to love more than just who a person is when you meet them. It’s often more critical to love who they’re trying to be. People are not static. They grow and develop over time. That’s just part of the human experience.

A transgender person faces more growing pains than most. They have to live their lives with a body and mind that are at odds. Just dealing with that is something that most non-transgender people struggle to grasp, but that means their growth process as individuals takes more turns than most.

For someone seeking to truly align the identity of their mind and body, it takes more than just growth or surgery. It also involves growing up in a world that is not very friendly to transgender individuals. That kind of growth involves a lot of hazards and their ability to navigate them reveals the kind of person they are.

For someone like me, who sometimes has difficulty surmising who someone is trying to be, a transgender woman provides a unique personal story. As someone with a strong appreciation for such stories, I can see an intimate appeal to that sort of connection.

Reason #5: A Transgender Woman Faces A Unique Set Of Life Experiences That Reflect A Unique Kind Of Strength 

This reason ties, somewhat, into the previous reason because it stems from that personal growth that a transgender person undergoes. In aligning their mind and their body into a singular identity, they undergo a difficult growth process. That process requires strength, namely a kind most cis-gendered people take for granted.

I wake up every day, look in a mirror, and don’t even think about my gender identity. I feel like a man. I look like a man. I have manly interests. I don’t have to put an ounce of effort into it. That part of my identity is not in conflict. I imagine if I woke up tomorrow in a woman’s body, I would be very confused and probably very distressed.

Dealing with that sort of disconnect requires strength and not just the kind that involves accepting their identity or undergoing surgery. Like I said before, it takes an uncanny amount of self-awareness to realize one’s identity. A transgender woman who made it to a point where she’s willing to date a guy like me reflects a strength that’s hard to put into words, even for an aspiring erotica/romance writer.

No matter who you are, having a firm grasp of your identity and being willing to share it with someone takes strength. A transgender woman would have more strength than most and for a guy with as many sexy thoughts as me, I think we could make a relationship work. I may never get a chance to try, but I’m comfortable saying I would be open to the experience.


Filed under gender issues, Jack Fisher's Insights, sex in society, sexuality

16 responses to “Five Reasons Why I WOULD Date A Transgender Woman

  1. Erica

    Kudos on a thoughtful perspective; I wish more cis people would engage in thought experiments such as this. Accuracy is not so important given the individual experiences we each undergo. More important is the genuine effort to understand the differences that not only describe transgenders, but that actually add to the beautiful diversity of humanity. You did that here. Thank you.

    • Thank you very much for your kind words. I don’t deny that I have a lot to learn about transgender issues. There’s probably only so much I can understand, as someone who is not transgender. But I believe it’s still an effort worth making. Thanks again for your kind words.

  2. Marias

    Hey, just from cis person to cis person: Some of your thougts are interesting and you seem to be self reflecting on your perspective of trans issues. This is a great thing. At the same time, there were some unfortunate implications in your text which regarding transness. That doesn’t mean you don’t mean well, but there are some ways in which you could improve your understanding of trans issues. Although I’m not trans myself I have been educating myself on issues trans people fight for, so I can share that knowledge with you.

    “The body says they’re a man.” – except it doesn’t. A body is not “objectivly” be linked with a certain gender, because linking bodies (and their sex characteristics) to a certain gender is nothing more than a social construct. A trans woman is a woman. Since she’s a woman and it’s her body, her body is a woman’s body. Only how she concieves her body is relevant, not the fact that some doctors assigned her male at birth or anybody who can’t get over that, since it’s of no importance whatsoever regarding her womanhood as valid. Since most people hold such transphobic assumptions (thinking assigned sex is important to a person’s gender) there is a lot of speculating of trans woman’s genitals in the media in sensational manner. It’s normalized – so everyone, including you and me have come across such tropes – but that doesn’t make this practice altogether less rude or degrading. In Short: When trans people already have the public spectaculating about their genitals in that manner, it’s not a good idea to wonder about a hypothetical trans woman’s “understanding of what it’s like to have both a penis and a vagina”. Maybe she does, maybe she doesn’t refer or refered to her genitalia as ‘penis’, even before she came out to herself as trans. Maybe she is experiencing disphoria by having somebody else refer to her genitals as penis – well, because of rude assumptions people way too generally make. Maybe she has not undergone surgey/ies regarding genitals for various reasons. Maybe she want’s to in the future and maybe she want’s to but can’t afford it, e.g. financially. Or maybe she just doesn’t want to and that’s just fine as well. Remember, genitals are something very personal, intimate to talk about – generalizing assumptions won’t help that matter. Just as generalizing assumptions of genitalia won’t make anyone’s sex life better. Some understanding of how genitals work, yes, I agree, will be quite crucial to enjoy sex, but to base that knowledge on mere assumptions just won’t.

    Since we all get used to transphobic messages in the media and for all of us it’s difficult to unlearn what we hear basically from everywhere, it’s important to think beyond stereotypes and see trans women as the unique individuals they are. Trans women can be very self concious but also insecure. They can be confirmed of their identities and can still be questioning at various points. All of them are valid and awesome. They are lovable for being individual wonderful people. Recently I came around an interesting article which gives great recommendations on this is possible without ignoring unfortunate assumptions, which may otherwise happen way too easy automatically. Even though your article seemed that you have not yet met a trans woman who you’d like to date and who’d like to date you and even though this article focuses on sexuality, I’m sure the tone and the backround of it will be interesting for you:

    good regards, Marias

    • Thank you very much for your kind and insightful words, Marias. I appreciate you taking the time to write them.

    • Emily Wells

      Hi Marias,

      I found your comment to be somewhat worrying for me – and way off course: “The body says they’re a man. – except it doesn’t.” and then you went on in depth about not linking a body objectively with a certain gender, because doing so is nothing more than a social construct.

      Well here is the reality for me and many of my girlfriends who are trans. Every morning when I wake up and look at myself, my brain sees a body that is male, not female. To correct this anomaly, I spend a good part of my morning ensuring I feel and look as feminine as possible – yes I know your response is but that’s social constructing gender!

      Who you are advocating for is people who are gender variant, gender non-conforming, gender atypical or gender queer (about 25% – 30% of the population). Your message is advocating not transgender people who are transsexual (about 0.3% – 0.5% of the population).

      People who are transgender (transsexual) typically have gender dysphoria, i.e. the condition of feeling one’s emotional and psychological identity as male or female to be opposite to one’s biological sex. I take HRT and do everything I can to change my body to the correct gender as it eases my anxieties. This is not a social construct – it is a reality!

      What your message actually tells me is that I am wrong to think I am female because the gender I know I am (female) is exactly the same gender (male) that I was declared to be when born – after all just look at your body. But don’t worry because gender doesn’t exist. You telling me that I am not a female as I feel I am. Basically, your message is exactly the same as we hear everyday from those who deny our existence i.e. there is no such thing as Transgender as it is a modern social construct.

      Perhaps we need less cis-people telling trans-people how we feel and more cis-people listening to trans-people when we explain how we feel.

  3. Sheila Matthews

    Being a transgender woman I loved this article. I found a man that loves me for me. That’s the most important part. He never makes me feel like anything less than who I am. Men you date and love transgender women are a special breed. Soceity will call them gay or bisexual because they love a transgender woman. They have to have a special courage. These men are truly the best of their gender.

    • Thank you very much for your kind words. I’m so glad to hear you found such love and happiness with someone special. As an aspiring erotica/romance writer, that helps remind me that real love exists and it’s worth celebrating. I wish you and your love all the happiness in the world. Take care!

  4. Sarah Lambert

    The love of my life was a cisgender man and I gave him my heart and soul. We were together four years and my best friend told him he would be doing the right thing in leaving me, so he did, at Christmas by letter in a black envelope.
    He broke my heart and I haven’t loved since. Trans women are as delicate and vulnerable as anyone, but we get hurt more I think, and that eventually makes us stronger. So I am strong, but alone, and a cisgender man did that to me. He damaged me and stopped me trusting people, and he lied about loving me. I will never forgive him for that.

    • I’m so sorry to hear that you got your heart broken. That’s a tragedy and a travesty, especially during the holidays. Nobody should endure that kind of pain. I’m sorry you had to go through that. But the strength you attest gives me confidence that you’ll endure. You’ll find love some day. A heart can be broken, but it can never be shattered.

      Thank you so much for sharing this personal story with me. I appreciate it and I wish the best for you and whatever love you find.

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  6. Raven

    Thank you for writing this. It helps me not feel so hopeless about dating men. I hope I find a man with an open mind like you someday.

  7. Danielle

    Thanks Jack, you’re awesome

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  9. Jessica

    Jack – you are a candle in an otherwise very dark world. Thank you for bringing me some hope 🙂

  10. Interesting article. I am 45. I never got married and had a string of horrible relationships. I agree with your reasons. I would date a Transgirl myself. I think they have a better understanding of things and since I am different (as you see in my picture), I can relate to the trans community on a certain level. I know what it is like being discriminated against for being who I am by people who don’t want to understand things. But yea, I like this article.

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