Dating is complicated when you’re transgender and for trans women who date men, you find yourself in a lot of scenarios where a man’s attraction to you is based almost entirely on whether or not your body falls into a specific range. If you’ve just come out as trans, a lot of the heterosexual men are going to be disinterested in you because you don’t “pass” for one reason or another. Maybe it’s the shape of your face, your lack of breast development, or even your overall aura. You can easily get the impression that once your body has changed enough, the reasons why a heterosexual man would reject you will suddenly become, at least to you, a moot point. So, you may feel that once you reach a certain point, there isn’t a real reason to tell anyone that you’re transgender. A lot of transgender women fantasize about reaching that day t where they no longer have to have that conversation. Where people perceive them properly as their gender and no longer have a reason to reject them.. But, as a trans woman, I’ve found that this aspiration is just that, a fantasy.  

Nicole Sanders and Justin Moldova are in a fascinating relationship in this most recent season of 90 Day Fiancé. Nicole had gender-affirming bottom surgery when she was around 20 years old, a good near-decade before she met Justin. For two years, they were in a relationship where they quite often had very passionate sex. The only problem was Justin didn’t know that Nikki was transgender, and he wouldn’t find out until they got into an argument one day where Nikki would finally tell him. Nikki wanted to find a cheap way to hurt his feelings and shift his paradigm, so she yelled, “I used to be a man” at the height of an argument. Justin was only 19 at the time, Nikki was 30. This news dramatically shifted Justin’s feelings about the relationship, and he left Nikki to return to his country, Moldova. 

As I’ve started publishing content discussing their relationship, I keep running into the argument that Nikki had no reason to tell him she was transgender because she’s post-op and it doesn’t matter. Furthermore, Justin is “rude” for feeling “traumatized” by this experience and the idea that his feelings shifted after receiving this information is simply transphobia that should not be validated. When I read these comments, it’s hard for me not to interpret that some of these people have not been in long-term relationships as transgender people or they aren’t really in a position where they “pass” and are thus in situations where their transness is something to tell. I feel that way because, like I said, being in a relationship where this never comes up is a bit of a fantasy that doesn’t align with reality.

I know that this may be a bit confusing for some, but even with my large online following, I am still pretty regularly in situations where people do not know that I’m trans. When I was “stealth” in my 20s, keeping that secret was more of an active decision. I was incredibly aware of what I looked like, how I came across, and how I was being seen. For me, stealth was survival, which meant that the way I carefully curated myself not to seem transgender was, in so many ways, life or death. Mind you, we’re talking about the late 2000s and early 2010s. Our society had less understanding of who transgender people were, and I was “passable,” so I decided to make my life easier by keeping that information to myself. And guess what? It worked. I got a lot of upward mobility because passing allowed me to enter certain rooms and make specific connections. As I pursued a more public career as an out trans person, I let go of the idea of stealth, but I still quite regularly find myself in situations where people weren’t able to put two and two together to figure it out. It isn’t intentional for me these days, but no one can say I’m hiding it, and for me that’s been very liberating, when compared to how things used to be.

When I was younger, I did a bit of “stealth” dating. Which, for me, meant that I went on a handful of dates with men who didn’t know that I was transgender. These were often men I met online who found themselves taken with me. Ironically, the thing a lot of men appreciated about me at the time was how straightforward and definite I was about what I was looking for. What was I looking for at the time? a long-term, monogamous relationship that could lead to marriage and family. I had this idea that if I kept my transness to myself, these guys would end up loving me so much that they really couldn’t justify not being in a relationship with me. I imagined that love would conquer all and that maybe they’d put aside their desires to be with a cis woman to be with me because of how much they loved me. But so many of these relationships ended the same way. Ultimately, these men felt hurt by the fact that I didn’t tell them, and for some of them it wasn’t even because I was trans. It was because I intentionally kept something from them. How can they trust I wouldn’t do that with other things? Sometimes, these men really did like me. They really were attracted to me and would absolutely have loved to date me, but they could not stomach that I was transgender and realized that despite having the same life plans, my transness made pursuing those plans a bit more complicated.

In my video, I said that it’s in a trans person’s best interest to disclose to their partners that they are transgender and that got a fair bit of pushback. I understand why some people feel that way. Some view the rejection of a transgender person “because” they’re transgender as a form of transphobia. As we’ve discussed on this blog a few times, I do not feel that way for a few reasons. However, the overarching reason I think this way is because I believe in saving my time. Going on dates with men who didn’t know I was transgender was a waste of time. It made sense to me at the time because I was dealing with the very bizarre reality that if men knew I was transgender, they decided to limit the type of relationship we had, often just to sex in private. Or they’d avoid taking me to certain places out of paranoia. Stealth dating allowed me to feel, at the time, that these men were treating me the way they’d treat cis women. Maybe for some men, that was true, but I figured out pretty quickly that men who disrespect trans women don’t often suddenly have mountains of respect for cis women. Yes, some of these men will mistreat you and say that they’re doing so because you’re transgender, but that’s an excuse. A man’s misogyny doesn’t shift based on whether the person is trans or cis. That’s one thing stealth dating truly taught me. Some men think they can get away with more when you’re trans, but those men are rarely more respectful of cis women. 

I think the very harsh reality is that when you’re transgender, dating will always be complicated. However, I’ve found it to be a lot less complicated the more comfortable I’ve been with myself. One of the most blaring issues in Nikki and Justin’s relationship is that they have a very different set of values. As a trans woman who raised conservatively, watching their relationship is interesting to me because I know there’s a part of me that could be in a relationship with a much more traditional man. But that part of me is less confident. It’s the part of me that feels very comfortable standing behind a man and allowing him to decide everything for me. It’s the part of me that doesn’t mind shifting myself and becoming more modest to satisfy the desires of my partner. The part of me that was comfortable making myself smaller for a man. The part of me that was stealth and very comfortable with that. But I’ve been there, and I wasn’t happy. Almost a decade later, I’m so happy I never married that guy.  

When I first started dating my ex, a liberal dude from a conservative town, his family didn’t know that I was transgender. In retrospect, when I was eventually outed to his family, our relationship only went downhill. Suddenly, his family wasn’t as warm and welcoming. I sat quietly in the corner for most of our family gatherings, and things were always on a fragile thread. His father was a conservative cop who listened to Rush Limbaugh and Fox News very loudly in his garage. I became very aware of the fact that his parent’s perception of a transgender woman was not positive. Suddenly, I was incredibly invested in ensuring that I contradicted their assumptions. It created this air where I’d become the stereotype if I ever stepped out of line. Mind you, it was already an issue that I was black. After I broke up with him, he dated other trans women, and one of those women contacted me to vent about the relationship. He had apparently become far less comfortable with openly dating trans women. While I didn’t notice it, his need for his partners to “pass” was pretty intense, and she felt those standards quite harshly because her appearance was why he was not open about dating her. I was shocked to hear this because I wouldn’t have assumed he felt that way, but in retrospect, it shouldn’t have surprised me.  

Justin is led by his insecurities the way many conservative men are. Nikki’s larger-than-life persona is off-putting because he wants a modest woman who cooks, cleans, and is submissive. While they’re trying to make this square peg fit into a round hole, they will both have to compromise to mesh with each other. You have to do that if you’re in a relationship like this. With that compromise will come a loss of identity. Nikki very clearly loves being Nikki Exxotica, a vivacious, cartoon-esc, sexy pop star, but she’d have to change that in order to maintain a long-term relationship with Justin, who is more attracted to women who are quieter and meeker. Compromise is common in relationships, but for the transgender woman, the compromise is almost always to be less public, be less seen, be more feminine, and be quieter. Some trans women will be able to accept that, but I learned long ago that wasn’t the life for me. I don’t think it’s the life for her either.  

Nikki and Justin have a lot of very obvious incompatibilities, but one of the reasons I believe Nikki remains in this relationship is that the optica of Justin are very validating to her as a transgender woman. He’s a heterosexual man who’s never been with a transgender woman. He’s a conservative white man with a traditional approach to relationships and there’s something very intoxicating for a transgender woman about being with a man like that: A man who’d never be with a man. Some trans women feel that if a man knows you’re transgender and approaches you, that makes him a “chaser”. A “chaser” is a guy who fetishizes transgender women. If you’re a trans woman who’s ever used a dating app or simply openly spoken about yourself as trans, you’ve met these guys. They’re often preoccupied on your transition and are often focused on your genitalia. A lot of them will lose interest in you when you have bottom surgery and can no longer fulfill their sexual fantasy. These men rarely want anything serious with a transgender woman and I know there’s something particularly intoxicating to Nikki about the fact that this guy proposed to her and decided to pursue a relationship with her. She likely feels that Justin is more genuine in his desire because he didn’t know that she was transgender and, before he found out, wanted to marry her. When you’re trans, the idea that a man could fall in love with you while knowing that you’re trans feels like a long shot, but if I’m being honest… that hasn’t been my own experience since I left these small conservative towns for the city.

Yes, being out as trans often comes with all of the issues I’ve described and then some, but I have found that as I became more social, men came to me pretty easily. Sure, some of these men aren’t interested in me once they know that I’m transgender, but I’d say most of them are, at the bare minimum, still interested in getting to know me. I went from being stealth to virtually requiring that men I dated had experience with trans women or were very confident about their attraction to trans women. I don’t like wasting my time and men who are inexperienced or typically not attracted to trans women can only offer me their hesitation and doubt. I completely understand Nikki’s frustration with Justin potentially not being sexually attracted to her. It can be anxiety-inducing to feel that someone you love isn’t attracted to you. However, it’s a bed she made for herself. She decided to keep the information from him, which means he wasn’t really ever given the chance to know exactly what he was getting into. So now, after the fact, he has to process that she kept something from him for 2 years, and even if he fully accepts Nikki as a woman, he now has to ask himself if his relationship with her reflects a certain way on his sexuality. And sure, you can say that what he’s processing is his own internalized transphobia, but who cares? Whether it’s phobia or not, it’s a position he has to process because we don’t live in a society that has gotten to the point where everyone accepts that not all women are cis. So, for most men in his position, there’s a bit of processing that will have to take place. Personally, I have a deep disdain for this process of processing because it puts me in a position where someone could be so into me, but not my body. It really sucks to know that someone likes you, but can’t accept you. And it sucks for you to be in a position where you feel you have to beg for their acceptance or show you aren’t like what they may have assumed. You end up being in a position where hard not internalize the idea that your transness is a problem. That acceptance will only come once you change yourself enough to make them comfortable. My transness is part of my history, and I cannot put myself in a position where my relationship is made or broken for things that I can’t change.  

Realistically, the only way for you to maintain a long-term relationship with someone who has absolutely no idea that you’re transgender is to first “pass” as cis, and then distance yourself physically from almost every person who’s ever known you who could know that you’re trans. Your transness doesn’t need to be all-encompassing and all-defining. It can be a footnote that doesn’t impact your daily life. But it will always be part of your history. It’ll be a part of how your family and friends remember you. It’s part of the timeline of your life and if you’re building an intimate relationship with someone; one where you’d potentially meet their family and friends and they’d meet yours, it’s just not realistic to think it will never come up.

Ignore all of the arguments about how you’re obligated to tell someone simply because they’re attracted to you. Ignore those arguments that say you owe men your entire medical history because they looked in your direction. Think more about saving your time. Think more about the pure intimacy and love you receive from that person who truly knows you. A man who accepts your past but loves who you are today. Who understands that while your path may have been different, it is just as valid. So much of the feelings trans women have about not sharing that information with men is based in the idea that straight men don’t typically date trans women or couldn’t potentially understand or be attracted to them. And in all reality, that’s become less and less of a reality. More and more men are opening themselves up to dating transgender women. Personally, I’ve not found it to be very hard to find men who were open to dating me. Perhaps it’s who I surround myself with and the city I currently live in, but I’d say when I tell men, about 80% absolutely do not care.

Having been in many closets throughout my life, I haven’t found them conducive to living a life where I feel happy and seen, even as a trans person who doesn’t wave a pink, white, and blue flag, who still struggles wearing pronoun pins, being out as trans has been one of the most productive things I could have done for my romantic life. The security I feel knowing that my partners are entirely on board with me cannot compare to the passing positive feelings I felt during stealth dating. Knowing that the love they have for me isn’t conditional is massive. Because I once thought it was impossible for me to find, I have a lot of sympathy for those like Nikki who still feel like the most secure relationship they can have is one that doesn’t start with transparency. My romantic life has changed very dramatically since I started looking at my transness as something people need to accept early on. I no longer have those “I just can’t do it” conversations that send me down a path of self-loathing. I never want my transness to be held over my head, so I don’t put myself in those positions. Most of my partners are men who didn’t know I was trans at first but who stayed with me once they knew. I befriended them for a bit, and I only told them after understanding their politics, feeling mutual attraction, and knowing they could receive that information without reacting violently. I understand things should be different, and I wish they were. Until then, I think it makes a lot of sense for trans women, especially, to be incredibly discerning when it comes to their partners. Not only for their safety but so they do not end up in relationships where their partners do not accept them and use that against them.

I hope it works out for them.