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Navigating the dating world as a trans woman

transgender Filmmaker Nyala Moon short film How Not To Date While Trans
Courtesy Nyala Moon

Filmmaker Nyala Moon on the precarious balance of disclosure and safety, challenging societal norms, and how her film advocates for a deeper understanding and empathy toward trans individuals' experiences.

In our society, there is one prevailing rule about being a trans woman and dating men. As soon as, and even maybe before, you meet someone, you MUST disclose to your partners you are trans. Then, they must decide if they want to have a relationship with you. And if you don’t tell them right away, you are a horrible person, and whatever happens to you is your fault. Simple, right? Well, yes, it is simple if you are not a trans person.

I was part of a new generation of teenage transgirls. The bell rang, and we saw Law & Order, Maury, and Jerry Springer episodes featuring trans women and characters. As exploitative as they were, just seeing these portrayals was the first time I saw someone like me on TV.

What people must know is that the younger you medically transition, the more passable you become. So, a lot of my friends and I had the blessing of starting to transition as teenagers. I was becoming myself, my actual self. And I was actually cute, and men thought I was pretty. There was euphoria in being able to transition as a teenager, but there was always an air of danger.

In my twenties, I was fortunate with two long-term relationships with guys who knew I was trans and were cool with it. However, I went on a lot of dates. So, because I went on a lot of dates, I had tried multiple ways of telling a guy I was trans. I would write it on my dating profile, but some guys don’t read it. Or, I would say it right before the date. Some guys are super friendly and still go on dates, often so I could give them a lesson on Trans 101. Then there were times I would wait for three dates to tell them, but some guys are hot, and I am human with human needs. So, between me and you, there isn’t a right way to tell some of your trans.

Most people would agree that you should talk to them immediately because of safety. However, many of the trans women murders were committed because of intimate partner violence; in relationships with trans women, these partners knew, yet it didn’t stop them from committing violence.

You could get harassed and attacked while walking to the bodega. Maybe someone looked at your face as the sun hit you at a certain angle and was able to clock your ‘T.’ The reality is there is no safety in existing as a trans woman. Any moment could theoretically be the moment that someone decides to make your day harder or, even worse, murder you.

I have always struggled a lot with the concept of disclosing. When I talked to cis people and some trans people about dating, they would ask if my date knows. If I said yes, then it would be a sigh of relief. I imagine they were thinking, ok, good. Nyala is going to be safe. Even though we know that isn’t true. In our society, we really don’t protect the vulnerable - women, children, the disabled, unhoused, or the elderly. So I know that being a trans woman, I am low on the docket. Just look at the life expectancy of the average trans women! (Gag, I’m in my thirties. Wish me luck!)

If you think about it, it’s damned if you do, damned if you don’t. And sometimes, in my dating history, I did! Being seen as I was just a girl was fun and amazing, as was going on dates and meeting people. The thing is that we live in such a hostile world for trans women. You become hyper-aware of how your transness is perceived by the world around you. It was seductive to just be a girl without all that noise. I craved those moments no matter how fleeting and ephemeral they were. No matter how painful it would become after I told them I was trans. I still crave those moments.

I was in a relationship with a guy who chose to be with me before and after my bottom surgery. We were in a four-year-long relationship. And I didn’t tell him for a few months. We met in college, and I was apprehensive about telling someone in my class. High School was rough because people knew and tortured me for it. But I say all of this to say that being trans and spilling the T is a complicated process that isn’t as simple as most people think.



I created my short film, How Not To Date While Trans, during a time when trans people disclosing came back up on social media. Of course, people were talking in absolutes. I was a year out of my film graduate program. I was writing a historical crime drama pilot called The Harvey Milk Girls. It was a true story of teenage trans sex workers who pretended to be vice cops and rob the johns. I was single and currently frustrated with dating and the conversation about dating trans women.

From podcast bros to Dave Chappelle, the conversation around dating or discovering having a trans partner was atrocious. TikTokers doing street interviews and asking drunk men on the same thing often produced negative responses, sometimes even with violence implied. I wrote How Not To Date While Trans because I want to be a voice for my community.

The point of the short film is there is no way to date while trans. I want to create something for other trans people to see and feel seen, just like I had when I saw the trans women on Maury. There was always quiet confidence in those women during those segments with “if I can, then you can, too” energy. That’s what I hope to inspire in other trans people with my work.

For cispeople, I hope that if you haven’t met a transperson, the character of Andie in the film could be that person for you. I use the trope of breaking the fourth wall because I wanted Andie to be your trans best friend. I hope through her, you can develop more empathy for people. I was inspired by Phoebe Waller-Bridge’s Fleabag and Spike Lee’s She Gotta Have It. I want to show a more complex experience to question the viewer's beliefs about trans people. Through my work, I hope that maybe the intimate partner violence might lessen. I hope to challenge the narrative by expanding the conversation on love and loving a trans person.

So I have this hunger to memorize our experience; maybe if no one can empathize with us, they know we exist because the internet is forever.

What's next in store for me? I just wrapped up the production of the first feature film, I Use to Be a Woman, a mockumentary about a de-trans person who is part of a Christian ex-LGBTQ+ group. I'm also writing my next feature, a blaxploitation film about a black trans woman who fights back. My latest short film, Dilating For Maximum Results, won the grand jury at Outfest and NewFest and is a part of the Whitney Biennial.

So, you can say I am obsessed with telling trans stories. Why? Because who else can tell our authentic stories and experiences other than us?

Nyala Moon is an award-winning filmmaker. Like and follow her on Instagram @nyalamoon.

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