Dating While Trans Feminine: The Troubling, Often Demoralizing Reality

TW: Trans fetishization, transphobia, self-harm

Edit 2/12/21: This piece in particular has received a ton of hateful comments over the past few months, so let me be abundantly clear—if you reject somebody solely on the basis that they are transgender, you are being transphobic.

This has absolutely nothing to do with anyone being “owed” anything (sex, romance, etc.) from anybody—it’s about the way in which our society has normalized transphobia, and particularly transmisogyny, to the point that a majority of cis people will openly acknowledge their refusal to date trans people.

If you refuse to recognize that blanket refusal to date a trans person is fundamentally transphobic, then this space, quite frankly, is not designed for you. Trans and Caffeinated is designed for the affirmation of trans folks, and for allies who are willing to learn.

One of the most trying battlegrounds in the day-to-day life of many transgender people is dating. For many adults, finding one or multiple suitable partners is an important part of life, hence why dating apps are so prominent and why so much adult socialization is centered around bars, where flirting with strangers is normalized. Though most adults will acknowledge that dating is frustrating and a bit exhausting, there is an additional level of complexity for transgender people that stems from our identity.

I always had difficulty connecting with romantic partners, but I didn’t always connect it to being trans.

Even before coming out, I found it extremely challenging to find a partner with whom I truly connected. I don’t think it’s bold to assert that a healthy partnership is built on a foundation of authenticity and trust, and before transitioning, I was unintentionally inauthentic. Though I’ve always valued honesty, I was not yet comfortable enough to fully accept that I was transgender, so I was unable to be completely honest about it with my partners. Even though there was much left unsaid, I am confident that my partners felt my hesitation to truly be myself, and my inauthenticity hindered my ability to form meaningful bonds. Beyond that, I perpetually teetered the line between wanting and wanting to be the women I dated, and this jealousy consistently threatened to poison my relationships.

Around the time I turned 18, dating became even more uncomfortable. As my transness became increasingly undeniable, I grew increasingly uncomfortable with my body and the way it worked. Though I did not see this at the time, I’ve since realized how frequently I projected my discomfort onto the people I dated. My frustration at the knowledge that I would never get my period led to an obsession with my partners’. I became so tormented by the monthly reminders that I would always be “less than” that I habitually increased engagement in self-injurious behaviors every time somebody I was seeing got their period.

Though I recognize now that this was emotionally manipulative, I often communicated this pain to my partners so that they would take care of my emotional needs. My discomfort also manifested itself as extreme jealousy about my partners’ sexual pleasure. I understood all too well that my partners experienced orgasms in ways I feared I never could, which troubled me immensely. I often became extremely uncomfortable and self-conscious during sex, knowing that the way I desperately wished I could experience sex was vastly different from my actual experience.

Me at age 18, during the brief period of time that I’d convinced myself I needed glasses to drive at night. Please excuse the eyebrows, I was trying something out.
When I came out as trans, dating got even harder.

As difficult as dating was before coming out, it was nothing compared to my experiences over the last four years. After I began to be read as female, one question I had to ask myself repeatedly was when and how to tell potential partners that I’m transgender. My journey to becoming the out, proud transgender woman you all know today was preceded by years of being petrified to tell people that I’m trans (shocking, I know!). At first, I wasn’t confident nor secure enough in my identity to brush it off when someone reacted negatively, so I hesitated to tell anybody at all.

For the first few years of my transition, I only really told people I was transgender when I thought I may have sex with them. With this approach, however, I was already emotionally invested in someone by the time we had this discussion, meaning that I had a lot more to lose if they reacted poorly. I quickly realized that handling the information in this manner led to a lot of unnecessary pain and upset.

About a year after I came out as trans.
My 21st Birthday — month 7 of my transition, around the time I started to be read as cisgender (which I am not)

Soon, I began to make a point of telling people I was transgender as soon as we made plans to meet up. This approach worked slightly more favorably because it enabled me to discover whether somebody was transphobic before wasting my time getting to know them. I was comfortable with this for a while, but I soon endured a series of particularly painful and insulting interactions that stemmed from my coming out. One of these in particular still troubles me today.

I was using Hinge one night and met a girl named Christina, with whom I hit it off immediately. I felt like we really connected, and we were rapid-fire texting for days. She was funny, electric, and I really enjoyed talking to her. She was bisexual, which typically reassures me that I will not be rejected for my identity, since the majority of negative reactions I’ve experienced are from straight men and lesbians insisting that it’s “not personal” but they’re just “repulsed by penises” (which, for the record, is also transphobic, because it reduces me to the shape of my genitals).

After a few days, I asked her to meet for drinks at a local pub to which she gleefully agreed. Per my rule at the time, it was then that I disclosed my identity. In my experience, most people have the common courtesy and awareness to not acknowledge my transness as the cause of their lost interest, but Christina was different. I mentioned my identity pretty casually, fully believing that she was an ally and assuming it would not be a problem. Even when she briefly stopped texting back shortly after, I thought nothing of it. Her response was utterly insulting.

I don’t know what was more baffling — her seeming lack of awareness about how rude she had just been, how completely candid and seemingly unashamed she was about rejecting me for being trans, or her assumption that we could be friends after she had just dehumanized me. I decided to adjust my approach yet again.

I made a change.

What I realized following that experience is that if I tell somebody that I’m trans immediately after meeting them, I’ll likely never know if it’s the reason they lose interest. In disclosing it early, I don’t give them the chance to become interested in a version of me that doesn’t exist, and I save myself unnecessary frustration. As a result, I have made a routine of coming out within the first conversation with people on dating apps, or when meeting people in person, within the first conversation after realizing they may be interested in me. I wish this were not something I had consider when dating, but it is an unfortunate and stressful part of dating while transgender.

Beyond the question of when to tell someone that I’m trans, the stress of wondering if a potential partner will reject me because I’m transgender and the pain of being rejected for this reason are enough at times to make me not want to date at all. When someone rejects me because I’m transgender, it is a transparent admission of their transphobia, a callous conflation of my gender with the shape of my genitals, and an attempt to invalidate my womanhood. It is that person saying to me, in no uncertain times, that they don’t see me the same way they see other women simply because I have a penis.

In one instance, a woman on a dating app told me that while she’s not into “pre-operative” trans women because “penis scares the heck out of [her],” she had never been with someone “post-op” and “wouldn’t even know where to begin with that.” Colloquially, someone like that is called a TERF (trans-exclusionary radical feminist), which is someone who doesn’t believe that trans women are “real” women.

You can’t even make this stuff up…

Being rejected hurts, especially when it is based on something that is so central to my identity as being trans. It is one thing to be rejected because we don’t have common interests, or we live too far apart, or we just don’t have a connection, and it is something else completely to be consistently rejected for something I cannot change. And to add insult to injury, it seems that many people lack the slightest hesitation or slightest bit of shame about acknowledging that my trans identity is their sole reason for rejecting me.

In addition to transphobic rejections, we’re also frequently fetishized.

On the equally offensive flip side of the coin is trans fetishization. I can’t even count how many times someone, usually a man and usually on a dating app, has fetishized me for being transgender. People have said things like, “I think it’s kind of hot that you’re a chick with a dick” and bluntly asked to give me oral sex as soon as I disclose that I’m trans.

Fetishization of trans bodies is so common that many pornography sites actually have whole categories dedicated to it, and many sites label these sections with disgusting, transphobic slurs like “She-males” and “Trannies.” Trans fetishization is equally as dehumanizing as rejection on the basis of trans identity because it is similarly a reduction of my identity to the shape of genitals — the difference in the case of fetishization is that this is the reason they want me rather than the reason they don’t. My body is not your pornography and it is not for your consumption. I am an entire human being — I have thoughts, feelings, desires, likes, dislikes, frustrations, and anxieties, and I am so much more than the shape of my genitals.

Word to the wise: Don’t tuck while you sleep.

One subject that I rarely hear discussed in relation to dating while trans is the possibility of damaging one’s penis by tucking incorrectly, tucking too often, or sometimes simply from getting an erection at the wrong time. In fact, I only really started reading information about this when I searched for it directly, and even then it was difficult to find.

Early in my transition, my bottom dysphoria (dysphoria about my penis) was far more intense than it is now. To stifle my dysphoria, I would often tuck even while I slept. Unfortunately, one of the most common times for people with penises to get an erection is while they sleep, and that was often the case for me. However, if the penis is restricted from facing forward when erect, this can strain the tissue and ultimately cause damage. This happened to me on multiple occasions and the effects compounded over time. At this point, my erections range from mildly to blindingly painful. Coupled with my Spironolactone (Testosterone blockers), which decrease my sex drive immensely, this pain inhibits my ability to enjoy sex, which is something I’ve only gained within the past few years.

I’m sure you know the old adage — “If you have pain during sex, just get your penis surgically split down the middle, get a cavity created inside your pelvis, and use the remaining tissue to form the walls of your new vagina!” — or something like that. Anyway, this pic is from my first bottom surgery consultation.

Even before beginning to experience pain, I consistently struggled with trying to explain to partners how differently transgender people experience sexual pleasure as compared to both cisgender men and cisgender women. For most people I’ve dated, I am the first transgender person they’ve been with. As such, I am the first person they’ve slept with who has a penis but is not a man, so their only frames of reference for pleasuring someone with a penis are experiences with cisgender men. Having to explain to each new partner how to make me feel good can be pretty exhausting, so sometimes I just let people do whatever they feel like instead of speaking up. Sometimes, this is frankly just easier.

Trans women face disproportionate rates of IPV.

As someone who predominantly dates women, I don’t have to deal with half of the problems that predominantly male-attracted transgender women do. While women often react with discomfort and occasional verbal aggression at finding out that I’m trans, it is nauseatingly common for men to react with physical violence when finding out that their partner is transgender. This does not mean that women never react this way, but it is far less common.

I frequently read stories of transgender women who are hospitalized or killed when a male partner discovers that she is transgender, and here’s my hard to believe yet completely true fact of the day — there are FORTY TWO states in which the “trans panic” defense is still permissible in court, a defense which legitimizes transphobic violence by asserting that an attacker “panicked” when realizing their partner is trans and attacked them in a “moment of temporary insanity.” In other words, transgender women in 42 U.S. states can be murdered by a partner for being transgender, and as long as their partner hires a semi-experienced lawyer, they may not face legal consequences. The “trans panic” defense was used to mitigate a murder charge as recently as last April.

Beyond this, transgender women are disproportionately victims of intimate partner violence (IPV), and their unique marginalization limits access to resources that could otherwise help them out of a bad situation. When law enforcement gets involved, they often make a bad situation worse, especially when the victim is a trans woman of color. Trans IPV victims are routinely re-victimized by police officers, who mock them for being trans, belittle them, or doubt the credibility of IPV accusations simply because the victim is transgender.

Many trans people are ostracized from their families and communities after coming out, so they frequently have nowhere to live when seeking refuge from an abusive partner. Trans people often face workplace and hiring discrimination, which means lower income and fewer options for housing away from their partner. Homeless shelters are hardly a safe haven for trans women, who are routinely rejected from entering women’s shelters for being transgender.

For transgender people who are read as trans, dating can be even more complex. Being a visibly transgender person often means transgressing conventional beauty norms and building self-confidence within a culture that unapologetically propagates the belief that “looking trans” and being attractive are mutually exclusive traits.

I don’t buy into the myth that “you have to love yourself before you can love somebody else,” but I certainly believe that self-confidence makes it considerably easier to be vulnerable and take chances, both of which are beneficial when trying to find a suitable partner. On top of this, and though I wish this weren’t the case, it is often harder to date as someone who’s read as trans because we live within an aggressively superficial society in which far too many people are unable to see beyond conventional gendered beauty norms to find someone outside of these norms attractive.

This 2017 survey of about 1200 people (3/4 of whom identified as cisgender and heterosexual) is pretty disheartening. I will, however, assert that the results would have been slightly more optimistic had the sample been a bit more diverse in terms of gender and sexual orientation.

Many trans people ultimately decide to only date trans people.

Many of these challenges arise from attempting to navigate a largely cisgender dating pool, so many transgender people ultimately limit ourselves to dating other trans folx. Although the dating pool is much smaller, this tactic greatly alleviates many of the risks associated with dating while transgender. Additionally, dating other trans people is often just easier because there are so many aspects of trans existence that I do not have to explain because they already understand. For instance, other transgender people frequently understand what it’s like feel dysphoric and how dysphoria can shape my experiences, so I don’t have to put energy into explaining this.

When dating other trans people, it is much easier to bond about identity and experience because there are so many aspects of my day-to-day life that are so oddly specific to trans existence that they are hard to explain to a cisgender partner. Trans people simply understand many of my thoughts and feelings firsthand in ways that for obvious reasons, a cisgender person never truly can. However, just because somebody is transgender does not mean that I will automatically have a romantic connection with them, and with an already small dating pool, this makes it extremely difficult to limit myself exclusively to dating within my community. As a result, I’ve never personally made this decision, though I know a number of trans folx who have.

In spite of all of this, we persevere.

Dating while transgender can be challenging and exhausting, but it is certainly possible. Plenty of transgender people find happy, loving, fulfilling, beautiful relationships with partners who love and respect them for who they are. To me, there is no quality more beautiful than being authentic and assured in your identity, and nothing shows self-assurance quite like a trans person dedicated to living their truth. Especially when dating cisgender people, transgender folx need partners who are dedicated to learning, growing, and understanding the world differently from many of the ways they were previously taught. My optimistic hope for the world is that more folx decide that this dedication is worth it, because not to brag or anything, but dating trans people can be pretty fucking awesome.

15 thoughts on “Dating While Trans Feminine: The Troubling, Often Demoralizing Reality”

  1. That was a unique, beautiful and educational piece of writing! Thank you for being unabashedly you and also you’re a damn good writer

  2. Beautifully written Arielle! This is the first of your blog posts that I’ve taken the time to read, and I’m so glad I did. I’m learning so much, just from the language you use and the opinions you have on transphobia, that I haven’t considered yet. There is so much that you know that I hope to know some day, and your sense of self-assuredness is greatly comforting to me. Not to put you on too much of a pedastal, you seem to be a really cool person, and I’m looking forward to reading more from you in the future.

    1. Thank you SO much for your kind words, I really appreciate you taking the time to read it 🙂 I’ll definitely be posting more in the near future, and I can’t wait to hear your thoughts!

  3. Arielle, you have done it again! This was seriously so beautifully written and honestly once I started reading, I couldn’t stop. The experiences you write about are so real it hurts, and the fact that you added the screenshots to just further shows that this is a real thing happening so often really hit for me! So many of my female friends have shared with me their experiences and trauma and honestly, its absolutely ridiculous how some people can be and act towards women. This goes for men as well. And the fetishizing? Oh man did I feel that one!
    Keep up the writing, I love the consistency and effort you put into your work. It really shows.
    Sending love!

    1. Everybody just knows me as a gay cis man but deep down I’ve secretly struggled with my gender identity my whole life and been afraid to materialize what I want from my life due to being from Texas and a traditional family and all. But people like you inspire me to do something about it! Stay strong <3

  4. thank you so much for reading and for your kind words. You never did or said anything transphobic, so there is no reason I would ever have put you in here — you have always been kind and supportive. Thank you for your endless encouragement and validation <3 your comments forreal had me tearing up at work

  5. This is excellent and I will be sharing this blog post with my sexology and sex counseling colleagues in the AASECT list-serve and American Counseling Association Sexual Wellness online group. We all need to step up our game in supporting trans and gender diverse people in any areas of life in which they request support from us as helping professionals, and recognizing specific challenges, such as the dating challenges you describe, are super important. Part of this is understanding the corrosive emotional impact of “micro-aggressions” such as the ones you show in the screenshots, as well as the threats of transphobic violence. I appreciate that you have written this article. I have learned from it. Big respect and thanks for all you do!

  6. I have used the dating website OkCupid. One of the helpful features is that you can get others’ opinions on a variety of things through their questions (including on LGBTQ+ issues and rights). But one thing that’s sad for me is the number of people who answer the question “Would you date a transgender person?” by saying “no” (and ditto with “no” answers to things like, “Would you date someone who’s bisexual?”). It’s also surprising, because I’d think that the majority of people in the “dating pool” where I live (New York City) would be young, progressive, and a lot more open to dating someone who’s bisexual or transgender or someone in the LGBTQ+ community in general. Those experiences, while helpful for me personally for whoever I consider dating (because being an ally is requisite, and displaying blatant transphobia in the “Would you date a transgender person?”question is a deal-breaker), gave me a glimpse into some of the transphobia that exists with dating. Still, this post really educated me–a ton–about the struggle of being romantically interested while being transgender. Thanks for writing this.

  7. Still love this with every read. And I think it might be worth something right up front (title, subtitle, second subtitle) that this is about dating while being an amab trans person. afab trans folx also do experience crappy stuff, but it’s really different than what we experience.

  8. This is an older post and I’m unsure if you’ll see my comment but I just wanted to congratulate you on arriving to you and for overcoming so much in the process. Emphasis on so much. I’m not a part of your community, but I’ve always been a loving person with a wide scope for spreading that live. However, I am admittedly uneducated and unfamiliar with trans everything and I’m looking to change that because I don’t want to feel any otherness when speaking or experiencing any women or men.

    I’m cis female who empathizes with your struggles, and I can relate to your mental health struggles. Thank you for this well written piece that helps me better understand you and your long journey to being you. You’re a beautiful woman and I hope you are enjoying everything good and bad about feminity and being a woman in this often confusing world. We are amazing creatures and I wish you well, Arielle.

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