Relationships with men; the biggest challenge in my life

10 Jul 2024

This is one of the hardest personal blog posts I’ve ever had to write. I’ve actually been sitting on this topic for weeks mulling over the content, the tone and the level of exposure I’m comfortable with. In the process I’ve realized that this topic is just too complex to fully capture in a blog post. I still feel like I’m so in the thick of it that new ideas and experiences are coming all the time. This is my best attempt at collecting thoughts on dating men as a trans woman so far.

The problem

I find myself in a conundrum. I have all of this energy and enthusiasm to give to a relationship, yet it is so hard to find the right place to direct that energy without getting hurt. I’m overwhelmed by time-wasters, liars, and people looking for “no strings attached” kinds of arrangements. Men are frequently trying to trick or bait and switch on me. Conversations with catfish are at an all time high. I am constantly on guard. The way folks interact with me on dating sites frequently conveys a somber image of how they see trans women in the world.

I’ve tried a lot of different dating websites and they all have varying degrees of common problems. Some of the straighter sites, like Tindr, have men that either don’t realize you’re trans when they indicate interest, or are bi-curious and prone to shyness/ghosting. Other sites on the gayer side, like Grindr, have people who know what they want, but in an overwhelming sea of incredibly agressive men that say some of the most revolting trans-misogynistic things you’ve ever heard. Pick any other dating site between this spectrum and you’ll get a varied mix of these experiences.

The plateau

Somewhere in the absolute mess of things I’ve been deeply optimistic that a bigger connection would come. Every once in a while there is hope for meeting someone that may become someone special, but a threshold always seemes to be reached, which I call “The plateau”.

Personal examples of the plateau from recent experiences

These are some examples of what I’ve been navigating recently. They have all happened or had developments in my life within the last month. I’ve ordered them in terms of how far the connection went before hitting its plateau.

Exhibit A I’ve had a couple chats with guys on dating sites and given them my phone number after days of exchanging messages. We text ‘Hi’ to one another, then they never message again.

These men have hit their plateau at getting a phone number.

Exhibit B I met someone off OKCupid who I got along with quickly over our shared professions in technology. We met one evening on a whim at a bar after chatting for a month and seemed to have some chemistry. After that night we continued talking for 3 more months without ever making plans again. He eventually admitted he never was interested in making firm plans, he just likes meeting on whims. He expected me to remain patient with that, and continue talking to him whenever he felt in the mood, like a penpal.

This man hit his plateau at making firm plans with people. Yet he’s all over the dating sites looking for his next chat buddy as we speak, talking about hanging out soon and travelling together.

Exhibit C Just last week, after expressing some frustration and despair over my loneliness one evening on social media, a man reached out and expressed his condolences for some of the dating challenges I was navigating. He told me that he was moving from Alberta to Toronto in just a few days and would love to meet and explore the city. He was from a small town and that never felt quite safe given his bisexuality, and wanted to start fresh in a more welcoming part of the country. We exchanged photos, chatted by phone and seemed to have common interests. For the next few days we flirted by chat as he first arrived and settled in to his new home. Only, as soon as he landed in Toronto there was never a new picture sent. After a couple days, I asked him to FaceTime with me that evening. Hours of silence later, he replied to say his mother was sick and he was flying back to Alberta (sick family is a very common bail out excuse for cancelling dates too). I said it was fine but reasserted the need for proof of existence in Toronto and he never replied again. I should have smelled the catfishing harder upfront and not engaged, as there were signs upon reflection, but I just enjoyed chatting to this person for a few days and let myself run a bit blind.

This man hit his plateau somwhere lower than a decent human being. He’s actively on dating sites lying to people and, worse yet, knowingly exploiting vulnerable folks at their low points.

Exhibit D My ex boyfriend and I ultimately had some strong disagreements about what constitutes the minimum treatment of a girlfriend. He felt it was possible to both tell me he loved me and flirt online in public social media spaces with other women all day, no matter how many times I told him it hurt me deeply and made me feel deprioritized. He always seemed to need one foot out of our relationship, no matter how much he asserted he loved and wanted me.

This man has hit his plateau at the thrill of the chase currently. I hope he grows up one day, because I do still care for him, but I have no business being near someone who keeps such emotional distance from their partners.

Emotional Tourism

All these stories have some common themes, namely a lot of emotional tourism. There is a lot of overpromising and underdelivering. Every guy has his own flavour of how he does it, but there’s always some limit on how far something can go.

I’ve written before about how often men would treat me like an NPC in their own game of life when I was navigating my own discretion. That treatment is far from over though; It’s just taken new shape. Now people fantasize lives with me they never actually want to live. It’s made me realize that often if a guy says he’ll buy you anything more than a drink or dinner he’s most likely lying. I’m not trying to say that a trans girl can’t ever get the red carpet treatment from a guy, but small actions amount to lot more than big words, so if a guy is doing more talking than acting, it’s a red flag 🚩.

What’s up with these men??

The road is paved with good intentions. I don’t think that all people who I engage with necessarily intend to be so limited in what they can provide. It’s just simply the nature of where they’re at, how they look at their own identities and where dating a trans woman fits into their hierarchy of needs. While the plateau differs from man to man, it is never high enough to establish something stable.

It is unfortunate for trans women that the group of people that love us most, straight men, are closed minded about their sexual orientation. The term gynephilia means to be attracted to femininity, regardless of gender identity or genitals. Being gynesexual is a straight act by closest label proximity. Bisexuals like both traditional genders, pansexuals like all the genders. Gynesexuals just like women. I have found understanding this can actually help guys feel less hung up on their orientation if they mostly think “gay” or “bisexual” are the only alternatives. Many men have forwardly told me they are straight, as though that’s going to surprise me. That’s actually my standard expectation.

Stigma against transfeminine-attracted men is brutally hurting our landscape. Yes, some of them are just jerks like cis women are dealing with too. However, many are decent people in the closet about their gynephilia. These plateaus I am seeing are many times about men not wanting to be overexposed with a trans woman.

A scary thought

I’ve wondered before if this plateau effect is something that can cause trans women to chase fixes for their perceived imperfections. Changing themselves out of a sense of feeling not feminine enough, and thus personally responsible for the plateaus they find in the men they encounter. Surgeries, botox, etc.. becoming an endless pursuit of improving chances through some bimbofication process. As though if men won’t do the work to become enlightened, it’s on us to chase being more passably female in order to find a committed partner.

In dark moments of low self worth I ocassionally find myself thinking about “transitioning harder/faster”. I think defining what that means is for another time though.

At an impasse

I’ve been reaching a point of losing hope and steam. Not so much permanently as temporarily, though. An exhaustion. I’m capitulating to this just being the way things are. No amount of diving harder into dating sites will relieve that. In fact searching right now might just be making it worse. I feel caught in a finger trap and the more I squirm and resist the tighter the grip forms around me.

I’m chasing serious connection, putting the importance of most other traits aside and still finding it leads to mistreatment. Being harassed, lied to, insulted and catfished just so you can navigate your way to getting a cuddle is not better than just staying out of this trouble entirely for a while.

I’m frustrated by the loss of creative time for myself. Even writing this blog took longer because I’ve been talking to guys some evenings in hopes of building something.

New strategies

I think there are a few things I need to strongly consider moving forward.

Less dating sites

I need to push myself out to more in-person social events for meeting people. Even perhaps consider exposing myself to speed-dating events that are lgbtq friendly enough.

More dating

Much as it hurts me to say, I think I need to walk before I run. I’m finding the pursuit of anything remotely serious just too emotionally exhausting and I’m wasting hours and hours. This means taking a bit more of hedonistic attitude towards meeting people right now. As much as I have all this energy I want to give and give and give to a relationship, focusing a bit more on just taking what I want from present experiences with people is a better approach. This might sound like I’m saying I intend to be more promiscuous, but in fact it might be a matter of accepting more first dates with lower expectations and holding higher personal boundaries on intimacy until I’m comfortable.

Dating more women

My challenges with dating cis and trans women is the subject of another blog. However, I would summarize it by saying I’m more romantically drawn to women than sexually. The ambiguity of roles in these situations, if we’re both femmes, tends to stress me out. I have yet to feel like I could be fulfilled by a relationship with a woman as the way I do by a man, but I can’t say I’ve tried hard enough yet to really know either. I know I find getting along and doing activities with women a lot easier. Plan formation is also far less time consuming. I’ll save more details about my past and present history dating women for another time.

More exercise

This is one I keep telling myself needs to become more regular in my life. Exercise and mental health are highly connected. Feeling like a loaf when I go through hard times navigating relationships isn’t doing me any favours. Feeling good in my body also means a lot to me. More than it used to before I started transition.

Still more self-reflection

Beyond this list of ideas I think I still nee more time to reflect on the approaches I take. Reflect on the criterias I filter potential partners on. Reflect on the internalized transphobias that I still wrestle with controlling my own sense of self worth. As much as I might feel at times like I’m trying it all, I may not be thinking outside of the box. No matter what my profile says about who I am and what I’m looking for on dating sites, I’m still the same person inside. If something about my own attitude and approach needs changing for success, its not going to be about changing the words on my dating profile.