My Very First Genderqueer Date

by Phil Hill
genderqueer dating

Ask anyone who knows me well and they’ll be able to describe my ideal partner in two words; male and older. Whether it be posting images of Ewan McGregor as my Man Crush Monday on Instagram, or mentally drooling over the older gentlemen who come into my workplace, it’s fair to say I have a ‘type’.

However little did I know that I would soon end up dipping my toe into the world of LGBTQ+ dating. 

My whole life I had identified as straight and female, believing my masculine ways were nothing more than me being a tomboy and that my occasional feelings towards women had simply been exceptions to the rule. But after many discussions with my therapist last summer we managed to get to the bottom of my true gender and sexual identity.

I now see myself as a person rather than a gender and although I still have a strong preference for older men, it seems I’ve become a bit more open-minded when it comes to whom I date!

That being said a few months ago I was at work and in walked someone who caught my eye. I could instantly tell they were born in an anatomically female body, but wearing masculine attire and adopting a rather male demeanour, I was fairly confident their sex and gender didn’t align. 

Luckily they knew my colleague, so I made it my mission to interrogate her about this mysterious stranger. After a brief conversation, I discovered their name, that they identified as male and that he was 19. 

At 26 and with most of my previous partners being between ten and fifteen years older than me, the thought of dating someone so young would usually be a deal breaker. However this time their age was practically irrelevant as I found something incredibly endearing about them being trans. Granted, unlike him I didn’t identify as male, but knowing we were both masculine individuals trapped in a female body made me feel some kind of connection. It was new and it was exciting. 

Later that day I tried to find him on Facebook but after having no luck I went back to the reality of single life. Yet two weeks later the guy in the glasses returned to my workplace. This time I was even more attracted to him and according to my co-worker, the feelings were mutual!

As I arrived home later that evening not only had he been successful in finding me on Facebook, but he had sent me a message asking me out to dinner just a few days later. Flattered and wanting to go on a date like I had never been on before I didn’t hesitate in saying yes.

Tuesday came and as I sat in the restaurant sporting my smartest shirt, perfectly quaffed hair and smelling of aftershave, I nervously awaited his arrival. 

I had always felt the need to play down my masculinity on previous dates as most men would rather a woman in heels and a dress than one in a pair of skate pants. But this time I wasn’t a woman and I wasn’t going to meet a cisgendered man. I was a gender non-conforming yet masculine individual going out to dinner with a trans guy. For the first time ever I felt I could go on a date and be my authentic self. 

Eventually, he arrived and for once it was my date that was more nervous than me! We began chatting and inevitably the conversation turned to gender. This was only the second time I had spoken with someone who was trans in real life and therefore understood some of the difficulties I was going through as a queer person, so in a midst of excitement, I had a million questions I wanted to ask! We spoke about everything from binders to clinics, to our parent’s reaction to us not being the daughters they thought we were. At times I felt like I was prying, but thankfully he was a very open book. 

Something that stood out to me about this date though compared to all my others was the massive sense of role reversal. From trying to make sure he felt as relaxed as possible, to my attempt at chivalry as I held the door open for him at the end, it seemed I was the one who had taken on the ‘male lead’; something I had never done on a date before. I assumed it was because I was older, but maybe it was because this was the first date I felt I had permission to be the real me and as a result felt a lot more self-assured… Either way, I quite liked it!

After a nice meal and an in-depth chat the date drew to a close and although I had had a nice time, I just didn’t quite feel that spark. But in all honesty I didn’t really mind, as although fate hadn’t bought me together with my Mr Right, in those few hours I had actually gained something far bigger; I realised that it is ALWAYS better to be yourself on a date and after months of trying to explain to those around me what I was going through regarding my gender, I had finally met someone I could talk to who genuinely knew how it felt.

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