Growing up, I’ve always hated how toys were divided between boys and girls. Especially given the limited number of things that were acceptable for girls to play with while boys would have multiple aisles filled with fun things like Lego, science experiments and action figures. Even back then, I hadn’t much liked how interests could be so rigidly divded.

Nor did I like being relegated to wearing frumpy school dresses when part of the uniform was a shirt and shorts. In fact, it was a point of contention back in primary school with my mother. During one of the school photos, she had demanded I wear the dress rather than what I was comfortable with.

It should come as no surprise that I was considered a ‘tomboy’ in school.

But though films and movies would have you believe I’d finally figure out the secrets of make-up and try to dress to impress in order to snag myself a man by the time I hit university, this never happened. Putting on make-up forever remains a mystery. Yes, I understand it’s socially expected that I be patting on a layer of foundation and giving my lips a touch of rouge, but it just feels completely antithetical to who I am as a person.

Why are women expected to powder themselves up to appeal to the not as fair sex? Why do we need to shave our legs and armpits? More than that, why was it fine for me to run around shirtless when I was a child but not socially acceptable now that my mammary glands have developed?

If women can’t free the nip, and it’s considered crass if the nodules can be seen through the shirt, then I’m voting for men to do the same. I don’t need to men nips peeking through their thin shirts. Nor do I want to see their rolls of fat as they take their shirts off during a run. Especially if women can’t do the same without it being seen as unseemly.

As the years have gone by and new labels have appeared, I did wonder if my antipathy towards gender stereotypes painted me as non-binary. I, certainly, wasn’t the image of the typical woman with typical feminine interests and hobbies. But the more I thought on why such a label was required, the more I pushed against it.

The whole idea of the divide between ‘masculine’ and ‘feminine’ simply didn’t make sense. And by choosing to be non-binary, I was also conforming to the idea that because I wasn’t feminine enough, I had to straddle the line between the two. Even though I’d come to terms with the fact I’d never have a flat enough chest, and suffer through monthly bouts of menstruating (I also wanted to be taller and skinnier, but let’s not go into beauty standards on this post).

Why couldn’t I be who I was – a woman who liked video games, books and horses?

And though the idea of whether I might be trans did cross my mind, the years of being mistaken for a boy because of my unisex name further solidified my gender identity for me – but also because I didn’t have significant body dysmorphia leading me to severe distress in terms of the body I had (although being more athletic and capable of doing backflips would have been a bonus. Unfortunately, I don’t think science is at the stage to give me the ideal body I want). Besides, I can’t have been the only one who has wondered what it might be like to be the opposite sex and the advantages that come with it.

On the other hand, biology is a strange beast. Yes, there are certain markers to differentiate males and females of a species, but none of it is universal. Female hyenas, after all, have more testosterone than their male counterparts. Male birds are more flamboyantly coloured to attract a mate.

Then, of course, if you throw in intersex individuals, the whole dichotomy between man and woman collapses in its entirety. After all, where do you put intersex people if the system is binary in nature?

From a dating perspective, meeting and chatting with people who have transitioned has certainly opened my eyes to a few things. And it’s definitely been a different experience to dating cisgendered men and women.

While I have yet to actually go on a date with a trans woman, some of our chats have been quite productive as we strive to seek a connection on shared interests. True, one stopped chatting when Starfield released and pivoted their focus on the latest release from Bethesda, but the other was enthusiastic about pursuing new skills and hobbies.

Neither one of them led me to suspect this was all a means to ‘threaten’ or ‘undermine’ women. They were people simply living their lives in a way that best suited them.

And both of them were much easier to chat with than the trans man I did actually meet up with two weeks ago as of time of writing. For the sake of simplicity, though, I’ll codename them Tip Top (because they’re as bland as white bread).

From the outset, Tip Top was a difficult person to converse with. They seemed to have an obsession with pushing aside any type of heteronormative narrative when it came to how relationships formed – while still falling within the traps of what differentiates romance from friendship. They also liked to unnecessarily explain or clarify things. For example: danmei novels, which are essentially BL (boys love) by another name.

Then, of course, there was the way they pushed aside their cultural and ethnic heritage. While I understood they had issues with their family (something they implied in relation to their transition), it bothered me to no end how they also rejected almost anything relating to, as they described it, ‘Western pop culture.’ Which was one of the reasons why they disliked trivia or word-association board games.

It was a difficult thing to process. Especially given my two loves: Disney and the written word. I’m a veritable thesaurus with how much I read (and write)! To have someone target the very things I love in the first meeting, well, it dismayed me. A lot.

But it also made me wonder how much Tip Top actually engaged with the wider world.

As I’ve shown in my travel posts, I love engaging with the various cultures across the world. Truth, as is almost always the case, is stranger than fiction. The events that have shaped the trajectory of the world is fascinating. And seeing the world through the eyes of different people was the EXACT reason I fell in love with reading in the first place.

Given the limited time we have in the world, and the fixed perspective we have, it is eye-opening for me to see how others might interpret the world. So, knowing that Tip Top purposely closed themselves off, was a difficult pill to swallow.

Although, I can’t say I was surprised.

In the past, I’ve known other people who, like Tip Top, seemed to have lived sheltered lives or who show no curiosity about the world they live in. All of their focus is turned inward, with many of their views coming off as narrow-minded. Especially when they espouse dogma they’ve, no doubt, taken from people around them rather than develop their own views.

It can even make them seem self-centred and entitled.

Perhaps, it was as Tip Top said, that they didn’t have many friends in high school. And hadn’t been keen to connect with anyone because they were only living ‘half a life.’ And yet, I’m sure there are certainly a lot of trans people out there who still managed to be socially engaging with those around them prior to taking hormones and/ or surgery.

In the end, our conversations stuttered over Sunday brunch as Tip Top only seemed interested in asking me shallow questions and then refusing to truly engage with any of my answers. Whereas I tried to coax out more about who they were as a person, focusing on what they said their hobbies were on their profile. A part of it, I felt, was their struggle with expressing their thoughts. For example, when I asked them to elaborate about a visual novel they were playing, they tried to hedge around many of the details. Even when I said I was fine about spoilers.

So many little things irked me about Tip Top.

Worse, I couldn’t shake the similarities I found between them and a person I used to know, who, in a last update, identifies as a Caucasian man. While I can accept the fact they’re trans (I introduced them to the concept of possibly being non-binary when we previously griped about the woes of being a woman), I take umbrage on the fact they’re trying to claim an alternate racial identity. Especially as they were born, and look, East Asian.

But I digress.

This is about Tip Top and our rather lacklustre meet-up.

After we visited the bakery, for them to pick up a hojicha latte (although they were lactose-intolerant and also suffered a mild aversion to gluten), we walked around a nearby park before I bid them farewell.

It wasn’t the worst meet up I’d been on but it certainly wasn’t a good one either. And it makes me exhausted thinking about trawling through the disappointments to reach the diamond I’m hoping for. There is something to be said about being single. And yet, the more I age, and the more my friends go their separate ways, the more alone I’m starting to feel.

Maybe it truly is time for me to get a dog.