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Dating as a Trans Woman

Updated: Dec 16, 2020

Dating is a part of everyone’s life, some are more successful at it than others. Can we all agree that it’s already hard enough without being born in the wrong body?

I think we need to start at secondary school, because let’s face it - holding hands at primary school does not count. And even if it did, I wouldn’t be able to tell you much about it.

Secondary School

My secondary school experience wasn’t the brightest - especially after being consistently labelled as gay, which definitely put obstacles in the way. If I’m being honest, I didn’t really care about it though. I knew I wasn’t ready for a relationship back then and I guess I’m still not ready today.

Don’t get me wrong, I did feel a little jealous of my girlfriends being in couples - and who doesn’t have their first crush in secondary school? But even back then, I knew I had to find myself before anyone even had a chance with me.

Of course, there were a handful of gay and bi guys in my school, but I paid no attention to them - well, half of them weren’t out yet. I don’t blame them though, neither was I.

Mind you, no one paid attention to me either! I mean, I was nothing like I am today personality wise - and I hope I have changed on the outside too. To everybody, I was a little shy Polish boy running from class to class with my girlfriends. I was rather insecure about potential romantic interests, because even I didn’t know who I was.

Sixth Form

So, then we move up into my sixth form college, I stayed in the same town, so a lot of people I went to school with were here too. I thought I would just blend in again and call it a day, but I guess the universe wanted something different from me.

At large, my dating life (or the lack of it) remained the same; until I decided to throw caution (alongside a vague LGBT flag) to the wind. During sixth form I felt much more comfortable with myself. My friends were amazing, and I was just able to be myself - I felt accepted regardless of my gender identity.

I decided to slowly show more of myself - no Karen, not more of my skin, more of my personality. And with that, came a little attention from guys. And not the ones in the closets - the ones in an apocalypse-style bunkers.

I mean, one tried to kiss me at a party - and no offence, but you’re a minger - so no.

Social media

Once I was expressing myself more through social media (after having left sixth form), my DMs started sparking with attention from some of my classmates - and that was just embarrassing, for them.

At this point, I was gearing myself up to come out as trans… so I was definitely looking a little more feminine, which draws people’s attention - especially guys.


When I went to Uni, I came out to a handful of people - which allowed me to also be more open with potential romantic interests.

This led me to dating this one guy for 4 months. BIG. MISTAKE.

You know what they say, you have to kiss a few frogs before you get to the prince… well this was a toad.

To be perfectly honest, he was a very kind guy - really respectful, mature, caring blah blah blah. But there isn’t much you can do when you don’t like his face. I used to tell myself “he’s good for me”, “he won’t hurt me” and “this is a sensible decision” - but that went out the window when I realised my worth. So, I sent him a text:

“Uhh please don’t message me again”

So that was that, and I went on to enjoy a lovely Christmas.

New year, new me

In 2020, I decided to focus on myself, and just have fun. I’m only a teenager once in my life, and I have to embrace this student lifestyle the best I can. This meant going on several dates, so many in fact, I had to double book one of my nights. But I’m glad I did.

I met this really nice guy who knew exactly what he wanted, he was a hard worker and hot af. Need I say more?

I don’t think I will be in a committed relationship anytime soon. I believe so many people spend so much time and effort into making something work - when in reality, we should be putting that effort into loving ourselves.

This goes for everybody: don’t search for love outside of yourself, when you can’t generate your own love.

Yes, yes, I get it - we all like a cuddle from time to time - but that’s what you get a cat for, otherwise they’re just an expensive fur generator.

Throughout my dating experiences as a trans woman, I always wonder:

First of all, why are these guys even interested in me? There are so many smart and beautiful cis girls out there - and not to get all depressing on you, but why would they even choose me over a cis girl? Alternative intentions come to mind - and it’s something I’ve always been wary of.

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