‘I started dating men for the first time at 47 – this is what it’s really like’

Chloe Kelly transitioned at 45, and decided to enter the dating market at 47. She thought she understood how men think. Writing for PinkNews, she says the reality has been very different…

Having your first date with a man at the age of 47 is quite something.

Sure, I have had dates before. I have had long term partners. I have even been married. But all of that happened when I was living as him.

Now, two years into transition, I have just started dating men for the first time and it is infuriating.

You would think that spending 45 years living as a man would give me the inside scoop. Some secret knowledge about how they think. But girls, I am as clueless as the rest of you.

At 45 I stopped fighting the truth that had quietly haunted me my entire life and finally accepted that I was trans. The shame. The denial. The low level sadness that felt like a dripping tap somewhere deep in my soul.

For most of my life I told myself I was a straight man.

Turns out I am a straight woman.

And frankly it is deeply inconvenient.

Life would be much simpler if I could just be a lesbian. But no. Instead I have found myself bewitched by those strange, hairy creatures we call men and I have absolutely no idea how it happened.

The confusing part is that I do not even seem to like them that much.

I find them annoying, boring and faintly ridiculous in an “aww bless” sort of way. Yet despite all of that I am also ridiculously attracted to them and spend an alarming amount of time wishing I had one of my own.

Like I said. Inconvenient.

So how exactly do you go about acquiring a man?

Honestly, I have no idea. Which is why I am writing this article.

The whole experience feels a bit like fishing. Except now I am on the other side of the water. Or perhaps in the boat. I am not even sure where I am anymore.

When I was dating women back in my previous life I always felt like I understood the rules of the game. With men, I have absolutely no idea what is going on.

One minute they are bombarding you with attention and messages.

The next minute they vanish without a trace.

The last time I was single was around 2010, and back then dating apps existed but they were not the entire ecosystem.

Now it seems that, like everything else in 2026, dating only happens through an app.

My profile does reasonably well. I am actually a fairly attractive woman, especially for my demographic, and I currently have over three thousand likes on my profile.

I refuse to pay for the premium version though.

Which brings us back to the fishing analogy.

I get plenty of nibbles. Reeling one of them onto the good ship First Date is another matter entirely.

There is another layer to all of this.

I am fortunate in that I pass easily in everyday life, and looking at my profile you probably would not know that I am trans.

Initially I did include it on my profile.

I removed it after 48 hours.

Let us just say the messages I received during that brief window left me feeling like I needed a shower in alcohol sanitiser. The fetish brigade found me very quickly.

So here I am. Forty-seven years old. Dating as an attractive woman. With significant interest from men.

And yet somehow it still feels almost impossible to actually get a date.

Is this because I have only six months experience dating as a woman?

Or is it because men now have so much choice on apps that they simply cannot be bothered to go on real dates anymore?

One harsh truth I have already discovered is that the men I am attracted to tend to have options. Lots of them.

They are handsome. They know it. But more importantly they have that cheeky spark that makes me smile when they turn the charm on.

Unfortunately, when they turn it off, it drives me completely mad and makes me want them even more.

The nice guys, meanwhile, can sometimes feel a little beige in comparison. Which is frustrating because logically I know they are probably the better choice.

This is not exactly a groundbreaking discovery for most women.

But it is a revelation for me.

Another complication is that my body now runs on oestrogen thanks to hormone therapy. The process is often described as a second puberty and honestly that description feels accurate.

Emotionally I sometimes feel like a 15-year-old girl discovering boys for the first time.

The problem is that I am simultaneously expected to function as a calm, composed middle-aged woman in everyday life.

So internally I might be thinking “he is dreamy” while outwardly trying to behave like a responsible adult.

Which means that yes, the confident ones, the cheeky ones, and the occasional charming disaster all get my overly enthusiastic right swipe.

In the past six months I have been rejected. I have been ghosted. I have been ghosted so many times that I now treat it as the default outcome.

And yes, I have cried.

Quite a lot.

But I keep going.

Because what I am really trying to do is compress an entire lifetime of romantic learning into the space of a few years.

Sometimes I wonder whether the men I date sense something slightly odd. A sort of Freaky Friday energy.

A teenage girl somehow trapped inside the body of a middle aged woman.

Then again, they probably have not noticed at all. What do I know?

Still, I will keep going.

Because like everything else in life, the more experience you gather, the better you become.

Somewhere out there, presumably, there is a man worth all this chaos. Until then, I will keep fishing. After all, I only need to land one good one.

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