Dating. Dating, dating, dating.

This is actually the first article I’ve tried to dictate properly since having my voice surgery.

It’s a wet Thursday afternoon in Cork, normal weather has resumed, and I’m trying to speak very gently because that seems to be the deal with my new voice at the moment. If I speak softly, it behaves itself. The minute I try to project, interrupt somebody, or generally behave like I have done on work calls for the last 30 years, it starts squeaking, fading out and rasping.

This is especially irritating when I’m on calls full of men and I desperately want to butt in and tell somebody they’re wrong.

I try.

My voice goes shrill.

Welcome to being a woman, I suppose.

Anyway.

Dating.

Dating, dating, dating.

This is something I have deliberately stayed away from for quite a long time.

There were lots of reasons.

The obvious one was that I had just come out of a 19-year marriage. Whatever happened at the end of it, you don’t spend nearly two decades building a life with somebody, having children, getting richer, getting poorer, raising a family and going through all the utterly mundane shit that eventually becomes a marriage, and then wake up the next morning ready to download Tinder.

Or whatever people download these days.

I wasn’t remotely ready to start thinking about somebody else.

There was another reason too, which I may as well be honest about.

Before I had my downstairs surgery, I felt horribly insecure about the idea of getting into bed with somebody.

I just didn’t want to.

I didn’t want to take my clothes off and feel like I was presenting somebody with a structural mismatch.

I know perfectly well there is a huge sexual marketplace for pre-op trans women. There are men who absolutely love that configuration. There are trans women who like having that anatomy and have no intention whatsoever of changing it. Good for them.

It was never me.

I didn’t want to be desired because somebody had a transsexual fetish. I didn’t want to be somebody’s exotic sexual experiment. And I certainly didn’t want to preserve bits of my anatomy because they made me more commercially marketable on OnlyFans.

I’d rather make my money with my brain.

So I stayed out of it.

But there was another, rather more complicated problem.

I had absolutely no fucking idea what I was anymore.

I had spent most of my life assuming I was a straight man.

And if I’m being completely truthful, I had occasionally wondered just how straight that straight man actually was.

I think I was pretty straight.

But perhaps not absolutely, mathematically, 100.0000% straight.

There may have been a tiny crack somewhere.

And transition wedged it open.

Suddenly I had to ask myself a question I had never seriously needed to answer before.

I know I like women.

But do I like men a little bit too?

Well, I have subsequently accumulated quite a lot of data on this question.

Mostly: no.

The amount of male attention I get now is completely fucking ridiculous.

And 99% of the men interested in me do absolutely nothing for me whatsoever.

In fact, quite a lot of them creep me out.

The idea of lying next to some sweaty farting bloke with a scratchy face who hasn’t brushed his teeth and then having him burp on me is not, I have discovered, one of my major erotic fantasies.

But then occasionally I’ll see some slightly beautiful, artistic-looking man and think, yes, actually, you look quite nice.

Cillian Murphy rather than Sylvester Stallone, shall we say.

So I’m not going to declare men entirely outside the field of play.

But women?

Women are different.

Women are just lovely.

They’re softer. Prettier. More interesting to look at. More attractive to me.

Although even that gets complicated, because I now understand something that femme lesbians have apparently been laughing about forever.

Do I fancy her?

Or do I want her hair?

Do I want to kiss her?

Or do I want to know where she bought that dress?

Or both?

Before transition, I would look at women in what I can only describe as a weirdly technical way.

A normal heterosexual man might look at a woman and think:

“Fuck, she’s hot.”

I would be thinking:

“She looks really hot. That dress is amazing, although I think it could do with two little darts in the back. I’m not convinced about those shoes either. And she definitely shouldn’t be wearing dark tights with that colour.”

Or I’d be studying her eyeliner.

How had she done the flick?

What colour had she used?

Why did that eye shape work?

This was supposedly me looking at women as a heterosexual man.

With hindsight, it was all rather suspect.

And my attraction to women was never quite like the version of heterosexual male attraction I saw around me either.

I wasn’t a bloke who sat around watching pornography. I didn’t spend my life mentally undressing women. That whole way of looking at women felt alien to me.

And during sex, all my life, I imagined myself as the woman.

It was the only way it worked properly.

So was I a heterosexual man attracted to women?

Or was I always, in some peculiar scrambled way, a woman attracted to women?

I honestly don’t know.

Perhaps trying to retrospectively classify yourself is a fool’s game anyway.

I know that I loved women. I know I loved the woman I spent 19 years with. Nothing I discover about myself now retrospectively changes that.

What has changed is that I can finally look at all of this without having to make it fit the old explanation.

Eventually I decided the only sensible thing was to get some data.

So I created profiles on a few dating sites.

One was exclusively for women. Another was mixed.

On my profile, the first thing it says is TRANS.

Literally the first thing.

I am not hiding anything.

And still, whenever someone attractive starts talking to me, there is a small part of my brain going:

You did actually read the profile, didn’t you?

You did spot the trans bit?

I don’t want to say it out loud because that sounds needy and strange.

And then there is another sentence I sometimes want to say:

You do realise I’ve had the downstairs surgery, don’t you? Matching collar and cuffs. There is no surprise structural engineering.

I don’t usually say that either.

Instead, you chat.

Chat.

Chat.

And sometimes:

Boom.

Gone.

I assume they went back, read the profile properly and thought:

“Oh. Jesus. Transgender.”

And that is completely fine.

It really doesn’t hurt me very much.

It is simply maths.

There is a percentage of the female dating population who will never date a trans woman. Fine.

Then there is a percentage who might find me attractive but haven’t actually read the profile properly.

Also fine.

Then there is whatever remains.

Statistical arbitrage.

It is what it is.

This was my experience of life. I was destined, apparently, to spend a large part of it as a man and then become a woman.

I’m increasingly at peace with that.

I loved the life I had before. I loved being a dad. I loved my family more than words can say.

And I love being this person too.

Those things don’t cancel each other out.

Anyway.

Back to my extremely scientific dating experiment.

On the mixed dating site I was absolutely inundated with men.

Inundated.

And some of them were really handsome.

Young ones too.

Twenty-five, thirty, forty.

And I would sit there staring at the messages thinking:

They do realise what I am, don’t they?

Do they know I’m transsexual?

Is this a kink?

Is this just something men do?

I genuinely had no idea.

Mostly I just let the messages accumulate and laughed.

Occasionally I would think about Stephen Bennett and wonder what he would have made of the fact that all these men were now trying to shag him.

That still makes me laugh.

The women were slower.

But on the women-only site I eventually started getting some traction.

And, somewhat to my surprise, some really attractive younger women started showing interest.

This introduced another problem.

I am 57.

I have my shit together.

I have a career.

I have a nice house.

There is food in the fridge.

I own furniture.

Bills generally get paid.

There isn’t a random mattress on the floor next to three empty cans of Monster and somebody’s vape.

Apparently these things become impressive if you’re young enough.

And I could feel it happening.

Some younger women would become weirdly impressed with me.

Which initially is lovely.

Who doesn’t like being admired?

But after a while, somebody kissing your arse becomes irritating.

I don’t want a fan.

I want an equal.

Then you look towards people closer to your own age and encounter another inconvenient truth about dating which nobody is really allowed to say out loud.

You still actually have to fancy them.

So I find myself trapped in a slightly ridiculous Catch-22.

The younger attractive ones sometimes seem impressed by me in a way I don’t particularly want.

The older ones might be more intellectually aligned, but I’m often not physically attracted to them.

And my God, the lesbian dating pool is small.

I now understand all those jokes.

Two lesbians meet on Monday and are living together by Friday.

Someone says they live 400 miles away and the response is:

“Oh great, you’re quite local then.”

I get it now.

There simply aren’t that many of us.

At one point, a few months ago, I actually did bring a woman home.

I haven’t written about this publicly before.

She was considerably younger than me.

And if I’m completely honest, the whole thing was an experiment.

I didn’t really know what I was supposed to do.

That is the truth.

Before, sex had fairly obvious mechanics.

Now?

Fuck knows.

I’ve never watched pornography, so I couldn’t even fall back on years of visual education.

I basically had to play it by ear.

But something happened that I had never experienced before.

As I undressed, I felt proud of my body.

Actually proud.

And then this woman started absolutely lusting over it.

She thought my body was fucking incredible.

She couldn’t stop looking at my breasts.

She kept telling me how amazing my torso looked.

And my brain practically exploded.

Because I never had a particularly good male body.

Now I apparently have quite a good female one.

There is something utterly surreal about being able to look back at photographs of this very masculine-looking man and then finding yourself in a bedroom while an attractive woman is losing her mind over your tits.

I chuckled about it afterwards for days.

I still chuckle about it.

Was I sexually enjoying the attention?

Or was I just getting an absolutely enormous ego hit?

Probably quite a lot of the latter.

If I’m being brutally honest, I was using the situation to answer a question about myself.

I had experienced a lot of hurt and rejection during transition.

And I wanted to be desired.

That was it.

I wanted somebody to look at me and think:

I fucking want you.

And she did.

In abundance.

She stayed the night.

In the morning I drove her back to her hotel and said goodbye.

She left her earrings in my house.

That made the whole thing even more absurdly real.

And afterwards?

It wasn’t especially fulfilling.

Partly that was physical. My newly reconfigured downstairs equipment was still pretty raw and wasn’t particularly ready for enthusiastic field testing.

But mostly I think the experience taught me something else.

Being lusted over was extraordinary.

It was flattering.

It was validating.

It was surreal.

But it wasn’t what I actually wanted.

What would have meant more?

A really, really good chat with somebody who also found me attractive.

That’s it.

A spark.

Which brings me to the rather awkward question of what I actually want from dating.

And unfortunately I know the answer.

I want a hot woman of about 45.

Clever.

Funny.

Someone who spars with me.

Someone who tells me I’m being stupid when I’m being stupid.

Someone who tells me I’m an egomaniac when I’m being an egomaniac.

Someone who laughs at my jokes when they’re funny and tells me when they aren’t.

Someone who makes me laugh.

Someone competent.

Someone different from me.

Not flashy.

Warm.

Sharp.

A little lighter than me.

None of that is especially new, as it turns out.

I’ve had enough life now to know what chemistry feels like when it works.

For me it isn’t grand romance or being constantly told how wonderful I am.

It’s sitting around talking absolute rubbish with somebody clever.

Taking the piss out of each other.

Both knowing you’re joking.

Both knowing the other person knows.

Then deliberately taking it another level deeper.

That sort of playful metacognition is probably one of my favourite forms of intimacy.

I want somebody who can do that.

But I also know I don’t particularly want to recreate my old life.

I like living on my own.

I like my little house.

I like having my own space.

The end of a very long relationship and splitting one shared life into two separate ones was traumatic enough that the thought of immediately building another giant merged life with somebody makes me slightly queasy.

I don’t need another person’s socks mixed into my washing machine just yet.

But would I like somebody sitting next to me in the evening?

Yes.

Would I like someone to cuddle up with on the sofa and watch television?

Yes.

Would I like someone to tell all my stupid thoughts to?

Very much.

Would I secretly quite enjoy somebody initially being really impressed by me?

Absolutely.

I’m human.

There’s a certain pleasure in the varnished version.

The competent woman.

The glamorous woman.

The one with the career and the stories and the nice house and all her shit apparently together.

But I’m also perfectly happy for the varnish to fall off eventually.

Because underneath it I am still a bloody nerd.

I will still get ridiculously excited about some stupid technical system.

I will still explain my agentic AI architecture to somebody for 25 minutes after they stopped caring at minute four.

In some ways Stevie and Stephen aren’t that different at all.

I don’t actively try to preserve bits of him or throw bits of him away.

I’m just this.

The systemsiness is still there.

The nerdiness is still there.

The stupid jokes are still there.

There is just confidence now that wasn’t there before.

Peace.

Truthfulness.

Openness.

Perhaps the simplest description I can give is this:

I am Stephen without the bullshit.

And I think I would be a vastly better partner now.

Lighter.

Kinder.

More giving.

More open.

Less guarded.

If I imagine being with a woman now, it feels completely different from imagining myself in a heterosexual relationship as a man.

It feels lovely.

I feel off guard.

I get to be chatty and stupid and soft and playful.

I don’t have to perform anything.

I get to be myself.

Yes, I know.

What an appalling transgender cliché.

But sometimes clichés become clichés because they’re true.

So perhaps that is where I am in the marketplace.

I don’t particularly want casual sex.

I never did.

I have never cheated on anyone in my life. Never two-timed somebody. Never been interested in pickup culture, hookup culture, Netflix and chill, or whatever the fuck everybody calls it this week.

That experiment was an aberration.

A hurt person wanting proof that she could be wanted.

And now I have the data.

Apparently I can.

Great.

Experiment concluded.

What I actually want turns out to be much less exotic.

A woman I fancy.

Who fancies me.

Who is clever enough to tell me I’m full of shit.

Who lets me tell her she’s full of shit too.

And then, hopefully, we both laugh.

That would do me.