Standing on the Edge: Dating After 50

Trying to navigate the dating world as a 50+ man feels… complicated.
Especially when you’ve been out of the game for 25 years. It’s a whole new ballpark — but somehow, the games are still the same.

Here’s the thing: I’m not here to play games. I’m not diving into that cesspool again. I’ve got better things to do with my time — things that bring actual joy, progress, and peace to my life.

Don’t get me wrong, I still believe that dating — and maybe even love — can add meaning and happiness. But putting in the effort to build a real connection? That part is hard as hell.

There’s one person I’ve been seeing — the one I’ve mentioned before. My comfortable distraction.
He’s 27 years younger than me, and yeah… that gap brings its own kind of chaos. Our values, our goals, our ambitions — they orbit in different galaxies. Sometimes it’s beautiful, sometimes it’s confusing, and often it’s frustrating as hell.

We both said we wanted to see where this goes. But finding time together? That’s been the real challenge.
We had our first little tiff about it — and since then, there’s been distance.

And here’s what I know for sure:
I refuse to be the one doing all the emotional labor again. I did that for 25 years. It drained me — mentally, physically, spiritually.

In my relationship with Kerry, if I didn’t start the conversation, the silence swallowed the room.
Didn’t matter if I was happy, sad, or falling apart — if I didn’t open my mouth, the night passed in silence.

And when I did try? When I asked simple questions like, “How was your day?” I got, “Same as every other day. Why do you keep asking?”
So I stopped asking.

I stopped asking if he loved me, too.
The last time I did, he yelled — “Why do you keep asking me that?”
So I never asked again.
And he never told me again that he loved me.

That silence became a weight I carried for years. It chipped away at my self-worth, my confidence, my ability to believe I was worthy of affection without earning it.

And now, when I’m with this new person, I feel those echoes.
When he cancels plans or gets too busy, I tell myself to be patient — he’s got a lot going on. But when I see him finding time for other people, those old wounds crack open again.

I spiral.
The same voices whisper: You’re too old. Too fat. Not enough. Not exciting. Not worth it.
And the darkness starts to settle in.

I don’t want to live in that place anymore.

My friend Dave says, “Well, you know what to do.”
Maybe I do. Maybe I don’t want to hear it.
Because the truth is, when he smiles, I don’t want to give up.

So here I am — standing on the edge again.

He’s starting his life, and I’m gearing up for retirement.
He’s chasing beginnings, and I’m craving freedom. I want to play, to live, to move, to change.
I don’t want to be tied down anymore — not to a house, not to an old version of myself, not to pain that doesn’t fit me anymore.

But damn… I still want to be seen.
I still want to be chosen.

What the fuck should I do?

— Standing on the Edge