Dating After 50 / The Dating Files: James and the Sudden Self-Improvement Phase

James arrived already mid-transformation.

You could tell straight away. The clothes were newer than the habits. The haircut had been booked recently, possibly in a mild panic. There was a definite sense of "I’ve decided to get my life together and I’m hoping you’ll notice"  which in theory is admirable and in practice is… revealing. It makes me wonder if this is only found in the "dating over 50" category, on the basis that younger candidates haven't had as much time to "let themselves go"!

He talked about eating better now. Going for walks. Making more of an effort. Wanting companionship. Wanting something settled. Wanting a woman in his life. All reasonable desires. All delivered with the quiet urgency of someone who’s only just realised this might require some preparation.

Because this wasn’t a man who had always taken care of himself and slipped slightly. This was someone who had neglected himself for years — gently, incrementally — and had only recently clocked that this might be an issue if he wanted to start dating again.

And it showed.

His smile arrived before his teeth did. Or rather, not all of them. The ones that were present looked like they hadn’t been introduced to toothpaste on a regular basis for quite some time. Not dramatic. Not shocking. Just… under-maintained. Like the dental equivalent of I’ll get round to it.

Then there were the trainers.

They were blinding. Immaculate. Whiter than white. So white they almost felt ceremonial. I complimented them (as I couldn't miss them), and he beamed and said, “Yeah — my nephew told me to get some new shoes if I was gonna start dating.”

He said this proudly. As though the nephew had cracked some ancient code.

Once you hear something like that, your brain quietly opens a new tab.

The jumper followed the same theme. New. Clean. Clearly chosen with intention. And when I mentioned it — again, politeness — he nodded and said something along the lines of yeah, I’ve been told I need to make more of an effort now.

Now.

There’s a very specific energy that comes with this phase. A slightly rushed quality. Like someone revising for an exam they didn’t realise was happening until five minutes ago. New shoes. New jumper. Fresh haircut. All good things. All very late.

What he hadn’t applied the same sudden discipline to, however, was his house. This emerged slowly, as these things always do, once the conversation drifted towards where we lived. Not addresses — just descriptions. He spoke warmly, but vaguely. There were phrases like “a bit lived in” and “I’ve been meaning to sort that”. The kind of language people use when they’re hoping enthusiasm will carry you past the details.

It rarely does.

By the time the picture filled itself in, it was clear the house had been treated much the same way he’d treated himself — as something to get round to later. Years of deferred maintenance. Things started but never finished. A general sense that comfort had quietly tipped into neglect without anyone noticing when it happened.

And this is where it really lands.

You can’t fast-track wholeness.

You can’t undo years of neglect with a decent jumper, a haircut and a pair of trainers your nephew recommended. You can’t suddenly decide you’re ready for a relationship without addressing the environment you expect another human being to step into.

Because when a man tells me he’s “making an effort now”, what I’m quietly listening for is where that effort stops.

Does it stop at the outfit? At the shoes? At the surface?

Or does it extend to the things that require consistency rather than compliments — like teeth, routines, houses, and the general maintenance of a life that doesn’t come with a repair list?

James wasn’t a bad man. He wasn’t obviously lazy. He was just very used to living in a way for many years that worked entirely for him. And now, having decided he wanted company, he was scrambling to retrofit a version of himself that might be acceptable to someone else.

That’s not transformation. That’s back-pedalling in new trainers.

There’s also something faintly unsettling about realising you’re being dated by someone who is actively upgrading themselves at you. Like you’re not a partner, but the incentive. The reward at the end of the self-improvement programme.

I don’t want to be the reason a man finally buys toothpaste.

What stayed with me wasn’t really the trainers, or the jumper, or even the teeth. It was the assumption underneath it all — that certain things could remain unfinished, unmanaged, or quietly ignored, and that a woman would simply adapt around them. That if enough visible effort was made out there, the rest would somehow matter less.

It doesn’t.

By midlife, houses tell stories. So do habits. So do the things we’ve chosen not to deal with. You don’t have to be perfect, but you do have to be complete enough not to hand someone a list of things you’re hoping they’ll overlook.

Or worse — quietly fix.

James is probably still improving himself. I hope he keeps going. I hope the effort lasts beyond the dating phase and turns into something steady and self-directed.

But I know this now:

I’m not interested in men who only start valuing themselves because they want a woman.

I want someone who decided they were worth the effort long before anyone was watching.

Join us next time to meet "David ", the one whose biggest priority was a physical relationship.