Dating After 50 /The Dating Files: What Fresh Hell Is This?

Welcome to The Dating Files and dating after 50— a loosely organised record of modern dating after fifty. Names have been changed, details have been blurred, and some men may not recognise themselves.

Are you looking for a "Harold"?

Dating after fifty is like trying to assemble IKEA furniture without the instructions, the Allen key, or the faintest belief in yourself. You know roughly what you’re aiming for, but the pieces don’t always fit, something keeps wobbling, and you’re left holding a few mystery screws wondering where it all went wrong.

This is part of The Dating Files — which is really just me trying to make sense of modern dating at this age, one mildly unhinged encounter at a time. Names have been changed. Details blurred. Some men may not recognise themselves. That feels appropriate.

For many of us in our mid-fifties and beyond, online dating has become the default. Not because it’s fun, but because apparently this is how you meet people now. What’s sold as a straightforward path to companionship often turns out to be more like a social experiment with emotional side effects.

And yet… here we are.

The thing nobody really prepares you for is the profiles. The optimism. The creativity. The sheer audacity. Photos are frequently from a previous decade. Bios are packed with phrases like “I love to laugh” (who doesn’t?) or “looking for my partner in crime” (what crime, exactly?). Everyone claims to be active, adventurous and emotionally available, which is fascinating, given the evidence.

Then there’s the tech side of things. Uploading a photo without accidentally sharing your Tesco delivery order. Trying to work out why the app keeps showing you men who live 200 miles away and list “motorbikes” as a personality. Decoding what “active lifestyle” actually means — is this long countryside walks, or does it just mean standing up occasionally?

And the messages. Oh, the messages. Opening lines range from the baffling to the deeply unfortunate. “Hey sexy.” “You look great for your age.” “What are you doing tonight?” at 8am on a Tuesday. It’s a lot.

One woman matched with a man who described himself as a world traveller. Turned out he’d been to Tenerife twice and the Bluewater car park. Another date spent the entire evening talking about her cats. Not having cats. Auditioning him for shared custody. At that point, you start to wonder whether you’re on a date or being assessed for a role you didn’t apply for.

Eventually, some people decide they’ve had enough of swiping and try a matchmaker instead. This is online dating with a clipboard, a consultation, and a bill that makes you briefly question all your life choices. Matchmakers promise carefully vetted matches, personalised introductions and the removal of endless scrolling. What they don’t promise is magic.

One man joked that after paying several thousand pounds, he expected violins, champagne and perhaps a dramatic entrance. Instead, he got a coffee in Costa and a woman who arrived ten minutes late and asked about his pension before he’d finished his drink. Romance, but make it actuarial.

Dating after fifty also comes with conversations younger daters haven’t earned yet. Ex-spouses. Adult children. Knees that click when you stand up. Chats that escalate from light flirtation to medical disclosure with alarming speed. At some point, one of you will mention an operation, a hearing aid, or the fact that QR code menus feel unnecessarily aggressive.

One couple bonded over their shared inability to order food without speaking to a human being. It could have been awkward. Instead, it was oddly comforting. Nothing says intimacy like mutual confusion and a waiter taking pity on you.

At some point, you do learn a few things. Be honest — it saves everyone time. Not every date is “the one”, but basic decency is non-negotiable. Trust the feeling in your stomach. Meet in public. And know when to take a break before you start resenting every man with a bathroom selfie.

Dating after fifty isn’t about perfection. It’s about curiosity, connection, and occasionally surviving stories you’ll dine out on for years. There is no instruction manual. No shortcut. No guarantee. Just a series of encounters ranging from mildly promising to absolutely not, each one teaching you something — even if that something is never again.

So if you’re swiping, matching, meeting, or quietly recovering, remember this: every awkward message, every baffling profile, every date that becomes a cautionary tale is part of the experience.

What fresh hell is this?

Apparently, dating. And somehow, against all logic, we’re still game.