Dating After 50: The Uphill Battle of a F.U.B.A.R. Date

Dating in One's Middle Years #4

Why read on …

If you’re dipping your toes into the murky waters of middle-aged dating, you’re not alone. I’m here to share the trials and tribulations of finding romance after 50—because let’s face it, this isn’t as easy as they make it look in the movies.

Whether you’re new to online dating or just enjoy a good laugh at someone else’s misfortune, this tale of a date gone F.U.B.A.R. (that’s ‘F*cked Up Beyond All Recognition’ for the uninitiated) should hit the spot.

Several months into this whole ‘Online Dating Nightmare’, I caught up with a friend and may well have been bemoaning the realities. I’d bought into the idea that dating after 40 (or even 50) was going to be as easy as riding a bike.

Like bollocks it was!

There were a few similarities, but mainly a legion of differences:

1. The saddle digs into your soft parts

2. You seem to be forever cycling uphill

3. It is always much hotter than Hades

4. Every time you think you’ve found a rhythm, the chain falls off, so

5. You keep skinning your shins on the pedals, and

6. Finally, the finish line never, ever comes into sight!

So basically, it was pure hell!

After yet another disappointing date, I decided to give up the whole dating game for a while and focus on something more reliable - 🙈 excessive exercise 🙈.

It seemed like a sensible plan, but as fate would have it, I ended up with a sore chest and shoulder from overdoing it. This led to a conversation with a friend, during which I asked if he knew of any decent physiotherapists. Here, he had no hesitation. “You need to see J. She’s awesome.”

He said they did CrossFit together, and she was excellent.

He also mentioned she was funny, stacked, took no prisoners, had some world championship titles under her belt (Holy Moley), and was an all-round legend.

I had no idea what ‘stacked’ meant, so I asked.

"She's strong, mate," he clarified.

Okay, I figured it would be good to have someone capable of alleviating my injury, so I took the number and gave her a call. After a quick hello, J asked what the problem was and then arranged to visit me the following day for a dig around.

She arrived, lugging the table into my apartment, and I stripped down to my boxers. Having endured a public school education, being body-conscious wasn't really an issue. J whipped out a jar of coconut cooking oil (errr, okay) and began to gently work it into my chest and shoulder. So far, so good—not too painful, and her sharp wit was a great distraction.

About ten minutes in, J mentioned she was going to dig a bit deeper into the knot. I was only partially paying attention but remember thinking, “I can hack it." I was wrong! Pulling my arm away from my body and, with it partially on the other side of her hips, she dug her fingers deep into the knot in my shoulder.

"Mother f****r," I exclaimed. "That smarts!"

There was laughter and a polite suggestion, “Time to man up, Mark.”

Zero empathy, clearly. I can't remember much else about the massage other than a clenched jaw, pain perspiration, and many sharp intakes of breath … all whilst apologising frequently for swearing and trying hard not to cry like a baby!

Despite the pain and my string of expletives, J managed to keep the mood light with her sharp wit and easy conversation. By the time the session was wrapping up, I found myself feeling oddly comfortable with her. It was this unexpected ease that led me to blurt out, "Would it be inappropriate to ask you for a drink?" It wasn’t something I’d planned, but I couldn’t deny the curiosity that had been piqued during her visit.

She said, “No,” so I did, and we fixed a time to go out that coming weekend.

As she packed up her table and left, I felt a mix of apprehension and anticipation. I’d surprised myself by asking her out and was even more taken aback by her accepting!

The next few days were a blur which kept me from overthinking everything … a pleasant change!

We exchanged a few texts and perhaps a voice note, eventually settling on a Thai restaurant in town. J was more ballsy than many of the other women I knew, so when the weekend finally arrived, I felt more intrigued than nervous.

Predictably, about an hour before we were due to meet, my nerves kicked in, accompanied by my usual overthinking. After discarding a small mountain of outfits, I settled on what I like to call a 'casual suit'—something that seems to be a concept exclusive to our generation. I hoped it struck the right balance of smart and relaxed, though I wasn’t entirely sure I’d pulled it off.

J had insisted on making her own way to the restaurant, so I drove there myself, mentally rehearsing how I’d greet her. To my surprise, when we finally met, the conversation flowed naturally, and I found myself genuinely enjoying her company. She was more than just the no-nonsense physio who had inflicted pain on my shoulder - she was sharp, funny, and had the kind of life experience that made for intriguing conversation.

I’d never sat down for a date with a double world champion before—well, there had been that teenage fantasy about the famous Romanian gymnast, Nadia Comăneci, but let’s leave that in the vault of embarrassing memories!

Without thinking, I slipped into my hyper observant mode - a habit I’d picked up in childhood when trying to understand people who weren’t immediately readable. I like to think I’m subtle about it, but with J, who knew?

We ordered food, and in a misguided attempt to impress, I opted for a dish I remembered fondly from a trip to Thailand years ago. It was เผ็ด or 'pet,' which translates to… well, let’s just say it was spicy. Very spicy.

Spicy Hot, Hot, HOT!

The moment I took my first bite, I realised my mistake.

Nothing screams 'I’ve got this' quite like the sight of sweat pouring down your bald head, drenching your face in full view of your date. To make matters worse, my crisp white shirt only served to highlight the deep, embarrassing shade of puce my face had turned.

I struggled to string together a coherent sentence as the fiery spices took hold. Grabbing my soda and lime in desperation, I tried to casually mop my brow, but there was nothing subtle about it.

J’s steely gaze met mine, taking in the show, and then she howled with laughter.

Ouch… she really didn’t take any prisoners!

I joined in, because what else can you do? But while my laughter was genuine, it was tinged with a healthy dose of self-pity.

I mentally ran through my pre-date checklist:

• Look Cool - FAIL

• Dazzle with my witty repartee - BARELY

• Impress her with my culinary bravado - FAIL

• Maintain any semblance of dignity - FAIL

• Avoid making a spectacle of myself - UTTER FAIL

After about half an hour, the effects of the spices were dissipating, but I felt the damage had been done. The conversation had been entertaining, and J had proven to be fun company. On the flip side, I’d made a complete twerp of myself.

We wrapped up the evening and went our separate ways. Once home, I immediately jumped in the shower to cool down from my fiery supper. As the water washed away the sweat and embarrassment, I reflected on the evening. Despite my mishaps, I’d had a great time and decided I’d like to hang out with J again.

Over the next few days, we exchanged the odd text.

Then came the call …

J was talking when suddenly she dropped something into the conversation that I felt gave me an insight into her personality.

Don’t ask me what it was because I can't remember for the life of me. For some reason, completely unbidden, I felt an overwhelming compulsion to share my thoughts. So, I said something like:

"That's interesting, may I offer you some feedback?"

I know, I know:

• Useful in a coaching session;

• Of value in a board meeting;

• Frequently necessary on a leadership course…

But about as welcome as a fart in a lift when trying to flirt; in my defence, I’m beginning to recognise I may well be terrible at flirting.

“Go on,” something in J’s tone should have stopped me - yet it didn’t!

I heard the shift, a bit like the way a sudden absence of noise subtly registers on your subconscious. Anyone who’s spent time in any wilderness will recognise it:

It’s Nature holding its breath.

As J’s tone hardened, I was momentarily caught off guard. I’d thought my comment was innocuous enough—something that might even deepen our connection. But the shift in her voice was unmistakable. She was irked, and I was suddenly acutely aware that I’d misjudged the situation.

It wasn’t the first time I’d been blindsided by someone’s reaction, but it never got easier. I’d spent so much of my life in environments where feedback was a constant, often necessary tool—something valued in professional circles and even amongst friends. But here, in this budding personal connection, my well-meaning ‘insight’ had clearly crossed a line.

J was firm, clear, and brutally honest as she made it known that we wouldn’t be seeing each other again. There was no room for negotiation or second chances. I could only sit there, listening to the line go dead, wondering how I’d managed to turn something so promising into yet another F.U.B.A.R. situation.

Reflection

Sitting there, staring at my phone, I couldn’t help but feel a mix of frustration and disappointment. How had I managed to turn a promising start into a complete disaster in just a few sentences? It was a humbling reminder that the skills that served me so well in one aspect of my life could be utterly useless - or worse, detrimental - in another.

Reflecting on the evening, I realised just how much I still had to learn about this whole dating after 50 malarkey. It wasn’t just about finding someone you could connect with; it was about navigating a minefield of unspoken rules and expectations - something that was proving to be far more complex than I’d imagined.

But despite the missteps and the painfully clear lesson that unsolicited insights are rarely welcome, I couldn’t deny that I’d enjoyed myself, right up until that last, ill-advised comment. The date, while ultimately a failure, had been fun, and that had to count for something.

So, what did I take away from this?

Well, I’ve learned to keep my ‘helpful’ feedback to myself unless explicitly asked for it.

But hey, at least I knew one thing for sure: I’d never make that mistake again.

Well, hopefully not.

And I’ve realised that maybe, just maybe, the key to dating in your 40s and 50s isn’t about being perfect, but about being open to the experience—no matter how many times the chain falls off the bike.

So here’s to the next ride - who knows, it might just be the one where I finally keep my big mouth shut. And if not, well, at least I’m learning as I go.

Maybe the next time, I’ll manage to navigate the bumps without crashing so spectacularly. Click here to follow along with my previous misadventures.

(If you’ve enjoyed this read, click the ❤️ button or drop me a comment - it really helps keep me motivated to keep sharing my disasters!)