Online Dating Over 40: How Important is Emotional Readiness (What Happens If You Ignore It)

Dating in One's Middle Years #5

Curious about what dating really looks like in your 40s or 50s?

Buckle up for another round of my somewhat misguided journey through the highs, lows, and sheer absurdity of the modern dating landscape.

I realise that at this stage, I may not be the best advertisement for the joys of midlife dating -more like a cautionary tale, really - but if nothing else, I’m committed to making you feel better about your own chances. 😎

Some time had passed since my last ill-fated venture into the dating arena, and the memory of just how draining the whole experience can be had faded just enough to tempt me back into the pool.

But, variety being the spice of life (whoever said that clearly wasn’t talking about dating apps!), I thought it might be time to switch things up a little. So, in a moment of either brave foolhardiness or foolish bravery, I switched from the dating app that rhymes with “Catch” to the one that rhymes with “Fumble.” (An ironic choice, as you’ll soon see.)

After a month of exchanging messages with a perfectly pleasant woman who lived about 40 miles away, I decided it was time to meet in person. Our conversations had been enjoyable enough, although there was one peculiar moment when she asked if I had attended a certain school. Now, as a former pupil of a boys-only school, I couldn’t help but wonder where this line of questioning was heading.

Warning Sign: When Your Date Knows Your School

Imagine my surprise when she named it correctly. It turns out she was sitting with someone who had known me when I was 16 years old, though she took protracted delight in making me guess their identity… it turned out to be the daughter of one my old school’s teaching staff!

The phone was handed over and I stumbled through the usual questions when one is surprised by a voice from the past.

• How are you?

• How’s your Dad? (code for: Is he still alive?)

• What have you been up to … FOR THE LAST 3 DECADES!?

I found this all a little odd but played along.

In hindsight, I probably should have seen that as a sign. However, as any observer of my floundering attempts to date will be realising by now, I’m perfectly capable of missing almost every social queue!

As many seasoned daters liked to tell me, a bit of mystery is exciting, but when it starts to feel like an episode of This Is Your Life, it’s usually a harbinger of less positive things to come.

Notwithstanding all of this, the day of our date arrived, and I climbed onto the bike for the single hours journey to our rendezvous. We’d agreed to meet at a quaint eatery in some nondescript town not too far from Bath.

My date appeared on time and, even better, was the person in the photos (here’s a previous episode where catfishing took place!)

We chatted pleasantly enough, but I couldn’t help but notice the place she’d chosen was eerily quiet, save for us and a solitary young waitress hovering nearby.

I sensed something was off but couldn’t quite put my finger on it.

She was animated, almost overly so—like someone who’d had one too many espressos. There was a strident edge to her voice, a frenetic energy that was both exhausting and slightly unnerving.

Despite her efforts to put me at ease with frequent touches on my arm, I couldn’t shake the feeling that something wasn’t quite right. This wasn’t the calm, confident person I’d been chatting with online. Perhaps she was just nervous, I told myself. First dates can be intimidating, after all. But as the minutes ticked by and her monologue continued unabated, I began to wonder if it was more than just nerves.

Finally, after 20 minutes of polite nodding and forced smiles, I couldn’t take it anymore.

“May I ask you a question?” I said, bracing myself for her response.

“Yes, of course,” she replied, her wide eyes a mix of curiosity and trepidation.

“Are you okay? You seem on edge,” I asked, as gently as I could.

I didn’t know it then, but those words would prove to be the trigger for an emotional deluge. Her face crumpled, and within seconds, she was weeping. Not just a delicate tear or two, but full-on, body-shaking sobs. In an instant, she latched onto my arm as though it were a lifeline, clinging to me in desperation as she cried her heart out.

And there I sat, frozen in a nightmare of my own making, trying to process what had just happened.

It’s one thing to make someone laugh until they cry on a date, but quite another to inadvertently unleash a torrent of pent-up emotions in a public setting.

As I glanced around the room, I caught the waitress’s eye.

She was glaring at me with such intensity that I half-expected her to march over and start walloping me with her order pad! No doubt she thought I’d said something horrible, not realising that my attempt at kindness had inadvertently opened a floodgate.

Then, in the middle of this emotional whirlwind, the bombshell dropped. My date, in between sobs, managed to reveal that the young waitress glaring at me was her teenage daughter. To say I was shocked would be an understatement. The thought that this entire scene had been playing out in front of her daughter made the whole situation even more surreal and uncomfortable.

The next ten minutes were a blur of me making soothing noises while she sobbed into my sleeve. I can only assume this poor woman had been carrying around a tremendous amount of sadness and that my attempt at honesty had somehow provided her with the release she needed. But as I sat there, trying to will myself invisible, I couldn’t help but reflect on the deeper issue at hand.

How empty and isolated must our lives be when a small gesture of kindness from a stranger—a few words of concern—is enough to break us?

It’s not that I blame her for crying.

On the contrary, I felt a profound sense of sorrow for her and for so many others like us, stumbling through life, trying to find solace in the chaotic world of online dating. We all have our wounds, and sometimes, it only takes a gentle prod for them to bleed.

Eventually, she released her grip on my arm, and we parted ways with a subdued farewell. As I walked back to my motorbike, I couldn’t shake the thought that so many of us are throwing ourselves into the dating pool in search of happiness, rather than first finding happiness within ourselves.

It’s like trying to fill a bottomless pit with a teaspoon—futile and exhausting.

So, here’s the lesson I learned on this particular date: you shouldn’t begin the process of dating until you’re truly content with yourself. Too many people jump into it, hoping that finding a partner will solve all their problems, but that’s not how it works. Happiness isn’t something that can be given to you by another person; it’s something you have to cultivate on your own.

In the end, I rode home feeling a mix of emotions—sadness for her, frustration with myself, and a weary resignation to the fact that this, too, was just another fumble in my ongoing quest for companionship.

And so, I prepare to dive back in, yet again, with the hope that maybe, just maybe, the next time will be different. Although, given my track record, I’m not holding my breath.

If you’ve enjoyed this story, make sure to subscribe for more updates. Next week, I’ll share the tale of 'The Pillion Passenger,' where I was surprised by someone’s rather forward nature.

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

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