Online Dating: Putting One’s Toe Back in the Water ...

Dating in One's Middle Years #1

Photo by Lidia Nikole on Unsplash

Putting My Toe Back in the Dating Pool!

A few months after my marriage ended, I began to hear my inner voice - the persistent, nagging one that whispers, “You’re ready for this again.”

Fool that I was, I decided to listen.

My friends at the gym, ever the enthusiastic cheerleaders, pushed and prodded me into action. With their insistence, I started to like the "idea" of dating again, particularly the seemingly safe realm of online dating. It appeared to offer a buffer, a digital moat to stave off immediate awkwardness.

After much deliberation, I selected a site that seemed to “Match” my aspirations. At 50, I wasn't looking for a quick fling, but something more connected, more meaningful. The site I chose boasted a highly detailed matching algorithm, promising to align me with someone compatible on a deeper level.

Naive optimism, perhaps, but it was appealing.

The process began with the tediously, dutiful completion of many questionnaires. These ranged from the mundane—“Do you like pets?”—to the slightly odd—“What’s your stance on the Oxford comma?”

True to form, I approached each question with the seriousness of a man applying for a mortgage. Each answer was painstakingly considered, each photo scrutinised for appropriateness and honesty. I was determined to present the best, most authentic version of myself.

Writing my profile was another challenge entirely. How does one encapsulate a life in a few hundred words? I agonised over every sentence, striving for accuracy without sounding self-important. I wanted to be honest about my past, hopeful about my future, and clear about my present.

It took bloody days, but finally, I felt it was right.

With bated breath and a sense of impending adventure/doom, my finger hovered over the button before I eventually made my profile live. The saying, “You have to be in it to win it,” came to mind as I clicked the button.

Immediately after, a wave of emotions hit me—excitement, fear, curiosity, and a touch of remorseful dread.

What would come of this? Was I truly ready?

I felt publishing my profile was the end of the journey, little realising it was but the start! It went live to the resounding sound of …

SILENCE; NADA; ZILCH; NOTHING; ZIP!

Having girded my loins rather as one might do before a boxing match, it was disturbingly anti-climactic!

Five days in, I'd had a few nibbles but even I, a man almost completely blind to the less transparent wiles of the opposite sex, could tell they were likely scammers. Most of these seemed to originate from Sub-Saharan Africa or South East Asia.

In no small amount of despair, I showed my profile to several of my female training partners. They were polite, but I could feel them rolling their eyes and holding back titters at my naivety. Their suggestions were kind but pointed—clearly, I had a lot to learn.

Back to the drawing board it would be!

The feeling of deflation was palpable. I felt the crushing weight of failure and the gnawing urge to quit, to scuttle back into the safe anonymity of my sofa with a takeaway and a large glass of wine.

It was tempting to abandon this venture entirely, to accept solitude rather than face the jungle of online dating.

But maybe, just maybe, there's something to be learned here. Maybe you've felt this way too—standing on the precipice of something new and terrifying, wondering if it's worth the effort.

Maybe, like me, you know deep down that you need a new plan, a new approach, and perhaps a bit more courage.

So, it was time to regroup and to rethink my strategy.

I invite you to come along on this journey.

The adventure hadn’t even begun!

Stay tuned for the next instalment, due in a week. Who knows? We might both learn something along the way.

… to be continued …