Chapter One – The Dog, the Date and the Moment I Knew: Oh God, This Is a Book

“They had to freeze the dog,” he said, his voice wavering as he tried to hold back emotion.

What? Surely this was not the pinnacle of my dating career. Fifty dates in, and now another disaster, involving the dog.

I sat there listening to yet another story of a tragic pet, a toxic ex, and a family death. My mind wandered, but this time somewhere constructive: could I write a book about these dating disasters? Would anyone be curious about a clumsy midlife plunge into internet dating and its improbable outcomes?

So, let’s start at the beginning. Maybe I should start by telling you who I am (sometimes I’m not sure either), why I’m writing this, and how I ended up here. I have enough first dates, relationships, and near misses to capture the occasional highs, the crushing lows, and the absurdities in between. Also, don’t worry, this is not a self-help book. I didn’t find spiritual alignment on a Shamanic retreat and feel the need to batter you over the head with my findings. And, just for the record, I am still single, or as a dear friend calls it, “untethered.” But my story takes unexpected turns.

What followed was not just a series of dates, but a slow and sometimes painful education in modern dating, ageing, and how easily you can lose sight of yourself while trying to be chosen. There were a lot of mainly awkward laughs, a few grimaces, one horrible heartbreak, and more than a few “what the actual feck?” stories along the way.

I was married for twenty-four years and have two grown-up sons finding their own way. Our relationship followed a predictable course: the initial flurry of excitement of a new relationship simply and slowly eroded away with life. Over time we became like passing ships, barely exchanging more than a Post-it on the fridge. Somewhere along the way, we stopped making time for us in every way that turns a partnership into more than just housemates.

The grand life shake-up then began with an awkward separation, followed by a rebound relationship, a reluctant reinvention, and nearly five years of on-and-off dating ranging from somewhat promising to utterly ridiculous.

Several years after my separation, I took a risky, year-long sabbatical in “Eat, Pray, Love” style, but with too much eating, quite a bit of swearing, and very little enlightenment. This was not some bougie, trustafarian style wander through Asia either. It was more about jolting myself out of a mundane routine, redressing the balance between life and love, and asking the big question: what next?

I thought that taking time out would also give me the headspace to write this book and tackle a long list of “one day I will” ambitions I had ignored for decades.

That year however, had different plans for me. Illness, a short but intense relationship, a house fire, family upheaval, and the loss of a close friend all intruded. I travelled quite a lot, but less than I would have liked. But, what it gave me was a thirst for more and a determination to make the dream of living further afield a reality.

The peculiar merry-go-round of dates, longer relationships, textationships, situationships, a very brief affair, and a friend with benefits, would also never lead me to where I wanted to go. Writing this book has given me the chance to step off that ride, reflect on the process, the lessons learned, and how it reshaped my view on love life and connection.

Midlife dating is bloody exhausting. The constant cycle of messages, hope, outings, and disappointment takes a toll. Then there is the money: subscriptions, petrol, coffee, meals, anti-ageing serums and the cost of hope. And the unusual behaviours of people in their fifties, still figuring out their dating goals or just forgetting basic decency and communication. It is a wonder anyone survives it with dignity and sanity intact.

I am not blaming anyone, because it is of course about human behaviour, mine included. I’m aware that women can be as strange as men, or worse and that in these times, social media dating advice plays a huge part in fanning the fire of complete confusion.

You may find me flippant and trust me, I am. But beneath the humour, I am a soulful, quietly romantic woman who believes in deep connection. I want someone who shares my values, is my best mate, lover, and partner in crime. But there is far more to it than that.

I haven’t listed every single date as that would be a very boring story. Many dissolved before they even started: no spark, no chemistry, no interest in a follow-up. A mix of coffee, banal chat, and polite goodbyes, often accompanied by brutally deleting all traces of them on the way home. Instead, I’ve focused on the dates that were eventful, bizarre, or that changed my perspective along my winding, often chaotic dating journey.

What follows is a trip through messy, confusing and humorous encounters. Behind the jokes and resilience sat the very basic desire to be seen, chosen, and understood. Over time, it became less about the stories and finding “the one”, and more about what I wanted from life.

Sometimes you have to go through all that to recognise what truly matters.

It was only during the whole process that I understood how my early experiences of love, attraction, and expectation shaped the way I approached connection in midlife, often without even realising it.

It also seems that just dating as we used to know it, is now not as simple as it used to be.

So, before diving into the whirlwind of internet dating, it feels only fair to step back and look at the dating world of the 1980s and 1990s, because that, in reality, is the only fair comparison I can make and is the last time I tried to date!