When I first became single after 23 years of marriage, there were lots of things I expected to worry about.

Would anyone find me attractive?

Would I remember how to flirt?

Would I accidentally call a date by my ex-husband's name?

Would I spend three hours choosing an outfit only to decide I hated all of them?

What I didn't expect was a conversation about sexual health after one drink.

One.

Drink.

I remember sitting there thinking, "Blimey, we've not even ordered a second round yet."

Now before anyone starts shouting at their screen, I know he was probably trying to be responsible. Looking back, he was probably just having an open and honest conversation.

But after being married for over two decades, my brain didn't hear:

"Let's talk about sexual health."

My brain heard:

"Right then, let's get the paperwork sorted."

Needless to say, there wasn't a second date.

Not because he'd asked the question.

But because it felt like he'd skipped straight to Chapter 10 when we'd only just finished Chapter 1.

Nobody Gives You The Rule Book

One of the strangest things about dating later in life is that nobody tells you the new rules.

When we were younger, conversations about sex weren't exactly encouraged.

Most of us weren't sitting around discussing STI testing over a glass of wine.

In many long-term relationships, the subject never even came up.

You met someone, fell in love, got married, had children, argued about whose turn it was to put the bins out, and carried on with life.

Then suddenly you're single again and someone mentions STI testing and you're sitting there wondering whether you've accidentally joined the wrong meeting.

For many people over 50, it's not the topic itself that's uncomfortable.

It's the fact we've never had to have the conversation before.

My All or Nothing Brain Takes Over

Of course, my brain immediately did what it always does.

It took one innocent conversation and created seventeen possible disaster scenarios.

What if I should be asking these questions?

What if I'm supposed to know this already?

What if everyone else got a dating handbook and mine got lost in the post?

Do I ask?

Do I not ask?

Do I assume they're fine because they were married for years?

Do I assume they're not fine because they've dated several people since?

What happens if something happens and then I think I've caught something?

What do I do then?

At this point my anxiety had practically created its own spreadsheet.

The reality is that many people are having exactly the same thoughts but nobody talks about them.

The Thing Nobody Wants To Talk About

Over the years I've spoken to lots of singles.

Some are incredibly cautious.

Others move from one relationship to another without giving it much thought at all.

I remember asking one gentleman whether he thought about protecting himself and future partners.

He shrugged and said:

"If I catch anything, I'll deal with it then."

Now maybe it's the mother in me.

Maybe it's the hypnotherapist.

Maybe it's just because I overthink absolutely everything.

But that answer made me wince.

Because it's not just about you.

It's about every person who comes after you too.

And while some things can be treated easily, others can stay with you for life.

Here's What I've Learned

I've learned that having a conversation about sexual health doesn't mean you're planning to jump into bed together.

It doesn't mean you're accusing anyone of anything.

It doesn't mean you don't trust them.

It simply means you're both adults.

Responsible adults.

The same way you'd discuss where you live, whether you want a relationship, whether you smoke, whether you want children, or whether pineapple belongs on pizza.

(For the record, that last one can end relationships.)

The timing matters.

The way you ask matters.

But the conversation itself isn't something to be embarrassed about.

We're Learning As We Go

The truth is, many of us are navigating dating after 50 without a map.

We're learning new technology.

New dating norms.

New ways of meeting people.

And sometimes having conversations we never imagined we'd need to have.

It's awkward.

It's uncomfortable.

Sometimes it's downright embarrassing.

But so was online dating the first time we tried it.

So was sending our first message.

So was walking into our first singles event.

And yet here we are.

Still learning.

Still growing.

Still hopeful.

And if there's one thing I've discovered on this journey, it's that confidence isn't pretending you know all the answers.

Confidence is being willing to ask the questions.

Even the awkward ones.

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