The Dating Experience
If you’ve found yourself single and dating after 50, I have a feeling you’ll recognise some of this. Dating has become a full-time job?
I honestly don’t remember signing up for this.
I thought dating involved meeting someone, having a conversation, maybe sharing a coffee and gradually getting to know each other.
Apparently I was thinking about 1992.
These days there’s online dating. Speed dating. Video calls before you’ve even decided whether you like someone’s laugh. Endless texting. Dating apps with names I’d never even heard of until recently. And somewhere amongst all of that you’re apparently expected to market yourself like you’re applying for a very competitive position.
“Tell us about yourself in 200 characters.”
Two hundred characters?
I’ve lived for more than sixty years. I’ve raised children, made terrible fashion choices, survived heartbreak, burnt countless dinners, travelled, learned a few lessons the hard way and developed a very strong opinion about supermarket trolleys with wobbly wheels… and somehow I’m supposed to squeeze all of that into two hundred characters.
Then there are the photos.
When exactly did choosing profile pictures become an Olympic event?
You don’t want one that’s too old because apparently that’s misleading. Don’t be that glamorous because then people think you don’t actually look like that or worse that you look like that every ordinary Tuesday. You probably shouldn’t use the one with your grandchildren because that’s their privacy. Definitely not the one where your ex has only been half cropped out. And heaven forbid you accidentally choose a picture wearing sunglasses because someone will inevitably ask, “Do you have one where I can actually see your face?”
It’s exhausting before you’ve even met anyone.
Then Come the Messages
I don’t know who invented the unwritten rule that every message requires an almost immediate response, but I’d quite like a quiet word with them.
You make yourself a cup of tea, fold a basket of washing, answer a phone call from your daughter, pop down to the supermarket for milk and by the time you look at your phone again you’ve somehow gone from “potential soulmate” to “clearly not interested.”
Or worse… you’ve been blocked.
Blocked!
We used to wait two days for someone to return a phone call. Now apparently forty-five minutes can be interpreted as emotional abandonment. Is that the rule when you are dating over 50.
Sometimes it all feels less like getting to know another human being and more like trying to keep up with a game where nobody ever bothered explaining the rules.
And I’ve been thinking about that lately.
I wonder if dating itself hasn’t actually become harder.
I wonder if it’s all the extra noise surrounding it that’s making it feel so exhausting.
Then There’s the Actual Date…Dating after 50…
And let me tell you… setting up a profile and replying to messages is actually the easy part.
Eventually someone suggests meeting for coffee, and suddenly you’re standing outside a café wondering if they’re going to recognise you, whether you’ve chosen the right outfit and if you’ve remembered to check there’s no spinach stuck in your teeth.
You take a deep breath, remind yourself they’re probably just as nervous as you are, and hope for the best.
Sometimes the best doesn’t arrive.
Over the years I’ve collected a few dating stories that still make me laugh, although I wasn’t laughing quite so much at the time.
The Financial Interview
We’d been chatting online for a little while and, if I’m honest, everything seemed perfectly pleasant. We had quite a bit in common, the conversation flowed easily and eventually decided it was time to graduate from our phones to an actual coffee.
We were chatting away when he suddenly leaned forward with all the seriousness of someone about to ask a life-changing question.
“So… if we’re going to catch up again, can I see your bank balance?”
For a moment I wondered if I’d heard him correctly.
“I’m sorry… did you say my bank balance?”
“Yes.”
Well… that certainly wasn’t on my First Date Bingo card.
I’d imagined we’d spend the next few minutes talking about travel, family or whether either of us had a dog. Instead, we’d gone straight from cappuccinos to capitalism.
For a split second I wondered whether this was a hidden-camera television show
I politely explained that my bank balance probably wasn’t something I shared with someone I’d only known for a couple of weeks. He looked genuinely surprised that I wasn’t immediately reaching for my phone.
As we kept talking, though, his question started to make a little more sense. He told me he’d been badly hurt in a previous relationship and had lost a significant amount of money. Suddenly I understood that this wasn’t really about my bank account. It was about protecting himself from ever being hurt like that again.
And honestly, I could understand that.
I just couldn’t help thinking there might have been a slightly more romantic way to discover whether someone shared your values around money.
Looking back, it still makes me smile—not because he wanted financial security…
But because sometimes our past teaches us perfectly reasonable lessons while also convincing us to ask some very unreasonable questions.
Borrowing Someone Else’s Face
I was sitting in a local coffee shop waiting for my date when a text message arrived.
“Sorry, something’s come up. I’m running a little late.”
No problem. I ordered another coffee and settled in to people-watch.
A few minutes later, a gentleman walked towards me with a smile. I smiled back, although I was a little puzzled. He looked vaguely familiar. There was definitely a resemblance to his profile photos, but something wasn’t quite adding up.
Before either of us had taken a sip of coffee, he smiled and said, “Before we go any further, I should probably tell you… those photos weren’t actually me.”
Well… that certainly wasn’t the opening line I was expecting.
“Oh?”
“They’re my brother.”
Apparently his brother had much better luck with women, a better job and, from what I gathered, considerably better photographs.
I remember stirring my coffee and thinking, This story is taking an unexpected turn every thirty seconds.
To be honest, I stayed.
Why not?
He’d made the effort to come, and despite the rather unusual introduction, he was actually pleasant company. I already knew there wouldn’t be a second date, though. For me, starting any relationship with a lie is a difficult foundation to build on.
We finished our coffees, shared one of those slightly awkward goodbye hugs that probably wasn’t necessary, and I genuinely wished him well. I politely explained that I didn’t think we were the right match, and we went our separate ways.
Or so I thought.
Before I’d even made it home, my phone had lit up with thirty-seven text messages.
Somewhere between the café and my driveway, he’d decided we were soul mates.
I, on the other hand, was mostly wondering whether I’d accidentally walked into the sequel.
A Small Detail
Another coffee date… by this stage you can probably tell that I was keeping Brisbane’s café industry afloat.
We’d been chatting online for a little while and everything seemed perfectly normal. We had a few shared interests, the conversation flowed easily and eventually decided to meet for coffee.
I arrived a little early, found a table and settled in to wait.
As I sat there, I noticed a gentleman wander past. He smiled in my direction, disappeared, then wandered past again a minute later with another smile.
I remember thinking, That’s odd.
A few moments later he walked straight over to my table.
“Hi Kay.”
For a split second I wondered whether he’d mistaken me for someone else.
He looked nothing like the age I’d been expecting. Now, I know age can be deceiving and some people look much younger than they are, but every now and then you simply know something isn’t quite adding up.
Trying not to sound too surprised, I asked, “Can I ask… how old are you?”
Without missing a beat, he smiled and admitted he was actually about twenty years older than the age on his profile.
“I changed it because I wanted to meet younger women,” he explained.
I wasn’t offended.
If anything, I found myself admiring the confidence. It was certainly… an optimistic strategy.
Then, just when I thought we’d reached peak awkwardness, he smiled and said he’d been hoping I’d look a little younger too.
“Younger than what?” I wondered. The woman sitting right in front of him? My driver’s licence photo? Or was he hoping I’d arrived looking like I should still be at my Year 12 formal?
By then I’d given up trying to make sense of it all and simply enjoyed my coffee.
The date didn’t lead anywhere, but it wasn’t a wasted afternoon. I discovered one of Brisbane’s best little cafés and came home with another story that still makes me smile.
What They All Had in Common
I’ve laughed about those dates many times over the years. In fact, they seem to become funnier every time I tell the stories. Friends always have a good laugh, someone inevitably says, “Surely you’re making that up,” and I have to assure them that, no, every word is absolutely true.
Although sometimes I wish it wasn’t.
But every now and then, usually when I’m driving somewhere or walking the dog, I find myself thinking about those people again. Not the funny bits. The people themselves.
Because if I’m being fair, none of them woke up that morning wondering how they could make a perfectly ordinary coffee date as awkward as humanly possible. None of them thought, Today I’ll ask to see someone’s bank balance, or I’ll borrow my brother’s photos, or I’ll quietly shave twenty years off my age.
They were simply doing the best they knew how.
Maybe not the best strategy…
But the best they knew.
The more I’ve thought about it, the more I’ve realised that dating after fifty isn’t really about two people meeting for coffee.
It’s about two entire life stories sitting across a tiny café table.
By the time we reach this stage of life, very few of us arrive with a blank page. We’ve all collected things along the way. Some of them wonderful. Some of them we’d happily leave behind if life gave us the chance.
We’ve loved people who stayed and people who didn’t. We’ve trusted the wrong person, worried about money, buried parents, watched children leave home and had our confidence quietly shaken along the way.
Maybe that’s what I was really seeing on those coffee dates.
Not strange people.
Just ordinary people carrying old hurts, old fears and old hopes into a brand-new conversation.
Then I Looked at Myself
And then it hit me.
I’d spent all this time noticing what everyone else was carrying into those cafés, yet I’d completely overlooked my own suitcase sitting quietly beside my chair.
The funny thing is, I wasn’t exactly arriving carefree either.
I’d already decided there were certain things I simply wasn’t prepared to tolerate anymore. I’d promised myself I wouldn’t ignore red flags, I wouldn’t make excuses for people and I certainly wasn’t interested in trying to rescue anyone. Looking back, maybe I was carrying my own little checklist into every first date.
Somewhere along the way I’d started asking my own quiet questions.
What if this ends the same way as the last one?
Hopefully, I won’t miss the warning signs?
Surely I don’t trust too easily?
None of those questions made me cynical.
They made me human.
Just like the people sitting across the table from me.
And perhaps that’s the thing I’ve come to appreciate most about dating later in life.
None of us arrive empty-handed.
We all have a suitcase.
The only real difference is what’s inside it.
Dating after 50 do we carry a Little Less Baggage
I’ve been wondering whether that’s really the challenge of dating later in life.
It isn’t pretending our suitcase doesn’t exist. By the time we reach our fifties or sixties, most of us have packed quite a bit into it. Some of it we’d never part with, and some of it we’d happily leave behind if life gave us the choice.
The truth is, every relationship, every disappointment, every wonderful memory and every mistake has quietly shaped who we are. They’ve made us a little wiser, a little more cautious and, hopefully, a little kinder too.
The problem isn’t carrying those experiences with us.
The problem comes when we let them do all the talking.
It’s so easy to let yesterday start making decisions for today.
The person who’s been hurt financially starts looking for proof instead of trust. Someone who’s been rejected wonders whether being themselves will ever be enough. The person who’s loved and lost quietly waits for history to repeat itself.
And if I’m honest, I’d caught myself doing exactly the same thing.
Not in the same ways, of course, but I realised I was walking into those cafés with my own quiet collection of “what ifs.”
Then one day I found myself wondering something completely different.
What might happen if, just for the length of one coffee, I rested my suitcase beside my chair instead of holding onto it quite so tightly?
Not because my past didn’t matter.
It did.
But because perhaps the person sitting across the table deserved the chance to introduce themselves before my past introduced them for me.
Maybe that’s all any of us can really do.
None of us arrive without a suitcase.
We simply leave enough room at the table for someone else’s.
