What nobody tells you about dating after 50
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I went back into dating in my fifties with what now seems like a remarkable degree of optimism.
I wasn’t naïve – quite the opposite. I’d been married, divorced, had relationships that worked until they didn’t, and one that taught me more about myself than I ever particularly wanted to know. Surely all that life experience had to count for something.
I knew myself better. I knew what I wanted. I definitely knew what I didn’t want. And presumably men in their fifties and sixties did too.
This was my first mistake.
Not because the men I met were terrible. Most weren’t. Some were lovely. Some were interesting. Some simply weren’t right for me.
And some provided material so good that it seems almost selfish not to share it.
Welcome to online dating
I began, as many single people now do, online.
Online dating after 50 is an interesting exercise in optimism, photography and geography. You create a profile designed to convey that you’re intelligent but not intimidating, independent but still capable of allowing another human being into your life, attractive without appearing vain, and fun without giving the impression that you’re spending every weekend at a music festival.
Then you wait.
Some of the men who contacted me were perfectly normal. Others raised questions.
One had chosen a profile photograph that appeared, from the angle and expression, to have been taken while sitting on the toilet. Perhaps it wasn’t. I decided not to investigate.
There were men who appeared considerably older than the age listed on their profiles, and others who lived on the opposite side of Australia. I live in Canberra. I’m sure Perth is lovely, but I was looking for someone to have dinner with, not establish a transcontinental relationship requiring frequent-flyer points.
Still, I persevered.
I tried RSVP. I tried eHarmony. I had conversations that disappeared without explanation, conversations that probably should have disappeared sooner, and occasionally conversations that led to actual dates.
Some were pleasant. Some were forgettable. And some were unforgettable for reasons nobody involved could possibly have anticipated.
I should mention that, despite everything, I never received a single unsolicited dick pic. Given the stories I’d heard from other women, I considered myself extraordinarily fortunate. The bar, it seemed, was already quite low.
Perhaps I needed professionals
After a while, I began to wonder whether the problem was me. Perhaps I simply wasn’t very good at picking men.
Given my relationship history, this wasn’t an entirely unreasonable concern.
So, I did what any sensible woman conducting an increasingly expensive longitudinal study into heterosexual relationships might do.
I outsourced the picking.
I joined a dating agency.
This was not a cheap experiment. Approximately $3,500 later, I had considerably higher expectations and a considerably lower bank balance.
There was something reassuring about handing the initial selection process to a professional. Surely people prepared to involve an actual matchmaker (and make a fairly substantial financial investment in doing so), were serious about finding a committed relationship. And perhaps a professional could identify something I had been missing.
The agency introduced me to David*.
David was intelligent and accomplished. We had some good conversations and dated for around three months.
He was also responsible for what remains one of the more peculiar experiences of my dating life: a seven-hour car journey during which we listened to no music. None. Seven hours.
I hadn’t previously realised how important music was to me until I discovered what it was like to spend most of a working day inside a moving vehicle without it.
Eventually, David and I went our separate ways.
The agency later introduced me to Mark.
Mark initially seemed extremely promising. Our first date was lunch by the lake. We talked for around four hours, and before lunch had even finished, he’d asked me to dinner. Our second date went so well that we were the last people left in the restaurant.
Excellent, I thought. Perhaps this was why people used dating agencies.
Then things became rather less straightforward. Communication became inconsistent. I often wasn’t quite sure where I stood.
And Mark had a particular expression he liked to use.
Stay frosty.
I’d never encountered this as a romantic sign-off before. “Sleep well”? Certainly. “Talk tomorrow”? Lovely. “Stay frosty”? Was I dating a man or being deployed on a covert military operation?
Eventually, I began pulling away.
Mark apparently noticed, because he ended things by text, telling me he needed someone “much fitter.” For context, I was a size 10-12.
Even the owner of the dating agency was horrified.
I was hurt, of course. But there was also something almost impressive about paying $3,500 for professional matchmaking only to be dumped by text with a critique of my fitness level.
Stay frosty indeed.
And something unexpected happened. I felt better about myself.
I’d gone to the agency partly because I wondered whether I couldn’t trust myself to choose men. Yet the men somebody else chose for me weren’t necessarily any more compatible than the ones I’d found online.
This was disappointing from a romantic perspective and not particularly impressive from an investment-return perspective. But it was surprisingly good news for my self-esteem.
Apparently, I wasn’t uniquely bad at picking men after all.
It had only cost me $3,500 to find out.
In the interests of thorough research, I tried speed dating
Having tried online dating and professional matchmaking, I decided the situation clearly required greater efficiency.
I went speed dating. If you’ve never been speed dating, the premise is simple. You spend several minutes talking to one person before moving on to the next.
Several minutes doesn’t sound very long.
It can be.
What I remember most clearly about the evening was that the women I spoke to were considerably more interesting than most of the men. I did, however, strike up a great conversation with one man. Unfortunately, he was the host.
Things became more complicated when I realised one of the men participating was someone I’d briefly chatted with on RSVP. I’d been rather nonplussed by our online interaction and had quietly allowed it to go nowhere. Now here he was. In the room. And he had recognised me.
Canberra is like that. There comes a point when online dating and real-life cease to be separate ecosystems and members of the cast begin wandering between them.
I did what any confident, mature, independent woman in her fifties would do.
I asked the host to rescue me. He did. The host and I exchanged messages afterwards and talked about meeting up ourselves. We never did.
Apparently, even meeting the host at speed dating is no guarantee you’ll actually go on a date.
Then there was the date whose identity I didn’t know
Some months after a perfectly pleasant date with a man I’ll call Ben, my phone pinged.
Ben had been nice. There was nothing wrong with him. I simply hadn’t felt much of a connection.
There had also been a slightly awkward moment at the end of our first date when, for the first time in my recent dating experience, it became apparent that I would be paying for my own meal.
To be clear, I don’t believe men are required to pay for women. But there is a particular little dance at the end of an early date when nobody is quite sure what’s happening with the bill, and this one had been sufficiently memorable that I remembered it.
I did not, however, remember Ben’s phone number.
I’d deleted it.
So, when a message arrived months later saying he’d like to take me out, “my treat”, I had one small problem: I had absolutely no idea who had sent it. There was an obvious solution to this. I could have asked. I did not.
At the time, Mark was occupying rather too much space in my head while simultaneously providing rather too little certainty about whether he was actually interested in me. And suddenly another man wanted to take me out.
Someone was paying attention to me.
It was flattering. So, I thought, why not?
This is how I found myself getting ready for a date without knowing who my date was. There is something quite liberating about having no idea who is about to walk into a café. There is also something deeply ridiculous about it.
I arrived.
I waited.
And then Ben walked in.
Ah.
My treat.
Of course.
Italy seemed a little premature
Then there was Tom.
Before we’d even met, Tom was talking about whisking me off to Italy. This was certainly more ambitious than coffee. He had plans to buy and renovate a villa there and spend extended periods of time in Italy. Somehow, before we’d established whether we actually liked one another in person, I appeared to have been tentatively incorporated into the European component of the plan.
I had mixed feelings.
On the one hand: Italy.
On the other: We had not yet met.Still, I admired the confidence.
We did eventually meet, and I really liked him. Tom was warm, cheeky and easy to talk to. Things moved quickly. After our first kiss, he told me he’d thought, “she is the one”. Given that Italy had already been discussed before our first date, perhaps I shouldn’t have been surprised. Not long afterwards, Tom and I were at my apartment, and things were progressing in a decidedly romantic direction.At this point I discovered that Tom had made a personal jewellery choice I had not previously encountered.
I will leave the precise mechanics to your imagination.
Suffice to say, there were piercings.
Plural.
I was still processing this new information when I heard something considerably more alarming.
A key in my front door.
My daughter has a key to my apartment. Apparently, on this particular occasion, she had also decided that knocking was an unnecessary administrative step.
There are moments in a mother’s life when time stops.
This was one of them.
I don’t remember ever moving so quickly.
Whatever your views on dating after 50, I can recommend one thing without reservation: If your adult children have keys to your home, establish a knocking policy. Preferably before anybody removes their trousers.Remarkably, neither the piercings nor the near-miss with my daughter marked the end of Tom and me. We continued seeing each other.
Much later, when things were almost at an end, we arranged to go out for dinner. I showered. Did my hair. Put on makeup. Chose a dress. Tom arrived wearing a T-shirt and shorts, looking as though he’d come directly from renovating his apartment.Because he pretty much had.
By this stage, Italy was beginning to feel like the least complicated part of the relationship.
Sometimes further investigation is required
Then there was Sam.
I really liked Sam.
He was sweet, attentive and thoughtful. He brought me flowers for my birthday, organised a picnic and communicated consistently. After some of my previous experiences, this felt positively revolutionary.
There was just one part of Sam’s life that remained strangely mysterious: His house.
I had never been there. In fact, I didn’t even know exactly where he lived. As the relationship progressed, little pieces of information began to emerge. There were cats. Quite a few cats. The house apparently needed cleaning. And decluttering. And repainting. At one point, steam-cleaning entered the conversation.
Still, no invitation and no address. Naturally, I became curious. Perhaps too curious. I would like to say that, as an emotionally mature woman in my fifties, I simply respected his privacy and waited until he felt comfortable inviting me into his home. I did not.
I surreptitiously worked out where he lived.
Naturally, I looked it up on Google Earth.
What I saw wasn’t particularly encouraging, but I decided to give him the benefit of the doubt. The images could have been old. Perhaps things had improved. There was really only one way to find out: I recruited my daughter. At some point during this process, it occurred to me that I had crossed an important threshold in modern dating and become what could best be described as a quasi-stalker. Nevertheless, we had come this far.
We did a drive-by.
As we approached the house, I tried to appear casual, which was ridiculous because I was in a car with my adult daughter conducting covert surveillance on a man I was dating.
Then I saw it.
The garden was so overgrown that the house was barely visible. There were neglected-looking vehicles outside, and the whole property appeared to have been waiting quite some time for somebody to love it. My heart sank. Suddenly the postponed invitations, cleaning, decluttering, repainting and steam-cleaning made considerably more sense.
The difficult part was that I really liked him.
He hadn’t treated me badly. Quite the opposite. He was sweet. He was attentive. There were things about him I genuinely adored.
There was no dramatic offence I could point to. No terrible date. No stay frosty. I simply looked at the reality of his life and knew I didn’t want it to become mine.
So, I ended the relationship.
Dating after 50, I was discovering, required skills I had never anticipated.
Resilience. Discernment. Optimism.
And, occasionally, reconnaissance.
Perhaps that was the real lesson
For a while, I thought successful dating meant becoming better at picking men.
Choose more carefully. Screen more thoroughly. Look for different qualities. Try a different website. Try a dating agency. Spend $3,500 on the dating agency. Try speed dating. Perhaps ask for photographic evidence that the profile picture wasn’t taken on a toilet. Maybe conduct the occasional drive-by. But eventually I realised I’d been asking something impossible of myself.
You cannot know somebody before you know them. A dating profile can’t tell you. Neither can a matchmaker, several minutes at speed dating or even a wonderful four-hour first date.
People reveal themselves over time.
So do we.
The real question became less “How do I make sure I pick the right man?” and more “Can I trust myself with what I discover?”
Can I enjoy a promising first date without writing the ending? Can I acknowledge that someone is a perfectly lovely person and still know they’re not right for me? Can I notice when something doesn’t fit without needing the other person to have done something wrong? Can I change my mind when new information arrives? And can I accept that a date that goes nowhere isn’t necessarily evidence that I’ve failed at dating?
Sometimes two perfectly decent people simply don’t belong together.
Sometimes a man stays frosty.
Sometimes a potential future in Italy presents itself before the first coffee.
Sometimes your daughter lets herself into your apartment at a spectacularly unfortunate moment.
Sometimes you find yourself conducting a drive-by.
And sometimes you turn up to a café without knowing who you’re meeting.
Perhaps the biggest surprise about dating after 50 was discovering that being older didn’t make me immune to uncertainty, disappointment, attraction, questionable decisions or complete absurdity. I wasn’t suddenly a wise woman serenely evaluating potential partners from a position of perfect self-knowledge. I was still human. But I did know myself better than I once had. I had a life I liked. I had family, work, writing, friendships, rituals and a home that felt like mine.
I wasn’t looking for someone to build my entire life around. I was looking for someone whose life could sit comfortably beside my own.
That turned out to be a very different proposition.
And despite everything, the awkward dates, disappearing messages, $3,500 professional matchmaking experiment, speed dating, romantic military terminology, questionable profile photography, quasi-stalking and unexpected jewellery, I’m glad I kept going.
Because dating after 50 wasn’t just frustrating. It was hilarious. It was occasionally confronting. And it taught me things about myself I couldn’t have learned by staying safely at home.
I did eventually meet an amazing man who makes me very happy.
He’s not appearing in this article.
Some things I’m keeping for myself.
*Names and some identifying details have been changed.
