Is This What Dating Men in Their 50s Looks Like?

I’ve been single for over seven years.

I gave up finding someone long ago because I got too comfortable being an independent, empowered single woman. Why introduce unnecessary drama into my life?

But recently, a reunion with an old friend triggered something in me. I decided to give online dating another shot.

I’m not 50 yet, but since it’s not too far off, I figure it might be best to look for someone older, in their 50s.

There were a few reasons why I thought men in their 50s would be a better fit:

If they haven’t had kids by now, they probably won’t want any — which is perfect since I don’t want any.

If they have kids, they’re likely older or young adults. That works for me because they now have their time back, and we can focus on nurturing our relationships.

They should know what they want, meaning no time wasted playing games.

With that mindset, I created my profile and got back into the dating scene.

The liar

My first match was 44.

Not quite the 50s I was aiming for, but oh well.

We had a few things in common, and he seemed genuinely interested in me. He asked many questions, checked in daily, and, most importantly, lived nearby.

If there’s one non-negotiable thing for me, it’s distance.

I refuse to date anyone who lives more than 15 km away. Life is busy — who has time to drive over 30 minutes just to see their partner? And if they live on the opposite side of the city, chances are they don’t want to move to my side, and I’m not prepared to move either.

I’ve seen this play out before. My girlfriend dated a guy who lived 45 minutes away. She could only see him on weekends, and he had a six-year-old daughter he saw twice a week. She loved living by the beach, but he wasn’t willing to move away from his child. It was a problem from day one. I wasn’t about to put myself in that situation.

Back to my first match.

After a week of texting, he asked me out. We met for dinner, and he picked a seat outside since it was a beautiful evening in Melbourne.

Great choice.

But when the waitress handed him the menu, he squinted at the menu, then stretched his arm out like he was trying to summon the words into focus.

I was surprised he was already battling with presbyopia at 44.

As we chatted, he told me about his spontaneous trip to Bali.

“Yeah, my kids are all grown up, so I figured I could just pack my bag and go.”

Adult kids! Tick.

“Are they working or still in school?,” I asked, assuming they must be around 20 or 21.

“Oh yes, working. My daughter is 30, and my son is 27.”

What?!

And he was 44?

He must have noticed my shock because he quickly corrected himself. “Oh, I’m actually 54, not 44. Stupid app — I don’t know how to change my age on there.”

Yeah right…

He admitted he lied to attract younger women. “Not 20-year-olds, but you know, somewhere around early 40s.”

“Oh, I guess you must be disappointed,” I thought.

If he had been honest, I probably would have swiped right anyway — he looked great for 54. But now? I’ll swipe left because no relationship should start with a lie.

The narcissist

Next, I matched with a 53-year-old commodity investor.

With my strong interest in personal finance, I was excited about the match. He had just returned from five months of travel, sold his property and bought a new one near the beach — he seemed to be doing quite well for himself.

And a new house near the beach? Another tick. Beachside living is my favourite way to live.

Although I am not physically attracted to him, I love talking to intelligent people. At this age, I need to broaden my dating criteria and aim for intellectual connection. Attraction will come.

But just when I thought this had potential, the conversation came to a screeching halt.

So far, I have been the only one asking questions; all he did was answer. There wasn’t any real back and forth, no curiosity from his side.

I dropped plenty of hints: “Oh, you like Canada? Which part? I’m from Canada too!” “When did you start investing? I’ve been learning a lot about it lately.” “Are you a twin?” (Because I saw his twin brother posting a photo of them together on the same app!)

I even asked what and why questions, giving him plenty of opportunity to say, “What about you?” But nothing.

Maybe I was expecting too much. So I stopped asking, thinking I’d give him space to show some interest.

Two days passed. Still silence.

Unmatch.

The egotistic cheapskate

Next up was a 51-year-old entrepreneur.

Great — I used to run my own business. I was always inspired by entrepreneurs.

We hadn’t talked much online because we were both ‘old school’ — better to meet in person than engage in endless texting.

Agreed.

He suggested a fusion Chinese restaurant near the beach. “I know the chef well. They do the best Chinese food. Check out the menu and see what you’d like.”

Intriguing. I loved good food, especially good Chinese. Let’s do this.

The menu startled me. A simple fried rice cost $35.

This better be life-changing fried rice.

I couldn’t help but wonder — is he going to pay? It’s our first date, after all.

As he walked through the door, disappointment hit me instantly.

He is not 5'10" as his profile suggested — more like 5'7" at best.

Another liar.

When it was time to order, he took charge. “Can I suggest a few dishes? I know what’s best.”

Sure, why not?

He went on to order four to five dishes, probably too much, but he insisted I had to try them. He also ordered a bottle of wine.

I wasn’t planning to drink that early in the day, but hey, Sarina, go with the flow.

Then he launched into why he was on the dating app.

“I have three kids. Divorced about a year ago because my ex-wife suddenly decided to become a lesbian!”

I didn’t see this coming. I wasn’t sure how to react, but he kept going.

“Yeah, with my best mate’s wife. Crazy, huh?”

I took a sip of water and braced myself for what was next.

“I don’t know why, but I seem to attract crazy women. My last ex was a total psycho — she threatened to kill herself if I broke up with her.”

Wait, what ex? Your ex-wife?

“No, the one after my ex-wife. I had to keep dating her because I didn’t want her to hurt herself. One night, she even stalked me while I was out with my mates. I couldn’t stand it anymore — I had to cut her loose. She was obsessed with me.”

I almost choked on my water. Obsessed with you?

The rest of his story was a blur because I zoned out. The only thing running through my head was how he would describe me as another crazy woman if we broke up.

I stayed for the meal out of respect but cut it short.

“Sorry, I have errands to run.”

We asked for the bill — $187!

He pulled some cash from his wallet and said, “I only have $80. Is that okay?”

I was speechless. What the f@#k?

I just wanted to get out of there, so I grabbed the bill and paid the rest.

He offered to walk me to my car, which, at this point, made no difference. Then, with full confidence, he asked, “When can I see you again?”

I turned to him and smiled. “Never.”

I got into my car, drove away, and felt awful about not spending that $100+ wisely.

Patiently waiting…

The world is changing, but people haven’t — at least not in the dating world.

I thought dating over 50 would mean meeting more mature, decent men. I was wrong. Many men prefer to stay boys, no matter their age.

At first, these experiences put me off, but now I find them quite entertaining. Human beings are an interesting species.

Maybe I needed to see the worst to set more realistic expectations. Or maybe my future partner isn’t on a dating app — he’s probably just wandering around a hardware store, waiting to cross paths with me.

Guess I’ll have to keep dating and treat this as entertainment until I find the one.