Dating in Your 50’s is More Painful Than a Root Canal

Thank God for AAA batteries

Iva Ursano
9 min readNov 10, 2021



Women over 50 who have had absolutely zero luck finding a good man to date, say “Yo”!

Girl. I feel your pain. Let’s face it. Dating at any age can be a tad stressful but dating in your 50’s? Oooph! What a shitshow that is.

Now I guess it also depends on where you live. I happen to live in a tiny town in a third world country (Guatemala), so ya. Send prayers, long lasting AAA batteries and chocolate please. I mean I imagine I could always check out a dating site for Guatemala city, maybe find a good man, and then hightail my ass there to visit him but I’m already exhausted just thinking about that. It’s 4 hours away on a good day.

Hard pass.

And it’s kinda hard to find a good man in the town I live in. Like it’s next to impossible. So for the sake of this blog, I’ll use my dating experiences from when I still lived in Canada and was regularly using dating sites.

And this isn’t just stressful for women. I’m sure men go through the same frustrations as we do? Surely. Buuuuut this article is from a woman’s viewpoint.

So there’s that.

Plenty of what…?

I remember when I left my last relationship ( I was 51 yrs old) I went back on the dating site to check out the cesspool, er I mean, the fish in the pond to find out what kind of choices I had. What a huge disappointment. I had been with my ex for almost 8 years (and ya, I met him on the same dating site) and all the men on this site were still there from 8 years ago (but then again, so was I).

That should have been a clear sign for me. Colour me desperate.

So after sifting through all the “Tom, Dick and Harry’s” I settled on a guy I knew for quite some time who was the ex husband an old childhood friend of mine. Conversation was light, fun and somewhat intelligent. He had a good job, was close to his children, seemed responsible enough. Had a good circle of friends. You know. All the things we like to check off when finding a new love.

3 months into dating I realized he was an alcoholic. Ugh!!



Iva Ursano