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Old Ladies No Ladies

Posted on September 6, 2022 by Steve Ainslie

For most of my life I have been attracted to older women. When I was a Freshman in high school, I wanted to date the Juniors and Seniors (there was no hope of that happening). When I was a Jr/Sr in high school, I wanted to date college girls.

When I was in college, I was attracted post-grad women who were past their sorority partying days and were ready for commitment.

Although I was attracted to older women, until I met my future wife, all of the women I dated were a few years younger than me. They were beautiful, sweet, attractive and young.

By the time I was 20, I had decided Into longer wanted to date “girls” who had no life experience. I wanted a mature partner, who had lived some life, knew who she was and what she wanted. I was kind of tired of being the “wise, mature, experienced” partner in the relationship. I wanted someone who was my equal when it came to maturity.

At 21, I met the woman I would marry. She was 19 years older than me. We fell in love and remained together for the next 29 years until she died.


I never intended to partner up with someone who was that much older. My wife always looked much younger than her age. When we met, I figured she was in her early thirties. But our age difference didn’t matter to me at all. I ignored it.

I always felt like I was in my thirties and she was a few years older than me. That never changed.


Fast forward to today.

I’ve got a totally skewed perspective on age gaps and dating. I’m still attracted to women in their 30s and 40s. I still feel like I’m 35. In my head, I look like I am too.

But clearly I am not. I’m 54. I look my age.

When I was on the dating apps, I was pleased to find attractive women to match with who were around my age. Most were in their late 40s to mid 50s.

I was less pleased to find that most of the women in my age range reminded me of senior citizens and my grandmother.

When they look at me, I wonder if I remind them of their grandfathers?


I am around a lot of old people at the pool everyday. Most are retirees. They have gray hair, old bodies and, in general, look their age. I feel like a young whippersnapper compared to them. Unfairness to them, I am probably 15-25 years younger than them so I am a young whipper snapper.

I’m impressed with their dedication and drive to stay fit. But I have zero attraction to any of them.


I occasionally run into attractive women at the pool. They bring their toddlers to swim lessons. Or they come swim laps during their work break.

They all look to be 30-50 years old.

In other words – younger than me. Some much younger and in a different chapter of their lives.


So I have concluded that it is unlikely I’ll be dating anyone – perhaps ever again.

I have no interest in dating someone whom I’m not attracted to. Similarly, why would an attractive woman who’s 10-20 years younger be interested in dating me?

They wouldn’t.


I’m writing this post to myself. It’s a reminder to not go back on dating apps looking for a unicorn to play a role in some fairy tale in my head about second chances, love and “forever”.

It might sound like I am depressed or in a negative head space. I can assure you I’m not. In fact, I feel fantastic about my life today as a committed solo guy.

I miss my wife.

I miss my old girlfriends.

I miss the time we spent together, the touching, the excitement and the love we shared.

I have many fond memories of those times.

I suspect I may never have them again. And if that’s true, it’s OK.


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