Skip to content

ainslies.org

a small, quiet life

Menu
  • Home
  • About
  • Archives
Menu

365 Days Date Free

Posted on March 2, 2023 by Steve Ainslie

It’s been about a year since I did my online dating experiment. I’m happy to report that I am extremely satisfied with my status as a non-dating single man. Having some time and distance has enabled me to look at my dating experiences in a new light.

First, and somewhat surprisingly, I have a warm fondness for most of the women I met. They were smart, attractive, interesting and accommodating. I realize now that they cut me a lot of slack as I fumbled around trying to “relearn” how to date after being married for 3 decades.

Second, I think I have a better understanding for why one woman ghosted me, two others said they didn’t feel a romantic connection, and why I didn’t feel a connection with several of them after meeting in person.

Third, and most importantly, I realize that I’m not interested in using dating apps and am only slightly open to dating at all.


Even when I think about my favorite dates with The Music Fan, I can now see that we probably weren’t ever going to be a good fit for a long term monogamous relationship. She was hot. And funny. And fun. I enjoyed being with her and undoubtedly felt my heart race when I thought about her. And now, I realize that she liked me too. But that isn’t enough.

As for future dating plans, who knows? I occasionally think about some of the women I see regularly at the pool or when dog walking. I have moderate curiosity about a librarian I run into occasionally. But, unless our circumstances lead to more conversations, reveal mutual interest and we have good timing, I suspect no dates will happen.

I am A-OK with that.


I had a good marriage and a great relationship with my wife. I have a lifetime of memories from our dates, our attraction, our love and our good times together – enough to carry me for a lifetime.

I was lucky. She was lucky. We were lucky together.

Now I’m in a much different place on the back half (or quarter?) of my life. I’d never repeat what I did when I was 21. I’m not the same person anymore.

I am proud of myself that I gave online dating apps a shot last year. I put myself out there, got uncomfortable and had modest success and failures. Now I know what that feels like and I don’t need to do it again.

As for the women I dated, I can honestly say that I hope they all find what they are looking for. I think some had already found it before I met them and I suspect many others will.

Recent Posts

  • Giving Up Fighting Mother Nature
  • If It Hurts Don’t Do It
  • Not Today
  • Work/School From Home? Sorta.
  • A Little More Reasonable
  • Stormticipation
  • Risk/Reward
  • An Unexpected Upgrade
  • “There’s A 50% Chance You Are Below Average”
  • Plumbing Logic
© 2026 ainslies.org | Powered by Superbs Personal Blog theme