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“Dating Is Supposed To Be Fun”

Posted on January 3, 2025January 4, 2025 by Steve Ainslie

Back when I tried dating again after my 29 year marriage and the death of my wife, I had several friends who regularly offered me dating advice and checked in to see how it was going.

After a few months, a half-dozen mediocre dates and a lot of wasted time trying to find matches online, I told one of my friends that this was starting to feel like a grind. I was putting in a lot of effort and not seeing much upside. He replied,

“Maybe you should take a break. Dating isn’t supposed to feel like work. Dating is supposed to be fun.”

He was so right. His words stuck with me as I thought about the six months I spent dating. Everything in my life was great – except dating.

So I took a break and haven’t gone back.


That was 3 years ago. I have a feeling I will never return to dating apps.

I’m open to dating someone I meet in real life, but since I’m not actively looking, it’s unlikely to happen.

Which is fine for me.


But lately I’ve been thinking about what I hear from others – on podcasts, in news reports, online and from members of the Solo community.

They all talk about how much dating sucks.

I’m not going to offer anyone advice on dating. I know what worked for me when I was a teenager 40 years ago. I have no great wisdom to share about dating in 2024.

Instead, I will repeat what my friend said to me, “Dating is supposed to be fun.” If it’s not fun, perhaps it’s worth asking if you can do something differently.

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