I'm jumping back into the dating pool

This time, I’m noticing what it actually costs.

Photo by Mika Photogenius on Unsplash

I used to think about turning my old dating adventures into columns — but never seriously.

It always felt a little off, like I’d be turning private moments into superficial click-bait. So I left it alone, and for much of the past four years I wasn’t in that world at all.

Then I got out of a long-term relationship and found myself back in these dating streets.

Now there are things the new me can’t unsee: how quickly time gets allocated, how expectations form almost immediately, how money starts moving in ways you don’t notice until you add them up later.

Seen in that light, talking about dating openly stops feeling like sleazy storytelling and starts looking like what it’s always been: another Money Talk.

And it’s rarely dramatic in real time.

One drink turns into another. A conversation runs longer than it needs to.

The downside is it adds up. Time, mostly. But money and energy too.

But the reality is I’ve got more of all three now than I used to. More time, more space and more resources. At some point, you’ve got to do something with it. I’ve still got to live.

So I’m back out here.

Not with any big plan or reinvention of how I do things. Just back in it, figuring it out as it goes, like most people do.

I don’t want Parker to make the same mistakes, so maybe keeping romantic lessons to myself isn’t the best idea.

Although she did fall over in her bed and play dead when I asked her thoughts about me dating again.

Still, think about how much money gets wrapped up in courtship, dating, engagements, marriages and divorces.

And how much of the fallout, emotional and financial, could be softened if people were just a little more honest early on.

I owe Parker that, in an age-appropriate way, whether she’s enthusiastic about it or not.

And I don’t mind dating. Not when it’s respectful and reciprocal. I learn people, I learn myself. I end up doing things I wouldn’t normally do, and I usually walk away with a story worth keeping, one way or another.

But dating has never been cheap, and it’s only getting more expensive.

Recent data from the BMO Real Financial Progress Index revealed that Americans spend $189 on an average date, including pre-date grooming and gas money, up 12.5% from $168 in 2025.

Forty-seven percent of singles say dating is not financially worth it.

We’ll see. This will be my first time truly dating in my 40s, so I’m interested in seeing what that looks like from here.

There’s a drawback to stepping out as this version of me, though, and it has nothing to do with my age.

It’s simply that I don’t move like most people anymore.

I’ve committed to doing things most people won’t, which naturally narrows the field. So the question becomes less about who’s out there and more about who actually fits the way I move.

That’s a much smaller number than it used to be.

And I feel it — in what it means for the wife and life I want.

But there’s only one way to find that person and build that life. So I’m back in these dating streets, embracing experiences.

Maybe I’ll write about a few of them along the way.