That Girl: Dating younger guys vs. older guys


I had a date this weekend. A “normal” date; whatever that means. We had great conversation and a couple of laughs over a few beers. It was a nice and welcome change from what I have been experiencing lately – low key. No horror stories.

To be honest, this column was the main reason I asked my date out in the first place. I mean, it ended up working out pretty well. He is cute and we had a fun time, and we may even go out again.

My initial motivation, however, was, “Hey, you have a dating column now… you need to actually go on dates consistently.” I need new material, after all, to keep all you readers interested.

That girl: Older men vs. younger men, Twin Cities Agenda

So I squeezed him in before a comedy show with one of my girlfriends – you have to have a contingency plan, right?


Clearly I’m still struggling with this whole dating thing. It’s overwhelming, and yet, often due to the repetitiveness of those “first date” questions, it’s not all that stimulating either… How can it be both stressful and boring? I don’t get it.

I’m pressing forward, though. Onward!

But I have a question. One that (maybe?) will help solve my previous conundrum: What age group should I be aiming for?

Here’s the thing: I’m in my early thirties. It is a challenging dating age. Most (not all, granted, but many) people my age are married, with children. I’m past what society considers “prime baby-making age.” Men looking to have a family would likely chase after a woman a good five years younger than me (or more). Which is okay… for me. Babies are kind of scary.

But I’ve also had some problems dating younger in the past (you can read more about that here).

There are some exceptions to the rule, of course. I won’t eliminate all younger men because of one douchebag; however, age is not always “nothin-but-a-number.” It’s a real thing, and a thing that certainly gets in the way of a real relationship. I cannot get past immaturity, or a lack of respect. Which, in my experience, does tend to improve with age.

Do I aim young in hopes of finding a mature one in the bunch?

That Girl: Dating younger guys vs. older guys

Or, do I go for an older, more stable man? He may have some extra baggage, sure. But don’t we all? It can be assumed, generally, that an older demographic, say 35+, is likely to have had a serious relationship in the past. Perhaps a marriage. Perhaps children, too. While this is totally fine with me, it is a complete shift in mindset. Exes and kids can add an extra element to dating. These men have a different set of priorities than their younger counterparts. They talk about things like the days they’ll have their kids with them, future plans (planning things months in advance! *Gasp!*), and financial goals, much more than the younger group.

Finding a single, straight man who is available is hard enough. But I want to narrow the search a little bit with age, don’t I? Or maybe not. Maybe I keep all options open. No age restrictions?

“It’s like a buffet,” a friend of mine told me. “Some things are good aged, like cheese. And some things you want fresh.”

Okay. Eliminate the age factor. Then what? How then do I filter in these stupid dating apps?

Maybe by interests? “Hey Alexa! Find me a man that likes cats and books!”

If only it were that easy.

Missed last week’s episode? You can find it here: That Girl: “Mom Knows Best”