January 20, 2022

Who Would Have Thought Dating in Our Forties Would Be So Hard?

Even in my most skeptical moments, I have always been a bit of a romantic. I have never stopped believing I would one day find my someone who would ride away into that sunset of bingo games and slowing down the freeway together with me.

Dating in our 40s.

I had no idea the difficulty that awaited, friends. 

When you’re in your early twenties, dating is so easy. You can fit everything you own into the back of your car, and it doesn’t matter too much where people’s families are from, what those you date want in their future, or even if you have a weirdo roommate eating pork rinds on the couch next to you, while you go to second base with your new special someone.

In your early twenties, you don’t know what your own red flags and problems really are yet, so you also have no idea what to look for when it comes to those things in a partner. Seems almost anyone could be a potential mate. After all, you’re young and just having fun. Plus, let’s not forget we all knew everything about everything when we first left home. There wasn’t much to learn about ourselves when we already knew it all.

In your late twenties, you’ve got more shit accumulated, but you can still move it all in a few loads with a borrowed pick-up truck. Maybe you’ve already gotten married. Hell, maybe you’ve already gotten a divorce. Maybe you’re thinking about having kids or perhaps you’ve got a couple rug rats already ruining the stuff you do own. 

You’ve finally figured out you didn’t quite know everything when you first left home. You’re aware that you’ve got some shit to work on, and you have an easier time finding people whose shit seems to match your shit. Your body still feels young. Your energy is still easy to tap into. Life is good. Love is easier.

Then there’s our thirties. There are two groups of people in their thirties. Those who get serious about life and families, and those who continue to play and think very little of those things at all. I was a part of the first group.

It seemed finding people to date in my thirties was easy since I had a small child, and so did most everyone else I was matching with on dating apps. In truth, adding more children to the brood, whether more of my own or someone else’s, fit right into the flow and idea of life. Since people only matched at that age who were on a similar path in life, we didn’t yet have to worry about too many of the trickier aspects of the future.

Our thirties were great because we still got to pretend we were young. We started finding our professional paths in life. We lived enough life to ditch those people we may have gotten ourselves stuck with in our twenties. We started moving up in jobs, housing, and maturity. All our stuff could fit into the back of a moving truck, and it still wasn’t too hard at all to mesh two lives.

We also understood ourselves more maturely than we ever had, and we all kind of rode this wave of self-improvement and endless hope together. It seemed most everyone I met in my thirties was working on themselves, and that was good enough for me.

But then…

Hello forties, and all you people who made it here currently single alongside me. Welcome to these turbulent, uncharted waters.

I would tell you what it’s like in your forties, but so far… I have not figured it out even a little bit. I honestly seem to get a little more frustrated and a little more confused with every person I try to meet.

So… Instead of blabbing on about something I know nothing about, I’ll tell you where I’m currently just… So… Fucking… Lost.

1) My kid is a teenager now. He’s about to start high school. I’m on the finish line, over here. I don’t want to start over with small children. Judge me for that, if you will. I just don’t. I’ve given everything I’ve got to raising my kid, and Daddy is tired. Of course, this eliminates dating almost anyone in their late twenties or thirties since they have small children or might someday still want them. 

2) I basically have my shit figured out at this point. I’m far more aware of what actually is wrong with me than I was ten to twenty years ago. I have learned what I can and can’t do when it comes to dating. I have learned what my red flags are. I have learned when it’s just not going to work, and I know the types of people who can’t handle me.

3) Anyone who is single in their 40s has mostly figured out the same things about themselves, too. They know when it’s just not going to work, and they know which types of people just can’t handle them. The honesty that exists in this awareness, for them and me, makes it so much harder to find what we believe is a compatible person.

4) On a similar note, I think many of us might just have our shit figured out a little too much now. We don’t get to enjoy the waning naivety we always did in the past as we look for partners. We have come to accept that we somehow can’t outgrow our mommy and daddy issues completely. We understand that parts of our childhood will affect us forever, as much as we wish otherwise. We understand that the person we find must be okay with the parts of us we know we cannot ever truly fix.

That’s kind of scary sometimes because before our forties, we were riding that self-improvement high and believed we could overcome just about anything.

5) People trying to date at this age are just… Tired. We all just seem to be at this weird burnout point. Our conversations on dating apps are half-hearted because the dating apps don’t work. Our dates are more boring than they used to be. Even sex with new partners has just kind of become a little more… Lazy. Can we all be honest about that? 

6) Photo filters. Dear lord, all the filters. I have so much to say about them that I think they need their own blog post. I’ll write that next.

7) Stuff. I have things now. Lots of things. An extra decade worth of things. I own a nice house, which I have decorated (to my tastes) every inch, some of which is expensive personal d├ęcor that I’m not going to move or get rid of. It’s a big house, yet I have no idea how to fit someone new into it. There’s no room for someone else’s pictures or art. There’s no room for someone else’s kitchen appliances or dish sets or garage junk.

Hell. There isn’t even a rentable moving truck that can move my stuff anymore. At this point, I somehow need a semi-truck if I were to move again.

8) Life. Work. Friends. All that kind of stuff. At this age, as a single parent, I have almost every minute of my life planned out. There are friend groups. There is family stuff. There is one-on-one kid time and extracurricular kid time. There is work and all the dynamics that go with that. There are side projects. There is home maintenance. There are trips. There are neighborhood events. There are holidays. There are bills to pay and taxes to do. There are things to learn. There are errands to run. There are appointments to keep. There are moments needed alone. And of course…

9) My hobbies. There are some hobbies I hope to one day share with my person, such as pottery, art, poker, or hiking. Then there are the hobbies I kinda must explain, such as my love for body painting. It’s a conversation that I can’t avoid with any person who could be a potential.

Summed up, it goes like this. “Young women come over, take all their clothes off, and I spend hours alone with them painting onto their bare skin.”

I mean, I know it’s a pure art form, the power of which lies in trust and the desexualization of nudity, but how on Earth do I explain that to someone new?

10) Finally, there’s just age in general. I’m feeling it and I know other people my age are as well. I’m closer to 50 than I am to 30 now. That’s a very strange thought to me. I honestly don’t think I could keep up with someone too much younger than me.

Sigh. Dating in our 40s. I don’t know, friends. 

As I write and think about these dynamics, it seems the ultimate frustrating factor is that for any of us to get to this point in life (still single), and to remain awesome (datable) people, we also each have had to create and build lives for ourselves that are full, busy, and don’t really have room for anyone else without a lot of effort and a lot of change. Am I off in left field?

I really want to date someone who is at a similar place in her own life. Yet, how do you possibly mix two lives that are so established and so full?

I dunno. Am I looking at it wrong? Is this a real problem, or is it just something I need to dig deeper and figure out? Is there a place I’m just not looking to find the right person? Do I need to lower my expectations? Do I just need to give up and wait until my 50s when so many of the children dynamics aren’t in play and nobody cares that you can’t have sex like you’re 20 anymore? 

I honestly don’t know the answers. 

What I do know is that when I moved into this new house, I did keep half the drawers in my bedroom and bathroom empty… Just in case I one day figure it out.

Dan Pearce | Dan Pearce Knows Nothing