7 Uncomfortable Truths Of Dating After 40

Whether you like it or not, dating changes the older you get.

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Dating is such an odd phenomenon. You’d think going out and finding a suitable match would be easier, especially as you get older, but it’s downright tricky. At least for some of us.

Maybe I’m picky, or perhaps it’s because I travel around a great deal, so actually finding someone worth telling Mom about is a difficult endeavor. Of course, if you’re like me, you probably have that one family member or friend who blows through relationships like dandelion seeds in a hurricane. Whenever you turn around, they’re with someone new, and it continues until you just stop learning names, because what’s the point?

I have so many questions for these people. Namely, how are you meeting so many strangers worth dating? Naturally, there are those who have deeper emotional issues and, rather than focusing on themselves and disconnecting from the dating world, they cram those feelings deeper and plow ahead to the next person, which will only compound the issue. There are others who are so mind-numbingly gorgeous that they can simply pick and choose anyone from a lineup of everyone, and then there are those who have some combination of money, sexual prowess, and pheromones they may or may not have ordered from the back of a plastic-wrapped magazine.

For the rest of us, dating, especially after that landmark “40” age, starts flagging us down on dating profiles like overripe zits on a teenager; it’s a challenge. I’m sure most of us expected to be in long-term, meaningful relationships at this age, and so we never considered asking parents and relatives what it would be like to date while over the hill.

And yet, here we are, and, as we all go (or at least as I’ve gone), there are some dating discoveries made along the way. If you’ve found yourself in a similar boat, chances are you’ve made some of these observations while searching for that special someone.

1. We All Have Baggage

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I’m not going to use the word “trauma,” as I feel that word is tossed around far too casually these days. Being locked in a basement by inbred hillbillies for a decade is trauma. Living with someone who wouldn’t pick up their dirty clothes is annoying.

At this age, we’ve all been through shit. Maybe it was a difficult divorce, or maybe your spouse unfortunately passed away. Perhaps your parents died at a young age, or you never even knew your parents. We’re not all made with the same ingredients, which leaves some of us sweeter, others bitter. Honestly, there are days I feel like a pineapple upside-down cake accidentally made with salt instead of sugar.

While our baggage is our own, it is important to know we aren’t necessarily special in that regard. Others are also coming in with their own struggles. It’s not a competition. I once dated someone who, whenever I opened up about some of the issues I was dealing with, immediately turned it around, pointing out that her issues were far worse.

I’m not going to tell you how to date anyone. That’s up to you. But it is so important to understand just about everyone you encounter, much like you, will have baggage. At this point in life, that’s just how it goes.

2. The Dilemma Of Kids

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In most relationships, you enter them hoping to become the other person’s one true love. The person they care for above all others.

That’s no longer the case when it comes to existing children. While it is a different kind of love, you will never be that person’s pinnacle. For some, that can be a difficult pill to swallow. You’ll forever, at best, be second place. Or third.

And even if you’re okay with that, dating someone with children, especially if you don’t have any of your own, is another unique experience you’re more likely to encounter as you date into your 40s and beyond. In some instances, the perspective mate’s children might already be in college or out of the house, while others might just be starting grade school.

I don’t have kids, so whenever the other person does, the potential relationship feels entirely different from when I was younger. Because you’re no longer dating just that other person, but that person’s children as well. Their say can make or break whether you’ll be given a long-term chance. I’ve been with women whose children immediately warmed to me, and we blended like Nesquik and milk. While for others, we were oil and water.

It’s a dating truth that, while not universal, you will likely have to get used to.

3. Status Is More Important To (Some) People

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When you dated in your twenties, it was almost exclusively based on if you found that person nice and attractive. Unfortunately, depending on who you are and where you live, those days are long gone.

When you’re dating in your forties and beyond, it’s often no longer good enough to be nice and attractive. You need to bring that person status. Whether that is having a solid paying job, can bump them into a new tax bracket, pay for their expenses, or offer them something they do not currently have and want.

It’s basically high school dating on steroids. When I was in high school, if you dated anyone who liked role-playing games, comic books, or was in the marching band, you were instantly labeled a nerd. A dork. Someone lower-tier. And then, if you dated a tall athlete who was likely to get some kind of athletic scholarship, or one of the girls from wealthy families who always wore designer clothes, that would elevate your high school status. Somehow, over twenty years later, those kinds of status dating games are back in full force.

This isn’t to say everyone does this. But it’s something you have to deal with, and often it doesn’t matter what the other person who’s judging you does. There’s an episode of Seinfeld where comedian Jerry is dumped by his girlfriend. When asked why, she said it’s because she caught his act and she can’t be with someone whose career she doesn’t respect. His response was, “But you’re a cashier.”

Unfortunately or not, what you can do for someone’s status when dating after forty is now often part of the equation

4. Politics Has Entered The Chat

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This one gets exhausting. At least for me, it does. Because you can meet someone who checks off most of your boxes, and yet if you do not entirely match their political agenda one hundred percent, they will immediately pull the plug.

For some, there is a need for political alignment. That makes sense. Now, I have no problems dating someone with whom I do not agree on everything political. Frankly, I’ve always found select ideas of most political parties attractive. But there are certain people who will shun me should I say there’s something I agree with from the opposite political party (personally, I find it rather narcissistic to think one party is 100% correct on everything all the time and all other parties are 100% wrong on everything all the time, but hey, that’s just me).

It never used to be that way. I think, realistically, that the fracture happened back during the Bush/Gore election, and it has been growing ever since, but maybe people older than me would say it happened with JFK or Nixon.

I just know that in modern dating after forty, there are going to be people with whom you match perfectly, but because politics is a major part of your/their personality, it simply won’t work.

5. How The Hell Do You Even Meet Anyone?

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Where is everyone meeting everyone? Like, seriously, how do you meet anyone? There are dating apps, but those just feel more superficial by the hour. And sure, you could go to a bar, but are you really going to meet a perfect match sucking down gin and tonics in the corner of a dive bar?

It feels like our parents had access to a “third space,” where they could meet others at local events, libraries, church, or any number of safe spaces. And yet the very concept of a third space, at least in the U.S., is elusive. Libraries aren’t the kind of meet-up space they once were, and unless you’re religious, swooping in on the “available talent” during mass probably isn’t the best look.

Modern activities feel, in many ways, intentionally segregated. Being a man and trying to meet someone at pilates is NOT going to end well. And don’t even think about going somewhere children might be if you don’t have children of your own. Women might have a little more wiggle room here, as men are far more likely to receive the “creep” label slapped across their forehead, but even so, the established boundaries can be difficult to cross.

And even those boundaries can be detrimental to women. Because men don’t want to receive the creep title or be blasted on social media for shooting their shot and failing, they are less likely to approach women at mixed social events. That puts more responsibility into the hands of women. In short, it’s all a mess that becomes so much more frustrating as you age.

But, seriously, where do you actually meet people? Asking for a friend (and maybe myself).

6. Natural Aging May Be Held Against You

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Maybe your skin isn’t as tight as it once was. Maybe you have more wrinkles around your eyes. Maybe you don’t have as much hair on your head as you used to. It’s all a natural part of the aging process, and yet it may very well be used against you.

Of course, there have always been beauty standards. That’s nothing new. But it feels like more than ever, your ability (or lack thereof) to hold off signs of aging affects your ability to date. Men might not like how certain areas of the body now sag, or heck, they might not like how much you’ve done to prevent aging (talk about a catch-22). Guys might find their dating perspective flake away with their hairline.

I don’t think this is necessarily different from when we were younger, as everyone has a type and everyone is attracted to certain looks. It just becomes more defined and more obvious.

7. Accomplishments Might Work Against You

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People like to be the center of their own universe, which means they don’t like it when others around them shine brighter. They certainly don’t like it if their significant other does. Again, this isn’t something that everyone does, but there will be those who see your accomplishments and back away from you because of them. Maybe they’re jealous, feel inferior, or just don’t want you to be “better than them,” but unfortunately, that’s the case.

I’ve lived in going on six countries and have traveled all over the world. I’ve seen and done things many people will not have the chance to do. It’s not something I bring up unless asked, because I don’t want to be the guy who spouts off about how Spain has fresh orange juice machines when visiting a 7-Eleven in Lansing or how Medellin has a mall dedicated exclusively to selling knockoff shoes when stopping by Payless. It’s obnoxious. And yet, I’ve come across people who don’t like that I’ve done so many adventures and will use it against me.

Maybe you’ve experienced the same. It doesn’t need to be travel; it can be education, awards, or having a New York Times bestselling novel. Being shunned for your accomplishments was never really a thing when we were younger. But now it is.

Guess it’s just part of getting older.