The Pluses — and Minuses — Of Dating Older Men


Some women in their 20s complain about “the men today” when it comes to dating.

For you younger women who are beginning to think all men are morons, I’m here to offer you a bit of hope: It gets better.

There are some big advantages to dating men who are in their 40s and 50s. I’ll let you know about those, but I’ll balance it out by telling you what’s not so great about dating older men.

(These are just general trends I’ve noticed. Please don’t mistake me for saying these points are true of all older men.)

+ 1. They’re better at chasing even though they’re slower.

The messages I get from men in their 40s and 50s on online dating platforms tend to be richer, like they’re trying hard to get me and my attention. They seem to have gotten the “For God’s sake, ask me a question I can answer” memo about how to start a conversation.

Younger men do ask questions, but the question is more apt to be, and I quote, “s’up?”

Ok, I’m exaggerating. Plenty of younger men write very nice messages. I’m just saying that about 100% of messages from men in their 40s/50s show effort.

When I go on dates with men in their 40s and 50s, I’ve generally found there’s less of a push to get in bed. It’s almost as if older men get that there are more important things than sex.

(Besides, as you get older, you realize that sexual compatibility can be ‘worked on’ and improved. It’s not a fixed “You either have it or you don’t”.)

Don’t get me wrong. Older men are still interested — very much so — in sex. I’m just saying that the approach is different. I don’t feel as if their every effort is made to steer me from the restaurant table to a bed as I did when dating younger men.

Then again, maybe older men are just better at being subtle about it.

+ 2. They don’t dawdle.

As we get older, there’s a consciousness of time going by…an understanding that our days on the planet are numbered.

If we’ve bungled our relationship lives in the past, we don’t have as much time left to get it right.

This plays out in two ways.

If an older guy isn’t feeling it, he isn’t as likely to waste time stringing a woman along or biding time just for the heck of it. He quickly lets you know he’s not feeling it and moves on. No time wasted.

When older men are feeling it, they seem determined to act on it quickly. They’re quick to go exclusive and seal the deal in terms of moving in or marrying.

My overall sense of older men is that they’ve finally got a lot of things figured out. They know what they want — and don’t want.

Of course that means you need to have your act together, too, if you want them to believe you’re worth their precious time.

+ 3. You know what you’re getting.

You’ve seen the fates of popular, high school quarterbacks who become below-average Joes.

You just have no idea whether that 20-year-old with the shaggy Justin Bieber haircut is going to go bald or not.

You don’t know if that ripped guy in his 20s is going to have a paunch and dad bod in his 40s.

But if you meet a guy in his 40s and he’s in shape, you know he’s that way. You know fitness is part of who he is, not just something he did before hitting the club on Saturday night.

Then again, if you’re dating at my age, you hopefully realize that physical features are fairly unimportant in deciding if a guy is right for you.

After all, shorter guys tend to be less likely to cheat. ‘Does not cheat’ trumps a head full of hair any day.

By the time a guy is in his 40s, you know whether he met his potential or not. You don’t have to wonder if the guy just talks a good game. You’ll know whether he did or didn’t follow through.

You wouldn’t have to hope that the young guy you saw playing video games in college and skating by with Cs finds his way in the world. You get to know that he has done fine — better than fine — in the work world despite sucking on academic exams.

Meeting guys when they’re older means you don’t have to worry about how they’ll turn out.

+ 4. Bonus: Snip, snip.

The great thing about dating older men is that many of them have had a vasectomy. Now that’s pretty dang nice.

If online dating apps had a question for that so we could know if a fella has or hasn’t had a vasectomy yet, that would be awesome.

-1: Ride or die isn’t cute.

Nowadays, I hear people referring to their significant others as their “Ride or die”. (Not sure why they don’t just stick with ‘boo’, but ok.)

If someone is my ride or die, I’ll be there for them when they have health problems. Naturally, I would prefer to put that off as long as I can, maybe get to be together a decade or so before the health problems start cropping up.

I once went on a few dates with a guy in his 50s who seemed pretty fit. He played tennis, fairly intensely, for several hours about 2 days a week, and he skied once or so a week during the winter.

A few dates in, he told me that he just found out that he had high blood pressure. I mentioned that I’d had to learn a lot of heart-healthy recipes in recent years to keep my own blood pressure down.

“I’m not going to bother,” he said. “It’s just easier to take the meds”, he said.

My interest in him disappeared.

I wish online dating apps had questions about that, like “Do you take any medications for preventable health problems? Are you doing what you can to be healthy so your woman doesn’t have to worry or take care of you as much?”

Yeah, I know, that’s not as sexy as knowing whether someone prefers mountains or beaches, but it sure would be useful to know this when dating older men.

It’s not about sickness and health. It’s about the actions that we do — or don’t take — that affect the people we supposedly care about.

-2: They’re stuck in their musical heyday.

Many men in their 40s and 50s seem stuck in the 80s and 90s when it comes to music. Some believe that any music written after their own heyday is of inferior quality.

(Hint: Just because something doesn’t match your preferences doesn’t mean it’s not good.)

An older guy I know was recently mocking an outfit that the pop singer Rihanna was wearing. Granted, her outfit made her look like a red M&M, but this guy’s favorite band back in the day was Motley Crue. Have you seen what they wore?!

“But the music was real back then!” he blustered.

I couldn’t help myself. I pulled up the lyrics to one of Motley Crue’s hits, “Girls Girls Girls”. The first lines read,

“Friday night and I need a fight.

My motorcycle and a switchblade knife.

Handful of grease in my hair feels right.”

I laughed and laughed about the greasy hair line. He didn’t appreciate it, but c’mon now.

Me, I have music on in my home from the moment I walk in the door after work ’til I go to sleep. I listen to a constant stream of music instead of watch TV. I keep up with music, often knowing the songs my students know.

If I cohabitated with a man in his 50s, I don’t think he could bear the 2020s pop or country or indie music I’d sometimes pipe into our shared home.

Maybe he put up with modern music when his teen-aged kids lived with him, but the default of many older men, when the kids aren’t around, seems to be to listen to music they liked when they themselves were in their 20s.

When dating older men, I start dreading having to listen to nothing but those ol’ classics when we drive together anywhere in the upcoming years.

Long road trips…dear gawd.

In the grand scheme of things, music is an unimportant feature when deciding who to date. I’m not sure it’s so much about musical taste as it is about being the kind of person who can’t find value in new and different things.

Getting stuck in musical ruts — or ruts of any kind — just isn’t super attractive to me.

-3: A full house isn’t cute, either.

Most older men I’ve dated have kids. On one hand, this is a very cool thing. There is nothing sexier than a good dad.


I’ve seen too many friends whose adult kids moved back in with them. I hear and see the struggles.

The 23-year-old kid mooches off the parents while working a part-time job, playing video games, leaving dirty dishes around, smoking pot in his room that smells up the whole house, coming and going when he wants even if that means his car lights and clatter wake the parents up when he comes in at 2am.

The older guy I meet might not have a kid living at home with him right now, but there’s a chance that one of his kids might move back in after college. I’ll deal with that hurdle if the time comes, but I’m sure not looking forward to it.

Bottom Line

If you’re frustrated because the younger men you’re dating seem immature, you could certainly look forward to dating men when they’re older. Some things might get better when dating older men, but some might get worse.

But here’s the real bottom line: It’s not about age. A good man is a good man, whether he’s 25 or 60, and even if he does listen to Motley Crue over and over again.

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