The Perils and Rewards of Dating Over 50

And how sex and age play into the process

Like everyone on the planet over the age of 50, with the possible exception of the Unabomber, I’ve had more than a few romantic relationships. I was married for 11 years, engaged for one, partnered with a lovely woman for five, and had a few shorter dalliances along the way.

What I suppose makes me a bit different is that during my 13 years of singlehood, I’ve dated a lot—more than 1,000 dates with more than 300 women. I realize those numbers are off-putting to some, especially women, but if you do the math 1,000 dates in 13 years means an average of seven dates with two or three women a month. And I'm not alone, I have listened to hundreds of my "mature" (over 50) peers about their dating experiences.

Does this make me an “expert”? I’ll leave that for others to determine. But I do think I have more information about dating over 50 than most experts. I look at it this way: who is the expert about baseball, someone who played for the Dodgers for 13 years, or George Will, a bow-tied columnist who writes about baseball?

Just to be clear, it would be lovely to find someone I could be in a long-term relationship with (Note: I intensely dislike the phrase “grow old with,” to me it connotes two elderly people drooling in wheelchairs together.) But until I do, this delicate, passionate, wonderful, and terrifying process of dating over 50 fascinates me.

There is a consensus that dating over the age of 50 isn’t always pretty. In my opinion it can (and should) be enjoyable most of the time, and interesting almost all of the time. After all, you’re meeting new people, hearing new stories, thinking about the possibility of new relationships, maybe even allowing yourself to drift off and think about sex. And you’re doing all this equipped with years of knowledge.

The great advantage is that you know yourself better than you did at 30. You know what you want, or at least don’t want, and you have less patience for BS so you know if somebody is a good match or not a lot sooner. Ideally, you are relaxed enough to view dating less as a referendum on who you are and more as a form of entertainment that could possibly lead to a lasting relationship. So why do so many people over 50—especially women—seem to dislike dating so much?

There are many good reasons.

  • It can be exhausting. If you’re a reasonably fit and energetic individual, getting attention from potential dating partners is fairly easy. You might even find yourself lining up several dates a week, which can be fun, but tiresome! I’m reminded of Roy Scheider’s character in “All That Jazz.” He’d look at himself in the mirror every morning and say “It’s showtime!” to ready himself for the day. Every date can feel like showtime, and not necessarily in a good way. I suspect many of us have done that—at 7 p.m. as we ready for our 8 p.m. date, we look in the mirror and say to ourselves, “Okay, got to be charming, got to be positive, make sure nothing between my teeth, don’t take out any photos of my ex.”

  • These days, thanks to the Internet, you can meet dozens, even hundreds, of people you never could before, and that is mostly a good thing. But of course online dating profiles are just snapshots, sometimes inaccurate or overblown, and there’s no substitute for meeting in person. And as exciting as it can be to meet new people, let’s be honest, a lot of these new people are dull-witted, out of shape, self-centered, narcissistic, and/or arrogant.

  • For women, dating can even be creepy. I’ve heard stories from women about guys who stalk, who propose after two dates, and then get livid if the woman politely says she isn’t interested in meeting again.

  • For men, dating can be an expensive habit. Despite all the admirable strides women have made in recent decades, there is still one physical limitation most women seem to have: reaching for their wallet. I’d guess less than 15 percent of the dates I’ve had offered to pay on a first or second date, and this includes women who made substantially more more money than I. (I’ve been asked how I know how much money these women have, and it’s not rocket science. If they live in a four-bedroom Park Avenue apartment,  talk about how much money their ex has, or about how they recently went to Paris for the weekend, one can draw reasonable conclusions.)

  • And perhaps the reason that looms largest is this: it’s difficult to find someone with whom you want to spend however much time you have left with. Sometimes it seems like a race against time. We say to ourselves, “Hey, I don’t have that many years left. How many false starts do I have to go through before I find ‘The One’, and when I do find him/her, will I even be up to the task of having a relationship?” At this age, most of us are metaphorically looking at our watches.

Considering the list, it is easy to see why not everyone in my demographic approaches dating with boundless glee and optimism. But I am here to point out that as we get older the misconceptions we bring to the dating process can interfere with what should otherwise be a good time.

Age Misconceptions

Many mature women seem to believe (wrongly I might add) that all men their age are looking for younger women. Not true. Not even remotely true.

Most rational men over 50 want women their own age for good reasons: 1) we enjoy the shared life experience that being on the planet roughly the same number of years offers; 2) unless we are idiots (and certainly some men are), we understand that trying to have a real relationship with someone 15, 20 or 25 years younger is a prescription for humiliation and heartbreak.  

Think an age gap doesn’t make much of a difference? Compare yearbook photos of college students in 1969 with those from 1966, long hair, tie-dyed shirts and Dashikis replaced crew cuts, ties and ladies circle pins.

I’ve had relationships with women six years older and 10 years younger, and both were pushing it, especially the younger one.

Men, if we think we look cool and desirable with a young woman on our arm, think again. We look ridiculous. Other men don’t envy us, and we are reviled by women our age for good reason. (Note: the only reason a woman wants a man 20 years older is money. Show me a “May-December” romance that has lasted for any reason other than money. Can’t be done. Donald Trump? Don Imus? Come on.)

And when the woman dumps the older guy, as she most likely will, the men run with their tail between their legs to age-appropriate women who should, and often do, say “No Thanks.”

The same is true of women and younger men.  Once a woman has gotten over the excitement of being a cougar, it will dawn on her that these younger guys have no real interest in them beyond sex, conquest, and perhaps also, money.

A study conducted a few years back found that political views mattered more than just about anything else when it came to finding a mate. Well, age has to be a close second.

It is understandable that someone who is getting older, particularly if their spouse of many years left them for someone younger, would think everyone is out there trolling for a young hard body, but it just isn’t the case. Most of us “mature” folks are looking for that common life experience. And most of us would prefer two soft bodies to being the only soft body in the room.

So Ladies, if you’re reading this, please try to stop worrying about men your age chasing women their daughters’ age. It’s happening far less than you believe.

Sex Misconceptions

On the other hand, what women over 50 might want to consider is the issue of sex itself in the world of dating. Many men in their later years still feel like they're 21, or at least very much want to feel like they’re 21. In other words, sex is important to them. I'm not saying it isn't to women (so ladies, don’t pounce on me (or rather do, in the right circumstances!), but it’s probably fair to say that, when it comes to sex, men and women generally have different timetables. This isn’t news, it’s just sort of astonishing that the dynamic is largely the same 30 years later.

I once thought women were more careful about when they would sleep with a man because they wanted to protect their "virtue" and would reason that if they didn’t sleep with a guy until they’d had several dates, the guy would “respect” them more (a term one hears often, whatever that means.) I still don’t understand the connection between sleeping with someone and respect. I mean I get it, but it always amazes me. I didn’t sleep with my ex-wife until we had dated for six months. I slept with my ex-fiancée on our first date. Both long-term relationships ended, having absolutely nothing to do with when we first slept together.

I once heard a wise old maxim that still rings true: men sleep with women to see if there could be a relationship, women sleep with men because they think there already is a relationship. So we have different emotional barometers. But as we get older, with that clock ticking in the background, waiting too long to see if there’s that physical thing doesn’t make much sense. Really, what exactly are we waiting for?

Sex is a marvelous thing, much more than a mere physical connection. But, it is NOT sacred. The more it is treated that way, the more weight it takes on, and the less fun it will be.

Obviously, the issue of sex is complicated and fraught with emotional land mines. This isn’t 1970 when people randomly jumped into bed with someone they just met. But it also isn’t 1870. My advice: if you’re attracted, and feel trust, go for it. Sure you might find that moment or partner didn’t pan out, but just move on.

Could it result in an emotional wound? Of course, but then a “committed” relationship or marriage may cause emotional wounds too, as any of us who have had relationships knows well.

Okay, now that we’ve put age and sex to bed, there are just a few other issues in this dating and mating game:


Expectations are more than half the battle in dating and relationships at this age. Truthfully, they probably constitute more than half the battle in most aspects of life.

If you genuinely expect to meet “The One,” you’re in for a tough slog. If a guy or woman has many of the qualities you seek but is missing a few, remember you are lucky and enjoy it. And realize that most people you meet and date aren’t going to result in that one wonderful long-term solution.

But you can develop friendships and even relationships with some. Take it easy on yourself (and your dates) in this process. If you go into it for the enjoyment of meeting someone new, someone you've had enough exposure to online or on the phone to want to meet, you'll rarely be disappointed. 

When you sit down for that first date expecting to find your soul mate, you’re in for a long evening.

Soul Mates

A word about soul mates:

The relationship world appears to be divided into those who believe there is one out there for them (I don't know, 85 percent?) and those who don't. I don't. I think believing in the concept of soul mates is simply depressing.

First, it may not be in the cards that you’ll actually find him or her. But does that mean your relationship life is a failure? Second, since most of you describe a former spouse or long-term partner as your soul mate, and that didn't work out, what is a soul mate anyway? Finally, choosing to believe there are hundreds, thousands of people out there with whom you could be happy is a much better way to live your life.


Finally, a word to all of my maturing sisters and brothers about singlehood: it is okay to be single.

You could be single for months, for years, or until you die. It may or may not be ideal, but it is okay. It is hard to find the right person at any age; some of us simply might not find that special person. That doesn’t make you a bad person or anything except someone who hasn’t found the right one.

The world will tolerate just about any type of relationship. It just doesn’t tolerate people who aren’t in a relationship. This is especially true of people over 50, according to society we’re not supposed to want to grow old alone. That said; NEVER ever admit on a date that you don't want to be in a long-term relationship. Never even say it out loud. It’s politically very incorrect. If you find that special person, that’s great. But if you don't, that is also fine. Not everyone has to be paired up to be happy.  

Joseph Seldner