Dating After 50: In Eight Steps

I never thought I’d be dating again at my age. Dating. Eeee. Someone spare me, please!

But we make mistakes, and we make them willingly, and they come to roost. Then: they go away, and we start dating again.


Step One

My last wife and I met online, through Yahoo Personals, just after 9-11. She was not the first woman I had met online; nor was I her first. We were old hats and it just came together—though I was surprised at how easily and how well. It seemed that, if we were not made for each other, we were certainly the most alike of any other people either of us had ever met.

It wasn’t perfect. We were different in subtle ways. But those minor differences all seemed manageable and correctable. We were both atheists, liberals, and the sex was outstanding.

What could go wrong?


I had dated several women after moving back to the South—most of them Southern. This was not by choice, but by geography and most people’s inability to move to a different location.

My friends tried.

“What kind of woman are you looking for?” they asked me after I left Los Angeles to come here.

I said: “Tall, smart, funny, thin, beautiful, and preferably rich. Other than that, I’m not picky.”

They thought I was serious and stopped asking. Then they got to know me. Oy-vay! The offers flooded in.

First up was a woman we’ll call Beaulah Mae. Just to get the flavor it.

Now that you’ve got that taste in your mouth—grits and ham hocks—we’ll call her Janet. She WAS tall, maybe 5-9, thin except for some rather enormous breasts which had suckled—get ready for it—seven children. Yes.

She had been pregnant nine times but lost two, the first and last.  The seven ranged in age from 25 to 7. All were boys but the youngest, who was the most darling little girl ever. Otherwise: all boys. Very much boys.

It should have been a clue—a red warning flag flapping in the winds of remembered boyhood.

The oldest lived away. He was the most responsible and made a good living after finishing college. He came home when Janet begged him to ride the other boys to behave. All of his younger brothers had gotten into trouble at one point, one seriously enough to go to prison for a while; the others were working on it. They stole things, broke things, got into fights, caused trouble, got thrown out of school—if they were still in it—on a regular basis. All but the youngest two, who were special little kids.

We bonded.

Janet’s husband had been a Baptist preacher who didn’t believe in birth control. When they met, he was a biker. Shortly thereafter, he found Jesus and made her start wearing floor-length dresses to church, nine days a week. She had to be a symbol of wifely propriety in the eyes of the Lord—and his paying congregation. He was their leader, their man of God, their teacher.

He and Janet had lots of sex. He called it her wifely duty. As a result, she got pregnant a lot. Then, just after she lost her last child, the preacher died in the bathroom, leaving her with the care of the remaining seven kids. She heard him thrashing around and thought he was kidding; but it was a heart attack and he was gone.

Janet plowed on in life, doing the best she could on welfare, WIC program food stamps, and a surviving widow’s social security checks from the dead preacher for his many left-behind children.

Despite all these continuing hardships, Janet was often a lot of fun. She was uneducated—the preacher didn’t believe in it—but smart.

Her kids were also smart—especially the oldest and the three youngest; until the eldest of those three young’uns fell under the influence of his older, middle brothers, and some wild kids in the neighborhood, and he started failing and getting into trouble all the time like the rest of them. It was difficult to see him succumb.

I hung in for longer than anyone imagined I would, but I suppose we were doomed from the get-go. It was only a matter of time.

We make mistakes, we make them willingly, we move on.

It wasn’t as easy for Janet. She became angrier at me than she had been at the preacher who died on her. Then she settled down, forgave me, and a few years later, some kid on drugs stabbed her youngest son in the neck—the nice smart one—and killed him.

Over twenty dollars.

He was special, a wonderfully curious explorer, and all-around good kid. But he was at the wrong party at the wrong time and was dead at 18. His younger sister has still not gotten over it.


My wife and I later ran into Janet and middle son #4 outside the courthouse. She was lobbying for a death sentence for the kid who stabbed her son. The middle son had turned into a handsome young man, looking sharp in a suit—there with solid support for his ever-grieving mother. I could see that she would never recover—not from that.

In a surprise off-guard moment, the suited son said, “In a way, I feel sorry for him.”

“Him” being the kid who had killed his little brother.

I thought this was one of the most profound realizations I had ever seen someone else experience; and I was happy that I was there to witness it, to hear the surprising wisdom of his thoughts, the maturity of someone still so young.

His mother thought differently. “He murdered your brother!”

The young man said with amazing calm. “But now his life is ruined, too. Over twenty dollars and being stupid one time.”

Janet repeated: “He murdered your brother!”

Nothing else was said other than goodbyes.

Step Two

Friends interceded again, sorry that they had made a questionable recommendation to begin with; but they applauded my diligence and quasi-paternal efforts.

In appreciation, they set me up with another of their friends we’ll call Madeline. Madeline and I had two or three lunches together before she told me, “I’m not sure I want to date a guy right now. I’m thinking I might like to try a woman for a change.”

She did, and they’re still together. They make a nice couple.

Step Three

Take some initiative, boy!

I signed up for Yahoo Personals. I met three very nice ladies. One was a former dancer with a great body, toned and lithe. We had some good foreplay sex, but at the critical moment she wiggled aside and asked, “Did you bring protection?”

“No, my gun is at home. Why? Did you hear a burglar?”

You see, at age 50, you don’t really think: Rubbers! Bring rubbers!

I hadn’t thought of bringing condoms since I was a teenager. As an adult, every woman I knew took The Pill or had had their tubes tied. They didn’t want seven kids.

They didn’t want one.

But she was right. And putting on a condom again after 35 years made me feel young again—and protected.

Then, out of the blue, she married some other guy.


I kept at the Personals and met a nurse, my third over the years. (I apparently was drawn to nurses.)  She was smart, had no southern accent, and lived in the tiniest house I have ever seen.

We swapped STD resumes, found each other to be in the acceptable range, and dated from spring to fall of that year with no discord whatsoever—as we had agreed not to talk religion or politics.

We took long, soaking baths together and she shaved my head the way she shaved other peoples’ private parts for surgery. Nary a scrape or scratch. We swam naked in her landlord’s pool when he was out of town, and I watched her feed her horses. I don’t like horses. Janet loved horses.

To me, horses are just an accident waiting to happen.

I haven’t given this one a name, yet. We’ll call her Deb. It doesn’t really suit her, but it’ll do. She won’t be in the story too long.

Deb was a tad on the serious side, but mostly fun. Very sensual. She was also a tad on the conservative side for my tastes, which might explain her lack of a sense of humor; but she had a good heart. Because of that—and some much better sex (she had been “fixed,” as she called it, because she really didn’t like kids)—all went well for a while.

But those conservative leanings eventually caused the end. To be fair, it was somewhat beyond her control.

Her parents came to visit. She had warned me that her dad could be a little crusty, but that he and Deb’s mother had been in love forever—first loves—and were kind of cute together. Even in their late 60s, his favorite bit was to come up behind her, his wife that is, while she was doing the dishes, grab her breasts from behind and say, “Can I help?” To which she would say, “You already are.”

It was cute. A little gross, and a lot sexist, but cute.

Since Deb told me that her father was a hobbyist woodworker, I brought him a special piece of black walnut, a section of limb from our oldest tree. He was quite appreciative and talked about some of the ways he might use it for inlays and such.

Then he said: “So, what about this n*gger who’s running for the Senate?”

Step Four

As those relationships wound down, I met another woman who said she was shy, but would be open to meeting for lunch. She owned her own landscaping business and was possibly looking to date again after a nasty divorce.

Probably gun-shy was more like it.

In her jeans and t-shirt with very short hair and no makeup, she had the tomboyish thing I always liked; but she was indeed painfully untalkative. Shy, after all.

We agreed to put a pin in it and ponder an actual date at some later time; but after a few emails, her communication abruptly stopped.

Step Five

Some more Yahoo Personals emails and…bingo! A hit! A real one.

We got married after seven years; then after another four years, she announced that she wanted a divorce.

We make mistakes, and we make them willingly, and they come to roost. I had known, I had seen, I had tried. I had ignored.

I had failed.

She told me to stop saying that, but I couldn’t shake the feeling of a lost future together. That was the failure. It was a failure of life itself, not a person.

In that failure, the person left and took the future by setting up house with a bodybuilder.

Step Six Oy-vay!

I “met” a few women who lived too far away, but mostly I got “viewed” by “mature ladies” in their Seventies who had lots of pictures of the grandbabies and great-grandbabies.

Perhaps it was a sign of the (new) times, but anyone my age or slightly younger was looking for guys younger than them—often by half. I saw this as another indication that society was coming around, that women were taking control of their lives—their likes and desires—and if they wanted to date younger men and it worked, good for them.

Meanwhile, I had the great-grandmas sending me messages.

Not what I was looking for. Still, I persisted. For years. Four years of reworking my profile, stressing my many, many good points (!), downplaying my bad ones (by not mentioning them at all), and trying to come up with new ways to say the same things (almost as hard as writing a synopsis of your own book).

Still, my unspoken bad points seemed to come across loud and clear in whatever I wrote, however I wrote it.

I got reamed twice by angry women.

One accused me of thinking I was smarter than everyone else because I mentioned that I was an atheist. She was pissed! When I replied politely, saying that I did not think she was stupid, she got even more pissed and blocked me.

The other one didn’t like my (younger-than-me) age range—a lot. But when I wrote back saying that I understood, she explained that she had been unceremoniously dumped by her husband for a younger woman. He had just up and walked out one day and she was admittedly bitter.

She apologized and I thanked her and wished her good luck.

For the record, I had not yet found out that my wife had left me for her younger body-boy.

Online dating had changed a lot in the ensuing decade-and-a-half from when my wife and I met. Many of the date seekers were women who had an ax to grind with men. There were lots of “Don’t contact me if…” disclaimers, along with tales of horrid matches, dates gone wrong, lousy men in general, et al.

I understood completely. I wouldn’t want to date those men, either, if I was into men. But I also didn’t want to date any women who were that angry—and happy to display their rage on a dating site where they were presumably trying to get a date.

Talk about counter-intuitive.

Then I started to notice that many of those women had been on those same sites for, well, maybe the entire four years of my search.

While I was also on those sites for four years.

Step Seven

Dating does not get easier as we age. I have learned this. I thought, in the beginning of this process, that with our age-induced wisdom, we could cut through the bullshit, be honest about our pasts, our futures, our needs and desires, and find common ground more easily than, say, when we were all in our twenties and thirties.

Turns out: in our twenties and thirties we don’t care! Mostly because we are interested mostly in sex. Sure, we say we are looking for more—a life partner, a soul mate, someone who also thinks pineapple on pizza is repulsive; you know, the important stuff—but ultimately, it’s about the sex. If we get lucky beyond getting lucky and connect, then the cycle begins.

But later in life, after one or two divorces, we become less interested in sex alone, and more interested in reducing complications—and that becomes complicated in and of itself. Life is complicated and, as we age, we realize that more and more, with greater clarity, and less patience.

It’s a good thing.

So we push on, perhaps with more rules, but with the aid of experience. The conflicting strains of desperation versus demands become more obvious, and those dating sites become less appealing. The people on them might be nice people, but what if they’re not? What if we go to all the trouble of setting up a meet in a neutral setting and there is no chemistry? What if, as happened to me the one time I agreed to meet a woman, she turns out to be a man?

Seriously: a transvestite. Not a trans woman, not someone in transition. Just a man dressed as a woman.

To quote Seinfeld: Not that there’s anything wrong with that!

Unless you’re expecting a woman.

Step Eight

I kept one online profile just to see if anything might change in the over-50 world of cyber romance. In my best estimation: it has not. So it’s back to real people!

This presents its own set of uniquely age-related challenges. A lot of men and women over fifty like being single. They’ve been the other route, perhaps more than once, and are relieved to be alone.

Honestly?  I can relate.

I have my time-tested and approved routines that make daily life more predictable—no crisis borne of another person’s internal angst or unresolved issues from “past lives.” No pending conflicts at the end of the day. No extended family get-togethers with even angrier distant relatives.

So here is the (new) world we live in as we “age out.” We can pursue whatever suits us with as much time and energy as we wish to expend; and if it doesn’t work out, we can try something else. If we want to attempt online dating, we can. If we find it to be disheartening and demanding, we can delete our profile. If friends introduce us to that rare single individual who wants to meet and see if there’s any kind of spark, we can go and meet. If it doesn’t work out, we can go home.

Home—where there is peace. Home—where there is comfort. Home—where there is no one to argue with except ourselves and our inability to completely get away from our pasts.

But our pasts fade, thankfully. With each passing day—and long night—we let those events and memories go. We learn to cherish the good times, but accept that they too are gone. And that’s okay. As each year passes and the next ones become “the best years of our lives,” we realize that the journey has been difficult, but rewarding, and we are where we want to be.

Ready, willing, and able to wake up tomorrow and live.

All of which makes us a better future partner for that someone who gets us, but isn’t us; who is delightfully their own person, but not so far away from who we are that we fidget and constantly ponder a way out; who is as fair and honest and real as they can be, and who brings that out in us. But thankfully, we are no longer in a rush.

Though some great sex would be nice on occasion.

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Glenn A. Bruce

Glenn A. Bruce, MFA, was associate fiction editor for The Lindenwood Review. He has published eight novels and two collections of short stories. He wrote Kickboxer, episodes of Walker: Texas Ranger and Baywatch. His stories, poems, and essays have been published internationally. He won About That’s “Down and Dirty” short story contest and was a two-time finalist in the Defenstrationism annual short story contest, and three time judge for Brilliant Flash Fiction’s annual contests. Glenn taught Screenwriting at Appalachian State University for 12.5 years and recently “retired” to focus solely on writing.

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