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What I’ve Learned from the Men in My Life That Women Often Miss (Even After 50)

By Shirley Goldberg December 04, 2022 Dating

The reality of stepping out there after a long hiatus – whether you’re divorced or widowed – is anxiety-producing. But what I’ve learned about myself and about men couldn’t have been experienced otherwise.

Who knows what you’ll glean from an hour or two (or 45 minutes, in a few cases) over coffee, a glass of wine or dinner?

And this is a good thing. Healthy, and perhaps even a tad heartwarming.

And fun, too.

All my encounters with men, whether male friends or dates, have been enlightening. So, here are some of the things I’ve learned, in no particular order.

Regardless of Experience, Rejection Smarts

“It’s still painful, getting rejected,” a friend of mine, who’s dated widely and works the room (as I call it), said. “Especially if you think you’ve read all the signals. You never get used to being rejected.”

What’s he really saying between the lines? I wondered. “Are you saying flirting is almost like leading a man on?” I asked.        

“Not exactly.” He hesitated and then elaborated. “When a woman flirts, I think she’s interested, and I’ll ask her out. I’m a man, it’s what I do,” he said with a hurt look.

I couldn’t really blame him for trying.

Women Are Not Tuned in to Rejection

“Women don’t really know what it’s like to be rejected all the time,” my friend said. “How many times have you risked rejection by asking a man on a date?”

With a start, I realized I could count on one hand the times I’d asked a man out. Two or three over a lifetime? Men put themselves on the line far more often than women do. And, men too, are riddled with doubt, whether they’re looking for companionship or their special person.

Practical Lessons

I’ve learned a few practical things from men. I know how to check the pressure in my tires, the value of really good paint and how to choose and apply it. Hint: Never shake the can, which creates bubbles.

I know how to pull baseboard off the wall without damaging it. I’ve learned some sexy rhumba moves and two complete line dances – which I forgot a week later. Also, I can play the first four notes to “When the Saints Go Marching In” on the harmonica.

Men with a Hobby Are Interesting Species

I especially enjoy the company of men who have a passion. Too many men have few interests beyond the sedentary, and no, I don’t count going out to eat. Right now, I have a musician friend with his own band, a writer who’s on his fourth book, and a welder, who’s been at his hobby for 40 years.

It’s particularly intriguing to watch and listen to these men talk about their projects. You can almost see the gears in their brain turn and click, and all of that elevates your spirits too.

Men Have Body Issues Too

Men have the same body hang-ups we do. The male character in my new novel-in-progress has lost a cool one hundred pounds.

To research this touchy subject, I spoke to a brave man about his body image before and after his gastric bypass. Although he felt much more at ease after losing weight, he preferred lights off in the bedroom.

“My wife has a tough time losing weight,” another friend told me. “Now that I’m trying to shake 30 pounds off, I have a lot more compassion for her than I used to.”

Other friends hate their chicken legs and wear socks to disguise skinny shins or a shirt at the beach to cover a thin chest.

Two Categories of Men

When it comes to dating in our 50s and beyond, men fall into two categories. Those who know what they want and those who don’t. This is obvious, you say? Not so fast.

A man can believe he knows what he wants, but if, at around the two or three-month mark in the relationship, he starts backing off, it’s a sign he has doubts. Which is reason enough to have a full life, so you don’t go all clingy.

Don’t Keep Him Hanging On

If you’re not interested, let a man go. Leading someone on is cruel and worse – it’s dishonest, especially if he’s paying your way.

I’ve been on both sides of this dating dilemma. A lopsided relationship, no matter which side you find yourself on, is not fun. Give it three dates at the most. You’ll know at that point.

Men Don’t Like to Feel They’re Being Used

No one likes to be used, but online dating lends itself more easily to bad behavior (ghosting, bread crumbing, for example) than most other social activities.

More than one man I met over wine or a beer felt obligated to announce he didn’t take a woman to dinner on a first meet. “Some ladies out there just want dinner, and they meet us guys so we’ll wine and dine them.”

Best to keep it casual and inexpensive on the first date.

Sensitivity to All Relationships

Men are as sensitive as women to family issues, misunderstandings with friends and troubled offspring. They can’t always let go, especially since many divorced and widowed men have no one to vent to.

Clueless About First Date Conversation

Many men who are dating for the first time aren’t great at asking questions. In fact, some blow it by dominating the conversation.

When you finally rise from the table, you realize you don’t know a thing about him, and he knows everything about you. You might want to give this clueless guy a second chance. Second dates allow a man to relax and focus more on getting to know you.

Interest Shows

If a man is into you, he wants to spend time with you. This goes for male friends as well as those interested in dating you. Your friends not only value you, they’ll be there long after your latest two-month relationship has fizzled, so cherish the friendship.

Men aren’t the pleasers we women are. There are times I don’t say no when I should, volunteer for projects or activities I have little interest in – and resent it later. Men don’t seem to have this problem. This is not a scientific survey and comes from my experience. Do you find it true?

Men Love Appreciation

Often, while we’re pursuing productivity and the occasional drudgery of our daily lives, we forget to show the men in our lives how much we appreciate them. And I don’t want to take anyone in my life for granted.

Acceptance is great quality and, when it comes down to what’s important in life, we all have room to be more open and accepting toward those we love and value.

Let’s Have a Conversation:

Do you think that even after 50, women are just missing some of the things about men? Men are sensitive, men love appreciation… Do you agree with some of the statements in this article? Which ones? Please share below and let’s have a conversation!

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The Author

Shirley Goldberg is the author of Middle Ageish and Eat Your Heart Out, both romantic women’s fiction with seasoned characters. Her website,, offers a humorous look at living single and dating in mid life. Shirley’s friends nag her to tell them which stories are true in her novels.

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