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Want to Finally Succeed at Dating Over 60? Make This One Attitude Shift

By Shirley Goldberg October 16, 2021 Dating

I recently had another of those relationship discussions with a few single friends. What they have in common is, they all have plunged into online dating.

And everyone agrees that online dating is more painful than a dental scaling and root planing of all four quadrants of your mouth.

With one exception.

Miranda (not her real name) has no complaints about internet dating.

She dumped her boyfriend of two years (I must mention that the breakup was not an easy decision, but this article is not about that subject), took a few months off to look around, and joined an online dating service. I’ll get back to her in a minute.

Why I Care About Relationships

Relationships fascinate me. Coming together fascinates me, why people stay together intrigues me, and breakups are the stuff I write about.

“Enough is enough,” said a friend when I picked her brain about her ex-husband. “15 years ago? I don’t want to go over the past. Why do you?” Frankly, she was irritated, and I didn’t blame her.

My persistence is a mixture of wanting to know more about my friends’ lives, combing for material, and wanting to understand the whys of people’s behavior.

I write, you see, and writers are curious. We wrestle with words and, in trying to figure out our characters’ motivation for acting the way they do, push to make sense of the relationship landscape.

Lots of Women Start Over

My stories weave around women of a certain age starting over, changing their lives, dating after a divorce or a breakup. By the way, several of my characters discover along the way that their women friends are more fun and less trouble than a man.

So, grabbing real-life examples from my friends is what I do. I ask friends and sometimes new acquaintances intrusive questions.

Which is how I learned Miranda was having a blast dating three guys.

Yes, you read that correctly.

Other friends gaped in astonishment – or Horror – at this revelation.

“How can she juggle three men?” asked a friend who’s met two men online. “Where does she find them? The guys I meet don’t let me get a word in edgewise.” Another describes the boredom, the misrepresentation, the lack of effort.

After a few weeks, Miranda narrowed the playing field down to two guys. “I like them both,” she says. “But my mom likes Bob (not his real name) better.”

How did her mom meet Bob? He invited her – Miranda – to lunch and, not wanting to go to his place by herself, Miranda asked if she could bring her mom.

“He must really like you,” I said.

Miranda puts a positive spin on her dating life, but she’s no push-over and won’t be rushed into taking the relationship to a level she’s not comfortable with.

Have Fun Instead of Making Lists of Your Wants and Needs

The other thing? Her behavior and her attitude are different from other women I’ve talked to who want a serious relationship.

They mention a desire for commitment after two or three dates. Or they focus on looks. “I can’t help it if I’m into hot guys who work out,” says a friend who’s had a score of unsuitable boyfriends over the years.

Others have strong ideas about a man’s profession, his financial status, and whether he knows his way around Tuscany.

Two refuse to go on second dates unless there’s chemistry. “If I’m not attracted the first time I meet someone, what will happen in six months?” says a friend who’s looking for the mythical love-at-first sight.

Miranda? No complaints. She’s usually game for a second date if a man makes an effort to get to know her. “I don’t want to think about how it will all turn out,” says Miranda. “Besides, I’m having too much fun right now.”

Enjoy Each Date and You’ll Enjoy Online Dating So Much More

Smack in the middle of one of these discussions, my brain whirled and clicked. The difference between Miranda and most of my other friends was her willingness to go along for the ride, enjoying the moment.

And that reminded me of Judith Sills’ book, A Fine Romance. Published in 1987, it’s nowhere near new, but the dating message is timeless.

Don’t get attached to the outcome, a piece of wisdom that is pretty much the approach to dating that is working for my friend Miranda.

I think it’s another version of that old cliché, “Don’t put the cart before the horse.” Imagine that.

At this writing, it’s been four months since Miranda met her two guys, and she’s whittled them down to one special man. Bob. Mother-approved.

Sounds like fun to me.

Please share one of your dating stories. Have you reluctantly given a man a second chance, only to find you hit it off? How do you feel about fellows who misrepresent themselves in their dating profiles? Please use the comment box 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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