I filed for divorce from the man I married three decades ago and jumped off a cliff with my eyes closed…and landed 1,700 miles across the country. I started over in Palm Springs with one tear-stained cocktail napkin and skinny margarita at a time.

My next leap?  Dating in a digital world.

I soon matched with a widower who was moving into a new house along with his young adult son.  

“He’s not going to college but wants to be an entrepreneur, so I’m financing him until he gets on his feet,” Daddy explained as he supports this kid’s dates, dinner and travel. When I reconnected with the widower again a year later, the unemployed kid was still living the good life on Daddy’s dime.  

EnablersRus, anyone?  Next.   

The best dates should be those where a friend suggests someone they know, right? So when my high school buddy set me up with his friend who’s vertically challenged and has the dark, brooding looks that match his career as a dark, brooding abstract artist, I quickly put on flats and watch him splash color on canvas.    

He’s the cheapest man I ever met. He took me to a restaurant only once, yet declared he had plenty of money to live the good life--evidently for a party of one.

He’s also the most temperamental. He knew I’d practiced yoga for 30 years, so decided to test my knowledge. “Can you name the eight limbs of yoga?” he asked one evening. When no Sanskrit words beyond “asana” and “pranayama” rolled off my tongue, he declared I didn’t really know much about yoga.  “You’re a dilettante,” he said with a satisfied smirk. 

A**holesRus. Next.

Another man was a perfect match for me on paper with his cute-guy, midwestern face. We both grew up in Kansas City and have acquaintances in common. But he’s so tightly wound that when things don’t go his way at a restaurant, even his Hendricks gin martini, up, can’t take the edge off. His looks could wither even the most seasoned server.

When we drove through the neighborhoods where we lived as kids, he mentioned that his father was a tightly wound Marine and there’d been a lot of pressure growing up. Probably true, but I wasn’t willing to stick around long enough to see his steely stare turn on me if I did something that didn’t meet his rigorous standards. 

I had one date with another man who dropped names of designers—"Are those Valentino sandals you have on?” They weren’t, but I was happy the dupes looked real. He talked luxury brands of cars with gusto and told me he lived in the toniest part of town, but when I checked, it was really “tony adjacent.”  

As I gave a parting embrace to mr. tony adjacent, I noticed the faint whiff of a social climber.

And, then, there was he of the poetry writing and picnic planning school of charm. He took me to his hometown and the beach where he learned to surf. He introduced me to his best friend who described my date as, “one of the nicest guys I’ve ever met.” 

So what happened?

As the weeks of hiking and hand holding rolled along, he did something that stopped me cold after dinner at my favorite Vietnamese restaurant. The lovely Denise was tending to all our needs like we were the only patrons there, and when the check came, mr. charming left her a 12 percent tip. 

I made up for his stinginess on my next visit, but did he misread the bill? A seventy-something’s eyesight isn’t what it used to be.

“I think you made a mistake with the tip,” I said to him later. 

“No, I think 12-18 percent is the norm, and 20 percent is for five-star service, which rarely happens,” he answered as I looked at him, dumbfounded.

I’d just read Delia Ephron’s book, Left on Tenth, and when she quizzed her new beau Peter on their compatibility, one of her dealbreakers was that he must “tip easily and well.”

Delia has the right idea.

My guy’s thriftiness carried over to his appliances, and he refused to run his dishwasher. About the third time I pulled a greasy plate out of his cabinet, I knew I’d never eat at his house again.

Are any of these guys all bad? No, and none are of the Netflix “Dirty John” variety. The tightly wound dude with the Marine father? He spends weekends with that father, who’s now in his nineties and needs help with meals and programming a new iPhone, bless his heart.  

Just because they’re not MY guys doesn’t mean they’re not someone’s love match. We all have baggage, and mine is filled with trust issues that lead me to approach some men like an FBI operative.  Reverse search on their phone number?  Check.  Google search on everything they’ve told me to verify if it’s true?  Check, check.  

“I wonder if I’ll ever be able to climb that wall you’ve built around yourself,” one guy mused after we’d had about a dozen dates.  I protested at the time, but when I dug deep, I knew I’d have to take off my protective armor and clear out the nuclear fallout of my failed marriage.  As Jack, my gay bff, says after every dating dip and dive, “You get back on that horse better than anyone I know!”

So nine years of dating later I ask myself, “Does the kind of man I want exist IRL??”  Giddyup…I plan to find out!

-Linda

A freelance journalist for more than 25 years, Linda L. McAllister (BA, MPA, MS) writes non-fiction magazine features after a career in corporate healthcare.  She is currently writing her memoir with a focus on dating after 60.  Working title? “Giddyup.”