Lifestyle & Culture

Late Dates #4: Looking for a Few Good Men


By Grace Cooper

“He was a dark-eyed man and I knew right away
It was gonna take a turn for the worst
So I said ‘hey, heart, if you’re gonna go crazy
Give a little warning first’

Idiot heart
I shoulda left you at home
You gimme nothin but hard love, bad luck
when you gonna leave me me alone?

Ooh, you’re an idiot
A lunatic a nitwit
And you make a fool outta me
Oh, you’re a sad sack
Subtle as a heart attack
Hey heart, when you gonna let me be?”

—”Idiot Heart

(Song by Carsie Blanton)

ASSUMING you’ve stabilized emotionally post-divorce—that is, found a therapist, a support group, or adjusted your meds—you might now be ready to take the plunge into the virtual reality of online dating pools. But before you leap, there’s much to learn in terms of maximizing safety and preserving sanity, for instance.

Do you have any idea what you want to find in a new relationship? Yes? Great! That makes it much easier to navigate this journey. No idea? Neither did I, but in another post, I will detail how I used 150-plus first and last dates to discover the good and the not-so-good aspects of me for the first time as well as what I’m looking for in a partner.

Ever since online dating began to catch on, various researchers and authors have explored the math and the science of dating sites, with the goal of cracking the code to maximizing your chances of meeting a good match. Largely, it’s a numbers game—the more dates you go on, the greater your chance of finding “the one.” But it’s more complex still. The dating sites themselves collect algorithms based on what they learn about you as you browse profiles and as you send “likes, or winks,” or email correspondence. Tinder launched in 2012 on the back of the explosion in smartphone use. Just two years later it was registering more than a billion “swipes” a day. The more you participate on the sites, the more the sites reward you with suitors who meet your algorithmic criteria—or so they claim. It’s no exact science, though—at least not any that works for the subscribers. Despite the limits I placed on a geographic radius, I used to shake my head at all the matches sent my way from far-flung towns 3,000 miles away, and Canadians who were unable to cross borders for two years during the pandemic. Tinder is one of several brands that falls under the Match Group umbrella.

Let’s start by choosing a site because there are dozens of them, although you might be interested to know almost all the services operate under multibillion-dollar international corporate conglomerations. Yet, they all have their somewhat unique process for matching you to potential suitors. Here is a decent description of the more popular sites with the over 50 crowd: “Top 9 Dating Sites For Seniors 50 And Over Looking For Love.”

I’ve only experienced Match and for a few years during the pre-vaccine Covid pandemic, I was a member of the Elite Singles crowd, so to comment on the other sites is outside my range of expertise. Basically, dating sites vary widely in price, in member subscribership, and ease with which you can customize such things as geographical distance, physical attributes, age range, personal interests, educational level and athleticism. Most of the sites will allow you to browse their membership somewhat, or even offer a free introductory period. Know that they all claim success in matching one single to another, and some even claim credit for many marriages. Yet my suspicion is that these claims refer mostly to the varying number of candidates that get dumped in your profile inbox daily. Sorting and culling the herd of potential dates is up to you alone. You must be realistic and proceed with caution, armed with solid information, and a sense of adventure.

Before you enlist, I recommend you dream up a fake name and create a Gmail account with that pseudonym. I am not suggesting you borrow the name Julia Roberts, or Christie Brinkley, but now is your chance to get creative. This will be your name for all email communication—on or off the dating sites. It will also be your name when you have your first date, and on the second date, if you still have any lingering spidey sense (ability to sense and react to danger before it happens).

How to present yourself in the best possible light? There is information aplenty on this topic, from dating coaches to psychologists, so Google away. Most all of them certainly emphasize the importance of choosing flattering photographs to post in your profile. We’ve all heard that men are visual creatures, and because first impressions are the bait you cast on these sites, success comes down to how well you show off the unique allure of wonderful you. Here’s a fun link to self-proclaimed “dating experts”—“a visionary, a soulmate specialist, a numbers cruncher and a miracle worker,” who are all in the business of guiding mostly men to successful internet dating: 16 Tricks to a More Attractive Profile Pic [Backed by Science!]

I preferred to steer clear of businesses such as these, but I did find their advice to “squinch” for the camera too funny not to share this article with you.

So you’ve signed up, checked all the boxes the sites suggest on hobbies, pets, kids, education, drinking and exercise habits; some sites ask for everything but your social security number. Alternatively, on Tinder one swipes left to reject a profile offering or right to offer to engage—ugh! Talk about reducing this whole thing to the most superficial aspect of a relationship—appearance. Tinder, owned by the Match corporation, grew out of the hookup culture. If that’s the type of relationship you seek, no judgment. Just know that personal safety is a real consideration. Everything from assault via an undisclosed STD-which are rampant, BTW to the possibility of physical assault should be enough to give pause to meeting men in this manner.

Please put safety first. I cannot tell you how many times I met a man online who seemed reasonable enough, but in person made the hair on the back of my neck stand up. I’ve been stalked and hacked and harassed more than once. Use your head, but always trust your instincts before you get your idiot heart in the game. ***Don’t feel obligated to reveal any more than you are comfortable revealing to any stranger you meet on the street. Be smart, and you’ll be safe while having some fun.

Now it’s time to compose the dreaded essay in which you must sum up what makes you, uniquely you, in just a few paragraphs. I like to write, so I had fun with this part, but most men and women struggle to capture their essence. I phoned a fellow writer I’d met online to ask for his opinion about what makes an appealing personal expository essay. His advice: Women tend to be very body conscious, but so are men, so don’t ever apologize for a few extra pounds. Pour yourself a glass of wine, relax, then write with abandon about yourself—just open up about what makes you laugh, cry, inspires you—no emotional filters allowed. Then, in the morning, edit it, but not the parts that show your fun and alluring side. He also suggested that posting a photo of yourself smiling your happiest smile is more attractive than a carefully curated glamor shot. And lastly, he advised against posting pics with your gal pals, children—and for goodness sake, envy shots from all your fabulous vacation photos are as obnoxious on Match as they are on Facebook. Be real!

Then you wait for the invitations to roll in. Or don’t wait. If you see someone interesting, send him a nudge. Email him with a clever question or comment on something interesting in his profile. Chances are, unless he is a misogynistic, narcissistic prig, he will be flattered and respond in kind. He may respond with a polite brush off, too, but nothing ventured, nothing gained. Don’t linger in the back-and-forth email phase for too long though. Few men aren’t looking for a bit of spicey conversation —especially the married subscribers posing as singles —but in-person dating reveals so much more of what you’ll need to know eventually. I used to answer all email inquiries, even if I had no interest in them, based on their profiles. I learned though, that to encourage them in this way is considered by many men to be crueler than to be ignored. On the flip side, some men, once encouraged are incredibly hard to shake loose. Best not to even start down that path.

However, here is a tip I learned the hard way. Always ask a few uncomfortably provocative questions before giving out any personal info or even agreeing to exchange phone numbers prior to a date. It’s best to see how a man responds when challenged BEFORE meeting in person. I’ve had one nutball threaten me with bodily harm for daring to suggest that he might not be healed enough to date after just losing his wife of 30 years a month prior.

And finally—the date! If you like him, whether for coffee or a SINGLE glass of wine, meet in a very public place. Do not accept an invitation for dinner on the first meet and greet. There is nothing more painful than deciding five minutes into a conversation that you’d prefer to be home washing your hair. Simultaneously smiling and chewing your way through a meal with a crashing bore is painful but easily avoidable. I’ve been tempted to hike up my skirt and climb out the ladies’ room window on more than one occasion when I’ve not followed that rule.

Introduce yourself by your pseudonym. By the end of the first date, or even the third if you aren’t sure about him until then, you can laugh as you reveal your real name. He will look confused, perhaps a bit scared, but that’s okay. Explain that you are no dummy, not desperate, have high standards, and respect yourself enough to use common sense. That’s a good headspace in which to begin any relationship with a stranger. If he’s legitimately interested in you—and not simply in what he can take from you—he will be flattered to know he made the cut. If he’s looking only for a nurse with a purse, for example, and knows you are not an easy mark, he will disappear faster than you can say, “Phew, Gracie! You dodged another bullet!”



—Grace Cooper (a nom de plume) left her long marriage a decade ago, and with it went all sense of her identity—but not for long. Now 67, she has begun chronicling her tales of looking for love in all the wrong places, and unexpectedly finding herself.

2 thoughts on “Late Dates #4: Looking for a Few Good Men

  1. grace cooper says:

    Thanks Jenny, but the best is yet to come – discovering yourself, using the wonderful world of dating as the vehicle. Think less Cinderella, pumpkins, and Prince Charming, and more Dorothy discovering her true heart’s desire with the help of some new male friends she makes along the journey to OZ.

  2. Jenny says:

    Brilliant article yet again! I think I’ll just stay home in my PJ’s and wait to be discovered by Mr. Right!

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