Lifestyle & Culture

Late Dates #18: A Reader Asks About Online Dating


By Grace Cooper

Recommended listening while reading: Girls Just Want To Have Fun by Cindy Lauper. 

Q: I AM in my 70s, long divorced and several years retired from my career. Recently I moved to a new town to be closer to my grandchildren, and where I have several close friends. I’m tempted to join a dating website for seniors, as a few of my friends are offering to introduce me to single men. What are the pros and cons of such a (bold, scary, potentially embarrassing) action? 

GC: Retirement, death and infirmity, and even Covid have diminished many previously robust social circles. The opportunity to meet single men of a certain age has become more complicated as we age. Online dating is an opportunity to cut to the chase—meeting men who are likewise searching for companionship. See my past columns about safely negotiating online dating websites. However, emotionally, there are a few things to keep in mind before you jump into online introductions. 

Ideally, you’ve been happily successful negotiating life as a single woman. That’s the ideal headspace from which to enter the late dating arena. After all, if you are too lonely, timid, insecure or too starved for adult male conversation, you’ll not survive the world of online dating. Take it from someone who knows. My first 50 or 60 dates had me rocketing between hope and despair on a daily basis. Muster every bit of self-confidence, dust off your sense of humor and develop a tolerance for the absurd . . . that’s when late-life dating becomes a fun and rewarding experience.

Here’s another important tip—late-life relationships can look like anything you want. Gone are the years in which you dated to mate. Presumably you’ve either successfully launched your prodigy into the world or made your peace with enjoying a child-free life. Adult children with whom you’ve not set appropriate boundaries can derail even the most promising new romance. Accept no “but Mom, at your age . . . ”

Rather, repeat after me:

*I am an autonomous adult.

*I have a right to seek companionship. 

*Babysitting my grandchildren does not count as companionship. 

*Only my adorable grandchildren can manipulate me and get away with it.

Dating simply for companionship, sharing of common interests, friendship, or friendship with benefits are all perfectly reasonable end goals for late-life dates. Be advised, though, that if you are a nurse with a purse, there may be men who pursue you simply because . . . so if your idea of fun is driving some financially insecure elderly man to his colonoscopy . . . well, then, who am I to judge? 

Next, I’d advise you to make a list of all the nonnegotiable qualities you seek in a partner, but also consider where we are in life. Those aggressive captains of industry, or tall stud-muffin athletes of yesteryear . . . whatever criteria you used to choose your former mate no longer apply past a certain age. The men are typically past their peak expiration dates, and most likely are in the process of adjusting to their new reality as “plain-folk-like-us living in aging bodies.”

For some good insight into what the aging male is experiencing in his later decades, read Understanding Men’s Passages: Discovering the New Map of Men’s Lives by Gail Sheehy. It’s an insightful look at how men often stumble as they negotiate “man-o-pause” and ideally learn to reinvent and reinvigorate themselves in their second half of life.

Which brings me to my last bit of advice: You retired from your career so that you could enjoy freedom from projects and responsibilities. Dating any man should not feel like you are being recruited for unpaid housework. This is your time to play again, so swipe left on any man who suggests “cuddling by the fire after a home-cooked meal” unless he’s doing the cooking. Then inspect his place as you would any fine restaurant. Is the kitchen clean and well organized? The wine glasses and cutlery spotless? The living room free from clutter and dirty laundry. Is his powder room fresh? The overall ambience should reflect the home of a man who can look after himself, not of one hoping to inspire you to feng shui his life. 

Hopefully, I’ve not discouraged you too much. As I mentioned, dating can be fun, or—with a good sense of humor—fodder for funny stories you’ll share with your lady friends on your next girls trip to somewhere wonderful. 



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.

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