How To Date Like a Middle-Aged Man, Especially If You’re a Middle-Aged Man

John McCaffrey
4 min readOct 28, 2020

I am a middle-aged man. I am happily married. I am pleasantly plump. And I am relatively energetic, particularly after an iced coffee and a powdered donut.

I am hoping, if God is on my side and the stars align, to live long enough to become a happily married, pleasantly plump, relatively energetic, ice-coffee-and-powdered-donut-loving older man.

But as that great mariner (and hopeless romantic) Popeye the Sailor Man likes to say, “I am what I am, and that’s all that I am.” And right now I am middle-aged. And from that point in time and from that vantage point, with caffeine coursing through my narrowing veins and sugar residue on my chapped lips, I humbly offer some dating advice to my comrades in sagging arms.

Why, you might ask, do I put forth such a topic at this time? Because more and more I am hearing a recurring lament from others in my patriarchal peer group as it pertains to romance:

If I only knew then what I know now.

Clearly, these gentrified gents think they have learned something about love over the years. And if that is indeed the case, then maybe it’s something that can be useful to other middle-aged men who are single and looking and did not get the wisdom memo when it comes to dating.

Also, perhaps, the information might be helpful and inspiring to all interested bachelors, no matter where they stand or fall in the aging spectrum.

So without further preamble, here are five tips to be distilled, displayed and disseminated to men who have the desire and the dash to ask the age-old question that has launched countless relationships and spurred just as many rejections:

Want to go out with me sometime?

Slow and Low

Like smoking pork for a barbecue, middle-aged men should go slow and low — take your time and at a simmering heat. Passion like fashion is the provenance of the young. You stretch and look around; no need to fidget and strive. No more beer bongs and shots in a dive bar; you are seated in a comfortable restaurant with napkins and taking your time to select a wine. You already know what you like. But if you want to try something off-menu you should have the confidence to order it and the equal confidence to send it back if it’s not right. Your wrinkles, your aches — these aren’t just signposts to the Inevitable but a reminder that you’ve accumulated an experience that gently commands.

Kind and Polite

Middle-aged men no matter what their income can afford to be two things: kind and polite. In amatory pursuits, brutal honestly like skinny jeans have no place in a middle-aged man’s armory. While we should not be conniving, we should curve the truth when it preserves joy and dignity in others. We all need a store of delusion to get up the morning and leave the house; likewise, we should permit others their hard-won delusions (which isn’t the same as fostering madness).

Quiet and Contemplative

You no longer need to speak up to be heard, because you know no one cares what you have to say anyway. Releasing self-importance and forgoing any desire to shout out your talents and accomplishments is not only personally freeing, but also uniquely attractive in a world tilting with narcissists. Always remember, actions speak louder than words. An empathic nod of the head, a genuine smile, a full belly laugh, will do more to boost your approval rating than any scintillating story or fascinating factoid you pull out of your conversation quiver. But if you do feel the need to talk, use your indoor voice, and even then bring it down a decibel or two. Strive to come off as measured, meditative, and slightly muted.

Patient and Balanced

Think Miyagi, not Kreese. If the reference confuses, you’re probably not middle-aged. But to add context, Kreese is the founder of Cobra Kai, the strike first, strike hard, no mercy dojo from The Karate Kid, the iconic 1984 martial arts drama film. Miyagi is sensei to Daniel, a true underdog, who employs the legendary “crane kick” to knock out Johnny from Cobra Kai and win the championship (and get the girl). While Kreese preaches offense and ruthlessness (sweep the leg!) to his students, Miyagi is all about teaching defense, patience and balance. The latter is the mental space for middle-aged men to inhabit on a date. Never reach for the breadbasket first, and always keep an even keel no matter the probing question or strike to your soft spot (is that a toupee?). Above all, be considerate and compassionate no matter the lack of chemistry or outcome. If connection is not in the cards, don’t force the issue and try to snatch victory from the proverbial jaws of defeat. Better to accept an unwanted ending with grace and dignity and a welcome chance to get home early and binge-watch a season of Cobra Kai on Netflix. Yes, Daniel, Johnny and Kreese are back!

Light and Easy

We started with a food analogy, and we’ll end with one. The result of going slow and low is a meat that falls off the bone. That’s you. Easy pickings. You’re open and honest and as transparent as cellophane. You don’t share too much about yourself that is complicated or controversial, but you also don’t hold back the truth as you see it to a complicated or controversial question. You just be yourself. And if the joke is on you, all the better. Think of yourself as just one more bumbling creature in a demented cartoon, who still has one serious choice: to provide light or to promote darkness. Choose light.


Originally published at on October 28, 2020.



John McCaffrey

John McCaffrey is a writer and a professor at The Rochester Institute of Technology.