Dating tips 101 for ‘older’ people

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Photo by Alex Iby on Unsplash

“Help!! I’m newly single at 50 and wondering: how do people this age date? I’m thinking I am too old to find someone.” Or, “The dating scene has changed sooo much since the 80s. How do I navigate it?” Or, “Thinking I’m gonna be single forever. Middle-age love is almost impossible to find!!!”

the last few months since I’ve been a Medium member (and author) I’ve read a number of articles by people 40-plus who are saying kinda the same thing. One story’s title was “How Do Old People Date?” which I bristled at a little because the writer was 50 and I am a few steps past that. But I quickly got over being bristly about it and forgave her. It’s perfectly understandable that women are taking turning 50 pretty hard (or 40, or whatever age) because of western society’s emphasis on youth, youthful “beauty,” vigor, and desirability. Even though it’s obvious if one pays attention, that there are plenty of attractive, active, fit, smart and engaging “older” people out there. They just might get passed over in the dating pool because of crow’s feet and a gray hair or two. Getting past the fact that some of us now have a few extra pounds or gray hair or whatever might be one way to actually find someone, if one wants to find love — or companionship, or a one-night hookup — in the “middle ages.”

Plus the ageism often works against us in the dating arena. One 60-something woman on Medium wrote about her meeting men online. She talked about one man who was older than she who commented on her wrinkles (apparently she was online and unfiltered). She gave him a well-spoken reply to his ridiculous comment and I cheered for her while sitting at my computer. “Yes!!” I said. “Good response to that jerk.” Seriously. I agreed with her, musing that men can be overweight, gray and/or balding, have lots of emotional baggage and can be total “frogs” with tons of warts (and not even near as cute as REAL frogs are) … and they can nevertheless attract mates! Whereas a woman can be slim, fit, beautifully coiffed and dressed and some men notice only the lines around her eyes. Seriously guys, that’s bullshit of the kind that might ensure your bed stays lonely and your nights are filled with Netflix, rather than a woman.

Those of us in our 50s now were in the 20s in the 80s and indeed it was a whole nuther world back in the day. Things have changed drastically, and I’m not just talking about the current worldwide coronavirus pandemic that has basically turned our lives upside down, changed the ways we do many things … including mating. Of course there too is the fact that our 20s era was a different stage in our lives: back then we were starting out in life, just having graduated high school/college, starting careers, and (some people, anyway) looking for a mate to share our lives with and possible reproduce with. Some people went straight from walking up the aisle at high school graduation to walking down the aisle in some church wearing a white dress and tuxes. We all have had our choices and now we all have our backstories of those choices.

Back then the dating game seemed like a lot of fun — and it was for some. Prospective partners were plentiful and the cup runneth over for those who were open to becoming involved. Of course that depended upon which level you wanted to be involved, as in, were you dating to marry, as a lot of people of our generation did — and as so many of my friends (plus my 20-something son) think we should still be doing at this ‘old’ age? Or were you dating just for companionship, sex, to have someone at your side to do stuff with but not with the goal of grabbing the gold ring (marriage minded in other words)? Did the Poison song, “Don’t Need Nothin’ but a Good Time” ring true with you as your personal life anthem?

Flash forward to the 2000s and many of those in the Boomer generation have found themselves single, through death or divorce or even never having gotten hitched. I’m not quite sure how they escaped that but apparently their techniques of scaring potential partners worked splendidly and they never did pair up “till death do us part”. These are the people now sitting in beers, crying in them and whining because they “could never find anyone” (you could find them, dude, you just frightened them all away with your negativity/baggage/drunken ranting and raving/woman-hating ways). Other singletons are sitting around doing the same because “he/she left me and now what am I going to do???” There seems to be a lot of them for whom the “til death” vows did not pan out.

To all my cohorts in the 40-and-up range (or whatever decade of life, as long as it’s legal), here’s some ideas. It isn’t impossible to meet someone at our age(s), to find compatible companionship to do things with — it just might seem that way. BTW, if it’s just a booty call with some silver-haired fox you are looking for, well, there are some of those people around who would enjoy a little action in the bedsheets. Trust me on this. It’s true some Boomers and Gen Xers look down upon the current “quick hook-up culture” of nowadays where people meet and move in together all in the same week (or, in some cases, weekend) which is definitely taking it a bit, ummm, fast. In fact, some “older” people are perfectly happy and settled in their own homes and prefer a mate/partner that lives in his or her own house, and that’s fine too. We all have different preferences and aims, just as we did at our younger ages.

Note: along with the tips I’d like to add that given that we are all aware that there’s predators everywhere, you MIGHT want to watch the settings in which you meet/approach people. Venues that are well-lit with other people around are the best. Most of us women don’t want to be approached by some man on a dark street (never a good move, guys, unless you want pepper spray in your eyes). Safety in numbers, you know. Be open, friendly, genuine in your compliments and try not to come across as desperate. A good attitude towards meeting people and in general is always a good thing.

  1. Dating apps (or online dating sites): Because I haven’t done a “online dating” thing in over eight years I’m not aware of the sites. Some of the old ones, like eHarmony and Match are still around. Most of us are aware of Tinder, etc., which personally repulses me because you’re judging people by a glance at a picture (that, I’m betting, is filtered and enhanced to show the person off to the best effect … and probably looks very little like the person actually does in real life). There are apps and sites for “those of a certain age,” like OurTurn, which I only know about because I get the ad on my phone while playing online games and I’ll bet there are some more that are tailored to the “silver-haired mature set.”
  2. “Virtual friendships:” as I just mentioned I play a few online games, like Words with Friends and Yahtzee with Buddies. Most of the people I play against on Words I chat with (some for several years) and we have some great conversations. I met a man while we were playing Yahtzee together three yeas ago and he actually hopped a plane to come visit me for a while. We had a lot of fun, though it was never going to “go anywhere” because he lives in a big city in Canada and I live in a small town in the U.S. and well, ya know, neither was going to move for the other.
  3. Bars/alcohol-drinking establishments. This was the popular meeting place for a lot of us in our younger days and remains so. Although admittedly the choices are narrower now for potential mates since a lot of middle agers have sunk so far into the booze or beer bottle that you have to struggle to pull them out … and sometimes it’s not worth the effort of trying. Been there, done that, it gets old. Some people understandably don’t like meeting dates in the bar and I don’t blame them. However, a bonus is that at our ‘older’ ages we have heard a lot of bullshit from people’s mouths (as in pickup lines from smooth-talking manipulators trying to get in our pants) and we can pretty much see through that and deflect it.
  4. Coffee shops: Probably better than bars, depending on whom you ask and again, what it is you are looking for. I’d like to think there are generally more intelligent people sitting around in (name of large-chain overpriced coffee shop) than in the average local watering hole. Many people use the wi-fi to work or other activities and others read. Yes, there is the possibility of getting overly caffeinated and then yet talking too much between your spaced-out tables, but maybe it’s worth it. Just a thought.
  5. Grocery stores: Yes, it can happen here. I recommend the “rotisserie chicken” method wherein you walk around the store with one of those delicious roasted chickens in your basket. Odds are good you might meet someone (okay, a man…probably) unless you’re in a store where there are a lot of uptight and stuck-up people. I add this one because it’s happened to me twice whee I’ve met two single men while carrying around the chicken. One was old enough to be my dad and the other I might have considered but didn’t because maybe I was seeing someone else at the time. But it was interesting and noteworthy. Either than or run your cart into an attractive person’s cart and then apologize profusely.
  6. Library: In the past (pre-Covid-19) I’ve had some great conversations with men in libraries, gotten a few phone numbers. and even one date. So if your local library is open (many are only curbside nowadays) I highly recommend if you see someone interesting, start up a conversation — while appropriately and responsibly masked and distanced, of course.

I realize these are probably nothing new those who have been treading this earth for a while. The pandemic just means we might have to get creative — and put some distance in between those we meet. Our “personal spaces” (the bubbles around us that constitute our comfort zones into which we only invite people we really like/are attracted to) have gotten wider this year and I don’t see that as all of a bad thing. Maybe less people are just jumping into bed together because of the safety factor. Perhaps they’re spending more time having “virtual happy hours” or “Zoom dates” which may be resulting in more of a mental connection before one gets down to getting physical (if that ever happens). It was my hope by writing this that some of you find some inspiration in these stories, or think of some scenarios of your own.

ven though it’s probably a long shot that someday you’ll be at the library and drop a book, or at the grocery store and knock over a whole display with your cart, or some other weird scenario, and then end up meeting a fantastic person as you laugh over your clumsiness like a scene from those rom-coms. I say it’s a long shot because I’m a skeptic these things ever happen (“their eyes met as he helped her pick up the cans of creamed corn she knocked all over Aisle 5 and they both saw a promising flicker of warmth in each other’s eyes… and then all of a sudden you hear violins playing in the background and hearts are coming out of your head” ….). I’m not saying it’s impossible because in this life who knows? A positive attitude while out in the world certainly can’t hurt. Cheers!

Experienced professional writer/freelancer and former newspaper reporter-turned-online writer/blogger. Thinker. “Old soul”, young hippie, empath.

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