By Caroline Andrews
Dating after 55 isn’t what it used to be. Then again, neither are we.
For many people, the last time they went on a first date there were no dating apps, no texting, no social media and certainly no googling someone before agreeing to meet for coffee. You met through friends, at work, at a party or perhaps across a crowded room.
Today, that crowded room may be a screen filled with profile photos, short biographies and a surprising number of men posing proudly with fish.
Welcome to dating after 55.
And, having ventured into the world of dating after 55 myself, I can assure you that some of this is written from experience. It can be exciting, intimidating, occasionally hilarious and, for anyone returning to dating after a long marriage or relationship, a completely different world from the one they remember.
The first adjustment may be the technology itself. Suddenly you’re expected to summarize an entire lifetime in a few paragraphs while selecting photographs that say, “This is what I actually look like,” but preferably on a particularly good day.
Then there is the profile.
You like travel. So does everyone else, apparently. Long walks, good food, family and laughter are also extremely popular. Almost everyone claims to love adventure, although one person’s idea of adventure may be hiking in Patagonia while another is trying the new Italian restaurant across town.
And what exactly does “young at heart” mean? That you still go skiing? That you own a motorcycle? That you know how to use Instagram?
Then come the photographs. There are vacation photos, golf photos, dog photos and the aforementioned fish photos. Occasionally there’s a photograph taken so long ago that you wonder whether it was scanned from a film negative.
Eventually, though, someone catches your attention.
A message is exchanged. Then another. Perhaps you move to texting, which introduces an entirely new set of questions. How soon should you respond? Is a thumbs-up a perfectly acceptable answer or vaguely dismissive? And when did punctuation become capable of conveying an attitude?
At some point, somebody suggests actually meeting.
First dates after 55 can feel remarkably similar to first dates at 25. You still wonder what to wear. You still hope the conversation flows. You still know within the first few minutes whether there might be a spark.
But there is one significant difference: By this stage of life, most of us know ourselves considerably better. We have lived a little. Or a lot.
We’ve built careers, raised families, travelled, experienced loss, made mistakes and hopefully learned from a few of them. We tend to know what makes us happy and, perhaps even more importantly, what doesn’t. That changes dating.
At 25, you may have been figuring out who you wanted to become. After 55, you’ve probably become that person. You’re not looking for someone to build your identity around. Ideally, you’re looking for someone whose life fits comfortably alongside your own. And those lives can be surprisingly complicated.
There may be adult children and grandchildren. There may be former spouses, long-established friendships and family traditions. There may be a beloved dog who sleeps on the bed and has absolutely no intention of negotiating that arrangement.
There are careers, retirement plans, cottages, golf memberships, travel dreams and two homes containing several decades’ worth of furniture.
Romance may eventually require logistics.
If a relationship becomes serious, questions arise that probably weren’t part of dating in your 20s. Does either person want to get married again? Do you want to live together? Whose house? Or perhaps neither house? Do you combine finances? How much independence does each person want?
And then there’s geography. Meeting someone wonderful who lives 45 minutes away may not have sounded significant when you were younger. After years of establishing a community, routines and friendships, 45 minutes can suddenly feel like a long-distance relationship.
Yet there is something rather wonderful about dating at this stage of life. The pressure to follow a prescribed path is largely gone. A relationship doesn’t necessarily have to lead to marriage, a shared mortgage and matching towels. Some couples marry. Some live together. Some maintain separate homes. Some travel together and happily return to their own spaces afterward. The definition of a successful relationship can be whatever works for the two people in it.
There can also be a refreshing directness to dating after 55. Time feels more valuable. Pretending to enjoy something you don’t simply to impress someone becomes less appealing. If you hate camping, this may finally be the age when you can confidently say so.
Of course, dating at any age requires some common sense. Meeting somewhere public, taking your time and being cautious about sharing personal or financial information are particularly important when meeting someone online.
But caution doesn’t have to mean cynicism.
For all the jokes about dating apps, awkward first dates and questionable profile photographs, technology has created opportunities that previous generations simply didn’t have. It allows people to meet outside their existing circles and connect with someone they might never otherwise have encountered.
That’s the nicest thing about dating after 55: Life can still surprise us.
There can still be butterflies before a first date, laughter over dinner, the excitement of a new message and the possibility that someone you didn’t know existed a month ago could become an important part of your life.
The rules may have changed.
Thankfully, some things haven’t.
Caroline Andrews is a
freelance writer and real
estate advisor with Engel &
Völkers Ottawa, specializing
in 55+ real estate.
