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Slices of Life: Dating after 50 — part one

No one plans to date after 50, but you never know the details life will hand you: divorce, death of a spouse, boredom, aloneness — it all leads to one thing.

You find yourself being half of a couple in a couple’s world.

Such a conundrum. You were once half the age of 50 and probably a couple, now you are twice as old and twice as alone — or at least it feels that way; it’s the hand you’ve been dealt.

Dating at 20 is one thing. It is beautiful. You are beautiful and the people around you (and willing to date you) are equally beautiful. 

You all wear the magical cloak of youth, and that cloak is dazzling and vivid — nothing short of spectacular. It is healthy. It has a head full of hair and a six-pack of abs. Your body literally exudes glitter.

Then, time passes. The years go by and take with then the newness of youth, not to mention the glitter. Aging happens. Gravity happens. Baldness happens. Weight gain happens. Wrinkles happen. Aches and pains happen. Suddenly, but not so suddenly you aren’t thirty-something anymore. You aren’t even forty-something.

Welcome to life.

As an added insult, you look to the seat beside yourself and find your ride or die has died or at least left the vehicle, bringing a whole new meaning to the term “empty nester.”

And you find yourself contemplating that dreaded four-letter word:


Dating in your teens and 20’s is flashy and bright. It is exciting! It is the norm. Everyone is doing it, so hop on board!

Dating after 50 isn’t quite what it was 30 or so years prior. To start with, the dynamics have changed. Oh, hell, everything has changed. Well, except for you. You remain a youthful example of glittery goodness — even at age 59 (or so).

Full disclosure here: I am not an expert on dating. I haven’t been on a date in more than 35 years. I definitely don’t have the resume or expertise to give dating advice, but I can make observations.

I’ve compiled a list of the differences between dating in your 20s versus dating after 50. There were so many variables, I couldn’t fit them all into one column, so here’s a start. Part two is forthcoming.

During the 20s: He’s got a fancy new car!

After 50: He’s got a fancy new golf cart!

20s: You look forward to creating a future together.

After 50: You look forward to an early bird dinner together.

20s: You look for someone with a nice package.

After 50: You look for someone with a nice retirement package.

20s: You hope for a partner who forgets about your flaws.

After 50: You hope for a partner who can remember what happened yesterday.

20s: You appreciate someone who can roll stiff joints.

After 50: You appreciate someone who doesn’t have stiff joints.

20s: You hope to find someone who is passionate about their career.

After 50: You hope to find someone who is passionate about pickleball.

Dating after 50, in some ways, is more complex than decades earlier. It involves grown kids and maybe even grand babies. There are ex-spouses and dead ones. Money affluence or shortfalls. Mortgages, second homes and retirement plans. Travel histories and hopes. Viewpoints on religion, politics, fine wine, sail boats, tattoos, pick-up trucks, convertibles and Harleys.

And, at it’s best, love, which is a feeling and a way of life that never grows old.

At least I hope not.

— Jill Pertler’s column Slices of Life appears regularly in the Times. She can be reached at