Online dating in your 60s

As I look in the bathroom mirror one last time, nervously checking my makeup, I wonder what on earth I’m doing, heading out to meet a stranger I know only from a photo, a short, snappy profile and a few witty texts.

“You’re so brave to put yourself out there,” girlfriends say, as they breathlessly await details of each encounter. But I don’t feel brave. Online dating is frustrating, annoying and hard work, with the occasional magic moment thrown in.

None of us expected to be alone and looking for love in our 60s. We’re supposed to be the happy couples on Facebook sipping Champagne in Paris for our 30th anniversary, or walking the Camino de Santiago together.

Yet here we are, through death, divorce or plain bad luck, forming a tight-knit community of our own, upbeat and hopeful the next person who “Likes” our profile will be The One.

Though I resisted online dating as the only way to meet someone, it may be true. Saying hello in public is impossible with everyone plugged into their phone, guys at the gym appear laser-focused on their routine, guys in the produce department are on the phone to their wives and the only people I’ve met in night classes are other fabulous 60-something women.

Yet everyone knows at least one successful couple who met online. Since it’s free, and you can maintain your anonymity as long as you feel comfortable, why not give it a whirl? At the very least you’ll have stories to share with friends and something in common with nieces and nephews.

To begin, you’ll need a smiling photo of yourself. Scroll through the guys on any dating site and you’ll quickly learn how not to present yourself — with an old, blurry photo, for example, or your arms around unknown women, ex-wife? daughter? Or a selfie in the mirror or a sunset … to mirror your inner soul, perhaps? And please, dudes, ditch the dark glasses!

Though the photo of Dimitri in his undershirt didn’t inspire, I must say I was tempted by his offer to whisk me to his beach house on a Greek island, complete with organic garden. “Please take a chance on me my sweet baby,” he wrote, “I will pamper you!”

Writing a profile is the hardest part, deciding who you are and what you’re looking for in a relationship. And it’s tough to stand out when we share similar interests: “Art, music, food, travel, literature, movies and everything in between,” said Thomas. A current favourite solved that problem by writing a one-word profile: “Solid.”

It’s time to answer hundreds of inane questions so the computer can choose some likely prospects. A 96% match may mean you both hate horror movies, you’d prefer not to date someone who’s really messy and you’d rather be considered normal than weird. I’m astounded by how many men on OK Cupid agree jealousy is healthy in a relationship, and say they’d date a woman in considerable debt. Ditto the number who say they’re “absolutely” ready to settle down and get married right now. Me, I’d rather take things slowly, but it would be wonderful to feel loved again, and find a great guy to cook with and travel the world.

Hit send and you’ll be deluged by men desperate to meet you. Enjoy the attention — you’re fresh meat to guys tired of scrolling past the same women day after day. In my first week I lined up three dates in one day. One was lovely, one creepy (turns out a friend dated the same guy six years ago) and the third promising guy vanished an hour before we’d planned to meet. Then there was the week of five Bills. To my friends they became Bill #1, Burlington Bill, retired principal Bill, etc.

Sadly, within a few weeks we all become the house not sold (is there something wrong with him?) and the “Likes” slow to one every few days, usually from guys who’ve just joined the site.

Here’s the really deflating part. In my experience, about 99% of the guys who look and sound perfect will never contact you. Do not take it personally, as you have no idea what’s happening in their lives. And 99% of the guys who reach out to you won’t interest you. It may be their horrible photo, the cloying “Hello Beautiful!” messages (it’s 2019, gentlemen), or because they’re interested in “hookups” and “non-monogamy,” which make my stomach churn. And would you date a sapiosexual?

At the same time, I’ve met, in person or virtually, lovely-sounding guys from all walks of life. They’re retired engineers, speech pathologists, gemologists, diesel mechanics, Morris dancers, software developers desperate to publish their novel and an astounding number of contractors. They’re financially stable and love their toys: the cottage, two bikes, two boats! Those still working stand on the edge of the precipice wondering when to jump and what retirement will look like. They’re the most keen to find a travel partner.

When I find someone interesting online, I suggest meeting for coffee to get the chemistry part out of the way. As a friend says, it’s just coffee, you’re not getting married! She also makes sure I let someone know when and where I’m going. And be cautious handing out your cell number, which many guys ask for immediately.

Unfortunately a lot of men seem to think endless texting (scintillating comments like “How are you doing today?”) is a better way to reveal whether we’re a match. This gets boring quickly. Then there are the bullies, charming, articulate guys who come on strong and profess to know everything about you and what you want simply by reading your profile. They’re the first to disappear.

Sometimes he’s just not meant to be. I was so looking forward to running off to Italy with Jesse until we realized he’s vegan, I’m an omnivore, and he’d be severely allergic to my cat. We never met.

When you actually finagle a date, there should be no shortage of things to talk about — after all you’ve got 120 years of history between you. Be prepared to feel as nervous and excited as a teenager. As we talk, a little ping! goes off in my head when we find common ground. I even met a guy who shares my obsession with horrible Hallmark romances. But starting from scratch is hard; it takes a long, long time to know if you’re a good match. Just pray you don’t end up with a guy who prattles on without asking a single personal question. Next!

There’s something else you should know about guys in their 60s. They’re not only stubbornly set in their ways (unlike us, of course!), but you may find yourself dating his kids, grandkids, aging and ailing parents, ex-wives and even ex-girlfriends. While the sex is great, it’s sadly not as effortless as it once was: they’ve got their secret blue pills, we’ve got our favourite lubricant. At least we’re old enough to laugh about it.

Oh, and before jumping into bed you might ask if they’re still active online. One more thing? Getting dumped in your 60s hurts just as much as it did in your 20s.

Though I’m convinced there are wonderful men out there, I wish I could tell you how to find them. I do know, however, that even if you don’t meet your soul mate, your forever guy online, you may still find yourself in a Havana nightclub enjoying electrifying jazz, listening to medieval music in an ancient church, skinny dipping in a frigid river and fielding dinner invitations from other couples.

Sure beats sitting home alone watching Netflix.

First published in the Toronto Star, July 6, 2019


  1. Loved reading this the other day. Daniel and I had a laugh over breakfast! Hope you are having a great summer so far.


  2. You are brave – but as you say there is someone out there for you !


    Sent from my iPhone


  3. Great article. Hope that sounds nice we met that you’ve met mr. good-enough. And how r u enjoying the summer?

    I’ve made some progress in getting the lexicon into bookstores. It ‘s available via indigo chapters, Renaud Bray, Archambault online and possibly in store, and amazon has it online via Renaud bray. And the mtl museum of fine arts boutique has it as well as Mtl’s historical archeological museum Pointe a Calliere in old mtl in their boutique as their current show is A Table, the history of French cuisine. In Calgary, SAIT’s bookstore may be ordering it too.

    I never heard back from the two Ryerson folks. I’m learning the ropes abt how to approach people and am very likely making mistakes and losing potential ‘influencers’. C’est la vie.


    Diana PS: you didn’t mention how you feel abt connecting with guys in other cities who use online dating sites. It’s an xtra hurdle. And what exactly is a hookup? Just meeting or a one night stand?


    • Happy to hear you’re making progress!! I’m thinking a hook-up is a one-night stand but didn’t have that conversation. !!! Hope you’re having a wonderful summer. I’m spending next week at Steve’s cottage-in-progress in the middle of nowhere … another test!!! xcy

  4. Great column!! Karen

    From: Cynthia David Reply-To: Cynthia David Date: Tuesday, July 9, 2019 at 12:03 PM To: Karen Davidson Subject: [New post] Online dating in your 60s

    > > cynthiadavid posted: “As I look in the bathroom mirror one last time, > nervously checking my makeup, I wonder what on earth I¹m doing, heading out to > meet a stranger I know only from a photo, a short, snappy profile and a few > witty texts. ³You¹re so brave to put yourself ou” >

  5. I expect fresh fruit and veg honest talk from you but not your single and dating online editorials…reading yours from osaka.cheers Charles
    Charles Ellis Esq

  6. Excellent column. On-line dating does take some nerve, and patience. Hang in there. Many people have had very positive experience finding romance on-line.

    • Thanks Bill! I’m sure guys have their own list of annoyances but havent heard them yet. Of course part of me’s thinking The One might read it and show up in my inbox. Ha! Connecting with lovely (of course) women instead. Hope you’re having a wonderful summer. xxcy

  7. Thanks for the dating tips. Responding to your finely-crafted piece as a guy, which is effortless as I happen to be one, the most common online dating issues I encounter are: photos and stated ages that would not pass as ‘current’; sunglasses (alas, women too); and the Princess/Prince thing: an overly romanticized expectation of perfection and completion. Successful relationships are hard work, and not meant to complete your sense of self.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: