I married my husband the year I turned 50. We met the old-fashioned way, via a mutual acquaintance. Our casual matchmaker was someone I had interviewed for a story a number of years earlier, a friend of a friend who was the wife of a colleague of my husband. I am using my own experience to illustrate how webs of people intersect in mysterious ways: Honestly, I’m not sure I ever would have run into my now-husband in the course of our everyday lives – our careers and friend groups are so different. I also use it to illustrate that you never know from where romance might come.

There are a lot of fish in the sea, and not just on ABC’s The Golden Bachelorette (which just hit the airwaves). According to a 2022 Statistics Canada survey, 30 per cent of Canadians over 50 were single (and not cohabitating). The late anthropologist Helen Fisher (author of Why We Love), found that older daters tend to be pickier than younger ones. “My hypothesis,” she told The Washington Post at the time, “is that the young have to reproduce so they are more likely to compromise.” So, feel free to be picky, Sherry!

To help us sort through the options open to older daters, our expert this week is Jen Kirsch, a Toronto relationship columnist whose work you may have seen in the Toronto Star or heard on iHeartRadio, Newstalk1010 or the CBC. Kirsch is very upbeat about the prospects for over 50s returning to the dating pool. 

“Back in the day, women who were divorced or lost a partner were less likely to date again,” she says. This was due to societal conventions; women were not expected to “move on” Kirsch thinks lockdown was an eye-opener: that the restrictions drove people to seek out companionship. “Following the pandemic, people wanted to meet someone else,” she says. “They were open and understood that there are different types of love, and they wanted to find a new life.”

“Where do I meet someone?” is the number one question she is asked. Introductions are great, she says, but “don’t wait around for your friends or your children to introduce you to someone. Chances are everyone has already gone through their list of available prospects for you.” That said, it never hurts to remind your friends you are looking for someone.

If you are not going out of the house, then start going out! “If you go to the same coffee shop every day, change it up. Go to another neighbourhood, and go outside of your comfort zone. Sit at the bar at a restaurant, even if you don’t drink. It is easier to strike up a conversation there.”

Conversation, she says, is a muscle you need to practise. “Plus you are expanding your network. You might become friendly with the bartender. Who knows who they know, who they could introduce you to?”

Kirsch gives examples of subtle ways to spark conversation with strangers. “I’m a big reader. If I have a book under my arm, people often ask me about it. I was holding the new Jeanne Beker book [Heart on My Sleeve] under my arm, and people stopped me to ask about it. I have a dog, and the dog park is an especially great place to strike up a chat.” Join a running club, go see a band, check out Eventbrite for free things to do right across Canada. “Common interests are a great excuse to connect with people.”

So what about dating apps? Kirsch is 40 – currently happily single – and she sees the apps as a complement to meeting people in real life. Her rule for apps is to use recent, undoctored photos. “Put up pics from the past six months,” she says. “Show yourself doing things you love to do. Use a close-up, and two full-length shots. Show your full body, as it is.” Your best currency is authenticity. “Relatable people are unapologetically themselves. That is what is most appealing to others.” 

Her second big tip about the apps is to move the conversation offline and into the real world as soon as possible. “Talking online isn’t real,” she says. “It is too crafted, curated and, most dangerously, you can build up something too much in your head before you know if there is any chemistry.” She tells a story of being introduced to a guy who has a place in Tuscany. “Because of that, I got carried away with the idea of travelling to Italy, right up to imagining a grand wedding. We get so in our heads, there is too much space to create an imaginary relationship that real life will never compare to. It is very dangerous.” 

The beauty of getting older is knowing who you are and what you want. The best way to know if a match will ultimately click? “If you are playing games, that is not the person for you,” says Kirsch.

Tinder.com is Canada’s most popular site, followed by the big hitters, Match.com and eHarmony.ca. There are costs associated with most sites (from about $12 a month up), with more matches and access to messaging and more photos available at different cost levels. eHarmony boasts an extensive personality test, which can be useful in and of itself in determining what you like and what you want in life. If the prospect of “swiping right” (the Tinder flip-book approach) feels like too abrupt and depersonalized a way to shop for love, there are some apps that cater specifically to an older demographic. I have heard close personal anecdotal stories of success on both OurTime.com and SilverSingles.com. Note that you have to sign up with a profile to even look around on the sites.

If you want a little hand-holding, there are coaches and introduction services out there to walk you through everything from creating a profile, to critiquing online responses and  setting up photoshoots. FriendofaFriend Matchmaking.com is a Toronto- and Hamilton-based online service that offers various levels and types of support (from $149 for profile creation to $549 for a complete coaching package). They also offer a boutique matchmaking service (pricing upon acceptance, with one to five customized matches per year). Coaching topics include examining past dating patterns, getting ready to date again, shifts in identity as we age, body positivity and issues of chronic illness and disability in dating. 

The thing I took away from my conversation with Kirsch, though, was her certainty that saying yes to yourself is the true first step. Get comfortable going out alone, get used to talking to people when there is nothing at stake. It is, indeed, freeing (though nerve-racking at first) to sit at a bar alone, with a book. Honestly, no one is thinking you are anything but cool for doing it. I also really like her personal mantra: “I’d rather have no company than bad company.” Most of all, don’t miss out on life waiting for Mr. or Ms. Right to come along. It is a truism that the more we like ourselves, the more other people like us back.

Always asking questions,

—Leanne Delap