Where have all my friends gone?
That question has been on my mind for some time. After enjoying a robust social life for most of my years, by my mid-50s, I found my list of close friends had shrunk to just two — both family. Following years of losing people to death, divorce and the slow drift of growing apart, I realized I was lonely. As the headlines about our modern “loneliness epidemic” reflect, I knew I wasn’t the only one asking where the connections went.
I decided to stop waiting for new connections to happen and to take action. I knew this wasn’t a personal failure, but a common experience in Toronto, where adult friendships can be notoriously hard to form. As part of the Star’s Better Friends series, where staffers join group activities to find social connection, I set out to test friendship-making apps that organize face-to-face events to see what actually works in midlife.
I am certainly not alone in being alone. A 2022 Statistics Canada study found that 40 years ago, almost half of Canadians saw friends on any average day; by 2022, that number dropped to less than 20 per cent. It’s the same story in the States: A 2021 study by the Survey Center on American Life found that in 1990, 27 per cent of Americans reported having three or fewer close friends. By 2021, that number had skyrocketed to 49 per cent.
My first foray into friend-dating apps was the morbidly named Timeleft. In this program, you have one-off dinners with about five women (or a mix of women and men). You show up at the assigned restaurant at the assigned time and have dinner with people you’re matched with by personality and interests, no commitment beyond that. I did this twice and met lovely women both times. We had dinner, shared some of our histories and a few laughs and then went our own merry ways. I don’t think I’d recognize any of them if I ran into them on the street now. I realized if I was going to form lasting connections, I needed more structure and commitment and to be prodded to continue making the effort.
Then Instagram fed me an ad for a different friend-dating app, RealRoots, with a greater time and money commitment and a more in-depth selection process. For this one, you sign up for a series of about six dinners around town with a group of women in your age group after answering multiple personality-matching questions. The dinners are facilitated by a guide whose job it is to spark conversation and keep it going if it lags. You’re also paired up every week with a different person from your group with whom you’re supposed to set up an additional one-on-one “date,” a coffee, a walk, a drink.
The first meetup was a gong show of multiple age-specific groups in the back of a big, loud restaurant in Old Town, waiting for direction, seating, a much-desired drink and any indication that things were going to smooth out and become enjoyable. About 20 of us sat at a long table and did a speed-dating sort of exercise, introducing and describing ourselves to the person across from us for timed short periods before shuffling seats and moving onto the next person. These little interviews that had to be shouted over the din and across the table to alternating strangers in rapid succession were exhausting, and before long, that was the only topic of shouted conversation.
“This is a bit crazy!”
“I know, it’s so loud!”
“I know!”
Some women declared that first night their last.
Those of us who stuck it out met again the following week at a west-end brewery. Our numbers had been roughly halved, and a few women from a younger age group were added to the mix. There were more conversation starters from our guide and more musical chairs, but less chaos. By the next meetup, the younger women had been moved out, and what remained was a group of about eight 45- to 55-year-old familiar faces — a group I found myself genuinely looking forward to seeing.
Some outings included activities, like pottery or trivia, before or during dinner. But the best times were when we were simply a small group of new friends getting to know each other — which happened more quickly and easily than I would have predicted. As the weeks went on, we shared the major milestones of our lives: divorce, coming out, life-altering partner illness. We kept up with big events on the horizon, too — third-wedding planning, job interviews, new puppies. We started a WhatsApp group to stay in touch. We even gave ourselves a name, too silly to repeat.
As the number of remaining organized, chaperoned dinners dwindled, the biggest question was whether this newfound camaraderie would survive without the app’s structure. At our final official dinner — this one without our guide — we all agreed we wanted to keep seeing each other.
And we have. Since then, even with no prompting from the app, we’ve kept up our dinners out and hosted each other for backyard hangs and birthday parties. We check in when someone goes quiet for a while. We share vacation photos, track career moves, and offer cheerleading when one of us needs it. Most importantly, we have a genuinely good time and laugh a lot whenever we’re together.
I keep wondering about the apparent effortlessness of it all. Did we simply get lucky with a group that clicked as well as it did? Or does it make sense that a group of women actively seeking friendship would enjoy the company of others in the same boat? Either way, I’m proud of myself for getting out there and taking a chance. It turns out friendship in midlife isn’t effortless — but it is possible, if you keep showing up.
