Last updated on 28 February 2025
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What’s so fascinating and frustrating and great about life is that you’re constantly starting over, all the time, and I love that.
I’m a member of a few Facebook and Meetup groups. Meetup in an online community organizer platform where one can connect with people with similar interests. Everything from athletic endeavors like cycling or hiking to political, religious, idealogical and age-specific groups (“Boomers coffee”) have “meetups”, usually within a few miles.
They even have different flavors of meetup groups for singles; By age, by interest, by location: “Outdoorsy Singles”, “Christian Singles,” “Single professionals.” . I know because when I moved to North Carolina after my divorce, I joined a few. At first it was simply a way to meet people in a new city where I knew close to no one. A big part of my motivation was meeting people to jumpstart my real estate practice here. While I was thriving in Michigan, that was not true so far in North Carolina. In fact, my real estate business was on fumes.

I came here to start life over, a new chapter in a new city. Having to meet people to recreate my real estate business was the perfect way to also feel adopted by my new hometown.
I noticed as I dipped my toes into the meetup water a sense of something I couldn’t quite put my finger on among many of the people I met. Desperation? Wounding? Not in a huge way, more subtly, like background music or a chill in an otherwise warm current.
The groups inevitably have a dynamic, outgoing leader, like one woman who leads a pickleball group, which while not necessarily a singles group is populated mostly by singles in their 50’s and 60’s, men and women, looking for connection like me. She is single, in her late 60’s or early 70’s, with a few marriages that didn’t work out in her back pocket. To describe her as outgoing would be like saying tigers have stripes.
She loves connecting people and every time I show up at the courts, she rattles off the names of a few single women who are supposed to show up.
I’m also a member of another meetup group whose members call themselves The Tribe, which caters to all ages and is not necessarily a singles group, although many of us who are members are.
This group builds community around events, from kickball to axe throwing to karaoke nights and themed dinners and parties, and, lately, some charity work.. There’s a smaller singles group that splinters off this one. The Tribe is made up of people in their 30’s to early 70’s who gather frequently at local restaurants, pubs and other venues for drinks and conversation. They also hold parties at members’ homes; I’ve been to a few birthday parties for members. It’s a mix of men and women too. Its purpose is creating community and deeper connections and friendships.
I’ve noticed as I’ve attended some of the events the undercurrent of grasping, a neediness that borders on desperation or maybe something else. And maybe now I know why.
When you get this age, with kids who are now adults with lives of their own, with careers either in full swing or winding down, and almost all with a few train wrecks in our recent and further past (usually divorces, sometimes career setbacks, often relocations, like mine), it’s not easy making new friends. For making new friends takes risk and effort with no guarantee of payoff.
This is a song about somebody else
So don’t worry yourself, worry yourself
The devil’s right there right there in the details
And you don’t wanna hurt yourself, hurt yourself
Looking too closely
Looking too closely
No no no no!– Fink
I consider myself introverted; at a party I’m more likely to stay on the perimeter than dive into the middle and introduce myself. That is if I even go. I’m more likely to gravitate to people I’ve spoken to or seen at an event before than seek out someone new. Even people I don’t particularly resonate with but just to talk to someone. As you might guess, I don’t last very long at these events either.
There’s one especially charming guy in this group. He is in his 30’s, relocated to the area about three years ago and is a fixture at every event. He has an uncanny memory for people and facts about them. And he lives for karaoke, despite not once being able to hit a key. I am not kidding. It’s as if he is writing the songs he sings in the moment, trying to decide what key he should be in. But it doesn’t matter. He is fearless and loves to sing. You can hear and feel it when he takes the mic. He and I share a love of college football and have hung out together at sports bars a few times. He is a very nice guy, well-liked by everyone in the Tribe and his kindness is beyond contagious. But I would hesitate to call him a friend. (If you read this and figure out who you are, please forgive me.)
I’ve realized this is on me. After all, he is the epitome of this friendly community. Yet I find myself comparing everyone new to the people I’ve come to love and call friends that I left behind when I moved from Michigan. Maybe I’m just less willing to trust and to put in the work to create friendships. I’m not mean about it. Some would call me aloof. I see it as wary. Why put in the effort to befriend someone and find out you don’t really resonate with them?
My divorce shook me and made me gun shy about putting myself out there to anyone. In fact, I’m more likely to retreat now to my one-bedroom apartment and to the predictable comfort of a book than seeking company. (Yes, I often feel lonely in case you are curious).
Even as I write these words, I’m sitting at my dining table in my apartment listening to Fink sing “You don’t want to hurt yourself.” Alone once again. With no plans to get out and interact.
When you’re young, you have both time and circumstances. For example, when my daughters were growing up and in school, my former wife and I had an easily accessible lab where friendships easily developed around a common factor: we were parents of children who saw each other at school events, clubs, meetings and sports. It was natural to strike up conversations that then flowed easily to “the next thing,” which could be getting together for drinks or coffee, most often in pairs. It was natural and there was no desperation, no neediness.
I might be wrong about the neediness I see in these present day meetup groups. It might be something else. Maybe wounding or a type of social PTSD. As if all the punches life has thrown have taken their toll on our souls. We are simply less willing to risk additional hurt even while we seek connection. It’s an odd place to be.
As if all the punches life has thrown have taken their toll on our souls. We are simply less willing to risk additional hurt even while we seek connection. It’s an odd place to be.
It’s a side of aging in America I never thought I would be a part of; solo, aimless, lacking social courage after heartbreak nor the ability to solve my own dilemmas.
Before you say get out and meet people, put yourself out there, it’s a numbers game, the more at-bats, the more likely we are to get on base, cut me some slack. Some of that is true. I’m not a fearful person. I’ve taken risks. Dealt with uncertainty. Fumbled, Struck out, failed epically. And gotten back up.
The effort it takes to manage our lives now aging and alone, paying bills, working, shopping, cleaning, cooking, getting enough sleep, taking care of our bodies, working out, seems to take more out of us than before. It’s like driving a clunky stick shift after years used to an automatic. I don’t know how my former wives and I did all we did; raising children and step children, taking care of homes, working full time and managing not to fuck up our careers and our kids (mostly) while also providing wholesome, delicious meals, packing great lunches, being confidants, gently guiding them around the obstacles of childhood.
Nothing in the universe can stop you from letting go and starting over.
Perhaps what I’m noticing as desperation or wounding in my Meetup group peers is merely a hope to jumpstart life once more after a setback. To find purpose once more. And the undercurrent of desperation is this fear of taking the risks of creating sustainable, authentic friendships and relationships. This is a culture that celebrates the young and strong and is not so supportive of middle-aged and aging adults. And even moreso single aging adults.
What if there is nothing to catch us if we fall?

I know my life is completely my responsibility. I’m not trying to shirk that. it’s up to me to find my own contentment, my own purpose. It just seems so much harder now. As I look back, I see places where I could have made different choices that might have changed where I am today. Mostly smaller choices rather than bigger ones. Places where I could have benefitted from pausing, even for a moment, and connected with my intuition a bit more fully, rather than acting as I have so often done out of habit.
But that’s so much spilt milk. The past is the past. No matter how much I long for do overs.
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