“Age isn’t a barrier to friendship. It’s an advantage.”
Hey Reader,
There's something that's really been bugging me from the replies I get from all of you. I want to address the Myth of the Expiration Date.
Too many of us act like friendship comes with an expiration date. Make your “real friends” in college, maybe add a couple at work in your 20s, maybe one or two more when you have your first kid and after that? Forget it.
But friendship isn’t yogurt. It doesn’t suddenly go bad after a certain date. (Though if anyone knows the real rules on food expiration dates, please reply and tell me. I say you can always add three days. My wife is stricter. Our fridge is a battlefield.)
Lately, I’ve been getting a slew of notes from some of my more “seasoned” readers explaining their struggles making friends at the ripe old ages of 46, or 55, or 72, or even 81. And for all of them, I say the same thing: it’s not too late.
🤝 The Friend
In 44 BC, the Roman philosopher Cicero wrote On Old Age: basically the world’s first anti–midlife crisis essay. His point was simple: stop whining.
Old age, he argued, isn’t decline. It’s freedom. You’re no longer chasing shallow pleasures or jockeying for status. You finally know what matters and that makes you better at friendship. You listen more. You cut through the small talk. You choose loyalty over popularity.
As Cicero put it, “Old age is the crowning glory of life.”
Most people assume making friends gets harder with age...fewer new faces, smaller circles. But Cicero flipped that idea 2,000 years ago: age doesn’t limit friendship, it sharpens it.
Clarity is the raw material of closeness, and it’s something only time can give you.
⚒️ The Fix
Stop treating friendship like a race you already lost. Ask yourself: What new circle could I realistically build in the next six months?
Think of the 65-year-old who picks up pickleball for exercise. Within half a year, he’s texting inside jokes, planning weekend games, and suddenly has people who’d drive him to the airport. Not because they “went way back,” but because they showed up now.
That clarity Cicero described...it makes later friendships go deeper, faster. What once took decades can click in months.
I’ve even seen it firsthand: my mom, who’s in her 70s, just started an adult education program in New York called Quest. Three days a week, she and her classmates teach each other all sorts of fun subjects and in the process, she’s built an entirely new circle of friends.
Deep friendship doesn’t take decades. It’s more like a second marriage: once you know yourself, you skip the games and cut to the good stuff. Six months of rhythm can feel like twenty years of history.
📚 The Reco
The Second Mountain by David Brooks
Brooks argues that the first mountain of life is about achievement — career, independence, checking boxes. The second mountain is about commitment: to family, to a vocation, to a philosophy or faith, and to community.
I’ll admit: I chased the first mountain extremely hard (and in some ways, I still am). But I also feel great about the fact that it’s now in my rearview — because it means I get to focus more on the second.
Brooks’ core argument is that our culture celebrates freedom and individualism, but real fulfillment doesn’t come from avoiding obligations. It comes from surrendering to them — from binding yourself to people, to places, to causes.
That’s friendship in a nutshell. You don’t feel alive by floating free. You feel alive by rooting yourself in others — and the second mountain is often higher, more joyful, and way more fun to climb with friends. The second mountain isn’t Everest — it’s the one you climb with friends and call a “hike.” More joy than grind.
These days I'm more of an audiobook guy, so linking to his book on Audible, between the near sightedness and the multi-tasking, audio is winning for me, Anyone else made that shift?
📊 Quick Poll
Do you feel like you’re still on the first mountain (career/independence) or climbing your second mountain (commitment/community)?
Click to vote — I’ll share results in next week’s newsletter.
And if this resonated or if there's someone who needs to hear this, please forward it. That's how we've grown from zero to 8000 of us together here in less than 3 months, and I appreciate every last one of you :)
Until next week, remember...
"Friendship is the ultimate life hack."
— Matt Ritter
PS: Last week’s poll results are in: going to watch your team narrowly edged out reality TV as the stronger fall friendship ritual. What does that say? Probably that we’re starved for the kind of weekly, everyone’s-talking-about-it watercooler shows that used to glue us together. (As a working screenwriter, I’m trying to fix that too 😉).
