During COVID, six childhood friends from West Roxbury tried to reconnect on Zoom. It was a disaster, so they went for a walk instead. Seven years later, they’re still walking five miles every Sunday, and one of them made a documentary about it.
Shaun and Chris talk with four members of the Old Man Walking Club: filmmaker and author Michael Connelly, Rad, Peter and Tim. It’s the most guests we’ve ever had on one episode, and the nonstop ribbing proves it. Under the jokes is a serious conversation about what happens when men let friendships fade, and what it takes to bring them back.
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In this episode:
- How a failed Zoom call turned into a weekly walk that has lasted seven years
- Why a walk builds more connection than a round of golf
- The “roast” culture: nothing is off limits, and they still make room for the hard stuff
- Peter’s Sunday “control-alt-delete” and what it does for the rest of his week
- Climbing Croagh Patrick in Ireland, and moving from childhood buddies to something closer to brothers
- Getting Robert Waldinger (Harvard Study of Adult Development) and Dan Pink into the film, plus the wives’ side of the story
- Writing your own obituary, learning to say yes, and Tim finishing all 48 of New Hampshire’s 4,000-footers
- Our three closing questions, answered by four guests
Shoutout: Former guest Sam Pressler of Connective Tissue co-authored Nobody to Call, a report on men without college degrees. Almost half of the men interviewed reported having no close friends.
Join us: We’re hosting a screening of Old Man Walking Club on November 16 at the AMC Rosemont in Rosemont, IL, with a Q&A with the guys afterward. [event link]
Sponsor: Mental – getmental.com
Learn more about MenLiving at menliving.org.


