“The conversations that change your life rarely happen sitting down.”

(2-3 minute read)

Hey Reader,

A few months ago, I stopped thinking of walks as exercise and started thinking of them as friendship infrastructure. Looks like Sheryl Sandberg was on my wavelength this week with her IG post about Call Me Maybe walks.

Lately I've noticed something:

The best conversations in my life rarely happen sitting across from someone at a table.

A few weeks ago, a buddy and I started doing a weekly stroller walk. No destination. Just two dads trying to get out of the house before one of our kids melts down.

And somehow we've had better conversations on those walks than we've had over dinners, coffees, and happy hours combined.

I don't fully understand why.

Maybe it's easier to talk when you're not staring directly at somebody. Maybe it's because silence feels normal when you're walking. Or maybe friendship just works better when there's somewhere to go.

Whatever the reason, I've become convinced that some conversations are meant to happen side-by-side.

👥 THE FRIEND: Steve Jobs — The Man Who Walked Through Every Big Decision

Steve Jobs was famous for walking meetings.

Walter Isaacson wrote that when Jobs wanted to have a serious conversation, he'd often suggest a walk around Palo Alto.

Not a conference room. Not a boardroom. A walk.

The older I get, the more I think he understood something most of us forget: some conversations need movement.

🛠️ THE FIX: Schedule One Walk-and-Talk This Week

This week, text one friend:

"Want to go for a walk?"

That's the whole assignment.

Not drinks. Not dinner.

Just a walk.

Worst case, you get some exercise. Best case, you end up talking about something that actually matters.

Here’s why this works better than coffee or dinner:

No awkward silences. When you’re walking, silence is natural. When you’re sitting across from someone at a table, silence feels like a failure. On a walk, it’s just part of the rhythm.

No time pressure. There’s no bill coming. No waiter hovering. You walk as long as the conversation is good, and when it naturally winds down, you’re done.

Side-by-side magic. Psychologists call it “shoulder-to-shoulder” interaction and there’s real research showing it produces more honest, less defensive conversations than face-to-face.

If you want to level up, make it recurring. Same friend, same route, same day. Let it become the thing you don’t have to plan.

👕 THE RECO: Sweet Cream Baby

A dear friend recently started a company called Sweet Cream Baby.
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Our friendship origin story is very sweet (pun intended) - my wife, Jess, and Lauren, the founder, met at the hospital three years ago, our kids are born 12 minutes apart and we lives eight houses down! We love them so I would support no matter what, but the product is amazing.
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We've been putting our boys, Julian and Brenner, through a pretty rigorous testing process (by which I mean: spit-up, snacks, playgrounds, and washing machines).

The stuff is ridiculously soft, made from certified organic cotton, and manufactured in Los Angeles.

Most baby clothes seem designed either for Instagram or survival. These somehow manage to do both.

If you've got a little one in your life, or need a gift for someone who does, buy some clothing. Use promo code "Larchmont" for free shipping :)

This week, don’t sit across from someone. Walk beside them. The conversations that change your life rarely happen at a table.

Until next Monday,

Matt Ritter

The Friendship Guy

“Friendship is the original life hack.”

🎧 Listen to The Buddy System on Audible​

⏩ Forward this to a friend who could use a good walk. They can join the Friendship Challenge here.