There's a sentence most people have said at least once this month.
"We should hang out sometime."
Said with total sincerity. And then… nothing.
Just the slow, quiet fade of something that could have become a friendship.
I've been watching this happen on the walks since 2022.
And what I've figured out is: it's not a skills problem. People obviously know how to send a text. They know how to suggest a place and a time. They know the move.
What they can't shake is the belief underneath the move.
The belief that wanting someone's company is a burden. That showing your hand and concretely signaling "I liked talking to you and I want more of that” is somehow too much. That the ask will tip some invisible social scale from "cool, chill person" to "cringe weirdo who wants something."
So instead, they leave the potential on the table. Both people do. And two people who would've been genuinely good friends fade into the bushes like Homer Simpson.
The Trail Tale this week is one of our most-read pieces. But the angle I want to take today isn't the mechanics or scripts of asking someone to hang out.
It's what happens when you stop treating your desire for connection as a liability. 🧡
From our walking villages in 16+ cities around the world:
Walk #198 in Austin, Texas. Hands up if five miles flew by. 🧡
Sacramento Walk. Nobody planned the sculpture cameo, but somehow this turned into a full-on photoshoot. ✨
Miami morning. The kind of Saturday that makes you forget you almost stayed in bed.☀️
Walk #7 in Aveiro, Portugal. The water, the views, the vibes. Jenna never misses. 🧡
(Don’t see your city? We post the photos in each Meetup group after the walk. Otherwise this email would be longer than a CVS receipt.)
🏆 In Sacramento, Megan Farrell shared that a brand-new attendee showed up because his therapist recommended The Board Walks. That might be one of the clearest signals that these walks are way more than a meetup. 🧡
🏆 In Detroit, one walker who had only attended one walk before showed up late and, instead of turning around, took a Lime scooter for the first time in his life just to find the group. The week before he had nervously joined strangers. This week, he was flying down the riverfront trying not to miss the conversations.
🏆 In Miami, Brian Hain shared that this was the first walk where every single attendee was a returning walker. He described the energy as warmer, more relaxed, and home-like than ever before.
The most popular piece we've ever published just got a second read from me, and I noticed something I glossed over the first time.
The framework — the five approaches, the scripts, the "what to do when they say no" — all of it works. But the part that actually unlocks the framework is a single reframe near the end:
Rejection isn't a verdict. It's information.
"Not aligned right now" is not "you're too much." It's not "I don't like you." It's just: the timing, the capacity, the context… doesn't match.
Once you actually believe that, the ask stops being a referendum on your worth and starts being what it actually is: a door you're offering to open.
The full piece covers the five approaches in detail (including one I've watched work dozens of times that feels counterintuitive the first time you hear it), the exact scripts that remove the awkwardness, what to do in the first hangout so there actually is a second one, and a funny secret behind it all.
If making friends as an adult feels harder than it should, this one's for you.
This week on The Board Walks, people brought these topics:
“If your life had chapters, what would this current one be called?”
“What's something society rewards that you secretly think is unhealthy?”
“What kind of person brings out the best version of you?”
“What's something almost everyone wants but people rarely admit out loud?”
“When do you feel most like yourself?”
Screenshot these. Steal with pride. Bring one to your next dinner party to shift the conversation from “meh” to marvelous.
Quick hits:
🔓 Your social life just got 5x better. The private, curated layer of the walks is now open. It’s starting to feel like a home for humans who love sending passionate voice notes and hopping on spontaneous calls. Heaven on earth?
🌍 Our pod is alive. Tap into weekly reflections from Elle and Cam… and we’re about to drop conversations with friends of The Board! (Know someone who’d be great on the mic? Reply and let us know.) Ear candy →
✨ Something we're noticing across cities: people keep coming back. First-timers are becoming regulars, regulars are bringing friends, and in some cities attendees are even stepping up to help lead. It feels like the kind of momentum you can't force, only grow.
Real connection still exists.
Sometimes it looks like coffee after the walk. Sometimes it looks like finally meeting people who ask better questions. But it always starts with a dose of courage.
The best conversations usually happen when no one’s trying too hard.
Have a whimsical week,
Head Gardeners of The Board Walks
P.s. The best peeps usually come from a friend forwarding this email. 👀
