Everyone who comes on a walk brings one topic to the trail.
A question, a knot they've been chewing on, a thing they can't stop thinking about.
We think of it like a conversational potluck.
You bring a dish, someone brings a dish, and by mile three you're all eating off each other's plates.
Some weeks the dishes are light. Some weeks someone shows up with a question so good the whole group goes quiet chewing on it. Our hosts collect them all.
This was a really good-dish week, so we felt inspired to round up 50 deep questions you can use for better conversations everywhere.
Let’s dive in… 🧡
From our walking villages in 16+ cities around the world:
Sacramento's quintessential summer day. Blueberry lattes before the walk, a fresh produce truck on a corner they'd never seen it on before, and regulars finally confident enough to lead the way themselves. ☀️
Aveiro today. 20 people, lots of regulars and first-timers, a walk that started at 10am and didn't wrap until snacks and drinks well after dark. One very tired pup. One very full heart. 🐶
Atlanta today. Another Saturday, another group of strangers who left as something closer to friends. 🧡
Nashville's very first walk. Five people, some of the rawest and most real conversations in a long time, and one request to bring a dog next time. 🎸
(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 Detroit, two walkers got so deep in conversation they had to physically stop walking to finish it, while the rest of the group waited a few minutes for them to catch up. As host Izzy put it, sometimes the conversation is good enough to keep you from walking.
🏆 In Austin, a newer walker admitted the walk has quietly become the one place they can go deep: "Not everyone in my life likes to talk about these things, and it can feel pretty lonely sometimes." Their existing friend group can't hold those conversations. This one can. 🧡
🏆 In Sacramento, a returning walker set a goal to do more than 15 pushups in a minute. At the end of the walk, the whole group circled up and cheered her through her reps. Summer goal, officially in progress.
We pulled together 50 questions that reliably turn "so, what do you do" into "no one's ever asked me that."
Some are gentle enough for a first hello (waffles or pancakes, defend your answer). Some will stop a person mid-stride. All of them have been brought by thousands of strangers, every Saturday, since we started hosting in 2022.
There's only one rule that comes with them: ask, then get out of the way. Lean in, say "tell me more," and let the silence do the heavy lifting.
Steal all 50. Bring one to dinner this week and watch the table change.
This week on The Board Walks, people brought these topics:
"What two things would you want to be buried with?"
"Can you have a society without money?"
"Where do you get your good ideas?"
"What advice do you wish you'd received as a kid?"
"How do you show yourself grace?"
Screenshot these. Steal with pride. Bring one to your next dinner party to shift the conversation from “meh” to marvelous.
Quick hits:
✨ At last night’s Salon, we had great conversations about Work & Ambition. Topics: implementing AI in your business, emotional blocks around being more visible online, and the quiet ache that comes with “making it” in life but still feeling like something’s missing. Join us next time →
🔥 Our socials are heating up. We’ve been sharing more bite-sized moments and reflections lately, and people are loving it. Join us on socials →
🤝 We’re looking for partners who want to help make real connection a weekly habit in 100+ cities. If you know anyone on our priority sponsor list and can introduce us, we’d be very grateful. Read the list →
You don't need to be interesting.
You need one good question and somewhere to walk it out.
We'll handle mile one. The trail handles the rest. And somewhere in the middle, a stranger asks you the thing you didn't know you were waiting to answer.
Have a whimsical week,
Founders of The Board Walks
P.s. Reply with the best question anyone's ever asked you. We're always collecting for the trail. 🧡
