You're at a coffee shop.
That person you met three weeks ago just walked in.
Your heart does the thing. You make eye contact. They smile, wave, and walk over.
"Oh my gosh, hey! How are you?!"
Great conversation. Ten minutes, feels like two.
"I should get going, but…"
This is it. This is where you either say it… or don’t.
“Want to grab coffee sometime?"
Not today.
You say: "Yeah, totally! Good seeing you!"
They leave.
You sit there, frustrated with yourself, wondering why you didn't just say it.
Most friendships fizzle out right here, in the moment someone has to make an ask.
This exact problem comes up on almost every walk: “Why is making friends as an adult so hard?”
Short answer: because we’ve made “want to grab coffee?” feel as heavy as “want to get married?” and everyone's waiting for the other person to go first.
Let’s break the pattern. 🧡
Before we dive into how to do this… let's celebrate the people who went first.
Photos from our walk chapters around the world:
Shoutout to our beloved regular Daksha for hosting the London walk while Cristina was out of town. Doesn’t this background look photoshopped?!
One ritual on the Austin walk is when Julia Grant walks around and says “Tacos?” until there’s a small hoard headed across the street.
Lots of talk about love on Valentine’s Day + a moment of spontaneity where one member stopped at the Ponce City Market piano and just started playing. Atlanta Walk #6!
Our crew in San Francisco grabbed some dim sum after 5 miles. Someone said “Want to grab lunch?” and half the group said yes. Easy peasy.
(Don’t see your city? We post the photo in each Meetup group after the walk. Otherwise this email would be longer than a CVS receipt.)
🏆 Half the San Francisco walk for doing exactly what this newsletter is about… they asked each other to hang out! After the walk ended, they got brunch together and planned a road trip. Alice's note: "super cute."
🏆 Cristina for hosting London Walk #20 on Valentine's Day. Someone came back for their second walk… on their birthday! One regular said "Love is in the air today." Someone else shared: "These walks have become fundamental for me. A space to pause, to be seen, to see myself more clearly." 🥺
🏆 Pratz in Atlanta for getting a job in Irvine and saying "I want to bring The Walks there!" When one of the first things you think about in a new city is how to recreate your community… you’ve found something special. Props to Sohil. 🧡
Nobody tells you that asking someone to hang out is a skill you can practice.
They just assume everyone magically gets it… but given how many people say making friends is hard, we're obviously in need of a refresher course.
After 400+ walks, here are 3 tried-and-true moves that actually work:
Make it specific and low-pressure.
Most people say: "We should hang out sometime!"
Nothing happens.
Try this instead: "Want to grab coffee next Tuesday around 10 AM? There's a great spot near me called [place]"
Or: "I’m going to the walk this Saturday morning. Want to come with?”
Specific. Low-commitment. Easy to say yes or no.
Use the "I Enjoyed X" bridge.
Instead of a random ask, anchor it:
"Loved your thoughts on [topic]. Wanna grab lunch and debrief more?!”
This tells them why you're asking. Makes it less scary.
One thing though: this only works if you genuinely mean it. People can sense when you're reaching out from loneliness vs. genuine interest. The vibe will feel off and nobody will know why.
Batch the asks.
If asking one person feels like a big deal… don’t make it one.
Ask three.
When you batch the asks, you stop putting all your emotional eggs in one basket and you get to practice, which makes it easier each time.
If one person says yes, you've made a friend.
If all three say yes, you're building a social circle.
This week on The Board Walks, people brought these topics:
“What’s an experience you really want to have but haven’t yet, and what’s been standing in the way?”
“What does friendship look like in 2026?”
“What inputs create a strong sense of community?”
"What makes you feel deeply connected to someone?”
“How do you handle the fear of judgment when you’re building something, sharing your voice, or putting yourself out into the world?”
Screenshot these. Steal with pride. Bring one to your next coffee date or group hang to shift the conversation from “meh” to marvelous.
Quick hits:
🎉 Social takeover: I couldn't be more geeked to share that we're posting nearly every day now. If you tag us, we will amplify you! This Friday newsletter + posting 4-7 times per week was my main goal for January, and by golly we did it. (Cam and I recorded a pod to celebrate.) Join the party →
✨ Expansion news: So many people have thrown their hat in the ring to host since we launched this newsletter, including some international folks! Excited to launch in 3-4 new cities soon. Apply →
✍️ Looking for a story: I’d love to write a profile on someone who feels like the walks were a turning point. Maybe they helped you build confidence, make a big life decision, start something new. If this is calling to you, listen to the nudge. Submit →
Lastly…
🔐 The Board is almost here. A curated inner circle of people who don’t leave conversations wondering “what if.” Join the waitlist.
The person you want to ask to hang out is probably thinking the same thing.
Two people can walk away from the same conversation, both hoping it turns into a friendship, neither willing to go first.
Both thinking: "Should I text them? Would that be weird?"
Both waiting for the other person to make the move.
So when you make the ask, you're not just being brave for yourself.
You're being brave for both of you.
That’s how friendships start. 🧡
Want to practice?
The walks are designed to make connection feel easier. The structure removes the pressure. The culture makes asking someone to keep talking feel normal.
And after a few weeks, you'll notice something surprising: asking people to hang out doesn't feel scary anymore. It just feels like the natural next step.
We’re currently walking in: Austin, San Francisco, NYC, London, Boston, Denver, Atlanta, Columbus, Detroit, Boone.
Have a whimsical week,
Founder of The Board Walks
P.s. If there's someone you've been meaning to ask to hang out… text them before you close this email. Yes, really. The worst thing that happens? They say no. The best thing that happens? You make a friend. Those odds are worth it. 🧡
