announcing the CHIT CHAT CHALLENGE

A.K.A.: it's okay to talk to strangers

Your AI-free reminder that you can find or create joy while also feeling fear, rage, despair, and other prickly crap.

“That comes to £19.39,” the bookshop clerk announced. I looked up at him, barely pausing before I said, “Well that was an awkward year,” because I have little-to-no filter, and a thing about wanting to interact with the people who sell me things. Because I have a thing about maybe I can make them laugh, or at the very least have a non-capitalist-transactional moment in their work day, even if work is in an indie occult bookstore. I didn’t think much before the observation slipped my lips, one that makes more sense in London, a city shaped by the events of 1939. He stared back at me, his eyes widening. Before I could start to social-anxiety spiral for saying stupid things he sighed out. “Whoah, that’s so crazy. I was just about to say the same thing. Like my mouth was shaping those exact same words!”

I cannot remember what I bought that day. I remember that man, that conversation, and how buzzy I felt afterwards.

Lately it seems like almost all of the internet wants to tell you about the value of everyone you don’t know. They want you to understand that connecting with other members of your Earth Crew will ease loneliness and bring joy and meaning to your life. Writers and editors in internetland are spewing forth about let’s connect! and small talk versus big talk. Even the talkers at TED have a lot to say about chatting with strangers.

So far, I’m not seeing anybody put their money where their mouth is (teehee) to throw down a challenge. So here goes: the Great Spring 2026 Chit Chat Challenge. Rob Walker of The Art of Noticing and I triple-dog-dare you talk to a stranger every day for ten days. Easy peasy. Bonus points for sharing your stories.

Starting Thursday April 23 for ten days, you will initiate a conversation with a person unknown to you. About anything. Or nothing. The particulars are totally up to you: fellow dog walkers, plane seatmate, the mail lady; the weather, the footie, the meaning of life.

The other 8,288,501,893 people that you share this planet with aren’t non-player characters serving to populate cafes and grocery stores or walk four-wide across the sidewalk. Their lives are as rich and storied as yours. They, too, occasionally awaken at 3am drenched in the cold sweat of existential angst, have never read the terms and conditions before clicking accept, and think farts are funny.

Our language fails us in differentiating relationships with people other than those very close to us. Partner can refer to the soul you’ve invited into your heart, with whom you choose to share your life, breath, and bed; or is someone you associate with in a business venture or other goal-oriented endeavor. Partner might be the ultimate intimate relationship or one that is perfunctory and temporary. Amazing that this lack of distinction has never proven problematic.

Words like spouse, sibling, parent are relational, telling us not necessarily about feeling and intimacy, but our technical ties to one another. In my world, “sister” can refer to one of three remarkably different humans. It tells you that we share genetic material from the same man and woman, but in no way indicates which one I may have multiple conversations with on three different social media platforms, four text message threads, and daily facetime/phone calls; and yet I know someone who hasn’t communicated with their sister in over two decades.

As far as the terms for our chosen people, those nestled closest to us are our besties, the core of who we call our friends. We have so very many levels of closeness and friendship but very few words to differentiate them, until the bonds loosen and friend blends into that nebulous term acquaintance. These are either people we kinda-sorta know or maybe have seen once or twice walking their dog. There is no slow fade, the next category of relationship to other humans is strangers.

To recap: there’s you, your ride-or-die peeps, your close peeps, some other peeps, and the rest of the 8,288,502,015 human residents of planet earth fall into the lump category of strangers.

The word stranger means someone you do not know, someone who does not belong. It comes from the Latin extraneus “foreign, external, from without,” someone out of place. It refers to the woman ahead of you in the bubble tea line at an art fair, the man walking towards you in an unlit parking lot at night, and a family you’ve never heard of tending a subsistence farm in a small village near Vladivostok. Again, not problematic semantics at all.

We can invite neighbor into the conversation, but that can also be confusing. That’s not always a feel-good vibe. I have a neighbor I’ve planted a flower garden with and another one we call “The Lady who Listens to Loud Cheesy Jazz and Doesn’t Pick Up Her Dog’s Poop.” No offense to cheesy jazz.

Big Stranger Danger will have you believe that everyone outside the ring of “acquaintance” is to be avoided at all costs. Our earbuds * headphones * audiobooks * podcasts * carefully-curated-playlists keep us burrowed safely inside of our own little bubble. Who needs actual human interaction when you have your true crime podcast besties?

My friends, we are all fellow crew here on planet earth. We’re all trying to get by. We’re all trying to find meaning. Let’s say you’re perfectly average in that you know 611 people, or roughly 0.00001% of the population. No disrespect to your 611 peeps, but are you really willing to say that one one-hundred-thousandth of a percent of humanity is sufficient to your needs? That none of the rest of the 99.99999% are worth connecting with?

Human connection is a free drug, a wellness miracle-cure safe from gifting in Coachella swag bags. Its value belongs to the participants (although the world may benefit from any cool collateral that comes from conversations).

If you’re not a regular stranger chit-chatter, this may feel funky at first. Fine. Feel it. But don’t let that stop you. You most likely won’t be rejected. You’re more likely to like your chosen stranger who will find you interesting and vice versa. Chances are greater that you’ll have a genuine moment of connection with another person, that you will both walk away feeling seen and keenly connected.

The aim of Chit Chat Challenge is to get us connecting. It’s not enough to read some stats and anecdotes about the power of talking to strangers. You actually have to do it. We’ve created this handy-dandy container to get you started.

Nothing is being asked of you today but to consider. I would never abuse your tender heart in such a way as to propose the idea of starting up a conversation with someone unknown to you, then declare you immediately set forth and chat. As you go through your day, think about the opportunities to connect, how your routines could set you interacting with others. Who will you choose? What might you say? How do you hope to feel?

Look to your inbox on Thursday, April 23 for more about how to get started, what to do, some tips, and inspiration.

I’m always open to ideas, suggestions, shenanigans, tomfoolery, collaborations, cheese, snacks, and field trips.

You can find my art here and here. I offer custom workshops and design. I am the proud guardian/custodian of a 17 3/4 year old cheeseburger named Patty.

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