The Lost Art of Random Conversations
You never know what's on the other side of an honest question
This blog is a space for honest stories, thought-provoking questions, and practical tools for personal and collective growth. It’s inspired by my work as a coach, facilitator, and founder of The Lost Art of Random Conversations — and by my life as another human doing their best to make sense of it all and enjoy the journey.
It’s the fall of 2019, and I find myself on yet another flight from Africa back to New York City. As always, my dad is patiently waiting for me in his Volvo station wagon.
On the flight, I chat with a couple of fellow passengers and befriend a KLM flight attendant, an older Dutch woman named Joan. The buzz of random conversations helps me push through exhaustion, an eight-hour time difference, and the emotional whirlwind of cultural re-entry.
When I land, my dad and I share a warm embrace at the curb before heading toward our traditional first stop back on U.S. soil:
Chipotle.
Because what better American re-entry meal than a burrito overflowing with guacamole? (Always remember, guac will cost $2 extra 🥑.)
As we leave the building, we hold the door open for an older gentleman who looks slightly puzzled. He’s wearing a medical mask and holding latex gloves in his left hand.
(Keep in mind—this was before COVID-19, so seeing someone in public with a face mask was unusual.)
As we cross paths, I take a deep breath, look him in the eye, and say:
“Excuse me sir, how is your day doing?”
He pauses. Looks down. Removes his mask. Then, with excitement in his eyes, he looks up and says:
“Well, this is the best day of my life. Thanks for asking.”
Woah.
My jaw literally drops. I glance at my dad, who looks just as surprised.
We stay silent, intrigued, waiting for the follow-up.
He continues:
“Today I became a grandfather! I just drove from the hospital, where my daughter and son-in-law had their first baby. I’m here getting lunch for all of us.”
Instantly, everything feels different.
My dad and I beam with joy—smiling, eyes twinkling, soaking in the moment.
“Congratulations!” we both say, nearly in unison.
“Enjoy the food!” I add.
He grins. Nods. Places a hand on his heart in appreciation.
As my dad and I walk toward the car, I glance over at him, still amazed.
The rest of our drive home is filled with conversation—about life, family, children, and the power of a simple, honest question.
Sparking Random Conversations
Something magical happens when we genuinely try to see someone, invite them into conversation, and give them space to be who they are.
Meaningful conversations are what life is all about for me.
It’s why I’m here.
To open myself and those around me to connection, curiosity, and the journey of being human.
That interaction in 2019 sparked a book title idea (which I am in the long and patient process of writing ✍️🤫):
The Lost Art of Random Conversations.
Turning a Moment into a Movement
Two years ago, I started hosting free, community-building events in Carbondale, Colorado.
I invite people to come together and have meaningful conversations with strangers (and soon-to-be friends).
To date, I have hosted 23 Lost Art of Random Conversations events with 231 curious people showing up to join me.
And every single time, we leave feeling more connected than when we arrived.
An Invitation for You
All of this… because I asked a man how his day was going.
We never really know what’s on the other side of an honest question.
So what might happen if, in your next conversation, you prepared to be surprised?
Let’s Keep This Conversation Going
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💙 Support the Work: If this resonates and you’d like to contribute, you can send a donation via Venmo: @LostArtofRandomConvo — always appreciated, never expected.
🌐 Explore & Connect: Want to go deeper? Learn more about my work and coaching offerings at www.tomkarrel.com.
And if you’ve had a random conversation that left an impact on you, I’d love to hear about it in the comments.
I really enjoyed the 5/6/2025 LARC event in San Diego. Huge thanks to Tom, Taylor, and Shannon for creating such a thoughtful space—it was structured enough to guide us, yet open enough to feel completely natural. That balance made it easy to connect with others, keep conversations flowing, and be reminded of how effortless it can be to talk with someone new! Thank you!!
I think about these events all the time. So fun, so authentic, and so refreshing to chat with people with no ulterior motives behind the interaction. (ie politics, religion, sales, sex) Thanks Tom!