• JKB

Talk to Strangers. They Might Have Candy.


My wife and daughters will tell you that I talk to strangers too much. They might be right. It's not a gross exaggeration to say that, if I run into a coffee shop to grab a quick cup, I will emerge minutes later knowing the life and times of my barista, where his great grandma is buried and his middle name. Katie and I once vacationed in Cabo with 2 close friends. I was given strict instructions not to make any new acquaintances because we wanted it to be a special time with our small social circle. But on day one, I went missing -- only to be found at the swim-up bar talking with an engineer from Johnson Controls who was thinking about retiring and driving a bus. True story. His name was Rob. I do this somewhat naturally (and too much) given my personality. But I also do it intentionally to avoid the trap of keeping my life small and predictable. Keeping life small is tempting (even for this extrovert). Schedules get full and our brains are predisposed to cut corners and manage energy. Conversations with unknown people can be nuanced, risky, boring, taxing, stressful...we'd rather have strangers on a podcast speak to us then stumble into some rando speaking with us (Sorry, Rob). But by saving myself from exertion, I could also make my life less interesting, less surprising, and less compassionate. So, I get to wondering: Why wouldn't I talk to strangers more? What happens when I do? How can I get better at it? Georgie Nightingall is the founder of Trigger Conversations, a London-based "human connection organization" that coaches people all over the world to have meaningful interactions. In her work, she's learned that a lot of people find it most difficult to initiate the conversation more than sustain it. The thought of approaching someone, making them feel unguarded, and conveying curiosity without an agenda is intimidating. Older people are better at it and the youngest among us don't seem to have acquired the skill or courage to do it (our online life has significantly altered our sociology). Yes, it's hard to start these interactions, but most of them prove enjoyable, enlightening, and often memorable. And there's more.

I don't think I'm overstating it to say that this practice can give you the tools to play your part in healing a fractured society.

This work is real communion. I don't think I'm overstating it to say that this practice can give you the tools to play your part in healing a fractured society. This isn't the spice of life, this could change how you live.


I believe the book I've recommended the most in the last 3 years is Malcolm Gladwell's Talking With Strangers. If you haven't read it, make it the next book you do. Gladwell explores all the ways we assume and misunderstand people. He stops short of lecturing us on how to end bigotry, exclusion, and categorization, but he makes a compelling case for how we all (yes, YOU and me) can live with a harmful delusion about other people's stories, motives, and potential. As we all re-acclimate to sharing air with each other, let's not allow our minds and hearts to remain in our uninformed, lop-sided comfort zones. So, some tips (many gleaned from this great article):

  1. Small talk has a purpose. Yes, it can be shallow, but it might be the way our species casts out widely in search of somewhere to dive deep. Small talk can be the way we intuitively ask each other, "What should we talk about?"

  2. Reframe. Everyone knows that starting a conversation with someone you don't know is weird. It helps us to know you know that. For instance, walk up to a total stranger and say "I know it's bizarre to just strike up a conversation with a complete stranger." Then, follow it up with an observation and a question. "But I really like your shoes. I'm tempted to order them right now. Where'd you find them?" This step is so helpful, I'll break it out into its own tip...

  3. Observe and ask. I'm tempted to barrage people with questions. If they don't know me, this can seem like an interview. Instead, I find it helpful to notice something in that environment, make a statement, then ask them. This can be as simple as "I see your name is 'Athena'. I think that's incredible. What was it like growing up with that name?!" or, it can be more external: "It's starting to warm up! Does that make you want to get away or is this why you live here?"

  4. Everyone is interesting. Don't go on autopilot with the small talk. Break the script. Lead the way by answering in unorthodox ways. You might respond to "How are you?" with, "Well, I'm a 7.4 out of 10 today." That invites curiosity. Instead of asking "How was your day?" you could ask "Has your day lived up to your wildest hopes and dreams?" This tends to unlock a little spark of each person's humanity.

  5. Ask open-ended questions. This is Conversation 101, but it bears repeating. When you do ask a question, try to steer clear of ones that ask for a "yes" or "no" response. "Do you think it's because of your last relationship?" is not as strong as "What do you think led to this?"

  6. Give up control. Follow their breadcrumbs without judgement or agenda. Respond and relate to it. Share how your life might reflect or contrast with what their saying, but then pull the thread a little more. You can't be surprised if all conversations stay on your map.

You don't have to apply all of these to have a powerful interaction with a stranger. There are plenty of other tips you could draw from. But I know applying just one of these ideas could open up someone's world to you, challenge your assumptions, start a new friendship, or make you more compassionate.

You're in the loop!