One of my favorite things in the world is engaging with strangers. It’s almost a competitive sport for me.

So much of our lives is spent passing by people who for all we know are interesting, passionate, good people we should have in our lives as friends. How are we going to reclaim that time and those opportunities if not by learning how to get beyond the superficial exchanges we normally have with strangers?

Here’s a running list of questions I use to strike up conversations that can lead to deeper connection (or at least a good memory for a day).

At the airport/on the plane

  • Where are you headed? (Note: don’t ask this if you are already on the plane with the person. It will make you look stupid)
    • Follow up from here to learn more:
      • Where are you from? From originally?
      • What’s taking you out to INSERT_DESTINATION_HERE?

At the store/coffee shop/restaurant

  • Anything interesting happen to you today? 
    • A good alternative to/response to “how are you doing?” from a store server. This brings in some specificity and jogs their mind for funny/challenging/cool things that have happened
  • What are you working on? 
    • Find a way to start a conversation about their craft, particularly if you won’t be distracting them. This leads into some good followup opportunities:
      • What do you find most interesting about your work?
      • What are the biggest challenges of your work? 

At an event/meetup

  • What brought you to the event? (or, “how did you find this meetup?”)
    • This is a tried and true one to get to know people’s work background, home base, and interests/values all in one answer. Branch out from here however you’d like.
      • BONUS POINTS: If there is a speaker giving a talk, always, always ask at least one good question. You’ll endear yourself to the speaker and audience if you do.

At a mixed social gathering (weddings, parties, etc)

  • How do you know my friend/the host/the bride/the groom?  
      • This is a great jumpoff point for sharing similarities. Other good questions to ask:
        • What is your favorite memory with INSERT_MUTUAL_FRIEND_NAME_HERE?
        • What is one thing you know about INSERT_MUTUAL_FRIEND_NAME_HERE that most people don’t?

At a family reunion

  • Heyyyyyy…. you….. Good to see you again. 
  • How are we related again?

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