How to Conquer Small Talk

More often than I’d like, I get into conversations that sound like this:

“Where do you live?
Ah, yeah, I’ve been there. I liked it.
What’s the weather like this time of year?
Sounds nice.
What do you do there?
Oh, that seems interesting.
Well, hope to see you again soon!”

It’s not that this kind of conversation is boring, it’s just… boring.

I do want the basic facts on another person’s life. If they’re the reigning Head Physician of Estonia, I know to stay away from my usual array of bad doctor jokes and inquire about Europe instead. And if the Head Physician tells me she has a stomach ache, I won’t try to give her medical advice. (Actually, Estonia doesn’t have a Head Physician - I googled it - but you get the point.)

Those context questions are good to start with. But if I only ask the “normal” questions - “Where are you from?” and “What do you do?” - I risk getting stuck in the Bog of Single-Sentence Answers. And if I ask one question after another, the conversation spreads out in all directions like an octopus on a rack, and neither of us say anything we haven’t said a hundred times before.

What can I do?

In this case, I decided to source the best questions I could find from Authentic Relating and Facebook data mines, and share them with you!

I now go into conversations with a few of these written on my arm, or phone. If the conversation gets boring, I pretend to check a text, pick a question, and voila - instant interest.

Try one and tell me how it goes!

All the best,

  • What are you passionate about

  •  What are you obsessed with right now?

  •  What would a perfect day look like for you?

  •  What was the best part of your day so far?

  •  What have you learned this week that you found interesting? 

  •  What is the biggest thing you’ve overcome?

  •  What's the best thing going on in your life right now?

  •  What’s something missing for you in your life?

  •  What do you want more than anything?

  •  What have been the 3 most valuable lessons of your life, and what experiences instigated those lessons for you?

  •  What is most real for you these days?

  •  Where & when do you get your best ideas?

  •  What's something you really value and appreciate about yourself (that you wish others appreciated more often)?

  •  What's something about yourself that you don't normally tell people you've just met?

  •  How would your friends describe you?

  • Why do you think we have met?

  •  What are three things that you and I have in common?

  •  What are you struggling with lately?

  •  How do you sense I can support you most?

  •  What’s something you really want me to know about you? Why?

  •  What do you really want to know about me?

  •  What’s something you’re afraid to share with me? Why?

  •  What do you think I think about you?

  •  The elephant in the room is…

  • Is there something you’ve dreamed of doing for a long time?
  • If you could wake up tomorrow having gained one new quality or ability, what would it be?
  • What do you value most in a friendship?
  • What is your favorite memory?
  • What is your earliest memory?
  • What activity in your life makes you the most nervous?
  • If you could do over one year of your life, which year would it be?
  • What makes you feel alive?
  • Do you usually follow your head or follow your heart?
  • Are you living your life purpose?
  • Do you have a morning ritual?
  • Before making a telephone call, do you ever rehearse what you are going to say?  Why?
  • If social media didn’t exist, how would your life be different?
  • What’s your relationship to anger?
  • What’s your relationship to spirituality?
  • What’s your favorite part of your body? Why?
  • What are you really fucking good at?
  • What is the number one reason that you think people want to hang out with you?
  • What is one way you like to be appreciated?
  • What helps you feel most fully in your swagger?
  • What is your most urgent priority for the rest of the year?
  • Who is the last person that deeply disappointed you? (What happened?)
  • Would you consider yourself an introvert, extrovert, or ambivert?
  • Would you like to write a book? (About what?)
  • Tell me about a friend from your past that you wish was still in your life.
  • What do you think happens after we die?
  • If your exes all got together and decided to psychoanalyze you, what do you think they’d say?

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