Thoughtful Questions for Deeper Conversation

Conversation Questions Beyond Small-Talk

I used to know someone who never once asked me ‘how are you’? She always asked something different and unique and she seemed genuinely interested in the answer.  It sparked so many interesting discussions and it was never boring. I challenged myself to come up with thoughtful questions to ask her too, each time we met.

Sometimes it feels like the art of conversation is fading, in a world where texting and DM’s are the primary form of communication. Deep discussions are replaced with memes and acronyms.

Actual conversation, the kind that engages you is not only stimulating but it’s actually essential. It’s binds our social lives and friendships, it helps us make decisions, it encourages the production, iteration and sharing of knowledge and understanding.  When we want to unpack complex subjects and perspectives, conversation – with it’s the give and take, asking questions and giving answers, clarifying mistakes – paves the way.

In fact, carrying a dialog is more important than ever, especially in today’s online climate where video calls replace office hallway connection and body language cues are restricted to facial expressions through a screen.

If you’re craving deeper discussions, and looking for ways to get to know someone in a meaningful way, beyond superficial small-talk, here’s a list of open-ended questions to incite interesting conversation.

  1. What are you excited about right now?
  2. What made you smile recently?
  3. What is something people are always surprised to learn about you?
  4. What’s the best thing you’ve ever bought?
  5. What is one thing you can’t live without?
  6. What hobby do you wish you were good at?
  7. What’s the strangest dream you’ve had recently?
  8. What’s the best prank you’ve ever played on someone? (or someone’s played on you)?
  9. What’s your secret talent?
  10. What’s the worst thing you’ve ever eaten?
  11. Which song would you make you dance at this very moment?
  12. What’s something you’re really into right now?
  13. What are three words that describe you?
  14. What’s your favourite way to unplug and relax?
  15. Who had the biggest impact on the person you have become?
  16. What gives you purpose in life?
  17. What are you most proud of?
  18. What’s the best gift you’ve ever been given?

Do you have any good questions to add to the list?

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