Meaningful conversation starters

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Tired of small talk? Here are 30 questions to spark a meaningful conversation:

  • How much is enough?
  • What are you grateful for?
  • What setbacks have you endured?
  • What accomplishments are you proudest of?
  • What’s a long-term goal you are working towards?
  • What dreams have you given up on?
  • What role have mentors played in your life?
  • How and when have you experienced transcendence?
  • What do you wish that you’d done differently?
  • What have you built?
  • What’s a story you’d like to tell?
  • In what ways would your college-age self be surprised by who you’ve become?
  • If money were taken care of, what would you be doing with your life?
  • What books have most influenced you?
  • What did you believe then that you disagree with now?
  • What help do you need?
  • What role has luck played?
  • What events have been most influential in your life?
  • What’s the contribution you seek to make in the world?
  • What are you currently most excited about?
  • When have you most felt a sense of belonging?
  • What has been your experience of loneliness?
  • What makes you come alive?
  • What for you would make an ideal day?
  • How would you define a rich life?
  • What brings you joy?
  • What do you worry about the most?
  • What habits have you recently changed?
  • In what ways do you fear that you fall short as a parent?
  • What is holding you back?