A better conversation tonight

20 questions for when conversation runs dry.

Take turns. Answer before explaining. Skip anything that does not feel right tonight.

  1. Which of our dates would you happily do again?
  2. What were you nervous about before meeting my friends?
  3. Which food from where you grew up would you want me to try?
  4. Where would you take me if we had next weekend free?
  5. What have you been wanting to learn lately?
  6. When did we last laugh so much we couldn’t finish the conversation?
  7. Who do you miss spending time with?
  8. Would you enjoy taking a long train trip together?
  9. What did you think our life would be like when we first got together?
  10. What helps you switch off after a difficult day?
  11. What would you like us to make more time for?
  12. Which place from your past would you like to show me?
  13. What’s changed about what you want from work?
  14. Which of your interests would you enjoy sharing with me?
  15. What are you looking forward to doing together?
  16. Who brings out a different side of me?
  17. What did your family treat as completely normal that you later found out wasn’t?
  18. At a wedding where we know almost nobody, what kind of tablemate would you hope to find beside you?
  19. What can you tell about my mood just from how I answer the phone?
  20. What’s a story your friends told me about you that you still think needs correcting?