Top 20 Conversation Starters

  1. Tell me about where you’re from.
  2. Who is the person who influenced your life the most?
  3. What did a (gallon of milk, candy bar, gallon of gas, etc) cost when you were younger?
  4. Which new technology have you found most helpful in your life? Which do you find to be the most annoying?
  5. Is there anything you regret not having asked your parents?
  6. What was the happiest moment of your life?
  7. What are you most proud of?
  8. How did your experience in *fill in the blank* (e.g. the military, growing up on the farm, being part of a large family) mold you as a person?
  9. What are the most important lessons you’ve learned in life?
  10. What is your earliest memory?
  11. Did you receive an allowance as a child? How much? Did you save your money or spend it?
  12. Who were your friends when you were growing up?
  13. What was your favorite thing to do for fun (movies, beach, etc.)?
  14. What was school like for you as a child? What were your best and worst subjects?
  15. What school activities and sports did you participate in?
  16. Do you remember any fads from your youth? Popular hairstyles? Clothing?
  17. What world events had the most impact on you?
  18. Tell me about the time you first fell in love.
  19. Tell me about the job(s) you had.
  20. How would you like to be remembered?