Questions to ask your best friend

Old friends know each other's present and almost none of each other's beginning. These questions fill in the years before you met, and put down on paper the ones you spent together.

Questions to ask your friend about their own life

Ask a few at a time. These work over dinner as well as in writing.

  1. 1.What was going on in your life when we met?
  2. 2.When did we go from knowing each other to being friends?
  3. 3.What is the best day we ever had?
  4. 4.What did you and your brothers or sisters get up to?
  5. 5.What is the stupidest thing we ever did?
  6. 6.What did we talk about for hours?
  7. 7.What has your own life looked like since we met?
  8. 8.What was your first day of school like?
  9. 9.What are you proudest of?
  10. 10.What are you still figuring out?
  11. 11.Who has shaped you most?
  12. 12.Who did you look up to as a young adult?
  13. 13.What do you want the next years to look like?
  14. 14.What do you value most in a friendship?
  15. 15.What were you like when we first met?
  16. 16.What has been hardest about loving someone for a long time?
  17. 17.What was going on in your life then?
  18. 18.What is your favourite thing we ever did together?
  19. 19.What was the daftest night we had?
  20. 20.What were you good at that nobody noticed?
  21. 21.How did your family shape you?
  22. 22.What has been the hardest chapter of your life?
  23. 23.What are you proudest of that you never talk about?
  24. 24.What was the hardest year of your life?
  25. 25.What work has meant most to you?
  26. 26.What has changed in you in the years we have known each other?
  27. 27.What do you want the next ten years to look like?
  28. 28.What song takes you straight back somewhere?
  29. 29.What kind of friend do you think you are?
  30. 30.What do you need from your friends that you never ask for?
  31. 31.What were we both like when we met?
  32. 32.What is the most beautiful thing you have seen?
  33. 33.What was going on in your life that year?
  34. 34.What did we do together that we would never do now?
  35. 35.What is the story about us you tell other people?
  36. 36.What tradition would you like us to keep going?
  37. 37.Which night out do we both remember completely differently?
  38. 38.When did we drift, and what brought us back?
  39. 39.Who else from those years do you still think about?
  40. 40.What was your first taste of freedom?
  41. 41.What did our group of friends get right about life?
  42. 42.What did we get very wrong?
  43. 43.How has your life gone compared with what you expected?
  44. 44.What did you do with your first proper pay?
  45. 45.What has been the hardest part of your adult life?

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Questions to answer about your friend

What you have watched them do is part of their story too. Write down the version only you can tell.

  1. 46.How do the two of you meet?
  2. 47.What was going on in both your lives back then?
  3. 48.What do you do together most?
  4. 49.What do they do for people quietly?
  5. 50.What is the best night or day you ever had with them?
  6. 51.What is the most ridiculous thing you do together?
  7. 52.What could you tell them that you could not tell anyone else?
  8. 53.What have they been frighten of?
  9. 54.How were they when you were struggling?
  10. 55.What do they see in you?
  11. 56.What did they never judge you for?
  12. 57.What can they fix?
  13. 58.What advice of theirs stuck?
  14. 59.What are they like in a crowd?
  15. 60.What are they like one-to-one, late at night?
  16. 61.What do they say that stung?
  17. 62.What do they always order, wear, play or say?
  18. 63.What do they dream about doing?
  19. 64.What did their family mean to them, from what you saw?
  20. 65.What does the family owe them?

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Common questions

What should I ask my best friend?
Ask what they were like before you met, the moment they knew the friendship would last, the hardest year they got through, and what they think you have never understood about them.
Are these only for old friends?
No. They work just as well for a newer friendship — most of them are about a life, not about the years you have shared.
How do we collect the answers?
Go Family Story emails each of you three questions a week by private link — you answer with a free account, no subscription needed — and keeps every answer in one shared archive.

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