Keepsake resources

Skills

Practical how-tos for interviewing and recording at home.

Upgrade the craft side of memory keeping with clear tutorials for interviews, audio capture, and editing basics.

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Guides

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Questions

40 funny questions to ask friends, family or a group

Funny questions that get people telling their best stories: school pranks, trips gone wrong, family inside jokes and pets with personality.

  • What's the most dramatic thing you did as a kid?
  • What's your most chaotic travel story?
  • What's the best inside joke in your family, and where did it start?
Questions

41 romantic questions for couples about affection and shared memories

Choose romantic questions about affection, shared memories and time together, with room for both partners to decide what they want to discuss.

  • When did you first feel loved by me?
  • What moment made you feel proud of us?
  • What does romance look like to you today?
Questions

60 philosophical questions about life, ethics and the mind

60 philosophical questions on identity, free will, meaning, ethics, justice, God and knowledge, with the classic puzzle behind each group and ten lighter ones.

  • If every part of you were slowly replaced, the way an old ship's planks are, at what point would you stop being you?
  • Would you plug into a machine that gave you a perfectly happy life, if you would never know it wasn't real?
  • If you had a ring that made you invisible, would you behave any differently?
Questions

60 uncomfortable questions for optional private reflection

Questions about choices, boundaries and unresolved thoughts. Skip any premise that does not fit; discomfort is not evidence that a question is useful.

  • What are you avoiding that you know you should face?
  • What is a truth about yourself that took years to accept?
  • What do you pretend not to care about but actually do?
Questions

Controversial questions that challenge assumptions

60 controversial questions about ethics, politics, technology and relationships, with ground rules for disagreeing without a fight.

  • Is revenge ever justified?
  • Should wealthy people be required to give away most of their money?
  • Is social media making society better or worse?
Questions

Conversation starters that make talking easy

Choose conversation topics and opening questions for everyday chats, new friends and groups, with examples and simple follow-ups.

  • What went well for you this week?
  • What have you been reading, watching, or listening to lately?
  • What was the best thing you ate this week?
Questions

Deep questions that open honest conversations

40 optional deep questions about who you are, turning points, love and trust, and what comes next, with advice on choosing topics and respecting a pass.

  • What do you wish people understood about you without asking?
  • Which moment in your life changed how you see yourself?
  • What does feeling safe with someone actually look like to you?
Questions

Embarrassing questions that keep it light

30 embarrassing questions about slips at school and work, social mix-ups and family stories, chosen so people laugh with the teller, not at them.

  • What were you saying when someone pointed out you were on mute?
  • Have you ever waved back at someone who was waving at the person behind you?
  • Which outfit looked better in your head than in the photograph?

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Recommended reading

More ways to keep going

Discover guides, questions, and articles to help your family tell better stories.