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Through years of listening, we've learned the secret to a meaningful conversation: it begins with asking the right questions.


Dr Dimity Dornan AO

We offer these suggestions to spark engaging conversations, inviting you to select the ones that resonate or to inspire your own. This compilation is unranked, allowing you the freedom to explore by category or browse at your leisure.

Questions for Everyone

  • Who are the significant people in your life?

  • What moments have brought you the most joy? The most sorrow?

  • Who has greatly influenced your life, and what have you learned from them?

  • Has someone's kindness ever significantly impacted you?

  • What vital lessons have life taught you?

  • What's the first thing you remember?

  • What's one of your favorite memories involving me?

  • Are there any humorous stories about you that your family often recounts?

  • Do you have any amusing stories, memories, or characters from your life you'd like to share?

  • What achievements are you most proud of?

  • Have there been times when you've felt particularly isolated?

  • Which memories would you choose to keep forever?

  • In what ways has your life turned out differently from what you expected?

  • How do you hope to be remembered?

  • Are there things you wish you had done differently?

  • What do you see for your future?

  • What are your aspirations for my future?

  • What hopes do you have for my children?

  • If this were our final conversation, what would you want to say?

  • To future generations listening, what wisdom would you share? What should they know?

  • Is there something you've never told me but wish to now?

  • Have you ever had questions about me you've never asked?

  • What advice would you give to your younger self?

  • What were your initial thoughts of me, and have they changed?

Friends or Colleagues

  • If you had the chance to interview anyone from your past or present, who isn't a celebrity, who would you choose and why?

  • What's your earliest memory involving me?

  • Has there ever been a moment when you felt negative towards me?

  • What is it that makes our friendship so strong?

  • How would you describe me? And how would you describe yourself in contrast?

  • Where do you see us in 10 years? What about 20 years from now?

  • Do you believe there's a chance we might drift apart someday?


  • When did you learn you were going to become a parent, and what was your initial reaction?

  • Was parenthood always a part of your plans?

  • Can you recall your emotions upon seeing your child for the first time?

  • In what ways has parenthood transformed you?

  • Through parenting, what insights have you gained about yourself?

  • What aspirations do you hold for your children's futures?

  • Can you remember the moment your youngest child moved out permanently?

  • Are there any cherished anecdotes about your children you'd like to share?

  • Where did you spend your formative years?

  • What characterized your childhood environment?

  • Who were your parents, and what were they like?

  • How would you characterize your relationship with your parents?

  • Did you ever find yourself in trouble? Can you recall the most significant misstep you made?

  • Do you have any siblings? What were they like during your upbringing?

  • Can you paint a picture of your appearance during your youth?

  • How would you describe yourself as a child? Did you generally experience happiness?

  • Could you share one of your fondest childhood memories? How about one of the most challenging?

  • Did you have a nickname? What's the story behind it?

  • Who were your closest companions? Can you offer insights into their personalities?

  • Could you envision and describe your ideal day during your younger years?

  • What were your aspirations for adulthood when you were a child?

  • Do you have any cherished anecdotes from your childhood?

  • What career aspirations did you harbor during your youth?

  • Did you find school enjoyable?

  • Can you describe the type of student you were?

  • How did you typically spend your leisure time?

  • How do you think your peers would remember you from those days?

  • Do you maintain friendships from that period of your life?

  • What are some standout memories from your academic years? Any particularly challenging moments?

  • Did any teachers leave a lasting impact on you? If so, what made them stand out?

  • Do you have any cherished anecdotes from your school days?


  • Where did your early years unfold?

  • Describe your experience of childhood.

  • Who stood out as your favorite family members growing up?

  • Can you recall any tales your grandparents shared with you?

  • How did your paths cross with grandma/grandpa?

  • What are your memories of my mom/dad/parent during their youth?

  • Were there any lullabies or songs you sang to me or your children? Would you mind singing one now?

  • Did your grandparents always follow the rules?

  • What’s the most mischievous thing your grandparents ever did?

  • How would you characterize your parents?

  • What were your impressions of your grandparents?

  • When people think of you, how do you hope to be remembered?

  • Do you feel pride when you think of me?

Romantic Relationships

  • Have you found your soulmate?

  • When did you first experience the sensation of love?

  • Could you share the story of your first kiss?

  • Describe your earliest significant romantic relationship.

  • Do you subscribe to the idea of love at first sight?

  • Do memories of past romantic partners ever cross your mind?

  • What insights have your romantic relationships bestowed upon you?

  • Can you recall individuals you felt slipped away from your life romantically?

  • Reflect on the most challenging breakup you've faced.

  • What stands out as the most memorable date you've ever had? Alternatively, could you recount your first date experience?

Marriage and Partnerships

  • Can you share the story of how you met your spouse or partner?

  • What made you realize that they were "the one" for you?

  • Could you describe how you proposed to them?

  • Reflect on the highlights and challenges of your relationship.

  • Have thoughts of divorce ever crossed your mind?

  • Have you ever experienced a divorce? If so, could you recount your experience?

  • What guidance would you offer to young couples navigating their relationships?

  • Do you have any cherished anecdotes from your marriage or about your spouse/partner?

Professional Legacy

  • Could you give me an overview of your profession and the tasks you undertake?

  • How did you initially venture into your current field?

  • Share your feelings about your current job—are you satisfied with it?

  • When you were younger, what career path did you envision for yourself?

  • What were your aspirations for your future career?

  • Reflect on the significant lessons you've learned from your professional experiences.

  • If you had the freedom to pursue any occupation, what would it be, and what motivates this choice?

  • Are retirement plans in your future? If so, when do you anticipate retiring, and how do you view this transition?

  • Can you recall any memorable anecdotes from your career journey?

  • What accomplishments or achievements in your career are you most proud of?

  • How have you made a positive impact or contribution in your industry or field?

  • Can you share a significant challenge you faced in your career and how you overcame it?

  • Reflecting on your career journey, what valuable lessons have you learned along the way?

  • Have you mentored or influenced others in your profession? How do you believe you've impacted their professional growth?

  • How do you hope to be remembered by your colleagues, peers, and those you've worked with?

  • What core values or principles have guided your professional decisions and actions?

  • Are there any specific projects or initiatives that you feel define your professional legacy?

  • How do you envision the future of your industry, and what role do you see yourself playing in its evolution?

  • What advice would you give to aspiring professionals entering your field?


  • When did you choose to pursue a career in teaching, and what drove that decision?

  • Can you recount your initial experience stepping into the classroom as a teacher?

  • How does the reality of teaching differ from your initial expectations?

  • Share a moment from your teaching journey that filled you with optimism.

  • What have been some of the most challenging or amusing occurrences in your teaching career?

  • How do you hope your students will remember you?

  • Did any teachers significantly influence your approach to teaching? If so, what valuable lessons did you glean from them?

  • Reflecting on your teaching career, what advice would you offer to your novice self in your first year of teaching?


  • What are your religious or spiritual beliefs? Can you share a bit about your faith tradition or spiritual path?

  • How did you first encounter or come to embrace your faith? Was it influenced by your family, personal experiences, or other factors?

  • Has your understanding of your faith or spiritual beliefs evolved over time? If so, in what ways?

  • Have you ever experienced what you would consider to be miracles or profound spiritual moments? If comfortable, could you share one of those experiences?

  • Do you believe in a higher power, God, or a divine presence? How do you personally experience this in your life?

  • What are your beliefs about the afterlife? How do you envision it, if at all?

  • If you were to encounter God or a higher power, what would you want to express or ask?

  • Have there been moments or challenges in your life that tested your faith? How did you navigate through them?

  • How does your faith or spirituality influence your daily life and decision-making?

  • Are there any rituals, practices, or teachings from your faith tradition that hold particular significance for you?

Serious Illness

  • Can you share with me your experience with your illness? How has it impacted your life?

  • Do thoughts about dying cross your mind? If so, what emotions or thoughts do they evoke? Are you scared?

  • When you think about your death, how do you imagine it? Do you have any particular wishes or preferences?

  • What are your beliefs about an afterlife or what comes after death?

  • Looking back, do you have any regrets or things you wish you had done differently?

  • Has facing illness changed the way you view your life and the world around you? In what ways?

  • Are there any last wishes or specific arrangements you'd like to make known?

  • If you could offer advice to me or others in our family based on your experiences, what would it be?

  • What are the most significant lessons you've learned from your life experiences?

  • Has your illness changed you as a person? If so, what have you learned about yourself?

  • How would you like to be remembered by your loved ones and the world? What legacy would you like to leave behind?

Remembering Someone Important

  • What was your connection to _____?

  • Could you share some details about _____?

  • What is your earliest memory involving _____?

  • What is your fondest memory of _____?

  • Can you recall a particularly vivid memory involving _____?

  • How significant was _____ to you?

  • If you're comfortable, could you discuss _____'s passing? How did it happen?

  • What has been the most challenging aspect of losing _____?

  • If you could speak to _____ today, what would you want to ask or tell them?

  • What do you miss most about your interactions with _____?

  • How would _____ want to be remembered?

  • Can you reflect on the major hurdles _____ faced in life?

  • Were there any areas where you and _____ didn't see eye to eye or had conflicts?

  • What about _____ always brings a smile to your face?

  • How would you describe your relationship with _____?

  • Can you paint a picture of what _____ looked like?

  • Did _____ have any favorite jokes or humorous anecdotes they liked to share?

  • Is there a particular story or memory about _____ you'd like to share?

  • What were _____'s aspirations and dreams for the future?

  • Is there something about _____ that you feel only you know?

  • How have you changed since _____'s passing?

  • What enduring image or memory of _____ stays with you?

  • Do you have any customs or rituals to honor the memory of _____?

  • What coping strategies have been most effective for you during your grieving process?

  • What are the most challenging moments you've faced in dealing with your loss?

© 2024 Talking Stories, Inc.

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