Questions to Ask Your Parents (or Loved ones) Right Now to Leave a Legacy

Card image cap

It can be hard to initiate meaningful and deeply personal conversations with loved ones. A great starting point is mentioning the incredible benefits of preserving their memories and life stories. Often, we are so busy with our own lives that we don’t spend time to learn about our loved one’s own journeys. As important to us are they are to us, we may know little of their background and what shaped them. We may be curious but don’t know how to begin to help them create and enduring digital legacy. Everyone has a unique story to share which is why we have created this comprehensive list of questions to help you get started. Go, set aside time with a loved one, grab a pen and paper or take out your phone and start recording their answers for posterity.

Family History:

1) Where did the family originate from? 2) When did the family emigrate? 3) Do you have a family tree? How far back can you go? 4) What can you tell me about your grandparents? 5) What stories did your grandparents share with you about their childhoods? 6) Are there any famous or infamous ancestors? What are their stories? 7) Who is the oldest family member that you can recall and what do you know about them? 8) Do you know of any special family heirlooms that have been passed down? 9) Who has them now and what are the stories behind them? 10) What do you know about your surname? 11) Is there is a tradition of naming children in your family? 12) Are there any recipes that have been passed down through generations? 13) What are your family’s unique traditions? 14) What should I know about our family’s medical history?


1) What is your earliest childhood memory? What made it so memorable? 2) What was it like growing up in your childhood location? 3) What was it like during the time when you were a child? 4) What type of home did you live in? A house or apartment? 5) Which of your birthdays is your favorite? 6) What is one of your best childhood memories? 7) What was a difficult moment in your childhood? 8) How would you describe yourself as a child? 9) Did you play any sports? 10) Did you learn to play any instruments? 11) What were your hobbies as a child? 12) Did you collect anything? 13) Did you have any nicknames? How did you get them? 14) What can you tell me about your siblings? 15) Who was in the household you grew up in? 16) Did you share a room with anyone? 17) Did you have any pets growing up? 18) What were your household members like? 19) Where did your household members work? 20) What was a difficult situation that the household faced? 21) What was a typical family dinner? 22) What religion was practiced by your family? 23) Did you have household chores? What were they? 24) Did you get an allowance? How much and what did you spend it on? 25) Where did you go to school? 26) Who were your best childhood friends? 27) What did you and your friends do after school or on the weekends? 28) What subjects were you best at? Worst at? 29) What were the schools you attended like? 30) What did you want to be when you grew up? 31) What were your hopes and dreams for the future? 32) Who were your heroes? Why? 33) Who inspired you most as a child? 34) What fads do you remember? 35) How do you think your household members would describe you? 36) Was your home strict or lenient? 37) What were the worst fights you had with your parents? 38) What was the most trouble you ever got in? What happened?


1) When did your education end? Why? 2) When did you get your first job? What was it? 3) What was the most unique job you ever had? 4) What was your worst job? 5) What was the best job? 6) How did you decide on your career? 7) If you could, would you choose a different career? 8) What was your first car? 9) What are some memories in the car? 10) When was your first date? What was it like? 11) What was the best date you ever been on like? 12) Who was your first serious relationship with? 13) What was the most difficult break up you went through? 14) When did you meet Mom/Dad? Where? 15) When did you know that you wanted to get married? 16) What do you remember most about your wedding? 17) Where did you choose to live? Why? 18) Did you dream of living somewhere else? 19) Who were your best adult friends? 20) How did you decide you wanted to have children? 21) What made you feel like you were ready to have children? 22) What was it like becoming a first-time parent? 23) Did you do anything your parents did that you swore you never would? 24) What happened the day I was born? 25) How did you choose my name? 26) What other names were almost chosen? 27) If I were the opposite sex what would you have named me? 28) What was I as an infant? 29) What did I do as a child that frustrated you most? 30) As a child, what did I do that you loved most? 31) What were some of your proudest moments as a parent? 32) Is there anything you did as a parent that you hope I do not?


1) What was your favorite book during your childhood? 2) What childhood toy was your favorite? How did you get it? 3) Did you have a favorite subject in school? 4) Which game was your favorite to play? 5) What was your favorite family vacation? 6) Did you have a favorite dish in your childhood? Who made it? Do you know how to make it? 7) What was a favorite childhood candy or treat? 8) What music was your favorite growing up? Do you still like it? 9) What was your favorite movie as a child? 10) Did you have a favorite TV show growing up? Have you watched it recently? 11) What was your favorite holiday as a child? What made it your favorite? 12) What was your favorite family activity? 13) What was the favorite place you lived? 14) What are your favorite books? 15) Do you have any favorite quotes? 16) What are your most favorite movies? 17) What TV shows are you favorites? 18) What are your favorite songs? 19) Do you have a favorite vacation location? 20) What are some of your favorite parenting memories? 21) What are your favorite foods? 22) What is favorite family tradition?

Reflection and Wisdom:

1) What decision do you wish you made differently? 2) What was one of your all-time best decisions? 3) What was one of the most difficult decisions you ever made? 4) Were there any moments that changed your life significantly? When did you realize the importance? 5) What was a difficult situation that you overcame? 6) What were the major challenges in your life? 7) How do you handle stress? Anxiety? Depression? 8) What do you wish you spent more time doing? How about less time doing? 9) What do you regret most? 10) What advice would you give yourself at age 20? 30? 40? 11) What have you realized in the last decade that you wish you recognized earlier? 12) What is the best advice that you have received? Who gave it? 13) What aspect of your life are you most grateful for? 14) What are some of your most unique experiences? 15) What did you find most unexpected about being a parent? 16) What were the hardest aspects of parenting? 17) What was most difficult about raising children? 18) How is being a grandparent different than becoming a parent? 19) Do you think childhood is easier now compared to your childhood? 20) What amazes or surprises you most about life today? 21) What do you miss most about the society of your childhood? 22) What were some of the most important life lessons you learned from your parents? 23) What principles do you live by? 24) What are most passionate about? 25) What do you think are your best traits? 26) How have you grown and personally developed over your life? 27) Have your views on religion and politics changed? 28) What book do you think that everyone should read? 29) What is the most important financial advice you have? 30) How much money does someone need to be happy? 31) Do you think that it is possible for money to buy happiness? 32) What is something that you are absolutely sure is true? 33) What is a secret you have not told anyone? 34) What are you proud of yourself for that you have not told anyone? 35) What advice would you like to see passed down to future generations? 36) What is the meaning of life?


1) How do you hope to be remembered? 2) What do you want to be known for? 3) What are three things about you that you want us to always remember? 4) What do you hope for your children? 5) What do you want or wish for your grandchildren? 6) What do you hope that I pass along to future generations? 7) What do you want your funeral will be like? 8) Do you want us to do anything special with any of your possessions? 9) Do you want us to continue any family traditions? 10) Are there any recipes that you hope we continue to make in remembrance of you? 11) How do you want us to continue honor you? 12) What are your favorite photos of yourself? 13) Where are your important documents stored? 14) Is there anything about you or our family that you want us to know? 15) What have you always wanted to tell me but lacked the courage to? 16) What have you wanted to ask me that you have not?