100 Questions to Ask Your Family This Christmas 2021

Post by
Scott Bair
100 Questions to Ask Your Family This Christmas 2021

It's almost that time of year--enjoying a filling meal with family members you may not see all too often. While we all have varying levels of closeness with our relatives, one thing is common with most people--when loved ones pass away, you wish you spent more time getting to know them better.

Here's a tip for this year:

Don't give yourself an opportunity for regret.

This holiday season, challenge yourself to ask your grandma, grandpa, parents, cousins, kids, second aunt--twice removed, just one of the following questions.

Getting to know someone starts with a single question. The more you know, the better questions you can continue to ask. And best of all, not only will you grow closer together, but asking someone to tell you about their life is one of the most effective and simplest way to make them feel cared about.

Early Years

  1. Describe the home you grew up in.
  2. What were you like as a child?
  3. Do you have memories of what your parents said you were like as a baby?
  4. What was a typical day like in your family when you were little?
  5. How does your family tend to show their love for one another?
  6. What would you say makes your family unique from other families?
  7. What did you do when you were bored as a child?
  8. What was one of your favorite activities as a child?
  9. How did you feel about school, and what type of student were you?
  10. Did you have a best friend, and if so, how did that relationship play out over the course of your life?
  11. When you were little, what did you answer to the question: “What do you want to be when you grow up?”
  12. What was it like growing up in your hometown?
  13. What was your favorite childhood holiday tradition?
  14. What are your favorite family vacation memories?
  15. Did you have a favorite or unique pet?
  16. What was a funny moment with your siblings?
  17. What’s a reason you got in trouble?
  18. What music do you remember from your childhood?
  19. What was a positive memory of your parents?
  20. What was a memorable birthday?


  1. What school(s) did you attend?
  2. What do you most remember about school?
  3. What was your favorite part of school?
  4. What was the most challenging part of school?
  5. What’s something few people know about your school years?
  6. Who was your favorite teacher and why?
  7. What do you still remember from school?
  8. Did you play sports?
  9. What were your favorite activities?
  10. Who do you remember from school?
  11. What are some major differences about school then to now?
  12. What did you do after school?
  13. Did you receive any special rewards?
  14. What would you eat?
  15. Did you have any team activities?
  16. What did you wear to school?
  17. What were some funny trends with your friends?
  18. What were your grades like?
  19. What do you know now about that time that you wish you could share with your younger self.
  20. Do you have any regrets with school?


  1. What was your first job?
  2. How did you enjoy working?
  3. What were all of your jobs that you had?
  4. What was your favorite job and why?
  5. What was one of the strangest things you had to do for work?
  6. What did you feel unqualified to do for work? How did you respond to the challenge?
  7. When you were a kid, did you think you’d have a job like you had?
  8. What were your bosses like?
  9. Do you have any fond memories of your co-workers?
  10. Do you still stay in touch with any of your co-workers?
  11. What interesting things did you learn about the industries you worked in that you didn’t know before?
  12. What are some achievements you are most proud of?
  13. What do you wish you did different at work?
  14. Were you typically early or late?
  15. Did you stay late or did you leave on time or early?
  16. What did you do when you ended work?
  17. What alternative career do you wish you would’ve tried?
  18. Do you think people should pursue what makes the most money vs. what makes them most happy?
  19. What are some life skills you still use that you learned from work?
  20. What advice would you give young people who are looking for their first jobs?


  1. What do you remember about your parents?
  2. What other family members helped raise you?
  3. What was your relationship like with your extended family?
  4. Can you describe your friendships through the years?
  5. How did you meet your spouse?
  6. How did you know they were the one?
  7. What was the proposal like?
  8. What did you most admire about them?
  9. When and where did you get married?
  10. What did you do for the honeymoon?
  11. What were the early years of marriage like?
  12. Where did you live?
  13. What are the names of your children? How did you come up with those names?
  14. What are special memories you have of raising your kids?
  15. Did you go on any memorable trips?
  16. What are some funny things they did when they were young?
  17. How did your friends change over the years?
  18. How was your relationship with your in-laws?
  19. What are you most proud of with your family?
  20. What advice would you give to people who are hoping to get married soon?


  1. What are the hardest decisions you’ve had to make?
  2. Who has been influential in your life and why?
  3. If you could change anything about yourself, what would it be?
  4. Do you believe in God? Tell me why or why not.
  5. What do you believe happens after we die?
  6. Why do you think bad things happen in life?
  7. What is the meaning of life?
  8. Is there something you’ve always wanted to do?
  9. What would you like to be known for?
  10. If you knew you were going to die tomorrow, what would you want to do today?
  11. What would you want your family to know you think about them?
  12. What are you most proud of?
  13. If you could spend a day with anyone, who would they be?
  14. What advice would you give to someone who is going through a hard time?
  15. What has brought you most joy in life?
  16. Have you been a part of any church or organizations?
  17. What music should I listen to?
  18. Where should I make sure to visit?
  19. How can I find out what my purpose in life is?
  20. Do you know that I genuinely love you?

Our goal at TimeWell is to help deepen the relationships between generations. We do that by providing the easiest and most fun way to capture these life stories and memories in a special way--with your loved ones' voices!

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