Best 100 Questions to Ask Your Family This Holiday Season 2022

Post by
Scott Bair
Best 100 Questions to Ask Your Family This Holiday Season 2022

"I didn't know that!" "Wow! I can't believe you did that." "Learning that gives me so much perspective for your upbringing..." Asking your loved ones questions about their past, preferences, funny moments and dreams for the future is the best way to grow closer together.

This Christmas and holiday season, pull a few questions to ask around the dinner table. And even better-be sure to record the answers! (P.S. you can record the answers for free with TimeWell. Sign up here.)

50 Questions to know them better:

  1. What is your full name and where did it come from?
  2. What is your earliest memory?
  3. What was your childhood like?
  4. What was your favorite subject in school?
  5. What did you want to be when you grew up?
  6. What are your hobbies and interests?
  7. What is your favorite family tradition?
  8. What was your most embarrassing moment?
  9. What was your proudest accomplishment?
  10. What was your favorite vacation or trip?
  11. What is your favorite family recipe?
  12. What is your favorite family story?
  13. What is your favorite thing about being a part of this family?
  14. What is your favorite memory with me (the person asking the questions)?
  15. What is your favorite memory with our family?
  16. What is something you've always wanted to learn or try?
  17. What is a lesson you've learned that you want to pass on to the next generation?
  18. What is your favorite book, movie, or TV show?
  19. What is your favorite song or musician?
  20. What is your favorite quote or motto?
  21. What is your favorite piece of advice that you've received?
  22. What is something you wish you knew earlier in life?
  23. What is something you regret not doing?
  24. What is something you wish you could change about your past?
  25. What is something you're proud of overcoming?
  26. What is something you're looking forward to in the future?
  27. What is something you're afraid of?
  28. What is something you're passionate about?
  29. What is something you're currently working on or trying to improve?
  30. What is something you wish you could change about your current situation?
  31. What is something you hope to achieve in the next 5 years?10 years?
  32. What is your biggest dream or goal?
  33. What is your favorite thing about your job?
  34. What is something you wish you could change about your job?
  35. What is your favorite thing about your community or town?
  36. What is something you wish you could change about your community or town?
  37. What is your favorite thing about your home?
  38. What is something you wish you could change about your home?
  39. What is your favorite thing about your family?
  40. What is something you wish you could change about your family?
  41. What is your favorite thing about yourself?
  42. What is something you wish you could change about yourself?
  43. What is your favorite thing about your friends?
  44. What is something you wish you could change about your friends?
  45. What is your favorite thing about your relationship with your partner?
  46. What is something you wish you could change about your relationship with your partner?
  47. What is your favorite thing about your relationship with your children?
  48. What is something you wish you could change about your relationship with your children?
  49. What is your favorite thing about your relationship with your parents?
  50. What is something you wish you could change about your relationship with your parents?

25 Questions just for fun:

  1. If you could have any superpower, what would it be and why?
  2. If you could be any character from a book, movie, or TV show, who would you be and why?
  3. If you could only eat one type of food for the rest of your life, what would it be?
  4. If you could swap lives with any animal for a day, which animal would you choose?
  5. If you could trade places with any historical figure for a day, who would you choose?
  6. If you could only listen to one album for the rest of your life, which one would you choose?
  7. If you could only watch one TV show or movie for the rest of your life, which one would you choose?
  8. If you could travel to any planet, which one would you choose and why?
  9. If you could only wear one outfit for the rest of your life, what would it be?
  10. If you could only have one type of ice cream for the rest of your life, what flavor would you choose?
  11. If you could only have one type of pizza topping for the rest of your life, what would it be?
  12. If you could only have one type of sandwich for the rest of your life, what would it be?
  13. If you could only have one type of soup for the rest of your life, what would it be?
  14. If you could only have one type of fruit for the rest of your life, what would it be?
  15. If you could only have one type of vegetable for the rest of your life, what would it be?
  16. If you could only have one type of cereal for the rest of your life, what would it be?
  17. If you could only have one type of candy for the rest of your life, what would it be?
  18. If you could only have one type of drink for the rest of your life, what would it be?
  19. If you could only have one type of dessert for the rest of your life, what would it be?
  20. If you could only play one sport for the rest of your life, what would it be?
  21. If you could only listen to one type of music for the rest of your life, what genre would it be?
  22. If you could only watch one type of movie genre for the rest of your life, what would it be?
  23. If you could only play one type of video game for the rest of your life, what genre would it be?
  24. If you could only travel to one type of destination for the rest of your life, where would it be?
  25. If you could only have one type of pet for the rest of your life, what would it be?

25 Questions about their perspective of you

  1. What is your favorite thing about me?
  2. What is something you admire about me?
  3. What is something you wish I would do more of?
  4. What is something you wish I would do less of?
  5. How have I impacted your life?
  6. What is something you think I am particularly good at?
  7. What is something you think I could improve upon?
  8. What is something you've always appreciated about me?
  9. What is something you've always admired about my personality?
  10. What is something you've always admired about my appearance?
  11. What is something you've always admired about my skills or abilities?
  12. What is something you've always appreciated about my values or beliefs?
  13. What is something you've always appreciated about my sense of humor?
  14. What is something you've always admired about my intelligence or knowledge?
  15. What is something you've always admired about my creativity?
  16. What is something you've always admired about my leadership skills?
  17. What is something you've always admired about my communication skills?
  18. What is something you've always admired about my problem-solving skills?
  19. What is something you've always appreciated about my sense of responsibility?
  20. What is something you've always admired about my work ethic?
  21. What is something you've always appreciated about my loyalty?
  22. What is something you've always admired about my compassion or kindness?
  23. What is something you've always admired about my sense of adventure or willingness to try new things?
  24. What is something you've always appreciated about my ability to adapt to new situations?
  25. What is something you've always admired about my resilience or determination?

From the team here at TimeWell, we wish you the best during this holiday season!

Want to try it for yourself?
Start for free today!

Keep your memories alive for your family.
No card needed to sign up.