60 'If...' Questions to Ask Your Friends & Family

60 'If...' Questions to Ask Your Friends & Family

Posted on
July 21, 2021
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When I was growing up my family had the 'If...(Questions for the Game of Life)' book series by Evelyn McFarlane. Most nights during family dinner someone would pick up the book and choose an 'if' question to ask. Sometimes there was just one question, other times each family member or dinner guest would take turns posing a question to the group.

I think this little ritual cultivated in me a strong inclination towards deep conversations. I feel that curiosity is an under-appreciated quality. I love being asked questions and I love listening to other people answer them even more. I think the answers to these 'if' questions give us a glimpse of how people are wired, what their motivations are, the way they think, how they feel, etc. Asking these kinds of questions allows us to know someone in more significant and meaningful ways than daily small talk about the weather and what is happening in our lives. Additionally, by default, you end up hearing some really great life stories you may have not otherwise heard from loved ones.

So, whether you are looking for Hinge date ice-breakers, ways to kill time on a road trip, or you want to know your mom better, here are 60 'If...' questions to get you started.

  1. If you could go back and live one year of your life over again, without changing a thing, which would you choose?
  2. If you had to be locked in a retail store overnight, which would you pick?
  3. If you could be exceptionally talented at anything in the world, what would you choose?
  4. If you had to pick the best kiss of your life, which one would win and why?
  5. If you could plan out the last meal of your life, what would be on the menu? 
  6. If you had to live in one outfit for an entire year, what ensemble would you wear?
  7. If you could eliminate one thing from your daily schedule what would it be and why?
  8. If you could go anywhere in the world right now, where would you go? 
  9. If you could pick 5 people to have dinner with (dead or alive), who would you choose to be at your table?
  10. If you could domesticate any animal and have it as a pet, what animal would you choose?
  11. If you were a breakfast cereal, which one would you be and why?
  12. If you could visit any period of history, when would it be and where would you go? 
  13. If you could speak any language fluently, which would you choose? 
  14. If you could meet any famous person, who would you choose and why?
  15. If you could meet any historical figure, who would you choose and why?
  16. If you could plan out the ideal Saturday what would you spend it doing? 
  17. If you knew you only had 1 week to live, what would you do with the time left?
  18. If you won the lottery, what is the first thing you would do with the money? 
  19. If you could live perfectly well without sleeping, how would you spend all your nights?
  20. If you were given the chance to go to the moon, would you go? Why or why not?
  21. If you could only choose one memory to have of us together, which one would you choose?
  22. If you could choose the very last thing you see before death, what would it be?
  23. If you had to trade houses with someone you know, who would it be?
  24. If you had to name one thing that scares you the most about growing old, what would it be?
  25. If you could have any view in the world visible from your bedroom window, what would you choose?
  26. If you could choose one thing to alter about human anatomy, what exciting alteration would you make? 
  27. If you owned a bar, what would it be known for? 
  28. If you could open up any hospitality business, what would it be? 
  29. If you had to give a new parent one piece of advice, what would you tell them? 
  30. If you had to lose one of your five senses, which one would you pick? 
  31. If you could live as anyone else in the world for one day, who would you choose?
  32. If you could make a career change now, what would you do? 
  33. If you could visit any person from your past that you’ve lost touch with, who would it be? 
  34. If you could talk to someone in your life that is dead, who would it be and what would you ask them about? 
  35. If you could change one thing about your partner, what would it be?
  36. If you could change one thing about yourself, what would it be?
  37. If you had to pick the thing you think contributes the most to human beauty, what would you say it is?
  38. If you had to kill off one of your exes, which one would you pick and why?
  39. If you had to name the single most erotic part of the human body, what would you say it is? 
  40. If you were invisible for a day, what would you do? 
  41. If you had to pick three books that have impacted your life, which ones would you choose?
  42. If you had to choose between fame and fortune, which would you pick and why?
  43. If a movie was made about your life, who would play you?
  44. If you could pick a music artist to write a song about your life, who would you choose?
  45. If you had to pick a song that reminds you of your mother, what song would you say?
  46. If you had to pick a song that reminds you of your father, what song would you say?
  47. If a genie granted you three wishes, what would you wish for? 
  48. If you had to give a prize for the most attractive politician, who would win it? 
  49. If you could have overheard a specific conversation between people, which would it be? 
  50. If you had to nominate one person you know for sainthood, who would you choose and why?
  51. If you had to rename each of your children, what would you call them? 
  52. If you had to pick a new name for yourself, what would you choose? 
  53. If you had to come up with a new national holiday, what would it be? 
  54. If you could develop one skill at a rapid pace, what skill would you choose? 
  55. If you had to choose the happiest moment of your life, what would it be? 
  56. If you could choose one superpower to have, which one would you pick?
  57. If you woke up suddenly because your house was on fire, what things would you save?
  58. If you could have any car you wanted, which car would you choose?
  59. If you could be an Olympic athlete, which sport would you want to compete in?
  60. If a fortune teller could accurately tell you the day you were going to die, would you want to know? Why or why not? 

On a related note: If you want to capture life story answers for yourself or a loved one, check out what Storii has to offer.