The Game Of Delving Questions

One of my favorite things to do whenever I’m in a conversation with people that I know really well (or, actually, people I don’t know at all) is to ask them questions, then follow up those questions with more questions, and keep doing this until someone physically stops me.

I like hearing people’s answers to questions they’ve never been asked, and (just as importantly) I like watching people react to being asked questions they’ve never been asked before. It’s an entertainment slam-dunk for me, so it’s pretty much all I do now when I’m in groups and there’s any sort of risk that the conversation is going to turn to something I don’t know anything about or if I’m about to be chastised for eating a disproportionate amount of the group’s snacks.

The spirit of the Game Of Delving Questions is essentially to learn things about people that you wouldn’t normally know, and the game will always work as long as it is within human nature to talk about oneself (this aspect of human nature has never once failed me).

My go-to questions in the past have been “what are the three characteristics you look for in a mate” and “which three animal body parts would you attach to your body if you could attach three animal parts to your body,” but eventually I ran out of new people to ask about mates and animal parts and had to come up with more, like “what’s your greatest weakness” or “what’s the closest thing you’ve ever had to a nemesis?”

I was recently asked for some sample questions by a friend so he could try them out on his friends, and ended up comprising this list of the usual questions I ask and some that I haven’t tested yet but seem like they’d be fun.

Bring them out to dominate the conversation the next time a group starts talking about a sports team you don’t know anything about or is getting dangerously close to discovering that you’ve eaten all the chips!

The Game Of Delving Questions

  1. If you could have three animal features affixed to your body what would they be?
  2. What are the top three characteristics you look for in a mate?
  3. What would be your motivation if you were to become a super villain?
  4. If you could Groundhog Day one day forever which day would you Groundhog Day?
  5. What is your greatest weakness?
  6. If you could change one thing about yourself what would it be?
  7. What is the most important thing in the world to you?
  8. If you could have one question answered by an all-knowing being, what would you ask?
  9. What is one moment that occurred in your life before you turned 18 that you would say helps explain who you are now?
  10. What’s the most in love you’ve ever felt?
  11. What’s your life philosophy in one sentence?
  12. What’s the closest thing you’ve had to a nemesis?
  13. What would your life look like in 10 years if you could control it?
  14. What’s the number one thing you’d need in your life to be happy with how it turned out?
  15. What’s your favorite gift you’ve ever received and why?
  16. If you could switch lives with one of your relatives, who would it be and why?
  17. What color would your soul be if it were a color?
  18. If you had 10 years to learn everything about one thing, what would you choose?
  19. What’s one thing you think you’re better at than most people?
  20. What’s the strongest memory you have that’s connected to a song?
  21. What was the most you ever wanted to be someone else?
  22. If you could have really good handwriting or really great posture which would you choose?
  23. If you had one month to travel the world, where would you go?
  24. What’s the worst thing you’ve ever lost?
  25. What’s the scariest animal encounter you’ve ever had?
  26. If you could turn into one inanimate object forever but you’d still be sentient, what would it be?
  27. What era would you most like to have lived in?
  28. What’s a feature of yourself that you used to dislike but don’t now?
  29. If you had to spend a year without speaking, what would you do?
  30. If you had unlimited funds to build a luxury hotel or restaurant, what would it be like?
  31. If they made a movie about your life, what would you want the central tension of the movie to be, who would the antagonist be, and who would play you?
  32. If you knew you could make one piece of art that perfectly expressed what you wanted it to, what would you make?
  33. If you could steal three characteristics from three different people you know, what would you steal and from whom?
  34. If you had to spend 6 months trapped in a windowless room with one person, who would you choose?
  35. If you had to diagnose your own “wants” and “needs” like a movie character, what would you say they were?
  36. Who’s voice is your favorite?
  37. If you could live inside one book, which would you choose?
  38. If you could know how and when you were going to die, would you choose to know?
  39. If you could make everyone who met you know one thing about you instantly, what would it be?
  40. If you could make your hair, eyes, and skin each any color you wanted, what color(s) would you choose?
  41. If you could design an alter identity for yourself, what would it be?
  42. If you could make one accessory or item of clothing your trademark, so much so that it would be synonymous with your name from that point on, what would you choose?
  43. If you could have one moment from your life on film to rewatch whenever you wanted, what would you pick?
  44. If you could create an award for one trait or action what would it be and who would the first recipient be?
  45. If you could make one pet peeve punishable by law, what would it be?
  46. If you literally had to give yourself a one-word nickname that had nothing to do with your actual name, what word would you pick?
  47. If you could choose one thing to keep in perfect condition until you died (sight, hearing, memory, physical fitness, hair) what would you choose?
  48. If you could either spend a week with your great-great-grandparent or your great-great-grandchild which would you choose?
  49. If you knew that the next sentence you were going to say was going to be broadcast to the entire human population, what would you say?
  50. What’s one way you hope to be different in 30 years, and one way you hope you stay the same?
  51. If you could jump to one parallel universe where everything was the same except for one difference (the sky is pink, the word “biscuit” and “fuck” have switched meanings, all buildings are made of jello) what quirk would you choose?
  52. If you knew that your last 5 years of memories were going to be erased but you could leave one message for yourself, what would the message be?
  53. If you could solve one mystery, what would you solve?
  54. If you had to pick one word to sum up each of the last four years of your life, which words would you choose?
  55. What song would you choose to be your own theme music?
  56. Do you think your birth order affected who you are, and do you think you would be different if you had a different birth order?
  57. Which parent do you think you’re more like and how?
  58. Which of your friends do you think is the most similar to you, and which is the most different?
  59. If you could be famous for one thing, what would it be?
  60. Who’s the most underrated person you know?
  61. If you were being forced to end every statement you made with a catchphrase like an 80s sitcom, what would you choose?
  62. What would you say is the biggest thing you’ve overcome?
  63. What’s the proudest you’ve ever been of another person?
  64. If you could make one person on earth know one thing, what would it be?
  65. If you woke up and realized you were the only person on earth, what would the rest of your day look like?
  66. What’s the biggest risk you’ve ever taken?
  67. What’s your most interesting scar?
  68. If you knew that tomorrow you would be bitten by a vampire and would look the exact same (including hairstyle, accessories, facial hair, and clothing) for the rest of eternity, would you change anything tonight?
  69. If you found out that you were being portrayed as the villain in a movie about the life of someone you know, who would you guess the movie was about?

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