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50 Dig A Little Deeper Questions

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This is an introverts dream right here. If more people asked questions like this, meeting people would be less awkward for a lot of people.

Here are 50 dig a little deeper questions to ask for any occasion:

 

  1. Do you prefer writing with black or blue pen?
  2. Would you prefer to live in the country or the city?
  3. If you could learn a new skill, what would it be?
  4. Do you drink your tea or coffee with sugar?
  5. What was you favorite book as a child?
  6. Do you prefer baths or showers?
  7. If you could be a mythical creature, which would you choose?
  8. Do you prefer reading paper or electronic books?
  9. What is your favorite item of clothing?
  10. Do you like you name? Would you ever change it?
  11. Who is a mentor to you?
  12. Would you ever want to be famous? If so, what for?
  13. Are you a restless sleeper?
  14. Do you consider yourself a romantic?
  15. Which element best represents you?
  16. Who do you want to be closer to?
  17. Do you miss someone at the moment?
  18. Tell us (me) about an early childhood memory.
  19. What is the strangest thing you have eaten?
  20. What can you see outside your bedroom window?
  21. What are you most thankful for?
  22. Do you like spicy food?
  23. Have you ever met someone famous?
  24. Do you keep a diary or journal?
  25. Do you prefer to use pen or pencil?
  26. What is your star sign?
  27. Do you like your cereal crunchy or soggy?
  28. What would you like your legacy to be?
  29. Do you like reading? What is the last thing you read?
  30. How do you show someone you love them?
  31. Do you like ice in your drinks?
  32. What are you afraid of?
  33. What is your favorite scent?
  34. Do you address older people by their first or last name?
  35. If money was not a factor, how would you live your life?
  36. Do prefer swimming in pools or in the ocean?
  37. What would you do if you found $50 on the ground?
  38. Have you ever seen a shooting star? Did you make a wish?
  39. What is one thing you would want to teach your children?
  40. If you had to have a tattoo, what would it be and where would you get it?
  41. What can you hear right now?
  42. Where do you feel the safest?
  43. What is one thing you want to overcome/conquer?
  44. If you could travel back to any era, which would you choose?
  45. What is your most used emoji?
  46. What is your favorite season? Why?
  47. How would you spend your ideal day?
  48. Describe yourself using one word.
  49. What do you regret the most?
  50. Invent your own word. What does it mean?