Things we would never ask each other in person.
  1. What is your social security number?
  2. Who did you vote for?
  3. How much money do you make?
  4. What is your net worth?
  5. What is the length/width/circumference of your penis?
  6. What illegal things have you done?
  7. What crimes are you wanted for?
  8. What is your favorite sexual position?
  9. Tell me about all the skeletons in your closet?
  10. Who do you want to be dead?
  11. What are your greatest fears?
  12. What are you most self-conscious about?
  13. What are your deepest secrets?
  14. What are you afraid of losing most?
  15. What do you dislike about me?
  16. How old are you?
  17. How much do you weigh?
  18. Are those your real boobs?
  19. What are your credit card numbers and expiration dates?
  20. What password do you always use?
  21. In what ways are you prejudiced?
  22. How did you lose your virginity?
  23. May I look through your purse/wallet?
  24. May I search your home/apartment?
  25. May I give you unsolicited advice?
  26. May I kick your pet?
  27. What kind of intrusive thoughts do you have?
  28. Are you a spy?
  29. What have you cheated on?
  30. What do you lie about?
  31. What STDs do you have?
  32. What are your health problems?
  33. How have you been intentionally mean, spiteful or vengeful?
  34. Which of your buttons may I press?
  35. Will you help me with this crime?
  36. What makes you feel ashamed?
  37. Are you liberal or conservative?
  38. Which family member do you hate most?
  39. Which traumas have you been through?
  40. Who have you had erotic dreams about?
    Suggested by @Alicia
  41. What does it take to make you have an orgasm?
  42. What medications are you on?
  43. What are you addicted to?
  44. What hideous sins have you committed lately?
  45. You don't by any chance happen to have six fingers on your right hand?