All Questions

  1. What unpleasant experience are you most proud of yourself for making it through?
  2. What about life 100 years ago appeals most to you?
  3. What would someone have to do to make you fall in love with them?
  4. What things do you think men are generally worse at than women?
  5. Who is the first to apologize after an argument?
  6. What seemingly insignificant thing contributes greatly to your happiness?
  7. If you had to commit a murder and get away with it, how would you do it?
  8. If you could magically make one food or habit healthy, what would you choose?
  9. What game show / reality TV show would you do best on?
  10. If you had to pick three people to do a cross-country road trip with today who would you choose?
  11. Which swear word do you use the most?
  12. How much would someone have to pay you to be a long distance trucker for one year?
  13. Which Winter (or Summer) Olympics event do you think you’d have the best chance at competing in?
  14. If you could send a one-sentence-message-in-a-bottle to yourself from ten years ago what would it be?
  15. If you could break up one couple in your life, who would you choose?
  16. What is your favorite article of clothing that you own?
  17. What is your most controversial dating opinion?
  18. If you were a cartoon character, what would you one outfit be?
  19. If you could travel to the past and change one event, what would you choose to do?
  20. In heaven, everyone gets unlimited ______.
  21. What purchase that you made in the last year had the most outsized return?
  22. What conspiracy theory is easiest for you to defend?
  23. What moment from your upbringing would you pick for the opening cameo in a biopic about you?
  24. What one word would you use to describe me to someone else?
  25. What is your favorite conspiracy theory? Where do you fall on the spectrum of thinking there’s some truth in it to just thinking it’s interesting?
  26. If you had to award yourself a superlative in high school what would it be?
  27. If you could be a part of any TV family which would you choose?
  28. What would you like to see in terms of what your country requires of billionaries?
  29. What is an aspect of fashion that men think looks good but women generally do not like?
  30. What do you have absolute faith in?