Dating Cards Questions

Tal Benisty
3 min readMay 23, 2023

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By School of Life

  1. What made you happy when you were a child?
  2. How good are you at turning people down who you don’t especially like?
  3. What do you most enjoy about relationships?
  4. What 3 books would you take as a good sign if a potential partner had read and liked them?
  5. How might you entertain a 5 year old child that a friend left you with for an hour or two?
  6. What attitudes to food do you find appealing in a partner?
  7. What type of traveling companion would you like an ideal partner to be?
  8. Describe the way you live: are you clean or messy?
  9. If you wrote a book, what would it be about?
  10. What moves you to tears?
  11. Describe your favourite childhood toy
  12. When are you most miserable and when are you calmest in an average working day?
  13. Sketch the course of three previous relationships you’ve had.
  14. What would the interior decoration be like in your ideal house?
  15. What is your most irritating work colleague like?
  16. Describe your political leanings without using the words ‘left’ or ‘right’.
  17. Describe your first kiss.
  18. What are you selfish about?
  19. How do you like to be comforted when you’re sad?
  20. Who would you like to go back and apologise to — and for what?
  21. What is your view of therapy? Have you ever had it, and what did it do for you?
  22. What would you have been like if I’d met you 10 years ago? What have you learnt since then?
  23. What are your parents’ strong points? What are their weaknesses?
  24. What do you think are your best qualities?
  25. What is your type?
  26. How would you describe your financial status?
  27. Complete the sentence “If someone seems to like me a lot, I tend to think that perhaps…”
  28. What type of friend are you?
  29. If you could magically invent a drug that could put you in any sort of mood, what would that mood be?
  30. What kind of fault are you particularly tolerant of in others? And which are you less tolerant of?
  31. How do you behave when angry: explode, get bitter, store the explosion for later, say nothing…?
  32. How strict would you be as a parent?
  33. How would you advise a friend who had just learnt their partner was having an affair?
  34. What changes in some aspect of your lifestyle are you currently contemplating or daydreaming about?
  35. With playfulness and generosity, point out to one another, how do you feel the other might be difficult to live alongside (remembering that we’re all difficult in some key ways)
  36. What do people seldom properly understand about you?
  37. What are you excessively anxious about?
  38. Describe your ideal relationship dynamic and the roles you and your partner would take?
  39. Describe a friend or acquaintance you are envious of and why.
  40. Pay each other two compliments, one, focusing on the mind, the other on appearance.
  41. In what ways are you slightly mad (bearing in mind that everyone is slightly mad)?
  42. What kind of people do you like as friends but not as lovers? And vice versa?
  43. What do you think people often don’t get right in their attitudes to sex?
  44. What is your view on having a family?
  45. Without thinking too much, complete the sentence: “The problem with most of the people I’ve been on a date with is…”
  46. What would you like to do better than your parents?
  47. What do you think might be most endearing about you?
  48. Complete the sentence: “When someone frustrates me, I tend to…”
  49. What are the main points you would like to be covered in a speech at your funeral?
  50. What would you love a kind person to come away thinking about you after you’d met them for the first time?
  51. What character trait would you like to be forgiven for?
  52. What character traits do you long to find in someone else and would help you feel you have discovered a soulmate?

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Tal Benisty

Head of Design at Circles. Formerly at Nexar, Cruise, Collective Health, Cooper, Designit, and IDEO.