Everyone who has dated since the advent of dating apps and dating websites in the early 2000s knows the dread of receiving a mindless starter like “Hey” or “What’s Up?” These are usually the same types of people who give one word answers or an “I don’t know” to the simplest of questions.

These types of openers and responses create a conversation dead space that is entirely palpable. There’s nowhere to go. You almost have to give random anecdotes and voluntary confessions to even keep the flow of chatter going. However, there is a much better way.

There are questions that not only open the door to great conversation, but increase the likelihood that the person you’re talking to will want to continue talking to you. Not all interesting questions need to be serious, though. Intersperse deep philosophical meanderings with random, quirky, stupid questions and enjoy the magic of a fulfilling dialogue.

  1. What is the single movie you’ve seen more times in your life than any other?
  2. What are your 3 most controversial opinions?
  3. What is one childhood memory that instantly makes you smile, laugh, or feel safe?
  4. If you could choose one object in your life that almost completely describes you as a person, what would it be?
  5. What is your most unusual and unpopular favorite food?
  6. What do you do for self-care and to relax?
  7. What is something that made you genuinely smile this week?
  8. What TV series have you watched beginning to end more than any other?
  9. What was your favorite, most treasured childhood toy?
  10. Were you named after anyone or anything?
  11. What is the most spontaneous night you’ve ever had?
  12. What is your zaniest drunk story?
  13. What is your zaniest sober story?
  14. What is an embarrassing memory you wish you could forget but you can’t?
  15. What is the best prank you’ve ever successfully pulled?
  16. When you were a kid, what was your dream career?
  17. How does your childhood dream career compare to your actual career?
  18. What is your favorite flavor of original Starburst?
  19. What was your favorite treat from the ice cream man?
  20. What is the most complex Lego set you’ve ever built?
  21. How many states have you been to in the U.S.A.?
  22. What is your favorite regional dish in the world?
  23. What is the most used app on your cell phone?
  24. Which member of the Simpsons family do you most relate to?
  25. What is your favorite quote or saying?
  26. Do you believe in life after death and what would your ideal afterlife look like?
  27. What causes and charities do you care most about?
  28. What were the last 3 songs you played on Spotify?
  29. What was your first and last concert going experience?
  30. Who are you more like: your mom or your dad?
  31. What is your favorite solo karaoke jam?
  32. What is the nicest hotel you’ve ever stayed at?
  33. What is the best Halloween costume you’ve ever donned?
  34. What is your favorite kitchen utensil and why?
  35. If you could only eat one culture’s food for the rest of your life, what would it be and what would be your favorite dishes?
  36. Can you name 3 animals that describe you as a person?
  37. What is your favorite household chore?
  38. If money were no object, what would you be doing at this very moment?
  39. What is your favorite article of clothing or accessory in your entire wardrobe?
  40. Do you believe in ghosts or have you personally witnessed any?
  41. What can you remember most vividly about your childhood home?
  42. What is your favorite natural scent?
  43. What is your favorite beach activity?
  44. Who is your oldest friend and how long have you known them?
  45. What was your favorite celebratory meal as a child?
  46. What is your single greatest accomplishment in life?
  47. What do you miss most about life and the world from 20 years ago?
  48. What are the most essential qualities in a true friendship?
  49. What was your worst disappointment in life and how did you deal with it?
  50. What website do you visit most frequently?

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