Getting to know someone new can either be exciting or scary (thanks to modern day’s increasingly difficult dating norms). When you’re getting to know someone that you don’t have a history or a mutual connection with, conversations don’t always come as easily, so things can get very awkward very fast. One of the easiest ways to get someone talking is to ask them questions about themselves. You’ll find that you can discover so much about a person from the questions you ask. One helpful tip is to try to keep your questions open so it gives the other person some room to respond. Doing this takes the edge off and makes your conversation feel less like an interview. From lighthearted to thoughtful, here are 99 open-ended questions to ask when you want to get to know someone better.

  1. What are your top goals or ambitions in life?
  2. What are some of your core values and principles?
  3. What motto or quote do you live by?
  4. What is your biggest dream that you are pursuing?
  5. What does your ideal future life look like?
  6. What is something you are really looking forward to?
  7. If you had unlimited funds to build a dream house, what would it include?
  8. What is one place you want to visit in your lifetime?
  9. Who is your biggest role model or inspiration? Why?
  10. What is one of your favorite memories from childhood?
  11. Where did you grow up and what was it like?
  12. What did you want to be when you grew up as a kid?
  13. Who is the funniest person you know?
  14. Who has been the biggest influence on your life?
  15. What songs or albums are included in the soundtrack of your life?
  16. What is your favorite book? What made it so impactful?
  17. What is your greatest accomplishment so far?
  18. What is the best advice you’ve ever been given?
  19. Name two people you really admire and why.
  20. What qualities do you value most in your friends?
  21. What is your favorite family tradition?
  22. Where is the most beautiful place you’ve traveled to? What made it so special?
  23. What is one of your favorite weekends or holidays you’ve had?
  24. Who is your favorite fictional character and why?
  25. What is something not many people know about you?
  26. What hobby or activity brings you the most joy?
  27. What life experiences shaped who you are today?
  28. What is the most thoughtful gift you’ve ever received?
  29. What random talents or skills do you have?
  30. What are you most grateful for in your life right now?
  31. What is your favorite item you own and why?
  32. What is your favorite meal or favorite food?
  33. What is one of the silliest or most embarrassing things you’ve done?
  34. What is something that never fails to make you laugh?
  35. What is your favorite place you’ve lived?
  36. What teachers or mentors made an impact on you?
  37. What pets have you had and what were they like?
  38. What is your most treasured memory of a loved one?
  39. What were your favorite subjects in school?
  40. What goals or dreams didn’t work out the way you planned? How did you adapt?
  41. What is one of your favorite stories or memories about one of your friends?
  42. What qualities or values do you admire most in others?
  43. Who is the most uplifting person you know?
  44. What songs do you love to sing out loud?
  45. What outdoor activities or sports do you enjoy?
  46. What is the most spontaneous thing you’ve done?
  47. What is something you’ve done that you previously thought you could never do?
  48. When do you feel most in your element?
  49. What are your favorite apps, websites or social media platforms and why?
  50. What is something you think everyone should do at least once in their lives?
  51. How would your friends describe you in three words?
  52. What stresses you out? What helps you decompress?
  53. What makes you feel nostalgic?
  54. What is your favorite book genre and some of your favorite books in that genre?
  55. What is one of the kindest things a friend or loved one has done for you?
  56. What are some of your favorite TV shows or movies and why?
  57. What are some small pleasures or indulgences you enjoy?
  58. How do you like to spend your weekends?
  59. What qualities do you value in a romantic partner?
  60. What has been one of your biggest learning experiences so far?
  61. What makes someone an excellent friend in your opinion?
  62. What do you geek out over or get really excited about?
  63. What is something that instantly puts you in a good mood?
  64. What hobby would you get into if time and money weren’t a factor?
  65. Where is the most awe-inspiring place you’ve been?
  66. What rituals or habits do you have in your daily life?
  67. What random facts or niche knowledge do you have from your hobbies and interests?
  68. What is something you know a lot about that you could give a tutorial on?
  69. Who had the biggest impact on the person you have become?
  70. What is one of your core beliefs or philosophies in life?
  71. What is your Heritage and are you proud of your roots?
  72. What do you hope people say about you after spending time with you?
  73. Where do you see yourself in 5 years from now?
  74. What are your typical weekend plans?
  75. What are you interested in that most people aren’t?
  76. What are your top 5 favorite apps on your phone?
  77. What’s your favorite thing to splurge on?
  1. Introvert, extrovert, ambivert?
  2. What always helps pick you up when you’re in a bad mood?
  3. What do you wish you knew more about?
  4. Favorite holiday? Least favorite?
  5. What TV show or movie do you think everyone should watch at some point?
  6. If you didn’t have to sleep, what would you do with the extra time?
  7. What’s your favorite zoo animal?
  8. What fandoms are you a part of?
  9. What fictional place would you most like to go?
  10. What is your favorite movie genre?
  11. What is your favorite season?
  12. What hobby have you gotten really into lately?
  13. What’s something you want to achieve before you die?
  14. What is your favorite music genre?
  15. What is a random fact about you?
  16. What is your favorite plant?
  17. Would you rather have key lime or coconut pie?
  18. What is your favorite holiday tradition?
  19. What is a favorite article of clothing you own?
  20. Tell me one thing on your bucket list?
  21. What is the weirdest dream you’ve had recently?
  22. What makes you nostalgic?