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100 interesting questions to ask to get to know someone better

Skip the small talk and ask these deeper, more personal Qs instead.

When we were younger, making new friends was simply a part of everyday life. However, it can be more challenging as an adult, especially when you factor in work stresses, cross-country moves and major life changes.

No matter if you’re looking for love, traveling somewhere new or trying to widen your social circle, the key to building meaningful connections is knowing the right questions to ask.

Hobbies and pop culture (think: books, movies, music and TV shows) are a good starting point since they are something we can all bond over, according to Susan Winter, relationship expert and bestselling author.

“Learning about who that person is and trying to find either common ground or something you are curious about can be extremely helpful,” Rachel Hoffman, chief clinical officer at Real, told TODAY.

But remember, our differences can often lead to the most interesting relationships. “If anything, learning about their interests and showing curiosity can be helpful in keeping the conversation exciting and intimate,” Hoffman said.

A good rule of thumb: Ask questions that will help you determine if this relationship is worthwhile — and make sure you really listen when they answer.

With the help of Winter and Hoffman, we've rounded up 100 of the best questions to ask to get to know someone — some funny, some deep. And yes, that means you won't find questions about the weather or their favorite color on this list.

  1. What's your friend/roommate/date like?
  2. How long have the two of you been friends?
  3. Are you still close with your college friends? 
  4. Are you still friends with anyone from your hometown?
  5. What do you like to do for fun? 
  6. What did you do this past weekend? 
  7. How do you de-stress after a tough day?
  8. What’s your love language?
  9. If you had to redo one year of your life, which one would it be and why?
  10. How do you typically celebrate your birthday and other holidays?
  11. Calling or texting?
  12. What was a major turning point in your life that got you here? 
  13. What’s your relationship like with your family? 
  14. Do you have any siblings? 
  15. If you had all the money in the world, how would you spend your time? 
  16. Do you have any upcoming trips planned?
  17. Have you ever been out of the country? 
  18. What's the most remote location you have ever been to?
  19. Are you a city person or a country person? 
  20. What’s your ideal sandwich? 
  21. Are you more of a work-to-live or live-to-work kind of person? How so?
  22. What's the most memorable place you’ve visited?
  23. What's something you’d like to learn?
  24. What are you most proud of?
  25. What line of work are you in?
  26. What are your favorite hobbies?
  27. What is it about that hobby that you find so interesting?
  28. Are there any causes that you are passionate about? If so, why?
  29. What do your three closest friends have in common?
  30. What are you looking for in the dating process?
  31. What are the qualities you most admire in a partner?
  32. What’s the worst date you’ve ever had?
  33. What’s the best date you’ve ever had and why?
  34. What have you learned about yourself from past relationships?
  35. What qualities do you admire about other people's relationships?
  36. How do you have fun?
  37. If you have 24 hours to do anything you want, what would that look like?
  38. What do you like best about yourself?
  39. What would you like to ask me?
  40. Do you have any pets?
  41. What’s your favorite meal your parents and/or grandparents make?
  42. What’s your favorite family tradition?
  43. What's your favorite season?
  44. Do you have a favorite holiday? 
  45. What's your zodiac sign?
  46. Do you believe in fate? 
  47. Are you an early bird or a night owl? 
  48. Deep dish pizza or thin crust?
  49. If you had one superpower, what would it be? 
  50. Who would you want to play you in a movie?
  51. What's your dream car? 
  52. Summer or autumn?
  53. Winter or spring?
  54. Skiing or jet skiing? 
  55. Beach or mountains?
  56. What’s your favorite aisle in the grocery store? 
  57. What's your favorite part of your day?
  58. How do you unwind at the end of the day?
  59. What shows are on your Netflix queue?
  60. Instagram or TikTok?
  61. What's the best concert you've ever been to and why?
  62. What genre of music do you listen to?
  63. Do you play any instruments? 
  64. Country or rock 'n' roll?
  65. Do you have a hidden party trick? 
  66. Do you like art?
  67. Have you been to any new art exhibits or galleries lately? 
  68. What’s your favorite museum? 
  69. Is there a museum and or art installation you want to check out?
  70. Are you an introvert or extrovert? 
  71. Which Hogwarts house do you belong in?
  72. Do you believe in magic? 
  73. 75. If you could have dinner with three people, living or deceased, who would they be?
  74. Do you believe in ghosts?
  75. Have you ever encountered any paranormal or supernatural spirits? 
  76. Which Avenger do you most identify with and why?
  77. Who inspires you most?
  78. 80. What’s the craziest thing you've ever done?
  79. Who never fails to make you laugh?
  80. When you’re feeling down, what always cheers you up?
  81. What’s your guilty pleasure? 
  82. Do you eat ice cream in a bowl, right out of the pint or in a cone? 
  83. If you were an ice cream flavor, which one would you be?
  84. What was your favorite childhood movie?
  85. Do you have a favorite Disney character? 
  86. Have you ever been to Disney World? 
  87. What are you currently reading?
  88. Who is your favorite author?
  89. What was your favorite book growing up?
  90. If you could be any character in a book, who would it be?
  91. What’s one book that would make a really great movie?
  92. What was the last movie you saw?
  93. Who is your favorite actor and actress?
  94. Have you ever met anyone famous? 
  95. Who is your celebrity crush? 
  96. If you could swap places with one person for a day, who would it be?   
  97. What's your biggest fear?
  98. Do you have any pet peeves?
  99. What's the best gift you've ever received?
  100. What's your favorite family tradition?