When a friend, acquaintance, or loved one invites you to join them for a feasting, it’s important that you always come prepared. While this oftentimes means coming equipped with a hostess gift, proper attire, and/or directions to facilitate your timely arrival, we believe it’s even more important to come prepared to converse.

As the Duchess of Windsor so candidly stated, “If you accept a dinner invitation, you have a moral obligation to be amusing… Nobody has the right to come to a party and sit there like a piece of furniture.”

Hear, hear, Duchess! We thoroughly conquer!

So to help you with your future conversing and dining experiences, we’ve compiled a list of 103 conversation starters. Some standard, some borderline inappropriate, all amusing and sure to start an interesting conversation with whomever you’re with.

It should be noted, though, that conversation starters are just that – a way to start a conversation! To merely go down the list without proper discussion or response from yourself completely defeats the purpose of having the list. So we suggest you dive in, and let the questions and probing flow in conjunction with the wine!

  1. What is something you’re obsessed with?
  2. What do you do to get rid of stress?
  3. What’s your favorite way to waste time?
  4. When was the last time you worked so much harder than you thought you were physically capable of?
  5. When you have free time, how do you spend it?
  6. When was the last time you reveled in doing absolutely nothing?
  7. Who is your oldest friend? How did you meet them?
  8. If you had intro music, what song would it be? Why?
  9. If you were an athlete and needed hype music to accompany your entrance into the arena, which song would you choose?
  10. What were you really into as a kid?
  11. What did you think you were going to grow up to be, when you were a kid?
  12. If you could have any animal in the world as a pet, which would you choose?
  13. Which animal do you think is your spirit animal/patronus?
  14. What three words best describe who you are at work?
  15. What three words best describe who you are when in your most relaxed state?
  16. What would be your perfect vacation?
  17. What would be your perfect day?
  18. What do you think of tattoos? Do you have any?
  19. Have you ever saved an animal’s life? How about a person’s?
  20. Would you consider yourself more of a Type A or Type B personality?
  21. If you could ever run your own business, what kind of business would it be?
  22. Have you ever spoke in front of large group of people? How did it go?
  23. Did you ever have a chronic dream that constantly appeared in your dreams? What was it?
  24. What’s the strangest/most intense/best dream you ever had?
  25. What’s something you know you feel controversially about?
  26. What in life brings you the most joy?
  27. Who in your life brings you the most joy?
  28. Who had the biggest impact on the person you have become?
  29. Where is the most beautiful place you’ve ever been?
  30. How often do you stay up past 3 a.m.? What you usually doing?
  31. Which is your favorite season? Why?
  32. Which do you value most? A great car or a great house? Why?
  33. Do you have a secret place you escape to when you’re feeling overwhelmed? Did you have one as a child?
  34. What do you bring with you everywhere you go?
  35. What’s the weirdest thing you do?
  36. How much time do you think you spend on the internet? Which site/app really gets you?
  37. Any recent news story really catch your attention?
  38. If you had to change your name what would your full new name be?
  39. Who would you consider the most successful person you know? Why? By what measurement?
  40. What is your guilty pleasure?
  41. When you have the house to yourself, what’s the first thing you do?
  42. How often do you curse?
  43. What’s your biggest fear?
  44. What do you fear is hiding in the dark?
  45. Which fads did you follow when you were younger?
  46. What’s your favorite room in your house?
  47. What was your favorite room/place when you were little?
  48. What’s on your bucket list? What do you want to accomplish before you die?
  49. What is the best place to take a date?
  50. What smell brings back great memories?
  51. What are you sincerely good at?
  52. What makes you nervous?
  53. Which TV show would you want your life to be life?
  54. 54. What’s your favorite television show currently?
  55. Would you rather binge watch or watch something as it comes out?
  56. Do you prefer books or movies?
  57. What was your favorite book as a child?
  58. Do you prefer physical books or ebooks?
  59. What is your favorite genre?
  60. Fiction or nonfiction?
  61. How fast do you read?
  62. Which book has influenced you the most?
  63. Which book do you think has influenced society the most?
  64. If you ever opened up a restaurant, what type of food would you serve?
  65. What is the strangest/best themed restaurant you’ve ever been to, or want to go to?
  66. How many countries have you traveled to?
  67. What is the most relaxing place you’ve ever been?
  68. Do you prefer traveling alone or with a group?
  69. Where do you want to go next?
  70. Which is your favorite mode of transportation? Train, car, plane, boat?
  71. What do you think of staycations?
  72. Do you prefer to do touristy things or go off the beaten path when you travel?
  73. Where do you typically get your recommendations when you travel?
  74. Do you think technology will save the human race or destroy it?
  75. What do you think the next technological advance will be?
  76. Do you care about fashion?
  77. What’s your favorite article of clothing?
  78. What’s the craziest, most outrageous thing you want to achieve?
  79. Which goals have you gone after and already achieved?
  80. Do you plan to grow into your parents? How have their accomplishments influenced you?
  81. What goals have you already failed? Are you going to reattempt any of them?
  82. Where do you want to retire?
  83. Any goals for this year?
  84. What’s your favorite thing about summer?
  85. What do you love most about winter?
  86. Does your family take seasonal vacations?
  87. Which holiday is your favorite? Why?
  88. What do you think of standardized tests?
  89. Are bigger or smaller schools better?
  90. What do you think of homeschooling?
  91. How has the education that you’ve received changed your life?
  92. What’s your absolute favorite food?
  93. Do you prefer savory or sweet?
  94. What food do you absolutely hate?
  95. What food do you eat even though you know you shouldn’t?
  96. What would you want your last meal to be?
  97. Time freezes for everyone but you for 24 hours, what would you do?
  98. If you have to relive one day of your life forever, which day would you choose?
  99. If you mind was an island, what would it look like?
  100. What does your own personal hell look like? How about your own personal heaven?
  101. A portal to another world opens in front of you, you don’t know how long it will stay open or if you’ll be able to get back after you go through. What do you do?
  102. If you were a king/queen what would your throne look like?
  103. If you were on the run from the police for a crime you didn’t commit, where would you go?