Best First Date Questions

So, you find yourself preparing to go on the infamous first date. Yikes! First dates are known to be one of the most awkward events in life. We here at hope that we can ease the burden of conversation that comes with being on a first date.

It can be easy to find yourself with nothing to talk about, just twiddling your thumbs over dinner simply because, other than the initial small talk about yourselves and the food, you aren’t sure where to go next with the conversation. Never fear! This list of questions is here to help! 

The point of this list is not to cause you to shoot questions at them in rapid-fire succession. The hope is that you can ask the questions as a launching pad. Use follow-up questions. Try to find common ground or common experiences with these questions. If one of the questions pushes you into a long conversation, then has done its job. 

*Pro-tip: Whenever they ask questions, remember to answer their questions with more than one-word answers unless you want the date to end early. Be patient, though, and give them the benefit of the doubt. First dates are awkward for nearly everyone.

Best First Date Questions

  1. If you could trade lives with one person for a day, who would it be?
  2. What is the last book you read thoroughly?
  3. What’s the weirdest scar you have? What’s the story behind it?
  4. Tell me the story of how you and your best friend met.
  5. What’s the last show you binge-watched?
  6. Do you believe in ghosts?
  7. Would you rather go horse-riding or scuba-diving?
  8. Who is someone that inspires you? Someone you aspire to emulate?
  9. If you had the opportunity to swim with sharks, would you take it?
  10. What do you like most about yourself?
  11. What’s one aspect of you that sometimes makes you insecure?
  12. What accomplishments are you most proud of at this point in your life?
  13. What food are you always a sucker for?
  14. Is there something you’ve always wanted to try but have been too scared to?
  15. What is the best vacation you’ve ever taken?
  16. Where would you travel if you had all the free time and money in the world?
  17. It’s a weekday afternoon, and you’ve got nothing on your schedule. Where do you go? What do you do?
  18. If you could describe your high school self in three words, what would they be?
  19. What’s one movie you love to watch and rewatch, even when you’ve got no one to watch it with?
  20. What’s the best Disney movie of all time?
  21. What was the first cell phone you owned?
  22. Do you have any bizarre talents?
  23. Where did you grow up? What were the best and worst things about growing up there?
  24. What are a few of your life goals?
  25. Are you into documentaries? If so, what kinds?
  26. If you were to make a podcast, what would it be about?
  27. What songs, artists, or albums have had a profound impact or shaped you in some way?
  28. Are there any fictional characters that you relate to on an almost spiritual level?
  29. What is your spirit animal?
  30. Do you have any cheesy pick-up lines, and have you ever used them on anyone before?
  31. If you could write a note to your younger self, what would you want to say?
  32. What’s a misconception others often have about you?
  33. What’s a valuable life lesson you have taught yourself or learned as a result of your own mistakes and collective experiences?
  34. What’s something you’d never imagine yourself doing?
  35. What are you most excited about in your life right now?
  36. Are there any extravagances in your life that you will never apologize to anyone for having?
  37. What do you want to be remembered for?
  38. Of all the books you own, what would you choose to take on a long plane ride?
  39. What do you do to keep yourself motivated?
  40. Do you create art? If so, what kind?
  41. What’s a global issue that you think more people should be focusing on right now?
  42. What’s something that comes easier to you than it does to most people?
  43. Have you ever been in love?
  44. What are you in the dating game for at this point in your life?
  45. What is something you probably take for granted?
  46. What’s your fondest memory with nature?
  47. Would you consider yourself to be a courageous person?
  48. What is one thing you do to make yourself happy and fulfilled?
  49. Would you consider yourself to be an optimist or a pessimist?
  50. What advice that you would give to another person, but struggle to follow yourself?
  51. What was the last epiphany you had?
  52. What habit do you hope to implement into your life in the near future?
  53. Have you ever kept a New Years’ resolution?
  54. Do you think you’re held back by fear? Where do you think you’d be if you weren’t afraid?
  55. What kinds of experiences constantly leave you breathless?
  56. If you could meet with any historical figurehead, who would it be?
  57. Do you believe in reincarnation? What do you think you’d be reincarnated as?
  58. If you had one day left to live, what would you spend it doing?
  59. What is a mistake you’ve made before that you’ll most likely make again?
  60. What was the best decade of the 20th century?
  61. What is the last movie that made you cry?
  62. How would your friends describe you when it comes to relationships?
  63. What do you think happens to us after we die?
  64. Where on earth would you happily live out the rest of your days if you had no obligations, money problems, or ties to anyone?
  65. If you could inhabit a celebrity’s body for a day, who would you choose to be, and why would they be a good choice?
  66. What’s the closest you’ve ever come to dying?
  67. When was the last time you laughed until you cried?
  68. Have you ever broken any bones? If so, what’s the story?
  69. What’s something you’d never want your mom to know about you?
  70. If you could solve one global issue with a single wish, which global issue would you resolve?
  71. What’s your guilty pleasure TV show/fandom?
  72. Have you ever indulged in some good, old-fashioned fanfiction?
  73. Do you have any nicknames?
  74. What’s your least favorite beverage?
  75. Do you have more of a soft spot for sweets or chocolate?
  76. What’s the dumbest thing you used to think was so cool as a kid/teenager?
  77. What’s your most-used emoji?
  78. If you won the lottery, what would you buy/donate to first?
  79. What high school stereotype would you still consider yourself to be a part of?
  80. What is your favorite season?
  81. Would you rather live in a perpetual summer or a perpetual winter?
  82. Which state in the U.S. would you never move to under any circumstances whatsoever?
  83. Who in your family are you closest to?
  84. What ingredients would go into the perfect burrito?
  85. Do you have any siblings?
  86. Would you say you’re more of a morning person or a night owl?
  87. What’s the best gift you’ve ever received?
  88. Do you think you’ve come to realize your full potential, or do you think it’s a continuous process?
  89. Would you rather travel to the Moon or Mars?
  90. How many times have you watched your favorite TV show?
  91. If you had to spend a year alone with only one other person on the planet to interact with, who would you want that person to be (famous, random stranger, or otherwise)?
  92. Do you cook? If so, what’s your specialty?
  93. What’s something you wanted so desperately as a child that you saved up all your money to pay for it?
  94. When’s your birthday?
  95. Do you think it’s the little things or the grand gestures that count the most?
  96. Do you believe in extraterrestrial life?
  97. What would you do in an apocalypse (zombie or otherwise)?
  98. What’s the most spontaneous thing you’ve ever tried?
  99. If you could transform into any animal, what would it be?
  100. When you were a kid, what did you want to be when you grew up?
  101. What is one of your strengths? One of your weaknesses?
  102. What was the worst job you ever had?
  103. Where do you see yourself at your 75th birthday party?
  104. What would you name your band, and what genre of music would it specialize in?
  105. Were Ross and Rachel really on a break?
  106. It’s New York City in the 1920s. What are you doing?
  107. If you could choose a decade to go through your teens in, what would it be?
  108. What would your superpower be?
  109. Rolling Stones or the Beatles?
  110. What’s the longest you think you could live without your phone?
  111. Would you rather live in Narnia, Hogwarts, or some other fantasy realm?
  112. What’s your favorite color?
  113. What are some qualities you admire in your friends?
  114. Do you speak any other languages?
  115. What’s your favorite 80s movie? 90s movie? 2000s movie?
  116. What’s your astrology sign?
  117. Do you believe in astrology?
  118. If you had to describe yourself in three words, what would they be?
  119. Where would you go on a solo road trip, and what would you bring with you?
  120. What’s one skill you still want to learn?
  121. Do you have any pet peeves?
  122. What’s one of the simple joys in life?
  123. Would you consider yourself a green thumb, or do you struggle to keep plants alive?
  124. What’s one thing you do every day to improve your life?
  125. Has a song ever made you cry?
  126. What’s one moment in your life that you’d love to relive?
  127. Has a book ever changed your life?
  128. Do you think people are inherently good or evil?
  129. Have you ever experienced heartbreak?
  130. Do you resent your exes or wish them well?
  131. Have you ever tried writing?
  132. Do you believe in magic?
  133. How do you plan to make your mark on the world?
  134. Is there anyone in this world you genuinely hate?
  135. Would you lie to keep your best friend out of prison?
  136. Do you think the childhood version of you would look up to the current version of you?
  137. What is the most underrated movie of all time?
  138. What is at the top of your bucket list?
  139. Do you think everything happens for a reason, or is it just chance?
  140. Do you think you’d be capable of murder?
  141. Who was your hero when you were a kid?
  142. Would you choose to live forever if you had the option?
  143. Would you consider yourself to be a minimalist?
  144. Do you get bored quickly?
  145. How comfortable are you talking about feelings?
  146. What was your first impression of me?
  147. At what age do you think it’s appropriate to settle down and start a family?
  148. Have you ever ghosted someone?
  149. What’s the best thing about your job?
  150. Where do you want to travel next?
  151. What’s your opinion on sweatpants?
  152. Have you ever tried to use The Force?
  153. Garlic bread or cinnamon rolls?
  154. Are you one of those people that screams when they see a spider?
  155. How often do you post stuff on Instagram or Snapchat?
  156. At the end of Inception, was Leo still in a dream?
  157. What’s more important: chicken nuggets or french fries?
  158. What Disney villain would you not mind being friends with?
  159. What’s the weirdest thing you’ve been caught doing?
  160. What are your staple ice cream sundae toppings?