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Interesting First Dates questions

First dates can be a tensing moment for both parties, it be tensing, nerve-wracking, awkward, exciting, disastrous and wonderful if done right.

On a first date, you are obliged to make a good first impression, you have to be funny, get to know about each other, ask questions, connect and communicate especially. It’s best to avoid some topics, be light on the questions and stay off your phones.

Remember you are not to barrage your partner with questions, it’s not an interrogation. When you have a topic in mind, ask questions surrounding the topic or randomly just pick a question when the date goes silent or drifting off this is just for pointers that might be your rescue.

To make things interesting you can both pick numbers to ask the other person, it helps each person be involved in the questioning and answering to make the situation more interesting.

Don’t just ask questions, also give answers to your own questions to keep the conversation going and ask a lot of casual questions to keep the vibe going, interesting and less tense. So on a first date and subsequent date, what kind of questions should you ask the other person for conversations to flow well?

Here’s a list of first date questions

  1. Are you a morning person or a night owl?
  2. What would your perfect morning or night be like?
  3. Are you more of an indoors or outdoors person?
  4. What’s your favorite thing to do outdoors? How about indoors?
  5. What do you like to do in your free time?
  6. What are some movies you really enjoyed?
  7. What was the last show you binge-watched?
  8. What TV series do you keep coming back to and re-watching?
  9. What was the last book you really got into? (If you’re into books yourself)
  10. Who is your favorite author?
  11. Who is the most fascinating person you’ve met?
  12. What’s your favorite restaurant?
  13. What’s your favorite alcoholic and non-alcoholic drink?
  14. What are you kind of obsessed with these days?
  15. What pets have you had?
  16. Do you prefer to work in a team or alone?
  17. What would be your dream job?
  18. What would you do if had enough money to not need a job?
  19. What’s the worst or best job you’ve had?
  20. What are some accomplishments that you are really proud of?
  21. What hobbies would you like to get into if you had the time and money?
  22. What’s Something You Want to Learn or Wish You Were Better At?
  23. What amazing adventures have you been on?
  24. Where have you traveled?
  25. What’s your favorite place to go to?
  26. What would your perfect vacation look like?
  27. Where’s the last place you’d ever go?
  28. Where’s the strangest place you’ve ever been?
  29. Where did you take family vacations to when you were younger?
  30. How many siblings do you have?
  31. What music artist do you never get tired of?
  32. What really cheesy song do you love?
  33. What song don’t you want to ever listen to?
  34. Is there any art or artist you would date if you could?
  35. Who’s your favorite actor or actress?
  36. What’s the worst movie you’ve ever seen?
  37. What TV shows did you watch when you were a kid?
  38. if you were to produce your own movie, who would you cast?
  39. If you had the power to change one law, what law would you change?
  40. If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?
  41. How did you meet your best friend?
  42. Among your friends, what are you best known for?
  43. Where would your friends or family be most surprised to find you?
  44. What’s the strangest way you’ve become friends with someone?
  45. What nicknames have you had throughout your life?
  46. If you could give yourself a nickname, what nickname would you want people to call you?
  47. What are some obscure things that you are or were really into?
  48. What are some things everyone should try at least once?
  49. What’s the best thing that has happened to you this month or year?
  50. What are you always game for?
  51. What do you do to unwind?
  52. What’s your favorite app on your phone?
  53. Who are your kind of people?
  54. What’s the silliest fear you have?
  55. What would be the best city to live in?
  56. What household chore is just the worst?
  57. What odd talent do you have?
  58. If you could give everyone just one piece of advice, what would it be?
  59. What would you like to know more about, but haven’t had the time to look into it?
  60. What country do you never want to visit?
  61. What wrong assumptions do people make about you?
  62. What has been the best period of your life so far?
  63. How have you changed from when you were in high school?
  64. What’s the most relaxing situation you could imagine?
  65. What is the most beautiful view you’ve seen?
  66. What’s expensive but totally worth it?
  67. When do you feel most out of place?
  68. What’s the most recent thing you’ve done for the first time?
  69. What small seemingly insignificant decision had a massive impact on your life?
  70. Where would you move if you could move anywhere in the world and still find a job and maintain a reasonable standard of living?
  71. Would you like to be famous? (If yes, what would you want to be famous for? If no, why not?)
  72. If you lived to 100, would you rather keep the body or the mind of yourself at 30 until you were 100?
  73. Before you make a call, do you rehearse what you are going to say?
  74. What are you most grateful for?
  75. What’s the most essential part of a friendship?
  76. When was the last time you sang to yourself or to someone else?
  77. If you knew you were going to die in a year, what would you change about how you live?
  78. When was the last time you walked for more than an hour?
  79. Best and worst flavor ice cream? What would make for an excellent new ice cream flavor?
  80. All modesty aside, what are you better at than 90% of people? It doesn’t have to be useful or serious, it can be something ridiculous.
  81. What’s the strangest phone conversation you’ve ever had?
  82. How much personal space do you need to be comfortable?
  83. What fad or trend have you never been able to understand?
  84. What do you like but are kind of embarrassed to admit?
  85. What’s your favorite smell?
  86. What skill or ability have you always wanted to learn?
  87. if you were to give your country a new name, what would that be?
  88. What’s the best meal you’ve ever had?
  89. Where was your favorite place to go when you were a kid?
  90. If you could go back in time as an observer, no one could see you, and you couldn’t interact with anything, when would you want to go back to?
  91. What’s something that most people haven’t done, but you have?
  92. What says the most about a person?
  93. What machine or appliance in your house aggravates you the most?
  94. What places have you visited that exceeded your expectations?
  95. If you opened a business, what type of business would you start?
  96. What’s the best road trip you’ve been on?
  97. If you found a briefcase filled with 1 million in 100$ bills in front of your door, what would you do with it?
  98. What’s the worst advice someone has given you?
  99. Besides your home and your work, where do you spend most of your time?
  100. If you could have the answer to any one question, what question would you want the answer to?
  101. What are your top 3 favorite things to talk about?
  102. What do you care least about?
  103. Where would you like to retire?
  104. Who is the most bizarre person you’ve met?
  105. What are people often surprised to learn about you?
  106. Would you rather live full time in an RV or full time on a sailboat?
  107. What would you do with the extra time if you never had to sleep?
  108. When you were a kid, what seemed like the best thing about being a grown up?
  109. What’s your go-to series or movie when you want to watch something but can’t find anything to watch?
  110. What were some of the turning points in your life?
  111. What companies made you so mad that you would rather suffer bodily harm than give them any more of your money?
  112. What small things brighten up your day when they happen?
  113. What sports would be funniest if the athletes had to be drunk while playing?
  114. What’s the most ridiculous thing you’ve done because you were bored?
  115. If you could send one letter to yourself in the past without the goal of making yourself rich (no lotto numbers, stock picks, etc.), what age would you choose and what would the letter say?
  116. How many other countries have you visited?
  117. What do you miss about life 10 or 20 years ago?
  118.  What’s getting worse and worse as you get older? What’s getting better and better as you get older?
  119. How often do you dance? Silly/ironic dancing counts.
  120. What habit do you wish you could start?
  121. Who besides your parents taught you the most about life?
  122. When are you the most “you” that you can be? In other words, when do you feel most like yourself?
  123. What’s the most spontaneous thing you’ve done?
  124. What’s happening now, that in 20 years people will look back on and laugh about?
  125. How much social interaction is too much?
  126. How different do you act when you are with acquaintances vs. people you are comfortable with?
  127. What were some of the happiest times of your life so far?
  128. Would you rather have an incredibly fast car or incredibly fast internet speed?
  129. What are the top three social situations you try to avoid most?
  130. What friendship you’ve had has impacted you the most?
  131. What’s something you’re interested in that most people wouldn’t expect?
  132. What do you do differently than most people?
  133. If you unexpectedly won 10,000$, what would you spend it on?
  134. What’s the Most Embarrassing Thing You Can Remember That’s Happened to You?


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