100 Questions Tag

Good conversation is very important in a romantic relationship!  Lust only lasts a little while.  Romance is time-sensitive.  Responsibilities are tedious.  But hey, good conversation is what makes the relationship last.  If you can master the art of good conversation, you’ll always be able to talk to your man, make him laugh, and draw him out for honest communication.

And of course, when there’s nothing specific to talk about, then it’s time to ask some questions!  You don’t have to stick to interview questions or invasive questions about his past.  You can have fun with some silly questions, interesting questions, or even deep philosophical questions that will tickle his curiosity.

Here are 100 questions to read over and ask your significant other, or a man you’re interested in dating.


  1. What do you wear when you go to sleep?
  2. What kind of animal would you pick, if you had to be attacked by one?
  3. What’s something a woman could do to lose points with you?
  4. Do you ever pee outside?
  5. What’s your favorite cartoon, as a kid and as an adult?
  6. What totally opposite career would you have tried in another life?
  7. Who was your first time and why?
  8. What’s the worst movie you’ve ever seen?
  9. What super power would you like to have?
  10. When was the last time you wrote a handwritten letter?
  11. What’s something unique you can do that most people can’t?
  12. Do you remember any stories you made up as a kid?
  13. If you could live as a woman for a day, what would you do?
  14. What’s your favorite breakfast, lunch and dinner?
  15. What animal would you like to be reincarnated as?
  16. What profession would you hate to try?
  17. Have you ever seen a ghost or seen suspicious activity?
  18. Do you have any enemies? Why?
  19. Who is your best friend and how long have you known each other?
  20. What would the book of your life be called?
  21. What’s your favorite color combination?
  22. Who was your favorite US president?
  23. What’s the last song you cried at or almost cried?
  24. What’s the weirdest thing you’ve ever eaten?
  25. What movie star should play you?
  26. What’s your most shocking fantasy that would make me blush?
  27. What’s your favorite song?
  28. What’s the last show or concert you went to see live?
  29. What’s your dream career?
  30. What’s something people always thought of you growing up?
  31. Do you have a dating profile, or if you don’t, what would you say?
  32. What’s the grossest thing you’ve ever seen?
  33. What’s a smell you love?
  34. Who was your first unrequited love?
  35. What game are you extremely good at playing?
  36. What’s your favorite exercise?
  37. Do you prefer tea or coffee (or soda pop)?
  38. What’s your favorite alcoholic beverage?
  39. What’s one decision you wish you could take back?
  40. What animated girl do you have a crush on?
  41. What’s an odd thing on your bucket list?
  42. What’s your favorite swear word?
  43. Do you know your ancestry?
  44. What’s the last big lie you’ve told?
  45. What’s the best compliment you’ve heard?
  46. Would you be willing to go to jail in place of your friend/spouse?
  47. Do you think parents should protect children from unhappiness?
  48. What’s the most annoying question you’ve heard?
  49. If you could live as a shape shifter, what pranks would you pull?
  50. Have you ever had a stalker?
  51. What’s your favorite TV show ever?
  52. What’s your favorite hobby to do or watch?
  53. What’s your board game or card game of choice?
  54. Who do you trust the most?
  55. Where do you see yourself in 10 years?
  56. Who taught you the most about life as a youth?
  57. Who do you wish you could meet in person, living or dead?
  58. What is a strange coincidence that happened to you?
  59. What’s your favorite corny joke?
  60. Have you ever been in love with two women at the same time?
  61. What’s something you’ve done that you feel guilty about?
  62. What would you do if you never had to work again?
  63. What’s your favorite way to travel?
  64. When were you the most scared?
  65. What would you want to ask a historian living in the future?
  66. What would you want to ask a historian in the distant past?
  67. What accomplishment are you most proud of?
  68. What’s the funniest thing you’ve ever seen?
  69. What weird activity appeals to you for no apparent reason?
  70. Who is your lucky star in life?
  71. Who is your main motivation in your life?
  72. Who was your mentor, or a teacher that changed your life?
  73. What’s your biggest weakness?
  74. What’s your best quality?
  75. What’s the most awkward moment you can remember?
  76. Who was your first pet?
  77. What kind of exotic pet would you like to have?
  78. If you were to create a TV show, what would be the theme?
  79. What’s the most offensive thing you can remember seeing?
  80. What dead person would you most dread being haunted by?
  81. What’s your favorite type of weather?
  82. What’s the worst injury you’ve ever had and how did it happen?
  83. What was the best day you can remember?
  84. Which sports team is your favorite?
  85. When was the last time you laughed so hard you couldn’t breathe?
  86. When was the first time you fell in love?
  87. Who has been your biggest supporter?
  88. Where would your dream vacation be?
  89. How did you start to change your life?
  90. Have you ever had a prediction come true?
  91. What did your parent(s) teach you?
  92. What’s your biggest fear?
  93. If pets could suddenly talk what would yours say to you?
  94. When’s the last time you’ve been amazed by a person?
  95. Have you ever cheated at something just to win?
  96. What’s a secret you’ve never told anyone else?
  97. What’s the most frustrating friendship you’ve ever had?
  98. When’s the last time you played truth or dare with someone?
  99. Who was your best friend in high school or middle school?
  100. What hobby or “vice” helps you cope with stress?


Remember, not only are these questions fun for him to answer (since men do love to talk!) but they also tell you a great deal about what’s going on in his mind.  Use the answers he gives you as a basis for learning him and determining what drives him every day.  Conversation is as simple as question and answer.  But don’t go for logic…go for the art of getting to know a person!

10 Magic Love Triggers That Make Men Fall Hard For You

Have you ever been near someone who gave you a strange spine tingling sense of excitement?

Have you ever felt those infamous little butterflies in your stomach fluttering around when your secret crush walked by?

Have you ever had the hairs raise on the back of your neck as someone you were in love with unknowingly brushed past you?

You can make him feel this way. Find out more and how to get 77% off our Feminine Enchantment program at the link below…

Click here to watch the video <<

Talk soon,

Matthew Coast

P.S. If you’ve been banging your head against the wall because you’ve fallen for a man who’s frustratingly unavailable…

Or if you’re being treated as an option with a guy and want him to feel like you’re “the one” he’s been looking for his entire life…

Then pay close attention to this video because here’s a secret almost nobody is talking and can change everything for you if you understand how to use it (and get a great discount on our most popular Feminine Enchantment program)…

Click here to watch the video <<

About The Author

Matthew Coast

What's stopping you from meeting Mr Right and having the relationship you want? Click here to take the quiz.

Leave A Response

* Denotes Required Field