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As someone who has been to several gatherings where everyone was silent and the energy was awkward, I can tell you for free that having several silence breakers in your repertoire is never a bad idea.
If you find yourself on a date with someone who you are sure loves reading and you have no idea what to say, I have created this list of questions that will definitely help you keep the conversation going.
Since you are on a date, there are some very sweet and cute questions you can ask your bookish date, or if you’d like to heat things up a little, I have also listed some slightly flirty questions for a bookish person that won’t put them off.
The majority of these questions are what I would describe as deep, but regardless of that, remember that you need to be able to read the room and decipher the type of energy that is being put out before you start firing off questions.
And I feel like a big sister saying this, but you definitely don’t want to bombard your date with questions.
Readers have different temperaments, but speaking as an introverted book lover, let me tell you right now that speaking rapidly in a way that isn’t nervous but rather tilting towards investigative is the biggest turn-off ever.
You definitely don’t want your date feeling like they have been invited to an inquisition, so take it slow, read the room, be natural, and if everything fails, let your date know that you are a bit nervous.
If they are interested in continuing the connection, you will see that they will be open to answering whatever questions you have.
1. If you could have dinner with any book character, who would it be and why?
2. What’s the most embarrassing thing you’ve done because you were too engrossed in a book?
3. What book would you recommend to someone who doesn’t like reading?
4. What’s your ultimate book-to-movie adaptation fail?
5. Do you have a favorite reading spot or do you just read wherever?
6. What’s your go-to snack for reading marathons?
7. Do you ever talk to book characters as if they’re real people?
8. If your life were a book, what would the title be?
9. What’s the weirdest place you’ve ever read a book?
10. What’s the longest you’ve ever stayed up reading a book?
11. If you could live in any book’s universe, which one would it be?
12. What’s your favorite book-related meme or joke?
13. What book character do you think would make the worst roommate?
14. What’s the funniest thing you’ve seen a book character do?
15. Do you have a book that’s so bad it’s good?
16. What book have you read the most times?
17. What book would you take with you if you were stranded on a deserted island?
18. Have you ever bought a book just because of its title?
19. Do you prefer books with one main character or an ensemble cast?
20. What’s your reading guilty pleasure?
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21. What’s the most ridiculous book cover you’ve ever seen?
22. Have you ever had a book crush? If so, who?
23. What’s the strangest book title you’ve ever come across?
24. What book are you currently pretending to read because it’s “in”?
25. Do you like books that make you cry, or do you prefer happy endings?
26. If you had to pick one book to read forever, what would it be?
27. What book have you read the most times?
28. If you could have any book author write your autobiography, who would it be?
29. What’s a book you think everyone should read at least once?
30. What’s the most unusual book genre you’ve read?
31. Do you ever judge people based on their bookshelf?
32. What’s your ideal reading environment: cozy blanket or sunny spot?
33. Have you ever bought a book just for its cover design?
33. What’s a book you think you’d be better off not reading?
34. If you could be any book character for a day, who would you be?
35. Do you have a favorite book that you always recommend to friends?
36. What’s the funniest book you’ve read? Why was it funny?
37. Do you have a book you’re embarrassed to admit you love?
38. What’s a book you wish you could unread just to experience it for the first time again?
39. What’s your least favorite book trope?
40. What’s your favorite book-related quote?
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41. Have you ever re-read a book just to understand a plot twist better?
42. Do you have a favorite book-related holiday tradition?
43. What’s the longest reading slump you’ve ever had?
44. What’s the most outrageous book title you’ve seen?
45. Do you keep track of what books you’ve read? How?
46. What’s the best book you’ve ever read on vacation?
47. Do you ever find yourself talking to books when no one’s around?
48. What’s a book you always keep on your nightstand?
49. Have you ever accidentally spoiled a book for someone?
50. Do you prefer book series or standalone novels?
51. If you had to live in a fictional world but could only take one item with you, what would it be?
52. What book character’s wardrobe would you want to raid?
53. Have you ever been inspired to start a hobby or skill because of a book?
53. If you could have any book character as a pet, who would it be?
54. What’s a book you’ve read that changed your perspective on something?
55. Which book do you think would make the best theme park ride?
56. Do you have a favorite book-related pun or joke?
57. What’s the most unusual place you’ve bought a book?
58. If you could rewrite the ending of any book, which one would you choose?
59. What’s the weirdest book recommendation you’ve ever received?
60. What’s your favorite book cover that you’d actually want to frame and hang?
61. Have you ever created a reading nook or special space just for your books?
62. What’s a book that made you want to travel to its setting?
63. If you could combine two books into one, which would you choose?
64. What’s a book that’s so unlike your usual taste but you loved it anyway?
65. What book have you read that you think everyone should avoid?
66. Do you prefer book recommendations from friends or from online sources?
67. What’s a book you’ve started but never finished and why?
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68. Which book character do you think would have the most interesting social media profile?
69. What’s the most surprising book plot twist you’ve ever read?
70. Have you ever read a book and then immediately started reading something else by the same author?
71. What’s a book that you think has a hidden message or deeper meaning?
72. If you could attend any fictional event or party from a book, which one would it be?
73. What’s the most memorable book-related gift you’ve ever received?
74. Do you have a favorite book that you think doesn’t get enough attention?
75. What’s the most bizarre book plot you’ve ever encountered?
76. If you could live in a bookshop or library, which one would it be?
77. What’s a book you would love to see as a graphic novel or comic book?
78. What’s a book that you think could be improved by adding a dragon or mythical creature?
79. If you could have a book-themed room in your house, what would it look like?
80. What book has the most unusual narrative voice you’ve encountered?
81. What’s the strangest book-related dream you’ve ever had?
82. What’s a book that you think should have its own theme song?
83. If you could ask a character from a book for advice, who would it be and what would you ask?
84. Do you have any book-themed tattoos or would you consider getting one?
85. What book’s world would you most like to see expanded into a series of spin-offs?
86. What book character would you most like to have as a coworker?
87. What’s the most unconventional book format you’ve ever read, like a book in a puzzle or a pop-up book?
88. If you could rewrite any classic book with a modern twist, which one would you choose?
89. What’s a book that you think could use a crossover with another genre?
90. What’s the most memorable book event or book launch you’ve attended?
91. Which fictional character’s job would you most like to have for a day?
92. What’s the most unusual setting for a book you’ve read?
94. What book’s ending left you with more questions than answers?
95. If you could add one of your favorite characters to your favorite book, who would it be and why?
96. If you could time travel to any period depicted in a book, which would you choose?
97. What standalone book have you read that you think could use a sequel or prequel?
98. What’s the most unique book-related collectible you own or would like to own?
99. If you could attend a fictional book club, which book would you want to discuss?
Dates are already incredibly nerve-wracking, but trust me when I say that they will be much better without the inevitable awkward silences. You’ll probably have a lot of them as you learn more about each other.
Save This For Later!
If you have a book club and you’ve been thinking of conversation starters that apply to any book, I have also written a post about questions that I think will be helpful for any environment.
