101

THE LADY'S MAN PRESENTS

QUESTIONS
TO KEEP HER TALKING
 101 QUESTIONS
TO KEEP HER TALKING
BY THE LADY'S MAN

© 2020 The Lady's Man

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TODAY
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Below are the 101

Questions
1. Can you tell when someone is lying / are you good with reading
people?
2. Do you have any habits you wish you could erase?
3. What is your most ridiculous fear?
4. Have you ever actually kept a New Year’s Resolution?
5. Have you ever set two friends up on a date?
6. Have you ever stolen anything? (Money, candy… hearts?)
7. What is the longest time you have stayed without internet?
8. if you could host a talk show, who would be your first guest?
(real or fictional; living or dead)
9. Do you play / want to play any instruments?
10. If you had an extra 1 hour to spend on yourself every day, what
would you do?
11. What would you do if you could be invisible?
12. What would you do if time stood still for a day?
13. If you were given the chance to become immortal, would you
take it?
14. If a genie came to you and granted you three wishes, what
would you ask for?
15. what’s the number one quality / trait that would attract you to
someone?
16. What’s something you find attractive that most people would
consider strange?
17. What's your weirdest deal-breaker?
18. What do you want the most: more free time, more fame, or
more money?
19. What is your ideal age for settling down? (why that early/ that
late?)
20. What was the best kiss / date of your entire life?
21. What’s the strangest date you’ve ever been on?
22. What’s one thing you’re deeply proud of — but would never
put on your résumé?
23. What’s something you’ve tried, that you’ll never, ever try
again? (food, trip, activity)
24. What’s the best compliment you’ve ever received?
25. What’s the one movie that you can re-watch over and over
again?
26. What’s your dream place / time period to live in?
27. What’s the best place you have visited to?1.
28. Do you believe in destiny?
29. What’s the wildest / craziest / boldest / most embarrassing
thing you’ve ever done?
30. Have you ever kissed a girl?
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The 101 Questions

continues
31. What’s the worst lie you have ever told someone?
32. What’s the most interesting class you have ever taken?
33. If you had to choose one, would you rather be pretty or smart?
34. What's the one bad thing that you regret never trying?
(drinking, smoking etc)
35. If you could trade lives with anyone in the world for one day,
who would it be?
36. What is the meaning of your name?
37. Do you prefer to have many friends or just a few close ones?
38. What's something everyone else loves that you think is totally
overrated? (harry potter, game of thrones, love?)
39. Who is the most important person in your life?
40. What are the three qualities that you value most in a person?
41. Do you think tour planners are better or doing it yourself is
better?
42. Have you ever gone on vacation by yourself?
43. What type of movies / series do you like to watch?
44. What is the last movie / series have you watched?
45. What is your favourite cuisine / snack / drink?
46. After a long day, do you prefer to hang out with friends or
spend time alone?
47. Do you like sunny or rainy days? / winter or summer?
48. What is the weirdest nickname you’ve got?
49. If you could try out any job for one week, what job would you
choose to try?
50. Are you usually early, late, or on time?
51. What is the best and worst thing about living in your city /
town?
52. Have your childhood goals changed as you've gotten older?
53. Do you have siblings? And do you get along with them?
54. Who are you close to most in your family (parents, cousins,
uncles/aunts)?
55. Are you a Marvel fan or a DC fan?
56. What’s the most romantic thing someone has ever done for
you?
57. What is the nicest thing someone has ever done for you?
58. What did you think of me the first time we met?
59. What’s your idea of a perfect date?
60. What according to you should be the most important thing in a
relationship?
61. Do you think there are soulmates or do we all have to work to
keep our relationships?
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The 101 Questions

continues
62. Do you think best friends can become lovers?
63. What’s the best and worst relationship you’ve ever been in?
64. Finish the sentence: life is all about…?
65. Where did you grow up?
66. What were you like, growing up?
67. Are you still in touch with your school friends?
68. What’s your most vivid/first memory as a child?
69. If you could turn back time and go back to one phase of your life,
what would that phase be?
70. Have you ever thrown a tantrum in front of your parents publicly
as a child?
71. Have you ever gotten lost as a child?
72. Do you think the end justifies the means?
73. Do you believe political correctness sometimes compromises
honesty?
74. Do you think too much self-acceptance can turn you into a jerk?
75. What are the people at your workplace like?
76. What would you say is one of your weaknesses?
77. What is something that you really like and something that you
really want to change about yourself?
78. What is the best or worst trait you inherited from your parents?
79. Who was your first crush? And what happened?
80. Would you rather date someone older or younger than you?
81. What are your hobbies?
82. Have you ever stalked someone on social media?
83. What is the weirdest food combination you’ve ever tried?
84. Have you ever been on a blind date?
85. Do you have any tattoos? What is it? / would you ever get a
tattoo? What would it be?
86. What are the top three things on your bucket list?
87. Which book would you recommend to everyone?
88. What’s something not many people know about you?
89. What’s something that most people don’t notice in you?
90. What was your favourite thing to do as a kid?
91. What makes you most uncomfortable about going out on first
dates?
92. Who do you count on the most?
9.3 If you were a parent, what would make you most upset on your
daughter? A tattoo, a nose ring or a bad boyfriend/girlfriend?
9.4 What is the silliest thing you’ve posted online? (a diss to a
boyfriend after breakup, over emotional reaction to something silly)
95. Do you usually make the first move or wait for the guy to do it?
96. Are you into being tied up or handcuffed? Or do you like it soft
and loving?
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97. What’s the best and the worst thing about being in a relationship?
98. What social customs do you wish would just disappear?
99. What is something about life that people don’t appreciate as much as they should?
100. What’s the biggest thing you have learned from your past relationships?
101. What do you think that two people must have in common to connect with each other?

FEW POINTERS BEFORE YOU

LEAVE
Although all of these questions described here would make her open up and make the conversation much
more interesting, you need to make sure that you build up some context before asking these questions.
Something as simple as the phrase "random question" can do the trick.

also, anytime you ask these questions, make sure you have your answers ready for those questions as well.
Because, if for some reason the girl fails to understand what exactly are you asking, you can give your answer
as an example of what you are really asking.

finally, don't be too eager to ask all the 101 questions to her. while all of our life we have been taught to stay
on the topic, while conversing with a woman, focus on NOT STAYING ON THE TOPIC. Let the conversation
develop on its own and make sure you have asked all the related questions and have told all the related
stories that come to your mind before you move on to the next question on the list.

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