Updated on January 4th, 2019
Love is a rollercoaster ride for sure. Often the person we fall in love with or start getting to know may not be as easy a person to decipher as he seems.
In fact, in the case of women they generally do not open up so easily to anyone they meet and men have a tough time finding out more about them. Not anymore as we are here to rescue you from this dilemma.
We are bringing you 101 deep questions to ask if you really want to get to know Someone. With this extensive list, you would quickly know how to break the ice with the one you seem to be interested in.
When you ask these questions intently you are most likely going to get interesting revelations which you may not get otherwise. You can then ardently studies her thought process and delve into her heart to establish a strong connection between you and her.
1. What’s your philosophy in life?
2. What is your biggest regret?
3. Are you religious or spiritual?
4. Can you pin point the moment in your life where you were the happiest?
5. Which parent are you closer to and why?
6. What was the best phase in your life?
7. What was the worst phase in your life?
8. Have you ever seen something you can’t explain?
9. What makes you feel accomplished?
10. What’s your favorite book/movie of all time and why did it speak to you so much?
11. What is a relationship deal breaker for you?
12. What is the strangest dream you’ve ever had?
13. Would you ever take back someone who cheated?
14. How do you feel about sharing your password with your partner?
15. When do you think a person is ready for marriage?
16. What kind of parent do you think you will be?
17. What would you do if your parents didn’t like your partner?
18. Who is that one person you can talk to about just anything?
19. Do you usually stay friends with your exes?
20. Have you ever lost someone close to you?
21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
22. What’s an ideal weekend for you?
23. What do you think of best friends of the opposite sex?
24. What is the darkest thought you’ve ever had? What about the darkest thing you’ve never told anybody?
25. Are you confrontational?
26. When was the last time you broke someone’s heart?
27. Would you relocate for love?
28. Did you ever write a journal?
29. Is there something out there, a thought, an idea, a current event, or a fear that you find deeply unsettling?
30. Do you believe in second chances?
31. What’s the one thing that people always misunderstand about you?
32. What is your idea of a perfect vacation?
33. What did your past relationship teach you?
34. Is there an activity that calms you? A place or a thing that makes you feel at ease?
35. What’s on your bucket list this year?
36. When have you felt your biggest adrenaline rush?
37. What is the craziest thing you’ve ever done and would you do it again?
38. If a genie granted you 3 wishes right now, what would you wish for?
39. Do you have a favorite book? A line in a piece of literature? A poem? Why do you relate to it?
40. What do you think about when you’re by yourself?
41. Does your job make you happy?
42. What did you want to be when you were younger?
43. Why did your last relationship end?
45. Can you remember a time in your life you felt the most alive? Tell me everything about that memory.
46. Where is your favorite place in the entire world to go?
47. What are your top five favorite movies?
48. What are some of your favorite songs?
49. What qualities do you admire about your parents?
50. How would you describe your best friend?
51. Tell me about the facts or harsh truths you choose to ignore but know you shouldn’t.
52. What’s something you can’t go a day without doing?
53. What is the first secret you ever kept from anybody? Which is the biggest?
54. What’s the craziest thing you’ve ever done for love?
55. What’s your biggest pet peeve?
56. Why do you think you’re still single?
57. What accomplishment are you most proud of?
58. What is one dream you have yet to accomplish?
59. What is your greatest fear?
60. Where do you find meaning in your life?
61. Who are five people you are closest with?
62. What is the greatest struggle you’ve overcome?
63. Tell me about the times someone broke your heart.
64. What’s the most exciting thing that’s happened this past year?
65. If your life was a movie or a book what would be the title to it?
66. What’s one thing that bothers you most about the world today?
67. Think about the people you love the most in your life, what do you do for them?
68. If you could change one thing about yourself what would it be?
69. If you could change one thing about the world what would it be?
70. If you could be anywhere other than where you are right now, where would you be and what would you be looking at?
71. What sport did you fall in love with?
72. What is the weirdest thing about you?
73. What was your longest relationship?
74. What would your best friend say is your best quality?
75. Who is your favorite historical figure?
76. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?
77. If you could tell your former self one thing right now what would it be?
78. What food could you not live without?
79. What do you think was there before the universe came into creation?
80. What’s closest you’ve ever come to being arrested?
81. What was your best birthday?
82. What’s one thing you wish you knew how to do?
83. Where’s one place you’d like to go that you haven’t been?
84. What was the last book you read? And When?
85. Is a life exclusive to pleasure (no suffering) worthwhile?
86. What are some of your own personal goals in the next 5 years?
87. What would you consider your greatest accomplishment so far?
88. If you could get away with anything that you do?
89. Who is your greatest hero?
90. Would you rather be loved or love?
91. Why are we here?
92. If heaven is real and you died tomorrow, would you get in?
93. Do you believe in fate?
94. Do you believe yourself to be truly free? If so, why? If not, what is holding you back?
95. If you had the ability to erase something that you did in the past, what
would it be?
96. What song makes you unconditionally happy?
97. If you could have anybody else’s life, who’s would you take?
98. What fictional character do you most relate to?
99. If I asked you at age 5 what you wanted to be when you grew up, what would you say?
100. If you were given a choice to choose your manner of death, how would you die?
101. If you could take us anywhere in the world right now, where would you take us?
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