We all have those intimate questions about our life that we are not so comfortable answering.

Maybe you don’t even know the answer to some of them, so this is a great opportunity to sit and think about them.

If you really want to know someone and to get close to them, you should ask them these questions but also be ready to answer them too.

1. Do you live the life you want to live?

2. If yes, why, or why not?

3. If you had one month of your life left, what would you do?

4. What has been your biggest mistake?

5. What would you change in your life?

6. What advice would you give yourself if you could go back to the past?

7. What are you avoiding doing in your life?

8. Do you have a true friend?

9. What is your biggest achievement?

10. Who in your life are you grateful for?

Portrait of daughter and mother with glasses at home

11. For what things in life are you grateful?

12. Do you love yourself?

13. If you could do anything in the world, what would that be?

14. What is the thing you are afraid of the most?

15. What were you supposed to do yesterday and you didn’t do?

16. What do you want to achieve in life?

17. Are you working every day to make your achievements possible?

18. Who is the most important person in your life and why?

19. What is the one thing you want to be remembered by?

20. Do you love your job or are you trying to love that job?

Portrait of beautiful young woman working in the office

21. Name five people in your life who you spend most of your time with?

22. Are those people really good for you?

23. What is the greatest limit imposed on your life?

24. Who inspires you the most?

25. Who do you hate the most?

26. What is the biggest disappointment in your life?

27. Who is the biggest disappointment in your life?

28. Would you forgive your partner if he/she cheated?

29. Why would you or wouldn’t you forgive them?

30. Have you ever cheated on someone?

woman caught while cheating her spouse

31. What bad habits do you have?

32. What was the saddest moment in your life?

33. Do you want a marriage like the one your parents have?

34. What things in your life do you want to forget?

35. Who is the person you hurt the most?

36. Is there something in your life you really want to do and you haven’t done because you are afraid to?

37. If you could move to any city in the world, where would you go?

38. When was the last time you cried?

39. When was your first kiss?

40. Who was your first love?

man kissing his girlfriend's nose in nature

41. Are you a good friend?

42. If you become a millionaire, would you quit working?

43. What is your greatest failure?

44. Do you judge other people?

45. Are you making choices for yourself or are you letting someone make them for you?

46. What makes you laugh until you cry and when did you last experience it?

47. If you could buy a one-way ticket to any location in the world, where would that be and why?

48. How do you want people to see you?

49. Are you happy or sad after a few glasses of wine?

50. When do you pretend to like something?

business couple talking outside

51. Where do you see yourself 10 years from now?

52. When was your first sexual experience?

53. What do you like most about the opposite sex?

54. What are your top three sex fantasies?

55. Why do you think you are attractive?

56. What do you like the most about me?

57. How do you remember your first love?

58. What was your first impression about me?

59. Would you leave me for of a popular person you liked?

60. What do you feel about your last girlfriend?

man looking thoughtful while holding glasses

61. What’s your biggest secret?

62. What is the one quality you like to see in other people?

63. Who was your first girlfriend/boyfriend?

64. How would you react if you found another person in your partner’s bed?

65. When are you planning to get married?

66. What makes you feel depressed?

67. What makes you angry?

68. How would you react if I said my doctor told me I had an incurable disease?

69. Would you be ready for a long-distance relationship?

70. How would you react if you had a child with a severe illness?

father sitting beside her daughter lying on a bed in hospital

71. What are your financial plans for the future?

72. How would you know if I was the right person for you?

73. Do you believe in God, and if so, why?

74. What are your personal goals?

75. What kind of childhood did you have?

76. What makes you insecure?

77. What do you expect from a love affair?

78. Do you want kids?

79. What expectations do you have of yourself?

80. What do you expect from your partner?

man kissing his smiling girlfriend on neck

81. What is your family like?

82. Who is your role model?

83. Do you gossip a lot?

84. What is your craziest memory?

85. What is your happiest memory?

86. What is one thing you feel you are really good at?

87. Have you ever broken the law?

88. Are you responsible?

89. Do you believe that you are supposed to meet some people in your life?

90. Who is the person in your life with whom you have the feeling that you are home?

young asian woman putting makeup on

91. If you could invite any person on the planet to dinner, who would you choose?

92. Do you want to be famous and why or why not?

93. Before you call someone on the phone, do you ever think of what you are going to say, and if so, why?

94. What does your perfect day look like?

95. When did you fall in love for the last time?

96. Who is your favorite superhero?

97. Do you anticipate how you will die?

98. Have you ever written a diary?

99. What part of your life are you most grateful for?

100. If you could change anything about the way you were raised, what would that be?

loving mother touching upset little daughter face

101. If you could wake up tomorrow with another quality or ability, what would that be?

102. If a crystal ball could tell the truth about you, your life, your future, or anything else, what would you want to know?

103. Do you have a dream you have dreamed about for a long time?

104. What do you appreciate most in friendship?

105. What is your most horrifying memory?

106. What does friendship mean to you?

107. What roles do love and attachment play in your life?

108. How close are you with your family?

109. Do you think you had a more fortunate childhood than other people?

110. What kind of relationship do you have with your mother?

happy smiling man hugging his lovely mother

111. Do you miss someone?

112. What is your favorite song and why?

113. What is your favorite book and why?

114. What is your favorite movie and why?

115. What did you want to become when you were a kid?

116. How many times in life have you been in love?

117. Are you OK with one-night stands?

118. What do you regret the most in life?

119. If you could change anything about yourself, what would that be?

120. What is one thing that you have done that’s made you proud of yourself?

Two attractive business woman walking down the stairs and talking.

121. If you could only keep one thing out of everything you have, what would that be?

122. Who do you think is very successful and why?

123. What is the best advice that someone gave you?

124. What turns you on?

125. Is sex really important in your relationship?

126. Do you like to flirt?

127. Do you need to be with someone in a relationship to have sex with that person?

128. Have you ever swum in a pool or the sea naked?

129. Would you ever play sexy games in bed?

130. Do you think you are a good kisser?

man wearing black top about to kiss woman

131. How many people have you slept with?

132. Do you think that sex is better if it is with a stranger?

133. Do you think that sex is better if you have been drinking?

134. Is alcohol important to you if you want to have fun?

135. What do you think about porn movies?

136. Would you ever watch porn with your partner?

137. What is your favorite sexual memory?

138. Do you think you are sexy?

139. What do you remember thinking the first time we met?

140. What’s the biggest decision you ever had to make?

man look thoughtful in living room

141. When did you feel most ashamed?

142. Who is the one person in your life you wish you hadn’t met?

143. Do you think that people change?

144. What is worse: to experience a failure or never trying?

145. What makes you different from other people?

146. What is the biggest promise you made to yourself?

147. What is one thing that happened to you that made you stronger?

148. Where is the place where you feel most safe?

149. Who knows you the best?

150. Do you like dancing?

romantic couple dancing in the kitchen

151. Do you sing in the shower?

152. Name one part of your body you don’t really like?

153. Name one part of your body you really like?

154. Can you save money or do you like spending it?

155. What is the best gift you ever got for your birthday?

156. Are you religious?

157. Did you like being in high school?

158. What is your favorite season of the year?

159. Would you like to have a pet?

160. Who gave you your name?

Mother hugs her baby at home

161. What kind of people do you especially like?

162. What kind of people do you definitely not like?

163. What is your secret skill?

164. What is your favorite toy from childhood?

165. What is the biggest embarrassment you had in elementary school?

166. If your house was on fire, what would be the first thing you would grab to save?

167. What is your dream destination?

168. What would be your worst job?

169. What is the bravest thing you have ever done?

170. What do you do when you don’t have any motivation?

man in pajamas lying in bedroom and typing on his phone

171. When did you last try something new?

172. What makes you want to be better?

173. What do you like to do, do you do this often and if not, why not?

174. Have you recently done something worth remembering?

175. What makes you excited?

176. What is your biggest problem?

177. When did you last go somewhere where you had never been?

178. What would you regret never doing?

179. What do you most want out of life?

180. What kind of influence do you want to leave on the world?

Audience applauding speaker at a business seminar

181. What do you like most about yourself?

182. Who do you think you can’t live without?

183. When you close your eyes, what do you think about?

184. If your life was a movie, what would its title be?

185. What does success mean for you?

186. If you could fulfill a wish for yourself, what would it be?

187. What do you owe to yourself?

188. When you think of a home, what are you thinking about?

189. What was the greatest adventure of your life?

190. If you abandoned your current life to achieve your dreams, what would you lose?

tourist with hat walking through outdoor market

191. What is your greatest strength?

192. What’s your biggest weakness?

193. What did life teach you yesterday?

194. On whose life did you have the greatest influence?

195. How many people do you love?

196. What are you doing for those people you love?

197. What bad habits do you want to get rid of?

198. Have you ever been crazy about some sport, band or book?

199. What is your biggest flaw?

200. Do you believe in love at first sight?

200 Intimate Questions To Ask A Guy Or Girl