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260 Deep Questions to Ask Your Girlfriend

by | Love

Jul 9, 2022

Have you ever found yourself wondering what makes your girlfriend tick? You are far from alone. I have the ideal questions you can ask your girlfriend if you want to get to know her better. 

Here are 260 profound questions to ask your girlfriend whether you both just started dating or have been dating for a while.

1. Chemistry or compatibility?

2. Do you hate the experience that shaped you?

3. Have you ever had a major friend crush?

4. Is there any ex you sometimes remember?

5. What can I do to make your life easier?

6. What gift do you wish to have?

7. What’s the most important day of your life?

8. Have you ever owned a teddy bear?

9. What do you enjoy doing that is peculiar to men?

10. Have you seen your period this month?

11. What’s your favorite color?

12. Have you ever needed anyone’s approval?

13. Would you prefer to go dutch on a date, and why?

14. Would you stick to your maiden name after marriage?

15. When do you want to start making babies?

16. In what ways do you show love without saying words?

17. How do you spend your spare time?

18. Would you forgive me if I cheated on you?

19. Lots of sex or money, which do you prefer?

20. Do movies with sad endings make you cry?

21. What can I do to make you happy?

22. Have you ever been ghosted by someone dear to you before?

23. Do you like going to see movies?

24. Who is your role model?

25. If you were a flower, what would be your name?

26. What’s your future ambition?

27. Do you ever want to get married?

28. Do you fear being rejected?

29. Is there anything you wished you did at a younger age?

30. When was the last time you burst into laughter?

31. Alone or unhappy and why?

32. What’s the strangest thing you have heard of?

33. What podcast would you recommend to me?

34. What was the most horrific nightmare you ever had?

35. What is one thing that you can never tolerate from me?

36. How would you convince me that your love for me is true?

37. What truth about me would you like to know?

38. Do you buy on impulse?

39. Have you had any infections before?

40. What is the most pleasant thing about you?

41. What’s your favorite outfit?

42. Can you tell me about a challenge you overcame?

43. How do you react to stress?

44. What questions would you rather ignore?

45. What irritates you about sex?

46. Have you ever cheated on your partner?

47. How did you lose your virginity?

48. What scares you the most?

49. Am I man enough for you?

50. Would you spend the rest of your life with me?

51. Who are you stalking presently?

52. Should I be worried whenever you go silent for days?

53. Would you go to bed in hunger due to anger?

54. How can I be a better man for you?

55. Am I too harsh on you?

56. Are you vulnerable enough with me?

57. What’s your best meal?

58. Do you think our love would stand the test of time?

59. Where would you love to go with me on vacation?

60. Do you drink and smoke?

61. When did you start developing feelings for me?

62. Would you do anything for me?

63. What are your core values?

64. Would your family accept me?

65. Should I massage you right away?

66. Do you sometimes have a sudden change in your emotional state?

67. Is there anything you would like me to do for you?

68. What’s the worst meal you have ever had?

69. What are your top 3 priorities in a relationship?

70. Are you sometimes worried about losing me

71. What’s the greatest decision you have ever made?

72. What humiliation have you ever suffered before?

73. Mention five things that are always in your bag when going out

74. Do you feel threatened when other girls are with me?

75. Why did you choose to be mine?

76. Do you know that I love you?

77. When are you coming to spend the weekend with me?

78. What’s the sweetest compliment you have ever gotten?

79. Which of your friends can you really count on?

80. If you discovered the worst about me, would you leave?

81. Have you ever had a second thought about us?

82. What traits do you look for in a man?

83. Am I the best you ever had?

84. What do you think is so special about you?

85. What are your insecurities in this relationship?

86. If today were your last day on earth, how would you spend it with me?

87. Is there anything you would like me to stop doing?

88. Which resolution do you intend to keep?

89. What is the best advice you ever got from your mother?

90. Which celebrity do you think you resemble?

91. In what ways do you feel loved by me?

92. Why would you cancel a date?

93. Have you ever ghosted anyone before?

94. How many kids do you want with me?

95. Am I always running through your mind?

96. What is the worst manner for someone to propose to you?

97. How romantic are you?

98. Have you been in love before?

99. Have you been on a diet lately?

100. Why are you always so beautiful?

101. What’s your greatest secret?

102. What drives you crazy?

103. What you do if your pregnancy test result came out positive?

104. What time of the day do you enjoy sex more?

105. When are you usually free during the day?

106. Which pick-up line made you fall for me?

107. Do you like adventures?

108. Have you ever tripped over your dress while wearing heels?

109. Would you trade me for anything?

110. Who were you crushing on in high school?

111. What’s your perfect dinner date?

112. What’s the funniest prank ever played on you?

113. What’s your favorite picture of us?

114. Do you enjoy my riddles and jokes?

115. Is any of your male friends asking you out?

116. Do you believe in fairytale endings?

117. Are you superstitious?

118. Do you think older men are attractive too?

119. Have you ever farted in my presence without my knowledge?

120. Who would you yell at for the slightest reason?

121. What was your favorite cartoon as a show?

122. Do you think fate brought us together?

123. What do you think of me?

124. Have you ever been forced into doing something you don’t want?

125. Which drink puts you in the mood?

126. Would you tremble if I touched your neck?

127. If you have extra money at the end of the month, what you are going to do with it

128. What was your childhood like?

129. What’s your deal-breaker in a relationship?

130. Have you completed a milestone recently?

131. Do you think a relationship should be 50-50?

132. Who would you be forever grateful to?

133. What do you fear losing the most?

134. Is there anything you would like to try out with me?

135. What experience in life made you develop a thick skin?

136. Are you a hopeless romantic?

137. What is love to you?

138. Would you give a second chance to an ex?

139. What do you desire more in this relationship?

140. Have you found your purpose yet in life?

141. What request would you make that I will not turn down?

142. What turns you on and off?

143. Will you let me know when I step on your toes?

144. Do I give you Déjà vu?

145. What makes you happy and sad at the same time?

146. Do you have any hidden talent?

147. What is your mantra in life?

148. What Guinness World Record would you like to break?

149. What kind of mother would you be in the future?

150. What habit would you want to outgrow?

151. Have you ever thought of breaking up with me?

152. What would you wear to feel sexy tonight?

153. What is your wildest fantasy?

154. Am I a priority to you?

155. Can you undress me while being blindfolded?

156. How would you save yourself from being hurt?

157. Who do you find handsome among my friends?

158. How long would you wait for me before moving on with another man if something separated us?

159. What lessons have you learned so far from your past relationship?

160. Do you believe in a twist of fate?

161. What story would you like to tell one day about yourself?

162. What do you not see as fun?

163. What genre of music do you not like?

164. Is there something that you spend your money uncontrollably on?

165. What do you think you are underrated for?

166. What’s your favorite hobby?

167. Have you ever taken revenge on anyone before?

168. Would you go dancing swimming lessons with me?

169. Do you have high standards or impossible expectations?

170. What would you be up to if you were not with me right now?

171. What do you admire most about yourself?

172. Do you have any regrets about your past relationships?

173. What is your favorite romantic book that you read?

174. How long do you spend getting dressed when going out?

175. What was your best subject in high school?

176. What’s your favorite season of the year?

177. What’s the weirdest thing a stranger has ever done for you?

178. Who is the best teacher you ever had?

179. Who do you look up to?

180. Who is your best celebrity couple?

181. What do you plan to do in 6 months’ time?

182. When was the last time you did something new for the first time?

183. Have you ever asked a guy out?

184. How do you find strength in your heart to do what others are discouraging you from?

185. What impact would you like to make on society?

186. If I could grant one of your wishes, what would it be?

187. Is it better to try loving someone and fail or to never have tried at all?

188. What makes your heart smile?

189. What can you live without—money or love?

190. What is the most special memory you have from the last 5 years?

191. Do you find peace in being with me?

192. How do you win my heart so easily?

193. Do you think things happen for a purpose?

194. How would you react to things I deny you of having or doing?

195. What are you most grateful for about us?

196. Will you always be there for me through thick and thin?

197. What can we do to sustain our romance?

198. What distracts you the most?

199. Do you like how I dress?

200. Have I ever made you feel special?

201. What length would you go to impress a man?

202. Do you agree that love gets better with age?

203. What would you do with the money you found on the ground?

204. Are you a hopeless romantic?

205. What’s the weirdest place you ever had sex?

206. Have you ever helped any man in a time of distress?

207. Would you lie about your age?

208. Have you ever bathed with a lover before?

209. Would you tell a man his zipper is down?

210. Which contest have you ever won?

211. Who is your hero?

212. Do you have a secret admirer?

213. What was the last thing that made you cry?

214. What is one thing you will never do in a relationship?

215. Do you think your past will haunt you one day?

216. What keeps your hope alive?

217. Is there something you used to enjoy doing but now have stopped it?

218. What were you like as a 16-year-old girl?

219. How would your family describe you?

220. What’s one thing that is out of your character to do?

221. Have you ever gotten so excited that you could not sleep at night?

222. What’s the best way you reward yourself after passing a test?

223. What principles do you live by?

224. Which of your friends influences you the most?

225. Would you date me if I were broke?

226. Where did you grow up?

227. Has anyone ever told you that you are good in bed?

228. What did you ever buy without using to date?

229. What’s your most awesome part of being a female?

230. How do you see girls that propose to men?

231. When was the last time you rolled on the floor laughing?

232. What do you have a flair for?

233. Has anyone walked in on you while bathing?

234. Why do men find boobs and butts inviting?

235. Can you keep eye contact for long?

236. What’s the most amazing cologne you have ever perceived?

237. What would you like our shared goals to be this year?

238. Do you have any activities you love doing with me?

239. Who among my friends do you dislike?

240. Do you smile when you think of me?

241. Have you had any serious relationships?

242. What’s one thing that you have done that is not ladylike?

243. What is your love language?

244. How do you know when you have found the one?

245. When was the last time you blushed after seeing my text?

246. Would you run away with me to somewhere no one else?

247. I get the hunch that you need my help. Is it true?

248. What 3 things would you do to make me feel happy today?

249. Winter sex or summer sex, and why?

250. Which would you like to live, reality or dreams?

251. Serious commitment or casual, and why?

252. Do you want a serious relationship?

253. Why did you end your last relationship?

254. What are your favorite social media apps?

255. What is your favorite romantic movie of all time?

256. Red wine or white wine?

257. Do you trust your gut?

258. What is the weirdest hobby you’ve ever heard of?

259. What was your first sex like?

260. Do you prefer to live for the moment?

Related: 260 Deep Questions to Ask Your Girlfriend

Wrapping Up

These 260 questions to ask your girlfriend will help you learn how to cultivate and maintain your relationship with her. They will also give you a better idea of who your girlfriend is and what you need in a lifelong partner.

By the time you finished getting answers to these questions from your girlfriend, you’re going to see how much you have learned about your girlfriend and you’ll be glad you did.

Photo by Pixabay on Pexels.

By Rachael Ukpebor

Rachael Ukpebor is an Editorial Assistant for Whatsdalatest. She graduated with honours from the University of Benin with a degree in Sociology and Anthropology. She covers beauty, relationship, and lifestyle topics at WDS, everything from best skincare and makeup hacks, to relationships. Her favourite music is Lovin' You by Minnie Riperton.

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