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300+ Amazing Questions to Ask a Girl to Win Her Heart

by Eugen Anderson
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300+ Amazing Questions to Ask a Girl to Win Her Heart

Good, unusual questions will help you keep a talk with a girl flowing. That is why we decided to compose an article of 300 great questions to ask a girl that will help you build firm, long-lasting relationships with your cutie and know her a little better. Are you ready to know what most of her friends and relatives have never known about? Let’s go!

When interacting with a girl you feel that the conversation has exhausted itself, you can rely on our list of 300 questions to ask a girl that will certainly light your conversation up. It is very important that you were really interested in knowing the answers for questions to ask a girl. It is better if you write down the questions which you would like to ask. Do not forget that your talk with a girl, which you are interested in, should not look like an interview. Prepare yourself that she will reciprocate the questions you ask her, meaning you should not ask questions, which you personally cannot answer fairly.

For instance, this year, you spent your holidays in the countryside or by the seaside, and you were so impressed with your vacations that you would like to tell an interesting story that happened to you while traveling. In such a case, you should opt for the next questions to ask a girl:

  • Do you like traveling?
  • Do you prefer active or passive recreation?
  • Where did you spend this summer?

After a girl has answered your questions, you can keep the conversation by answering them, too. In such a way, you make the interaction go on, and your dialog will be lively and engaging.

Our lists allow you to choose the most interesting questions to ask a girl, and also they will help you to generate new conversation topics in your head, depending on what you would like to figure out about her.

All non-banal questions to ask a girl are divided into several categories to facilitate your choice.

50 Interesting Questions to Ask a Girl to Get to Know Her Better

Would you like to know a girl better? This selection of interesting questions to ask a girl will help you build a breezy conversation and let the girl see that you are really interested in her – and this is a very good foundation for taking your interactions to the next level.

Question #1. What good has this day brought to you?

Question #2. Who do you engage better with: boys or girls?

Question #3. Do you have a best friend? Who is that: a boy or a girl? How long have you been friends already?

Question #4. Can you save money or do you prefer to spend them at once? What is the most expensive thing you collected money for?

Question #5. Are you fond of traveling? What country do you fancy to visit?

Question #6. What is your Zodiac sign, and do you believe in the compatibility of astrological signs?

Question #7. Do you always manage to do what you have planned to? And how often do you plan your daily routine?

Question #8. Can you keep your word and deliver on promises? And how do you react when somebody fails to uphold their promise?

Question #9. Are you a resentful person? How long can you entertain resentment?

Question #10. If you have a spat with someone but you know that you are wrong, will you admit your guilt?

Question #11. Do you smile often during a day?

Question #12. Does a financial status of a family matter to you? Do you believe that two loving hearts can achieve everything together?

Question #13. Did you have the first love in your school life, and are you still communicating with that boy?

Question #14. Do you have a cherished dream? Do you plan to realize it? When?

Question #15. How would you spend your free evening: would you lie comfortably on a sofa and watch your favorite series or have a party night with friends?

Question #16. Do you think the friendship between a girl and a boy is possible?

Question #17. Do you prefer to wake up early or sleep in? What time do you usually go to bed?

Question #18. Are you a pessimist, an optimist or a realist?

Question #19. How would you react if something went the way you did not want? For example, would you upset if your friends called you and canceled a long-planned meeting, or a concert of your favorite band was postponed to the next year?

Question #20. Do you quickly get used to people and the environment around you?

Question #21. How do you respond to criticism that heads your way?

Question #22. What foods do you like and dislike?

Question #23. Do you have habits which you would like to quit and why?

Question #24. Are you for a healthy lifestyle? Are you into sports?

Question #25. Are there any actions you regret you have ever done?

Question #26. What games did you like playing as a child?

Question #27. What cannot you deny yourself?

Question #28. Are you ready to live abroad for the rest of your life?

Question #29. Do you know what your name means?

Question #30. How did you become acquainted with your best friend?

Question #31. Do you like communicating via SMS?

Question #32. What musical instrument would you like to play?

Question #33. Who do you take after more: your mother or your father?

Question #34. Do you remember the first book that you read by yourself?

Question #35. Do you remember the best moment of your life?

Question #36. Do you know why your parents gave you exactly this name?

Question #37. Do you eat what you want to eat or what is healthy?

Question #38. Do you envy people which are more successful than you?

Question #39. Do you like sunbathing or do you prefer to stay in shadow?

Question #40. Do you like to stay in bed for a bit longer on Sunday mornings?

Question #41. Do you love dancing? What dance styles do you prefer?

Question #42. Are you usually calm or impatient?

Question #43. How do you prefer to interact with people: face-to-face, via a phone or over the Internet?

Question #44. What do you like more: working alone or in a team?

Question #45. How many books do you read per month?

Question #46. Do you consider yourself a good person?

Question #47. How often do you tell lies? Do you lie for a good cause?

Question #48. What traits of character do you hate in people?

Question #49. Do you think you are naive?

Question #50. Do you scold yourself if you do something wrong?

50 Romantic Questions to Ask a Girl You Like

If you like a girl and want to attract her attention, then take advantage of these questions to ask a girl which will help you find out her preferences when it comes to relationships with the opposite sex.

51. What scents of men’s perfume do you like most?

52. What traits of character should your ideal man have?

53. Imagine that your boyfriend and your best friend invite you to go for a walk on the same day. Which one will you choose?

54. How long did your shortest and longest relationships last?

55. What is the most important thing in relationships between a boy and a girl?

56. What do you like most: to give presents or to receive them? What is the best gift that you have ever been given?

57. Do you believe in love, and do you agree that it is possible to love several times during a lifetime? Have you ever loved seriously?

58. What do you think a perfect first date should look like?

59. Imagine you love a boy, but he does not feel the same towards you and offers you to be just friends. Will you agree?

60. Do you love children? How many kids would you like to have in your own family?

61. Do you believe in love from the first sight?

62. Are you a romantic person? If so, how is it expressed?

63. Do you like to keep silence together with your boyfriend when you are alone?

64. How would you like to spend your honeymoon?

65. Did you ever have an office affair or a holiday romance when you traveled abroad?

66. What attracts you most in a man’s appearance?

67. Do you like when a boy massages you?

68. Do you like when your boyfriend calls you by a pet name?

69. What do you think of open relationships?

70. Do you prefer to have meaningful relationships with a boy?

71. Have you ever felt in love at first sight?

72. Was there a boy in your life who did not guess that you liked him?

73. What do you think about jealous men?

74. Do you love hugs? When did you last hug with someone?

75. Do you think that it is the boy who should take the first step?

76. If we had a chance to travel together, where would you like to go?

77. How much time does it take you to start trusting a stranger?

78. Do you like spontaneous meetings?

79. When did you last have a romantic candlelight date?

80. Do you love to look at stars, hugging with your boyfriend?

81. Are quarrels important in the relationships?

82. Is free space important for you when you are in relationships?

83. In your opinion, how often do couples need to show their love in relationships and say “I love you”? Is it important? Or it is better to prove your love by actions?

84. What flowers do you like?

85. When did you last dance a slow dance? Let’s dance?

86. What are the girl’s and the boy’s responsibilities in relationships?

87. Do you think it is necessary to get better for each other every single day in relationships?

88. How much time does it take to find out whether a person suits you or not for further relationships?

89. When did you last confess your love to someone?

90. When you are in love, are you ready to make crazy actions?

91. How can you describe your feelings when you are in love?

92. Over time, even a strong amorousness passes. But what will come after that – a true love or just a habit of being together?

93. What type of boys do you like most: brunettes or blonds?

94. What is more important: intelligence or handsomeness?

95. What do you think about kissing on the first date?

96. What do you think ideal holidays look like?

97. How do you draw attention to yourself?

98. In what setting can a boy win your favor?

99. What compliments do you usually hear from men?

100. What words would you like to be whispered in your ear?

101. What is the very first thing you pay attention to when meeting a boy for the first time?

102. Do you visit dating websites?

50 Deep Questions to Ask a Girl to Make Her Think

Try these deep questions to ask a girl if you do not mind spending a couple of hours reflecting on different subjects together.

103. If you could travel in time, what epoch would you like to return?

104. If you went to a desert island, who or what would you bring with you?

105. If it was the last day of your life, how would you spend it?

106. Do you dream of visiting other planets? Do you believe that alien creatures exist?

107. Do you believe that the soul can transmigrate from one body to another?

108. Did it ever come to your mind that you had already lived before? If so, who were you many years ago, in your opinion?

109. Have you ever witnessed paranormal phenomena? Did you see ghosts or something else what you cannot describe?

110. Did you ever experience situations that seemed to have happened to you before? How often do you feel deja vu?

111. Did you ever have moments when you thought about something, and then it happened after some time?

112. Imagine you like a boy, and another girl also likes him. But this boy cannot decide between the two of you. What will you do in such a situation?

113. If you see that a stranger gets suddenly sick on the street, will you call an ambulance or will you pass by as if nothing wrong had happened? Were such situations in your life?

114. What is more important: emotional or physical intimacy?

115. Were there such situations in your life when you wanted your boyfriend to do something but he hesitated? Did you help him become more decisive?

116. Imagine your friend told you the truth about your common friend. After that, you meet this person, and he lies to you, and you know about this. What will you do? Will you say him that he is lying to you and you know the truth? Or will you save your breath and listen to him as if nothing were wrong?

117. What would you choose: to be rich but lonely or to be poor but happy?

118. How often do you give credence to your intuition? Did it ever let you down?

119. When you see a person for the first time, can you detect at once whether he/she is kind or evil?

120. What motivates you to keep on and reach your goals?

121. If you could change this world for the better, what would you start with?

122. Do you feel when a person makes you a compliment just to flatter you? How do you respond to this?

123. Do you believe in something that nobody else agrees with?

124. Is there any book, film or series that changed your attitude to life?

125. Is there any phrase or quotation that has become your life motto? Why is it so important for you?

126. If you try to make peace with someone but they do not want to make it up with you, will you continue your attempts to put up in some time?

127. What is more important: what you say or what you do?

128. What animal would you like to turn into?

129. What event that has already happened in your life would you like to change and why?

130. Who would play the main character in the movie about your life?

131. In your opinion, what are the main differences between men and women?

132. Do you believe in fate?

133. Where would you like to find yourself in five years?

134. If you had a free plane ticket, where would you fly to?

135. If you were a millionaire, what present would you give to your best friend?

136. If you could create something extremely beautiful, what would it be?

137. If you had five dollars for charity, how would you spend them?

138. If you met a goldfish, what three wishes would you make?

139. Do you have any talents or skills that you do not currently use?

140. What talent would you like to have?

141. How would your life change if you could see the future?

142. Where would you go to get acquainted with new people if you were alone?

143. What did you hanker for ten years ago?

144. Do you want to live forever?

145. Would you like to know the sex of your future baby or would you prefer it to be a surprise?

146. Do you believe that your fate can be predicted?

147. Would you like to learn to read other people’s mind? Whose thoughts would you like to read?

148. Would you like to be cloned?

149. Would you like to start your life all over again?

150. Do you have special places where you prefer to be alone? How often do you come there?

151. Did you have the same dream several times? What was that dream about?

152. Did you ever get in such situations when you could die but survived by a miracle?

100 Good Questions to Ask a Girl to Start a Great Conversation

If the previous lists of questions seem useful to you, then have a look at other 100 good questions to ask a girl and get to know her a little better.

153. Were you in your childhood the same as now?

154. Were you popular at school, and if so, why?

155. Did you have a favorite toy?

156. Did you have secrets from parents?

157. What foreign languages would you like to speak?

158. At what time of a day do you feel the biggest surge of energy?

159. In what sphere would you like to make your name?

160. How would you prefer to spend most of your time?

161. What professions would you like to master?

162. What season do you like most: a summer or a winter?

163. What is the best New Year gift that you have ever received from your parents?

164. What film can you watch over and over again?

165. What book did you read last, and why did you choose exactly it?

166. What famous person inspires you most of all?

167. Who is your favorite actor or actress?

168. Who is your favorite singer or singers?

169. Who is a leader in your family?

170. Do you love to celebrate your birthday?

171. What musical instrument would you like to learn to play?

172. If you had a chance to do a movie, what would it be about?

173. Would you invite me to your birthday party?

174. Would you change your current job for a more interesting but less paid one?

175. Do you have tattoos?

176. Has somebody ever brought you breakfast in bed?

177. Do you like adventure holidays?

178. Do you see colorful or black-and-white dreams?

179. Do you keep a diary?

180. Have you seen any celebrities in a real life?

181. Do you always read all the books to the end?

182. Could you marry a man that is much older or younger than you?

183. Do you go shopping because you need to buy something useful or just because you like the process?

184. Do you put down your ideas?

185. Do you dye your hair?

186. Is it easy for you to apologize?

187. Do you easily cope with slings and arrows of life?

188. Do you like chatting on the phone?

189. Do you love large, noisy parties?

190. Do you feel right when you are in one company with children?

191. Do you like shopping?

192. Have you ever worn not comfortable shoes just because they are attractive?

193. Do you usually finish the job that you started?

194. Have you ever stolen a boy from your best friend? Or vice verse: has ever your best friend taken your boyfriend away from you?

195. Have you ever written stories about yourself?

196. Have you ever composed poems? Have you shown them to anybody?

197. Are you a predictable person?

198. Do you allow your friends to come to your place without a call?

199. Do you get embarrassed when answering the strangers’ questions?

200. Do you usually have difficulty in finding a necessary thing, or is everything in its place in your house?

201. Do you often look in the mirror?

202. Are you an extrovert or an introvert?

203. When you achieve something, do you share your joy with others or prefer to enjoy your success alone?

204. Have you ever had precognitive dreams?

205. Were there situations in your life when nobody listened to you but you turned out to be right in the end? What situations were they?

206. What would you prefer to have: a lovely appearance or high intellect?

207. Do you like to go naked when there is nobody else in your house?

208. Have you ever got a peep of amorous twosomes?

209. Have you ever debunked a betrayal?

210. Have you ever taken a boy with you for clothes shopping?

211. In your opinion, who must dominate in a relationship: a boy or a girl?

212. What do you like most: when a boy talks to you rudely or gently?

213. Have you ever come to a boy on the street to get acquainted with him?

214. How often do people get acquainted with you on the street or in public places?

215. What will you never forgive your boyfriend for?

216. When did you first kiss with a boy?

217. If a man goes wrong, will you give him a second chance?

218. Is there anything that you have long wanted to do but still do not dare to?

219. Have you ever spied on a boy you like?

220. Have you ever noticed that you love girls? Have you ever had romantic relationships with a girl?

221. Are you jealous?

222. If using a 10-score scale, how would you rate your attractiveness?

223. Were there cases in your life when a boy loved you, but you did not feel the same? And vice versa: were there situations when you were deep in love, but he did not return the affection?

224. Is there something that you would like to know about me but do not have the courage to ask?

225. Did you ever have to lie to come off clean?

226. Could you drop everything and flew forever to another country to start your life with a clean sheet?

227. What do you think about changes in your life? Is it difficult for you to change a job, a residence, and a lifestyle?

228. What is your favorite sleeping position?

229. When it comes to competitions, do you prefer to compete with an equal opponent or with a weaker one?

230. What is your superiority over the others?

231. In what clothes do you prefer to sleep?

232. Do you entertain the idea that you could marry a man of a different race, religion or nationality?

233. If you decided to write a book, what would it be about?

234. If you had a tattoo on your body, what would it be and where?

235. How will you name your kids?

236. Does your mood depend on the clothes you wear?

237. Who were you closer with as a child: with your father or your mother?

238. What do you like most: sunrises or sunsets?

239. How long would you like to live?

240. How did your parents meet?

241. How do you feel when you are teased?

242. What was the most positive change in your life?

243. What are the strongest and weakest sides of your character?

244. What do you like more about the games: their process or their results?

245. What traits of character do you like most about yourself?

246. What was your maximal weight?

247. What are the good qualities that you owe to your family education?

248. What kind of underwear do you like most? Does its color matter to you?

249. What are your favorite male and female names?

250. What is the silliest thing you have ever done in your life?

251. What were you like in your childhood: an enfant terrible or a calm child?

252. What do you usually say to yourself when you panic?

25 Funny Questions to Ask a Girl

If a beauty you communicate with has a sense of humor, and you want to turn a serious conversation into a positive and joyful chatting, then take advantage of these 25 funny questions to ask a girl.

253. You wake up in the morning as if nothing had happened and suddenly find out that there is a spider creeping on your face! What will you do?

254. You stand at a bus stop waiting for the bus, and suddenly a strange boy comes to you, kisses on your cheek, and goes immediately away, without saying a word. How will you react?

255. You are in public transport wearing a short skirt. Suddenly you notice that there is a visible hole in your stockings. Will you continue your ride as if nothing had happened or will you get off on the next stop to buy a new pair of stockings in the closest store?

256. The guy you know has hurt your feelings, and you could not forgive him for a long time. But you decide that you will forgive him on his birthday if you slam his face into a birthday cake. On the birthday, this guy has two cakes (a cream and a chocolate) to atone for his offense. Which of the cakes will you eat together and which will you slam his face into?

257. What funny nickname were you called as a child?

258. Your younger sister has a birthday. And your family decides to have a themed birthday party. Each of you should have an unusual dress. Everybody took their costume so that there are only 2 variants left: the hot-dog dress and the fat ballerina dress. Which one will you choose?

259. Can you imitate somebody’s accent or voice? Suppose you have such an opportunity, whose voice would you like to imitate and what for?

260. What would you prefer: to be able to fly or to get invisible?

261. What other things can you simultaneously do while talking on the phone?

262. How do you clasp buttons: from up to down or vice versa?

263. At what price would you agree to shave bald?

264. How do you prefer to eat ice cream?

265. What is your funniest photo??

266. What is the most foolish thing you have ever purchased?

267. What was the funniest record in your school diary?

268. What is the funniest declaration of love you have ever had?

269. When you put the shoes on, which leg do you start with: left or right?

270. What cartoon character or superhero can you compare yourself with?

271. Would you like to change places with anybody or become a man for 1 day?

272. Would you like to be a magician? Whom would you turn into a frog, and whom – into a charming prince?

273. Can you touch your nose with a tip of the tongue?

274. Do you sing while taking a bath?

275. Do you talk in your sleep?

276. What would you do if you met your twin?

277. Do you have a habit of going to the last page without reading the book to the end?

25 Funny Would You Rather Questions to Ask a Girl

We also prepared a list of questions that will help you turn your interaction into an interesting and enjoyable game of questions. If you want to laugh loudly together, this pack of would-you-rather questions to ask a girl is everything you need.

278. Would you rather be a little pig or a huge rat?

279. Would you rather have a mustache or bushy eyebrows?

280. Would you rather have 20 cm nails or 20 cm eyelashes?

281. Would you rather have male arms or male legs?

282. Would you rather be a toilet brush or toilet paper?

283. Would you rather kiss a boy with big lips or big eyes?

284. Would you rather shave bald or shave your eyebrows off?

285. Would you rather wear a fur coat in Sahara or a swimsuit in Antarctica?

286. Would you rather laugh without a stop for the rest of your life or would you rather blink eyes for the rest of your life?

287. Would you rather be married and have two husbands or would you rather be in a marriage where your husband has two wives, one of which is you?

288. Would you rather wear only clothes without shoes or would you rather wear only shoes without clothes for the whole life?

289. Would you rather be a cross-eyed model or a large-eared wealthy lady?

290. Would you rather eat 5 dollars in order to get 100 dollars or would you rather give 100 dollars to someone who can eat five dollars?

291. Would you rather have a piggy nose or shark teeth?

292. Would you rather have the same eyes as your grandfather or your grandmother?

293. Would you rather wear body-hugging or oversized dresses for the rest of your life?

294. Would you rather go to the toilet that is very dirty and stinky or would you rather go to the toilet that is clean but with a huge hungry alligator sitting there?

295. Would you rather not wash your hands for three months or not wash head hair for three months?

296. Would you rather wear a tutu during a month or wear one holed sock during a month?

297. Would you rather eat cat food for a whole month or eat 100 grams of fresh grass at once?

298. Would you rather sleep in a baby carriage until the end of your life or wear diapers for the rest of your life?

299. Would you rather answer questions by spouting poems or by singing songs?

300. Would you rather bite a live toad at any part of its body or ride a sheep for 100 meters?

301. Would you rather have a body like that of an Afro-American and a head like that of a European, or have a head like that of an Afro-American and the body like that of a European?

302. Would you rather take petrol in your mouth and spit it out or eat a live spider?

What else questions can you ask a girl?

On our website, you can find even more interesting and funny questions to ask a girl. These include:

  • 200 best would you rather questions to ask a girl – If you want to have a good time together, then these questions will definitely perk your moods up.
  • 150 deep questions to ask a girl – if you want to delve into a deep conversation and better understand the inner world of your interlocutor, this series of questions is the real thing.
  • 700+ never have/ ever questions to ask a girl – is another pack of unusual questions that will help you know your girl and friends a little better.
  • 500+ truth or dare questions to ask a girl – is a question game with actions и.

Conclusion and tips

To ask means to demonstrate that you are interested in a girl and are willing to devote her all your time solely to her. But if you constantly ask questions, she will soon get tired of you and stop the conversation. Our tips will help you to avoid this:

  • Some questions should be asked only in a particular context. You should choose an appropriate situation and ask a girl what is most relevant at the moment.
  • React to the girl’s answers. Express your emotions. Make her compliments. Sometimes you can even make a kind joke about her, where convenient.
  • A good question is that which makes a girl think over the answer. Therefore, when you find a point where your interests coincide (such as favorite films, books, hobbies, etc.), try to ask what you both are interested in.
  • When you get an answer to the posed question, continue to ask directive questions on this subject or keep on the topic of your conversation. If you do so, your interaction will be full and engaging, and you will also notice that a girl gets interested in you, too.
  • If you see that one of your questions provokes interest in the girl, let her speak her mind. Listen to her attentively, and when she stops speaking, it means that she has fully answered the question and waits for you to continue the conversation. You can keep on the topic or ask what you have not yet asked on this or that subject.
  • Try to avoid monologues, when only she talks and you keep silent. If she has answered your questions for more than 5 minutes, then let her have a break for a while and take the initiative of a storyteller. Only by doing so, can you ensure a full information exchange and turn a monolog into a dialog.
  • You should be quite brave to ask the girl questions. Being brave and open describes you as a decisive person with transparent intentions.
  • When it comes to raising questions, you should not only prepare for that thoroughly but think over question formulations, too. To do so, you should build the scenario of your meeting and prepare a number of questions you would like to ask, but remember that she will definitely readdress these questions to you, making you answer them too. So choose only such questions which you personally are willing to answer.
  • As a rule, the purpose of a dialog, that always follows the “question-answer” scheme, will be the analysis and investigation of your talk partner. It means that you should pick up such questions which will help you to know the maximum information about her within a limited time. By doing so, you will quickly reap the benefits of your interaction.
  • To have more reasons for interaction, try to spend more time with the girl. Go to the cinema, get together with friends, take your pets for a walk, go to a gym, arrange picnics on weekends or go to the countryside. With having many activities to do together, you will not face any difficulty in finding the right questions to ask a girl. Events, taking place in your life, will help you discover new topics for communication, and you will never get tired of each other.