Trying to figure what the best questions to ask the girl you like can get pretty frustrating. There are a billion different things to ask or talk about, but we’ve decided to make it simple for you by setting up a list that will put you on the right path. Make it easy to talk and keep a deep conversation flowing, gentleman.

    The goal of these questions are to find out if she interests you. Not only that, you will become much better at conversing. These questions will allow you to be real, more thought provoking and giving a deeper insight into her and probably yourself too(She’ll most likely reciprocate the question). So whether you’re looking for random questions or some with substance, here is our list!

    *Updated September 2017*

    250 Best Questions To Ask The Girl You Like

    1. What type of guys do you feel attracted to?
    2. Where do you see yourself in the next 5 to 10 years?
    3. What is your definition of emotional intimacy?
    4. What has been the most embarrassing moment in your life?
    5. Which type of people you don’t like?
    6. Do you believe in true love?
    7. What characteristics do you desire in your guy?
    8. Have you ever had to make a decision that has greatly impacted your life?
    9. Where do you consider good places for couples to be romantic?
    10. Would you be okay if I accept that I still have feelings for my Ex?
    11. Are there people that don’t like you?
    12. What are your hobbies?
    13. Tell me your 3 weaknesses.
    14. If today was your last day, how would you spend it?
    15. What is the most romantic experience you have ever had?
    16. Would you be willing to break the law to save your family member?
    17. What excites you about (enter the name of the city where you are on the date)?
    18. What would you rather be; extremely attractive and poor or extremely rich and less attractive?
    19. What would you rather have; win a lottery or have true love?
    20. How would you like to spend $10 million?
    21. If you boyfriend cheats on you, what would you rather do; cheat on him or slap him?
    22. Who was your first crush?
    23. If I was an ice cream, how would you eat me?
    24. Describe your best holiday experience, especially the features that make it the best for you.
    25. What is your idea of true love?
    26. Have you had any fears in your childhood?
    27. What are your favorite movies from your childhood?
    28. Are you close to your family?
    29. How many siblings do you have? Do you like them?
    30. What makes you smile?
    31. If you are given the opportunity to visit any country in the world, which one would you visit?
    32. Tell me about the weirdest relationship you have had.
    33. Tell me about the most romantic experience you have had.
    34. What is your favorite color?
    35. Who is your favorite Hollywood actor/actress?
    36. What is the best gift you have ever received?
    37. What is the most thoughtful gift you have ever given?
    38. What are you nicknames?
    39. Are you a morning person or a night owl?
    40. What combinations of fixing makes your perfect burrito?
    41. At what age did you start enjoying coffee?
    42. What are two of your bucket list items?
    43. While growing up, were you closer to your dad or your mom?
    44. Do you like adventures?
    45. Do you get bored easy?
    46. In daily life, do you prefer routine or spontaneity?
    47. Do you believe in love at first sight?
    48. Can you describe your first kiss?
    49. What is the habit you are most proud of breaking?
    50. If you are made the ruler of the world, what would you change?
    51. Tell me 3 physical features you are complemented a lot on.
    52. What is the funniest moment of your life?
    53. Do you have any favorite quotes from successful people?
    54. Which genre of books do you like the most?
    55. Do you have any favorite writers?
    56. Which TV series do you like watching?
    57. Are there any causes you strongly believe in?
    58. Name any 5 things you hate and tell me why.
    59. What is the worst injury you have ever had?
    60. What is your favorite activity for the New Year’s Eve?
    61. What questions would you like me to answer?
    62. To you, what do a perfect life consists of?
    63. Is there an age where you think being a virgin would be awkward?
    64. What is your biggest goal in life?
    65. Do you think you can have emotional intimacy without physical intimacy?
    66. Do you have feelings for your Ex?
    67. Have you ever kept a New Year’s resolution?
    68. Do you have any favorite catchphrases?
    69. Where is your happy space?
    70. What is in your fridge right now?
    71. Have you ever been out of the country?
    72. Describe your ideal vacation.
    73. How long did you most intimate relationship last?
    74. Do you regret any of those intimate experiences with that person?
    75. What are your point of view of the world? Liberal/conservative, atheist/spiritual
    76. What are your thoughts about having relationship with the same gender?
    77. Do you follow your mind or heart?
    78. Do you have any opinion on politics?
    79. Do you like playing any sports?
    80. Do you like watching any sports?
    81. Do you think past matters in a relationship?
    82. Have you ever had a one night stand?
    83. Do you believe in love at first sight?
    84. Do you believe in soul mates?
    85. Do you like pets?
    86. Do you have any pets?
    87. What is the weirdest thing about you to most people?
    88. What do you like the most about yourself?
    89. Do you like to dance?
    90. Which is your favorite song?
    91. Who is your favorite fictional character and why?
    92. If you could meet a famous dead person, who would you meet?
    93. How do you think your friends would describe you in three words?
    94. If you could have a superpower, what would it be?
    95. What is the best advice you have ever received?
    96. Are you sexually open minded?
    97. Have you ever experimented with drugs?
    98. Have you ever kissed a girl?
    99. What is your biggest goal in life?
    100. What impact do you want to leave on the world?
    101. What is your star sign?
    102. Where would you most like to travel to?
    103. What’s your favorite childhood memory?
    104. What’s your favorite food?
    105. What’s your favorite season?
    106. Do you have any brother or sisters?
    107. If you could only eat one food for the rest of your life, what would it be?
    108. If you had to go to into space for six months, which three items would you take with you?
    109. Which celebrity is your style inspiration?
    110. What’s your idea of an ultimate romantic evening?
    111. If you could spend a day as any celebrity, which one would it be?
    112. Who’s your favorite fashion designer?
    113. If someone were going to cook a meal for you, what would you like him or her to cook?
    114. What was the last thing you binge watched on Netflix?
    115. If you could see any band live right now, who would it be?
    116. What’s your favorite season?
    117. What’s your least favorite food?
    118. Are there any books you want to read?
    119. What’s your favorite book of all time?
    120. Could Rose have moved over on the board in Titanic to let Jack on?
    121. If you could live in any other time period, which one would it be?
    122. What’s your favorite sport?
    123. What’s your least favorite sport?
    124. If there was only one day left on Earth, how would you spend it?
    125. When you have a day off work, how do you spend it?
    126. If you could be an animal for a day, which one would you be?
    127. Which female celebrity is your biggest role model?
    128. What really annoys you?
    129. What makes you dislike a person?
    130. When you first meet a person, what do you tend to notice about them?
    131. What are the top three items on your bucket list?
    132. If you won the lottery tonight, how would you use the money?
    133. Do you drink alcohol?
    134. If you do drink alcohol, what’s your favorite cocktail?
    135. Are you a morning person or a night owl?
    136. What’s the one meal you want to cook?
    137. Can you bake at all?
    138. What inspired you to choose your job?
    139. If you could create the perfect pizza, which toppings would you add to it?
    140. What’s the best gift anybody’s ever given to you? Why?
    141. Is there a topic you feel really passionate about it?
    142. What is your proudest achievement?
    143. Do you have a bad or funny dating story you want to share?
    144. Is there an experience you’ve always wanted to try?
    145. What would make you never want to see a date again?
    146. If you could choose between Christmas and Easter, which holiday would you choose?
    147. If you could buy one item of designer clothing, what would it be?
    148. What’s the one New Year’s resolution you plan to stick to this year?
    149. If you could do any job, what would it be?
    150. Which job would you never, ever do?
    151. Are you a spontaneous person or do you like staying organized?
    152. What’s the craziest thing you’ve ever done?
    153. Which three words would your family use to describe you?
    154. Are you into salty or sweet food?
    155. What’s the best piece of advice your grandma ever gave to you?
    156. If you could go back five years, what would you tell your past self about the future?
    157. Is there a family tradition you enjoyed as a kid?
    158. If you could go on a road trip tomorrow, which three places would you have to visit?
    159. What’s the worst job you’ve ever had and why?
    160. When you were younger, what did you think you’d do when you’d grow up?
    161. Do you have a secret talent?
    162. What’s a talent you’d like to try and adopt?
    163. If you could choose an actress to play you in a movie, who would it be?
    164. Do you think you look like anybody famous?
    165. Are you more like your mom or your dad?
    166. What characteristics do you look for when you’re choosing a friend?
    167. What are the three qualities you look for most when you’re choosing a partner?
    168. If you were stranded on an island, which person would you want to take with you?
    169. Are you more of a city girl or a country bumpkin?
    170. Do you think you could cope without your cell for a week?
    171. If you had to live with just three apps on your phone, which ones would they be?
    172. What’s your idea of a perfect day?
    173. If you went to college, what was your major?
    174. Is there anything you regret career or education wise?
    175. Did you enjoy high school?
    176. What job do you have?
    177. Would you rather watch a movie or watch a TV series?
    178. Do you have any cool trips coming up with your friends or family?
    179. What’s your favorite book?
    180. What’s the most embarrassing nickname you’ve ever had?
    181. How many family homes have you had?
    182. What drives you most in your career?
    183. Do you think you’ll stay in the job you’re currently in?
    184. Which U.S. city could you never move to?
    185. If you had to choose one city to move to tomorrow, what would it be?
    186. Would you rather live alone or have a roomie?
    187. What’s the one thing someone could do to stop you pursuing a relationship with them?
    188. Have you ever managed to stick to a New Year’s resolution?
    189. What’s your morning routine like?
    190. How do you like to stay fit?
    191. When you’re feeling sad, where do you go to make yourself feel happier?
    192. If something’s made you mad, what do you do to calm down?
    193. Are you afraid of flying?
    194. Would you be more impressed by a grand gesture or a small one?
    195. Which country would you least like to visit?
    196. Which subject were you really good at at school?
    197. What was your worst subject at school?
    198. Was there a teacher who inspired you the most at school?
    199. What was your favorite toy growing up?
    200. If you could return to one period of your life, which one would it be?
    201. What do you feel is the luckiest thing that’s happened to you?
    202. If you had a superpower what would it be?
    203. How would you use your favorite superpower?
    204. Is there a movie or book that’s really moved you?
    205. What do you think is the most irritating song?
    206. Which celebrity irritates you the most?
    207. If you could say one thing to Kanye West, what would it be?
    208. What do you feel is your greatest strength?
    209. Are you the type of girl who cries at a sad movie?
    210. What is your favorite vegetable?
    211. If you could dress in the style of one decade, what would it be?
    212. Do you like to dance?
    213. Are there any mistakes you’d never want to be again?
    214. Would you rather be twice as rich or twice as happy?
    215. Would you rather be twice as smart or twice as attractive?
    216. Tell me about a time you felt really nervous?
    217. Is there anything weird that really annoys you and you can’t explain why?
    218. Which friend do you think knows you the best?
    219. Do you know all the dance movies to any cheezy songs?
    220. What do you think is the best TV show of all time?
    221. Would you rather ask permission to do something or apologize for doing it?
    222. Would you rather have unlimited love or money?
    223. Which song have you listened to the most?
    224. Which celebrity would you like to trade lives with?
    225. What embarrassing story do your friends still tease you about?
    226. Do you prefer going to parties or spending time with a couple of people?
    227. Do you like surprise parties?
    228. What’s the worst age you’ve been so far?
    229. If you could be any cartoon character, which one would you be?
    230. What scares you the most?
    231. If you could choose three people to have dinner with, dead or alive, who would it be?
    232. Do you like watching the news?
    233. Are you a fan of politics?
    234. Who did you vote for in the last election?
    235. If you were a guy for a day, what would you do?
    236. Do you think it’s easier being a guy or a girl?
    237. What’s the nicest compliment you’ve ever received?
    238. What’s the weirdest thing anybody’s ever said to you?
    239. Who’s the strangest person you know?
    240. Who’s the quirkiest person in your family?
    241. If you could marry a fictional character, who would you choose?
    242. Do you listen to your head or your heart?
    243. Do you always take your parents’ advice?
    244. Have you ever done anything illegal?
    245. What do you want to be doing in five years’ time?
    246. Do you still talk to the person you had your first kiss with?
    247. Do you cry at weddings?
    248. Who’s your celebrity crush?
    249. Would you choose to have the power to read someone’s mind?
    250. Did you ever cheat on an essay or a test?
    Taylor

    Taylor

    Technology has affected his generation like no other. His life experience has brought him to every avenue of life and writes about the tech that is involved.
    Taylor

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