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Questions To Ask A Girl: 250+ Mind-Blowing Ways To Break The Ice

Questions To Ask A Girl: 250+ Mind-Blowing Ways To Break The Ice

When you’re out and about with the guys, there’s hardly anything you aren’t comfortable talking about. You spend hours debating over sports, PlayStation games, and your friend Jason’s weird rash he acquired after a night out. But, what are some questions to ask a girl?!

You can’t ask her about De Bruyne’s midfield display in the latest Manchester City game. Everyone knows girls hate talking about sports – even though she would probably tell you that was De Bruyne’s best performance of the season so far… Don’t worry, that was just sarcasm.

Anyway, it’s completely normal to feel all sorts of nervous when you’re talking to someone you really like. Whether you’re making small talk with your cute neighbor across the hall or you’re trying to make a move on a girl you locked eyes with at a bar, that awkward silence seems inevitable.

Or, does it? Think about it, when you ask her something along the lines of “what’s up” or “how’s it going” you’re not leaving her much choice to say anything other than “nothing much.” Instead, hit her with your best “what’s the worst pick-up line you’ve ever heard?”

Not only are you going to make her laugh and charm your way into her heart, but you’re also going to make her go on an entire rant about weird things guys have said to her before you appeared and swept her off her feet. It’s a win-win situation, don’t you think?

This must be your lucky day because we’re bringing you a bunch of mind-blowing questions you can ask a girl in all sorts of situations – when you’re texting or talking in person, when you’re trying to score a date or when you’re already on a date, and when you’re doing everything in between.

Questions to ask a girl when you’re texting

Questions To Ask A Girl 250+ Mind-Blowing Ways To Break The Ice

Find me a guy who’s equally skilled at making a girl smile at a bar and making her blush over a simple text message? Let’s be honest, most guys can only do one of these things, and making her blush over a text typically isn’t the one we’re talking about.

The art of flirting and romancing a girl over a simple text has brought many guys to their knees. One poorly worded text or one wrongly interpreted emoji can undo every “he’s so charming” and “he’s so funny” you’ve earned until that moment. It’s a tough world out there, guys!

But, once you figure out how to swoop her off her feet with the right combination of compliments and questions… You will become the master of charming your way into the heart of any girl you lay your eyes on. You might think that sounds a bit exaggerated and dramatic, but it’s not.

And, you have nothing to worry about if you’re not the most skilled conversationalist in the dating department. We’ve got your back with a bunch of questions you can ask a girl when you’re texting your way into her life. Grab your phone and get to work, why don’t you?

Make her smile with these quirky questions

1. Are you a pineapple on pizza type of girl or are you normal? *Bonus points if you send a picture of your favorite pizza toppings.

2. Are you Italian? Great, what’s your stand on the ketchup and pasta debate?

3. Do you have a favorite restaurant? How funny, that one’s my favorite, too. Would you like to join me for dinner this weekend?

4. What’s one book you’ve read AND LIKED, but you’re too embarrassed to admit because everyone else hated it?

5. While we’re on this topic, what’s one movie you’ve watched AND LOVED, but decided to keep your mouth shut because everyone else hated the cast and the acting?

6. What’s your favorite childhood cartoon? We should watch it together so that you can show me what the fuss is about, don’t you think?

7. What’s your favorite Disney movie? And who’s your favorite Disney character?

8. Have you ever dressed up as one of your favorite Disney characters for Halloween? Omg, can I see the pictures, please?

9. How do you feel about my outfit? I was thinking about changing my shirt, what do you think? (Then take the opportunity to send her a selfie.)

10. How do you feel about me drinking my coffee ALONE on a Sunday afternoon? *Send her a picture as proof and ask her to join you.

11. What are your plans for today? Weird, I can’t seem to find my name anywhere on the screen, I must’ve understood something wrong.

12. What was the most delicious thing you ate today? Would you mind letting me change your answer? I happen to know a really good place…

13. What does an ideal Sunday look like for you? Weird, those were my exact plans. Care to join me?

Make her blush with these frisky questions

14. Where would you rather be right now – at work doing whatever you’re doing or at a cafe having coffee with me? You’re allowed to take a break during the day, right?

15. What three things would you bring on a desert island with you? Funny, I can’t seem to find my name on the list…

16. When are you free? And don’t give me that “I’m never free, I’m always expensive” answer because I would really like to take you somewhere special. Are you in?

17. What’s your New Year’s resolution? Mine’s to charm my way into your heart. *Bonus points if you add a couple of heart emojis

18. What are your plans for the weekend? Would you mind if I joined you, or if we made completely separate plans for just the two of us?

19. Where would you want to be right now granted you could be anywhere in the world? Funny, I was hoping you’d say in my arms but I guess Paris works, too.

20. What are you working on at the moment? Weird, and here I was thinking you were working on asking me out for a date later this week.

21. Incredibly important question alert! Did you smile when you received my message or did all my efforts go to waste?

22. What’s the best question you can ask a girl when you’re trying to make her blush?

23. Well then, what’s the worst question you can ask a girl when you’re trying to impress her with your charm?

24. “What would you do if I was with you right now?” That’s exactly the type of question I would never ask a girl if I was trying to impress her with my charm. But, umm, is it working?

Get to know her better with these thought-provoking questions

25. What would you ask a guy if you knew his answer would be “yes” without a doubt?

26. What’s the first thing you notice when a guy approaches you? Asking for a friend…

27. What’s your biggest red flag when it comes to dating a guy?

28. And what’s your biggest green flag when it comes to dating a guy?

29. What’s one thing you’re scared of even when you know it’s completely irrational? I’m not talking spiders, I’m referring to something along the lines of a zombie apocalypse or a deathly virus that wipes off half of the planet…

30. What’s one thing you’re so terrified of you can’t even watch it on the big screen?

31. What’s the last movie you’ve seen? Can you imagine you’re a movie critic and you’re trying to tell the world why they should check it out? Great, you have fifteen seconds to send me your answer.

32. What was the last restaurant you visited? Can you imagine you’re a food critic and you’re trying to tell the rest of the world why they SHOULDN’T check it out? Great, you have thirty seconds to send me your answer.

33. What’s one thing that keeps you up at night? One thing that makes you go “here we go again”?

34. What’s one thing you’re stressed out about but you would never admit to anyone because you don’t want to be that girl? Trust me, you’re free to be that girl when you’re talking to me.

35. What does a day in a life of *insert her name* look like? I’m serious, I’m ready to learn everything about you.

36. What does your dream date look like? A cute picnic by the river or a romantic dinner in the big city?

Questions to ask a girl when you’re talking face-to-face

Questions To Ask A Girl 250+ Mind-Blowing Ways To Break The Ice

While most guys do have a better chance at swooping a woman off her feet when they’re talking face-to-face, that doesn’t mean that most guys know how to use that chance to their own advantage. Don’t shoot the messenger, the messenger’s just trying to help.

Let’s not forget about that time you froze up and uttered a barely intelligible “hey” when Jessica from the marketing department decided to make a move on you. Don’t get me wrong, even the most confident of guys forget their name when their crush walks into the room so Jessica didn’t stand a chance…

Anyway, there are times in your life when you have to get your act together and ignore that little voice inside your head that’s saying “you can’t do this.” We’re here to help you figure out the hows and whys of the best face-to-face interaction with a girl you’ll ever have in your life.

Forget about saying things like “hey”, “nothing much”, and “how about you”. There’s hardly anything a girl can say after you hit her with these incredibly lazy conversation killers. Trust me, you have a better shot at scoring a date after you tell her she looks horrible than after you tell her you’re “good”.

Don’t worry, there are plenty of thought-provoking questions you can ask a girl when you’re feeling stuck. Pick your favorite and see what happens when you give her the space to talk about something other than the weather. Let’s dive in!

Test the waters with these intriguing questions

37. Who has the biggest influence on you? And, I’m not talking about TikTok influencers like Addison Rae, I’m talking about people whose content has inspired you to become a better person or to do something better with your life.

38. Who’s one person in your life you can always rely on? One person you can call in the middle of the night when you need someone to bail you out of jail or take you to the nearest McDonald’s because you’re craving a BigMac?

39. What would happen if you received a letter from Hogwarts? What would be your reasons to accept and what would be your reasons to decline?

40. What are your favorite emojis and what do they say about the type of person you are?

41. What’s the last photo you took on your phone and do you have an interesting story to explain why you took it? If you don’t, you can totally make one up to make it seem more important than your average selfie.

42. What’s one movie or TV show character you seem to relate to the most? Mine’s Ross Geller from the Friends and wouldn’t it be hilarious if your’s was Rachel Green?!

43. What do you think, what were you like in your past life?

44. What’s one song you could listen to on repeat for the rest of your life?

45. What’s one song lyric you relate to the most at this stage of your life?

46. What’s the best period you could travel to if you found a way to travel back in time?

47. While we’re on the topic, what’s the worst period you could travel to if you found a way to travel back in time?

Make a good impression with these gripping questions

48. What do you prefer: the past or the future?

49. What vegetable would you describe yourself as, and why?

50. What fruit would you describe yourself as, and why?

51. What’s the best question to ask a girl when you’re trying to make a good impression on her?

52. Would you ever change your name, and if you would, what would you change it to?

53. What’s your favorite animal?

54. What animal sound would pick if you had to pick a sound you could use for the rest of your life instead of your own voice?

55. Which animal would you make a documentary about, and what would be the title of that documentary?

56. Which animal would make a documentary about you to show how you’ve been treating them for the past couple of years? Mine would be a spider and it would be a documentary about a weird human that screams and cries every time he sees one.

57. Which three words would your dog use to describe you?

58. Would you ever agree to fly to space? What would be the main reason for your decision?

59. What’s the first thing you would do the moment you arrived at your destination in space?

60. What’s the first thing you would do the moment you figured out you were in a zero-gravity zone?

61. What’s your opinion on aliens? Do you believe in them, have you ever looked up any documentaries about them, and have you ever been abducted by them?

62. What would you rather experience: an alien abduction or a zombie apocalypse?

63. What’s your least favorite planet and why?

64. What’s your favorite planet and why?

Make her giggle with these cheeky questions

65. Do you prefer sleeping alone or with someone by your side?

66. How many dates before a guy gets to kiss you for the first time?

67. What’s the worst question to ask a girl when you’re trying to make her giggle?

68. What’s the best question to ask a girl when you’re trying to make her giggle?

69. What’s one thing a guy should know about you before he asks you out on a date?

70. What’s one thing a guy should do to get you to agree to go out on a date with him?

71. What’s the perfect location for a date?

72. How does it feel to be the most beautiful girl in the room?

73. How does a guy like me compete with other guys standing in line to get your attention?

74. What are your plans for tonight and are you planning on bringing a plus one?

75. Do you believe in love at first sight or do you need me to walk past you once more? Be honest, how many times have you heard that one before?

76. Do you have a favorite restaurant to have breakfast at or should a guy just bring you some coffee and pancakes in bed?

77. How many times have you thought about kissing me tonight?

78. What do you think, how many times have I thought about kissing you tonight?

79. What would you say are the three most attractive things about you? If you mention any of the ones that are on my mind right now, I might just have to buy you a drink.

80. What would you say are the three most attractive things about me?

Questions to ask a girl when you’re on a date

Questions To Ask A Girl 250+ Mind-Blowing Ways To Break The Ice

Guys, guys, guys… You have it pretty easy when it comes to leaving a good impression when you’re on a first date. While girls have to spend hours plucking every rogue hair they have on their bodies, getting their glam on, and picking the right outfit, you just have to show up on time.

And if you iron your shirt, pick up the bill, and avoid talking about your exes – you are guaranteed to have her eating out of the palm of your hand by the end of the night! But, when it comes to scoring a second date you have to brush up on your flirting techniques and make the conversation a bit more interesting.

And no, you’re not leading the conversation if you’re talking about yourself for the majority of the night or when you’re adding a quick “how about you” after answering her carefully crafted questions. Sorry to disappoint you, but you’ll have to do a bit more work than that.

The entire dating dilemma comes down to one question: “Did she like you enough to agree to go on a second date with you?” And you have a higher chance for a positive answer if you make sure to listen, engage in the conversation, and ask her questions that will give her the opportunity to speak.

And if you’re not the best guy in the game, we’ve prepared a couple of ideas you can use to your own advantage. Scroll down, find something you like, and show up on your next date with nothing but confidence and a hidden ace up your sleeve.

Start the night with these engaging questions

81. What’s something you can’t live without, besides me?

82. When was the last time you laughed so hard you were genuinely afraid you were going to pee your pants?

83. While we’re on the topic; when was the last time you peed your pants?

84. What would you bring to a desert island if you were stranded there with me?

85. What would you bring with you if you woke up one night and realized your house was on fire?

86. When was the last time you traveled alone and how did you feel?

87. What’s the craziest travel story you have?

88. What’s the craziest, most out of character thing you’ve ever done? And most importantly, have you lived to regret it?

89. What’s your biggest pet peeve in a relationship?

90. What’s your biggest pet peeve on a date? And would there be a chance for me to score a second date on the off chance nothing is annoying about me?

91. What’s one talent you would love to have just because it would make you incredibly happy?

92. What’s one talent you would love to have just because it would make you a lot of money?

93. What’s your favorite thing to do when you’re home alone?

94. What’s your favorite place to visit alone? A place that doesn’t make you feel like everyone’s staring at you and judging you for being there without anyone by your side?

95. What’s your idea of a perfect weekend? What would you say if I told you that’s exactly what I had in plan for this Sunday?

96. What’s on top of your to-do list right now? Let’s do it together!

97. What’s your go-to song when you’re looking for something sad?

98. What’s your go-to song when you’re looking for something to dance to?

Win her over with these sweet questions

99. What’s one book you would recommend to every guy you’ve ever met?

100. What’s one movie you would recommend to every girl you’ve ever met?

101. What does it feel like to be in the center of attention everywhere you go?

102. What does it feel like to be the most beautiful girl most guys have ever seen in their life.

103. What question do you ask a girl when you’re trying to win her over?

104. What’s the last thing that made you so excited you couldn’t fall asleep?

105. What’s the last item you’ve purchased? And would you give me a recommendation for it?

106. What’s the last song you’ve heard on the radio and thought “I have to listen to this song again as soon as I come home?”

107. What would your “Miss America” gown look like?

108. What would be your “Miss America” talent?

109. If you could invite three celebrities, dead or alive, to your house for dinner, who would you invite?

110. If you could date one celebrity, dead or alive, who would you date?

111. What does Ryan Reynolds have that I don’t!? *Bonus points if you make her laugh!

112. What’s the most spontaneous thing you’ve ever done?

113. What’s one thing you can’t live without?

114. What’s the best present you’ve ever received? Who was it from?

115. What’s the one present you would love to receive for your next birthday?

116. What’s something you’ve never dared to do but secretly dream of doing?

117. What’s one piece of advice you would give your fifteen-year-old self if you could?

118. What’s something you’re passionate about?

119. What’s something you would love to change about yourself? Physically, mentally, emotionally?

Spice things up with these playful questions

120. What’s your favorite time of the day? Good, I just wanted to check when’s the best time to ask you on a second date.

121. Have you ever kissed a guy because you lost a bet?

122. When was the last time you were on a nude beach? And would you consider going there again?

123. How many days have you gone wearing the same underwear? You’re not allowed to lie your way out of this one!

124. Which celebrity do you think you look like?

125. Which celebrity do you think I look like? *Fingers crossed she says Ryan Reynolds!

126. Which celebrity do you have a crush on? Honestly, if you don’t say Ryan Reynolds I’m going to be offended.

127. What’s one thing you would love to change about me right off the bat?

128. What’s one thing you wouldn’t want me to change about myself?

129. What’s the best question to ask a girl when you’re trying to spice things up and score a second date?

130. What’s more important to you: beauty or brains? *Bonus points if she compliments you and says you have both.

131. Do you prefer being called “baby” or “babe”? Asking for a friend.

132. How on Earth does someone like you end up being single? You’re the most beautiful girl I’ve ever seen. *A cute compliment never hurt anybody.

133. How does a guy like me ask a girl like you on a second date?

134. What’s in your mind right now?

135. What’s on my mind right now?

136. What would you say to a guy who’s wondering whether he can kiss you?

137. What would you say if I told you I wanted to kiss you this entire time?

138. What’s your biggest deal-breaker on a date?

Questions to ask a girl when the conversation runs dry

Questions To Ask A Girl 250+ Mind-Blowing Ways To Break The Ice

When you’re trying to gauge a girl’s interest never be the guy who thinks all his work is done the moment he sends the “hey, how are you” text or the moment he utters the “did you fall from heaven” line. While these might be horrible conversation starters, that’s still pretty much all they are.

Don’t start a conversation with a girl (or anyone for that matter) if the only thing you’re capable of is hitting her with one-word responses, the dreaded “K” texts, and occasional questions that don’t get any more interesting regardless of how much effort she puts in.

While it’s completely normal to have your conversation run dry because you’re nervous or because you’re so enamored with this girl already that you just want to take her home and look at her for the rest of your life… You should put a bit more thought into what you say and how you say it.

So, what’s the best way you can avoid those moments of awkward silence? For starters, ditch the one-word responses and questions like “how about you.” Listen to what she’s talking about, show interest, and ask her something that relates to what she just said.

The moment you feel stuck and don’t know what else to add to the conversation, feel free to suggest one of these fun questions games. Not only are they such a great way to learn more about each other, but they’re also a foolproof way to reduce the pressure of knowing what to say at all times.

Make things more interesting with “would you rather” questions

139. Would you rather have everyone read your search history or your thoughts?

140. Would you rather have your date brag about their accomplishments or complain about their failures?

141. Would you rather be able to read my mind or read my texts?

142. Would you rather kiss your worst enemy or not be allowed to kiss your boyfriend for the rest of your life?

143. Would you rather be able to ctrl + f to find anything you’ve ever lost or ctrl + x to cut anything out of your life?

144. Would you rather be a unicorn or a mermaid?

145. Would you rather have your farts smell like roses or your breath smell like lemons?

146. Would you rather compliment people for the rest of your life or have people compliment you for the rest of your life?

147. Would you rather have a motivational coach everywhere you go or a therapist every time you’re going through something?

148. Would you rather have a bouncy castle save you every time you fall or a raincoat that floats over your head at all times and protects you from the rain?

149. Would you rather fart butterflies or burp rainbows?

150. Would you rather be with someone who’s incredibly handsome or incredibly smart?

151. Would you rather be with someone who’s poor but makes you happy or rich but makes you sad?

152. Would you rather experience being on the edge of a sneeze that never comes or having an itch you can never scratch?

153. Would you rather have the information on when you will die or the information on how you will die?

154. Would you rather have your favorite artist play a concert for you or your date’s favorite artist play a concert for him?

Get to know her better with “have you ever” questions

155. Have you ever gone skinny dipping with someone you just met?

156. Have you ever had a pregnancy scare?

157. Have you ever lied about your age?

158. Have you ever lied to get out of trouble?

159. Have you ever cheated on someone?

160. Have you ever been cheated on?

161. Have you ever gone to a party with someone you just met?

162. Have you ever been arrested?

163. Have you ever gotten a speeding ticket?

164. Have you ever stolen anything?

165. Have you ever drunk-dialed an ex-boyfriend?

166. Have you ever lost a bet?

167. Have you ever gotten robbed in a foreign country?

168. Have you ever broken a bone?

169. Have you ever been on a TV show?

170. Have you ever been on a blind date?

171. Have you ever kissed someone you just met?

172. Have you ever had a crush on a friend?

173. Have you ever had a crush on a professor?

174. Have you ever used a fake ID to get a drink?

175. Have you ever flirted with someone to get a drink?

176. Have you ever kissed someone you shouldn’t have?

177. Have you ever used someone else’s toothbrush?

178. Have you ever clogged someone’s toilet?

179. Have you ever traveled to a foreign country with someone you just met?

180. Have you ever kissed someone on a plane?

181. Have you ever pranked someone?

182. Have you ever returned something you already wore?

183. Have you ever left a hate comment on someone’s Instagram post?

184. Have you ever liked someone’s Instagram post on accident?

185. Have you ever gone two days without showering?

186. Have you ever gone two days wearing the same underwear?

187. Have you ever slept without any clothes on?

Play the “21 questions” game

You’re unsure of how to play this game? We’ve got you covered!

The “21 questions” game might be one of the greatest ways for two people to get to know each other better. If you notice the conversation running a bit dry, this game might be your best bet to save the day.

How do you play this game? It’s super easy – one of you picks the question, and both of you answer the question as honestly as you can. You can take turns picking the questions you would like the other person to answer, and you can have as much fun with it as you want to.

188. What’s the wildest experience you’ve ever had in your life?

189. What year of your life would you love to go back to, and why?

190. What’s one thing you would change about your life?

191. What’s the best movie you’ve ever watched?

192. What’s the best book you’ve ever read?

193. What’s the worst habit you have?

194. What’s your biggest regret?

195. What’s your biggest flex?

196. What’s your dream job?

197. What’s your dream destination?

198. What’s your dream wedding venue?

199. If you could be a part of any TV show or move family, which family would you be a part of?

200. If you could be in a relationship with any TV show or movie character, which character would you pick?

201. What’s one question a girl would never answer?

202. What’s one thing you would never do?

203. What’s your biggest social media pet peeve?

204. What’s your favorite sport to play or watch on TV?

205. What’s your favorite color to wear?

206. What’s your favorite food?

207. What’s your favorite dessert?

208. What’s your favorite drink?

Questions to ask a girl when you’re hitting it off

Questions To Ask A Girl 250+ Mind-Blowing Ways To Break The Ice

There’s hardly anything more exciting than being in the middle of the date with a girl of your dreams and getting that gut feeling telling you “we’re really hitting it off.” She’s laughing at your jokes, resting her hand on your shoulder, and playing with her hair. All the signs are there, but…

You don’t want to jump to any conclusion and break your own heart once you realize that her “it’s getting late, maybe we should go” didn’t necessarily mean that she wants you to go with her. Or even worse, that her “talk to you soon” didn’t mean that she wants you to ask her out on a second date.

Nobody said this dating thing would be easy, but there’s no reason why you should give up now that you’ve come so far. Forget about every piece of dating advice your eternally single friends have ever given you, you know better than to listen to anything they have to say.

After all, let’s not forget that it was your friend Jason who told you that “your mother seems nice” meant that the girl you were dating at the time wanted to get married, have your children, and become best friends with your mother. Doesn’t that sound a bit foolish after all these years?

While you could always be direct and ask whether she likes you or not, there are other questions you can ask a girl when you’re feeling like giving up on your flirting techniques. We’re all keeping our fingers crossed for you!

Spark her interest with these riveting questions

209. What’s the story behind your first kiss?

210. What’s your favorite song to sing when you’re having a shower?

211. What’s the best pick-up line you’ve ever heard?

212. What’s one question a guy should ask a girl when he’s trying to spark her interest?

213. What’s one thing everyone should know about you?

214. What’s the weirdest secret you’ve ever kept?

215. What’s the strangest present you’ve ever gotten from someone?

216. What’s your opinion on ghosts?

217. What’s the funniest name for a dog you can think of on the spot?

218. What’s the best name for a cat you can think of on the spot?

219. What’s the weirdest conversation you’ve ever had with someone who was trying to flirt with you?

220. What’s the scariest “I hate being a female” moment you’ve experienced?

221. What’s one thing every guy should know about the art of flirting?

222. What’s one piece of advice on flirting that’s guaranteed to work?

223. When was the worst date you’ve ever been on?

224. What’s one thing everyone should know about you?

225. What’s one thing nobody can ever know about you?

226. What would you do if you were a man for one day?

227. What would you do if you were the president of a country for one day?

228. What would you do if you were a member of The Royal Family for one day?

229. Which animal would you talk to if you were able to talk to animals for one day?

230. Where would you live if you could live anywhere in the world?

231. Would you go bungee jumping with someone you just met?

232. What’s your craziest “meeting a celebrity for the first time” story?

Fire her up with these flirty questions

233. What’s the story behind your last kiss? Would you let me change that story?

234. What does the perfect “I do” moment look like? Don’t mind me, I’m just taking notes.

235. What’s one song you wish was written about you? My writing skills aren’t as good as Ed Sheeran’s but that’s not something that would stop me from trying.

236. What’s the most attractive quality you’re looking for in a boyfriend? Or a husband, I might just stick around a bit longer?

237. Do you believe in soulmates or was it just me that felt this rush of emotions the moment you walked into this room?

238. What’s one question a guy can ask a girl when he’s trying to impress her with his flirting technique?

239. What’s one thing that gives off that “I’m in love” vibe? How do you know when you’re in love with someone?

240. Do you ever get butterflies in your stomach when you meet someone special? Or is that just me?

241. What’s the most attractive thing a guy can wear? Because I was feeling pretty confident when I walked out of my apartment wearing this outfit but I would love to hear your opinion on it.

242. What’s your opinion on relationships and marriage? Are you a “forever in love” or a “forever sounds too long” type of girl? Looking at you right now, I would definitely pick the first one.

243. What makes you feel attractive? I’m thinking that task shouldn’t be too difficult for you, but I would like to hear your take on it.

244. What’s your experience with unrequited love? I’m finding it hard to believe someone would have the guts to reject the most beautiful girl in the world, but hey, stranger things have happened.

Score another date with these endearing questions

245. Would you ever change your life up-side-down for the love of your life? Would you quit your job, move to a cute cottage by the river, and live happily ever after for the rest of your life? Asking for a friend…

246. How many times have you been in love? And I’m not talking about your average “I really like this guy” type of love. I’m talking about “I can’t imagine my life without this guy” and “I don’t know how I lived without him up until this point” type of love.

247. What’s the weirdest concert you’ve ever been to? Was that the artist’s fault, your friend’s fault, or yours?

248. When was the last time you stayed awake for the entire night? What were you doing?

249. When was the last time you slept through the entire day? What was the reason behind that decision?

250. What was the best Valentine’s Day present you’ve ever received? And how can a guy top that this year?

251. What was the best Valentine’s Day date you’ve ever been on?

252. What does your dream Valentine’s Day date look like?

253. Do you say “I love you” first when you’re in a relationship or do you wait for the guy to say it? You’re giving me so many ideas right now.

254. Which one do you prefer: watching the sunset with a guy you just met (but consider incredibly handsome) or watching the sunrise with the guy you just met (but consider incredibly handsome)?

255. Which one do you prefer: a spontaneous picnic date on the beach or a planned-to-a-tee fancy candlelight dinner at a fancy restaurant date?

256. What’s the most romantic question a guy can ask a girl when he’s trying to score another date?

Questions To Ask A Girl: 250+ Mind-Blowing Ways To Break The Ice