301 Questions To Ask a Guy To Get To Know Him Better in 2025
If you’re looking to strengthen your connection, finding the right questions to ask a guy will help deepen your bond. Whether you’ve been together for years or you’re stepping back into the dating scene, asking questions will help you learn more about one another and develop a stronger level of trust and intimacy.
Better Health describes intimacy as the ability to be emotionally connected and supported. It allows you the opportunity to be vulnerable and talk through your feelings and emotions. Finding the right questions to ask a guy can open that door to intimacy and lead to thought-provoking and fun conversations. So, what are interesting questions to ask a guy? We’ve rounded up a list of the best questions to ask a guy to get to know him better and deepen your intimacy.
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- Romantic Questions To Ask a Guy To Get To Know Him Deeper
- Flirty Questions To Ask a Guy To Make Him Laugh
- Spicy Questions To Ask a Guy
- Juicy Questions To Ask a Guy Over Text
- Questions To Ask a Guy You Like
- Questions To Ask a Guy To Get To Know Him Over Text
Romantic Questions To Ask a Guy To Get To Know Him Deeper
No matter how long you’ve dated your boyfriend, there are still plenty of great questions to ask a guy to get to know him better. Find deep questions to ask to take your romance to the next level.
1. What’s your love language?
2. Have you ever been in love before?
3. What does being in love feel like to you?
4. What did your last relationship teach you?
5. Do you believe in soulmates?
6. Have you ever had your heart broken?
7. What’s the most romantic thing you’ve ever done?
8. What’s the most romantic thing someone’s done for you?
9. What’s something you wish you had done differently in a past relationship?
10. How do you show someone you love them?
11. What’s the biggest lesson love has taught you?
12. What makes you feel truly appreciated in a relationship?
13. What kind of physical touch do you find the most comforting?
14. How important is romance in a relationship to you?
15. What do you envision your ideal relationship looking like?
16. Do you enjoy surprises or prefer predictable affection?
17. Do you want to get married someday?
18. How do you feel about having kids someday?
19. What kind of partner do you hope to be in the future?
20. Where do you want to live with your partner in the future?
21. What’s your idea of a perfect date?
22. What’s your biggest fear when it comes to relationships?
23. Do you like cuddling or are you more of a space person?
24. How do you handle conflict in relationships?
25. What’s a small gesture that melts your heart?
26. What helps you feel safe to open up emotionally?
27. What’s one emotional need you wish more people understood about you?
28. What song would you want to slow dance to?
29. When do you feel most vulnerable?
30. What does commitment mean to you?
31. How do you flirt when you really like someone?
32. Can you fall in love quickly, or does it take time?
33. When was the first time you ever knew you really cared about someone?
34. What’s your definition of “home” when it comes to a person?
35. Do you have a romantic fantasy you’ve never told anyone?
36. Do you think love is more about chemistry or compatibility?
37. What’s your favorite memory of us so far?
38. Have you ever had a love that changed you?
39. What’s something you admire about me?
40. How do you want to make someone feel when they’re with you?
41. Do you think we’re emotionally compatible?
42. What makes you fall in love with someone?
43. What song makes you think about love every time you hear it?
44. What’s your idea of growing old with someone?
45. When do you feel closest to me?
46. Do you think two people can love each other forever?
47. Where would you go for a romantic getaway?
48. What’s something you’ve never told anyone about your views on love?
49. What do you think makes us special?
50. How would you describe your ideal partner in one sentence?
Flirty Questions To Ask a Guy To Make Him Laugh
Asking flirty questions is a great way to keep your relationship fun and exciting. So, what are some flirty questions to ask a guy? Here are some of the best flirty questions to ask a guy to spark some romance.
51. If I were a dessert, what would I be — and don’t say boring vanilla ice cream!
52. Be honest, did you practice your flirting in the mirror before talking to me?
53. On a scale of 1 to 10, how single are you right now?
54. Are you this charming with everyone, or am I just special?
55. What’s your go-to “make her fall for me” move — and is it working yet?
56. If we were in a romantic comedy, which scene would we be in right now?
57. Do you believe in love at first sight, or should I walk by again?
58. How did you get so good at making me smile — natural talent or years of training?
59. Would you survive a date with me, or should I send you a warning label first?
60. If we got stuck in an elevator together for hours, how would you entertain me?
61. What’s more dangerous, your smile or your flirting skills?
62. Can you cook, or should I prepare to survive on takeout forever?
63. Do you come with a manual, because you’ve got my mind all confused?
64. Have you always been this smooth, or is this just for me?
65. What’s the cheesiest pickup line you’ve actually used — and did it work?
66. If you could steal one thing from me — besides my heart — what would it be?
67. What’s your secret to looking this good, or are you just lucky?
68. If I challenged you to a flirting competition, do you think you’d win?
69. When are you going to admit that you think about me more than you should?
70. If we were the last two people on Earth, what would you say to break the ice?
71. How many girls have you made laugh today, or am I your favorite target?
72. If I dared you to kiss me right now, would you chicken out?
73. Do you prefer me sweet, sassy, or a little bit of both?
74. If you had three wishes right now, would you use one on me?
75. If I gave you my heart, would you know what to do with it?
76. What’s the most romantic trouble you’ve ever gotten into?
77. Have you always been this cute, or is it just the lighting?
78. If you were a superhero, what would your flirting superpower be?
79. When are you taking me on that dream date you’ve been planning in your head?
80. If you could teleport us anywhere right now, where would we go — and why?
81. Is your flirting strategy always this sneaky, or am I just an easy target?
82. If I let you steal a kiss, would you give it back?
83. What would you do if I texted you “I’m bored… fix it”?
84. If you had to choose — candlelight dinner or spontaneous adventure?
85. Can you handle a girl who flirts as much as you do?
86. If you were writing a book about us, what would the title be?
87. Do you believe in fate, or are you just good at making your own luck?
88. Should I let you win this round, or do you like a challenge?
89. What’s more fun — teasing me or being teased by me?
90. If you could only use one word to describe me, would it be “trouble”?
91. Do you ever get tired of being this adorable, or is it effortless?
92. How long did it take you to perfect your “make her melt” smile?
93. What would you rate your kissing skills — should I be curious or concerned?
94. If I told you I was cold, would you offer me your jacket or your arms?
95. What’s the craziest thing you’d do just to impress me?
96. Do you think you’re winning me over, or should you try harder?
97. If I got lost, would you come find me, or would you get lost with me?
98. What’s the most daring thing you’ve ever done for a girl?
99. Can you guess what I’m thinking right now, or do you need clues?
Spicy Questions To Ask a Guy
Although these might come off as random questions to ask, adding some spice into your relationship will keep things fresh and exciting. Not to mention, these questions can further your trust and intimacy. Pose spicy questions to ask a guy to keep things exciting!
100. What’s the sexiest thing a girl can wear?
101. What’s your secret guilty pleasure?
102. Do you believe in love at first sight — or should I walk by again?
103. Have you ever been caught in the act?
104. What’s your biggest turn-on?
105. Where’s the craziest place you’ve made out?
106. Are you into more dominant or submissive vibes?
107. How do you usually flirt?
108. Have you ever had a dream about me?
109. Have you ever had a one-night stand?
110. What’s your favorite spot to be kissed?
111. Boxers, briefs, or nothing at all?
112. What’s one thing you’ve always wanted to try in bed?
113. What’s the dirtiest text you’ve ever received (or sent)?
114. What’s your ultimate fantasy?
115. Do you like talking dirty?
116. What’s your go-to move when you’re flirting?
117. Have you ever filmed yourself doing something naughty?
118. How many people have you kissed?
119. Have you ever used toys or handcuffs?
120. What’s something you’ve done that you wouldn’t tell your mom about?
121. Do you like rough or slow and sensual?
122. Have you ever gone skinny dipping?
123. Have you ever had a secret affair or fling?
124. Where’s the most adventurous place you’ve ever had sex?
125. What’s the kinkiest thing you’ve ever tried?
126. Are you a lights-on or lights-off kind of guy?
127. Have you ever had sex in public?
128. What’s the most spontaneous thing you’ve ever done?
129. Do you get emotionally attached after hooking up?
130. Do you like to make the first move or be pursued?
131. What’s one thing you wish girls knew about guys and sex?
132. What’s something you’re secretly good at?
133. What’s something physical that turns you on instantly?
134. Have you ever had a friends-with-benefits situation?
135. Do you enjoy giving or receiving more?
136. How do you like to be teased?
137. Would you rather cuddle after sex or fall asleep right away?
138. Do you like it when a girl takes control?
139. How do you show someone you really want them?
140. Can you handle a girl who makes the first move?
141. What’s a fantasy you haven’t told anyone about yet?
142. What’s your biggest weakness when it comes to girls?
143. What’s something non-sexual that you find incredibly attractive?
144. What kind of lingerie turns you on the most?
145. Do you believe in sexual chemistry at first sight?
146. Have you ever had a crush on someone you shouldn’t have?
147. Have you ever had a crush on someone older?
148. What’s something naughty you’ve always wanted to try but haven’t?
149. What’s your go-to line when you’re into someone?
Juicy Questions To Ask a Guy Over Text
Bring up juicy questions to ask a guy to learn something new about your partner. These scandalous questions, or even would you rather questions, are a great way to further your connection.
150. What’s the most random thought you’ve ever had about me?
151. What’s the last thing you thought about before you went to sleep?
152. Be honest — have you imagined kissing me?
153. What’s something a girl has texted you that made your whole day?
154. What kind of texts turn you on the most?
155. What’s your biggest turn-on — that you don’t usually admit?
156. If I dared you to send me a flirty selfie, would you?
157. Have you ever screenshot a message from a girl because it was that hot?
158. How do you flirt over text?
159. What’s one thing you want me to say to you, but haven’t yet?
160. What would you do if I showed up at your place with no explanation?
161. What’s your favorite thing to hear during a steamy conversation?
162. Want to swap secrets?
163. Do you ever reread spicy messages?
164. If you could kiss me anywhere right now, where would it be?
165. What would you say if I asked you to tell me your fantasy?
166. Ever had a late-night text turn into something more?
167. Are you more of a “sweet talk” or “talk dirty” kind of guy?
168. How far would you go on a first date… if the vibe is right?
169. What’s something you wish more girls did over text?
170. What emoji do you use when you’re thinking dirty?
171. What’s the sexiest thing you’ve ever imagined while texting?
172. Do you like slow, teasing conversations or straight-to-the-point?
173. If I dared you to tell me a spicy secret over text, would you?
174. Would you rather FaceTime flirt or keep it text-only?
175. Have you ever caught feelings after a spicy conversation?
176. What’s your guilty pleasure when it comes to girls?
177. What’s the first thing you noticed about me?
178. Have you ever sent a text that you immediately regret?
179. Have you ever pictured us kissing?
180. What’s the most risqué photo you’ve ever sent?
181. What’s your type? Or should I already know the answer?
182. Would you rather wait for the right moment or just go for it?
183. What’s your go-to move when you’re into someone?
184. What’s something you want to tell me but haven’t dared to yet?
185. What would you do if we were alone right now?
186. What’s one thing you could text me right now that would totally turn you on?
187. What’s your favorite compliment to get from a girl?
188. Do you save flirty texts or delete them immediately?
189. What’s your guilty pleasure when it comes to texting?
190. What’s the hottest conversation you’ve had over text?
191. How fast do you catch feelings?
192. What’s something that would catch you off guard — in a good way?
193. What kind of texts make you smile without trying?
194. What would your reply be if I texted, “I’m in the mood…”?
195. Would you rather sext or have a spicy voice call?
196. Would you rather cuddle or kiss right now?
197. What’s one question you’ve been dying to ask me?
198. Would you rather make out in a car or sneak kisses at a party?
199. What’s the most spontaneous thing you’ve ever done with someone?
Questions To Ask a Guy You Like
If you’re looking for interesting questions to get to know someone, these questions are great for exploring a new crush’s interests and personality. Pose these fun questions to ask a guy when your relationship is still new and exciting.
200. What’s the worst job you’ve ever had?
201. What’s your dream job?
202. What’s your favorite childhood memory?
203. What’s your go-to joke?
204. Tell me about the most embarrassing thing that’s ever happened to you?
205. What’s your guilty pleasure?
206. Are you a morning person or a night owl?
207. What’s a recent embarrassing memory that you have?
208. What are you likely to buy when you spend money for fun?
209. What’s your favorite pizza place in town?
210. What’s one food you hate?
211. What’s one food you love?
212. What’s the weirdest flavor combination you enjoy?
213. Are you a dog person or a cat person?
214. Who would you trade lives with for a day if you could?
215. How did you meet your best friend?
216. What would you tell your younger self?
217. What’s your favorite meme?
218. What do you think makes a healthy relationship?
219. What’s the funniest thing that’s ever happened to you?
220. Do you consider yourself a spiritual person?
221. What’s a fun activity you want to try but haven’t yet?
222. What’s your favorite movie genre?
223. What’s the worst pickup line you’ve ever used?
224. When was the last time you laughed so hard you cried?
225. What’s on your bucket list?
226. Who was your favorite fictional or cartoon character as a child?
227. If you were stuck on a desert island, what three items would you bring?
228. What’s the best hidden talent you have?
229. What’s the worst hidden talent you have?
230. What’s one song you could listen to repeatedly?
231. What’s your favorite comedy movie?
232. What’s your favorite video game?
233. What’s your most prized possession?
234. What’s the biggest life lesson you’ve learned?
235. What’s your idea of the perfect Saturday night?
236. What would you do if you had one million dollars?
237. Who is your favorite person to spend time with?
238. Who is your biggest hero?
239. What’s your weirdest habit?
240. What book or movie had a profound impact on you?
241. What was the worst date you went on?
242. What was the best date you went on?
243. What are you passionate about outside of school or work?
244. Do you remember your first crush?
245. What are some of your favorite ways to relax and unwind?
246. Are you a competitive person?
247. What role does family play in your life?
248. What’s your biggest fear?
249. Would you survive a zombie apocalypse?
250. What’s something you want to know about someone by the third date?
Questions To Ask a Guy To Get To Know Him Over Text
Sometimes, texting is the most consistent way to keep a conversation going. Whether you’re looking for questions to ask your guy friends or questions to ask a guy that you barely know, these questions are great for asking over text.
251. How was your day?
252. When do you feel the happiest?
253. Do you have a favorite genre of movies?
254. If you could switch bodies with the president or your favorite actor, which one would you choose?
255. If you could listen to any song on repeat for a week, what song would it be?
256. What would your chosen superpower be?
257. Would you rather be a rock star or a movie star?
258. Do you have a favorite meme?
259. Do you have a go-to recipe?
260. If you could meet any of your heroes, who would you choose?
261. Do you prefer cats or dogs?
262. What’s your picture-perfect breakfast?
263. What are you thinking about right now?
264. What’s the best thing that happened to you this week?
265. What’s something you’ve done recently that you’re really proud of?
266. What’s your favorite GIF?
267. How would your best friend describe you?
268. What is the most radical opinion you have?
269. What’s the weirdest thing that happened to you this week?
270. What are you most proud of?
271. What’s the best vacation you’ve ever taken?
272. What’s the scariest thing you’ve done?
273. What emoji makes you think of me?
274. Do you like to take naps?
275. What would be on a playlist you’d make for me?
276. What’s your favorite thing to cook?
277. How would you describe yourself in three words?
278. How would you describe me in three words?
279. Who has had the biggest impact or inspiration on your life?
280. What do you like to do on the weekends?
281. What’s your biggest goal or dream you’re still working to achieve?
282. How would you describe me to your friends?
283. What’s the best piece of advice you’ve ever received?
284. What unnecessary products do you find necessary in your life?
285. How do you express yourself creatively?
286. Guess what emoji I put next to your name on my phone?
287. Where do you want to be in 5 years?
288. What’s the most useless advice you’ve ever gotten?
289. What’s your biggest pet peeve?
290. What’s something you’ve always wanted to ask me?
291. What’s your favorite thing about your group of friends?
292. Would you ever stay friends with an ex?
293. What cause do you care about the most?
294. What are your five most frequently used emojis?
295. What is something that never fails to make you smile?
296. Do you prefer calls or texts?
297. What is the last brave thing you did?
298. What do you wish you had more time for?
299. What does happiness mean to you?
300. What kind of conversations do you enjoy the most?
301. What would you tell your younger self?
From spicy questions to deep questions, there are tons of interesting questions to ask a guy when getting to know him better. Whether you’ve been dating for a while or you’re looking to take your relationship to the next level, asking the right questions will help develop intimacy, build trust and turn up the heat in your conversations.
For even more fun things to do with your guy friend, check out other experiences happening on Classpop!
