231 Questions to Ask Your Girlfriend, From Fun to Deep

Most question lists fail the same way. You open one on your phone, read six questions out loud in a row, she answers each in about four words, and by the seventh it feels like a job interview neither of you applied for.

The questions aren’t the problem. The pacing is. One good question plus three real follow-ups will get you further than twenty questions fired off in sequence. So treat everything below as a menu, not a checklist. Find one that makes her stop and think, then stay there.

They’re sorted by mood, because what works on a long drive is not what works at 1am, and neither is what works three weeks into dating.

Fun and light questions to ask your girlfriend

Low stakes, easy to answer, good for a car ride or a queue. These are the warm-up.

1. What’s your comfort movie, the one you’ve seen so many times you don’t need to pay attention?
2. What food combination do you genuinely love that other people find disgusting?
3. What’s the most useless skill you’re weirdly good at?
4. If you had to eat one cuisine for the rest of your life, which one?
5. What song do you know every word to without ever having tried to learn it?
6. What’s the pettiest thing you’ve ever held a grudge about?
7. Which fictional world would you actually want to live in, not just visit?
8. What did you want to be when you were seven?
9. What’s the worst haircut you’ve ever had?
10. What show could you rewatch forever without getting bored?
11. What’s a trend you fully committed to and now regret?
12. If you could instantly master one skill, what would you pick?
13. What’s your go-to karaoke song, assuming there’s no way out of it?
14. What’s the strangest thing you believed as a kid?
15. Sweet or savory breakfast, and how strongly do you feel about it?
16. What’s the last thing that made you laugh so hard you couldn’t speak?
17. What household chore would you happily never do again?
18. What’s an opinion you hold that you know is indefensible?
19. If your life had a theme song playing when you walked into a room, what is it?
20. What’s the best gift you’ve ever been given?
21. Which animal would you be, and don’t pick the flattering one?
22. What’s something everyone loves that you find genuinely overrated?
23. What’s your dream vacation, ignoring money entirely?
24. What’s the weirdest thing you keep for sentimental reasons?
25. What would you name a boat?
26. What’s the most embarrassing thing in your search history right now?
27. If you had to give a 20-minute presentation with no preparation, what topic?
28. What’s your most irrational fear?
29. What’s the last thing you looked up because you were too proud to admit you didn’t know it?
30. What’s a small thing that instantly ruins your day?

Deep and personal questions to ask your girlfriend

These ask about values and formative experiences rather than facts. Don’t open with them, and don’t ask more than two or three in one sitting.

31. What makes you feel safest?
32. What are you proudest of that nobody ever congratulates you for?
33. What would you change about the way you were raised?
34. When was the last time you surprised yourself?
35. What do you want your life to look like in ten years, specifically?
36. What do you actually need from me when you’re stressed, as opposed to what I usually do?
37. What’s a belief you held strongly five years ago that you’ve since abandoned?
38. Who has shaped you most, and would they know it?
39. What’s the hardest thing you’ve had to forgive?
40. What do you wish people understood about you without you having to explain it?
41. What’s the loneliest you’ve ever felt?
42. What are you most afraid of losing?
43. What does a good life look like to you, in your own words rather than the standard ones?
44. What part of yourself are you still working on?
45. What’s a decision you made that changed the direction of everything after it?
46. Who are you around when you stop editing yourself?
47. What compliment have you never been able to accept?
48. What do you think you’re underestimated for?
49. What’s something you wanted badly and are now relieved you didn’t get?
50. How do you know when you trust someone?
51. What’s the most useful thing therapy, a book, or a friend ever told you?
52. What do you do when you’re disappointed in yourself?
53. What’s a version of your life you sometimes think about that didn’t happen?
54. What would you tell yourself at nineteen?
55. What’s something you’ve never said out loud to anyone?
56. What kind of tired are you most often?
57. What do you think you’ll care about at sixty that you don’t care about now?
58. What’s a fear you’ve mostly outgrown?
59. What does forgiveness require, for you, before it’s real?
60. If you could know the honest answer to one question about your own life, what would you ask?

Flirty questions to ask your girlfriend

Flirty works when it’s specific to her and to you. Generic flattery gets generic answers, so name the actual thing.

61. What did you first notice about me?
62. When did you know you liked me more than you were letting on?
63. What’s the smallest thing I do that you like most?
64. What’s your favorite photo of us and why that one?
65. What do you think about when you can’t sleep?
66. What’s your ideal night in with me, in full detail?
67. What do you wear when you want to feel like the best version of yourself?
68. What’s the most attractive non-physical thing about a person?
69. Have you ever told a friend something about me you’d be embarrassed for me to hear?
70. What’s something you want more of from me?
71. What’s the best compliment I’ve given you?
72. Which of our inside jokes is your favorite?
73. What’s a place you’d want to kiss me that we haven’t been yet?
74. When do you feel most wanted?
75. What’s the first thing you’d do if I came home two days early?
76. What’s something I do that you’d never admit you find attractive?
77. What was going through your head on our first date?
78. Would you rather be surprised or be in on the plan?
79. What’s your favorite way to be touched that isn’t a kiss?
80. What’s a text I’ve sent that you kept?
81. What do you miss most about me when I’m away?
82. What’s the most romantic thing anyone’s done for you?
83. If we had one day with no phones and no obligations, what would we do?
84. What do you think I find most attractive about you? Then let her be wrong and correct her.
85. What’s something you’ve been wanting to tell me but haven’t found the moment for?

Questions about your relationship

These are the maintenance questions. Worth asking every few months, not because something’s wrong, but because it’s much easier to fix a small thing than a resentment.

86. When do you feel most loved by me?
87. What’s your favorite memory of us so far?
88. What was your honest first impression of me?
89. What do we do well that most couples don’t?
90. What’s one thing about how we communicate that could be better?
91. Is there anything you’ve been putting off telling me?
92. When do you feel most secure in this, and when do you feel least?
93. What do you need more of from me right now?
94. What do you need less of?
95. How do you want to be treated after an argument?
96. What’s a small thing I used to do that I’ve stopped doing?
97. What do you think is the biggest difference between us?
98. How do you want us to handle money as this gets more serious?
99. What does support look like to you on a bad week?
100. What’s something you’ve compromised on that you’d rather not have?
101. What do your friends think of us?
102. How do you want to spend our next big anniversary?
103. What tradition should we start?
104. What’s the best trip we’ve taken, and what made it that?
105. How can we make more time for actual dates rather than default evenings?
106. What’s something new you want us to try together?
107. What do you think we argue about most, and is that the real thing?
108. How do you want me to bring something up when I’m annoyed?
109. What did you learn about relationships from watching your parents?
110. What would you want to be true about us in five years?

If the answer to number 105 is “I don’t know, we should do more,” that’s the most common answer there is. It’s also the one most likely to quietly become a problem. Our piece on why regular date nights matter covers what actually makes the habit stick.

Getting to know her better

Past logistics and into patterns. Good for the stage where you know the facts about each other but not yet the shape.

111. What does your ideal ordinary day look like, start to finish?
112. Which friendship shaped you most?
113. What would you do with a completely free year and enough money to cover it?
114. What’s a subject you could talk about for an hour with no preparation?
115. How do you make decisions when both options are fine?
116. What’s your relationship with your family actually like, not the summary version?
117. What were you like at fifteen?
118. What’s the best thing about your job and the thing you’d change first?
119. How do you recharge when you’re depleted?
120. What’s a rule you live by that you’ve never articulated?
121. What do you spend money on that other people think is a waste?
122. What do you refuse to spend money on?
123. What’s the most spontaneous thing you’ve ever done?
124. How do you feel about where you grew up now, versus when you lived there?
125. What’s something you’re better at than you give yourself credit for?
126. What’s a hobby you dropped that you miss?
127. Who do you call first with good news?
128. What kind of people do you find easiest to be around?
129. What’s the hardest you’ve ever worked at something?
130. What was the best year of your life so far?
131. What smells or sounds bring you comfort?
132. How do you feel about being the center of attention?
133. What’s something you’ve changed your mind about recently?
134. What do you do when you’re angry and can’t say so?
135. What’s a book, film, or album that genuinely changed something for you?

Romantic questions to ask your girlfriend

Softer than flirty, less heavy than deep. These are for the good end of an evening.

136. When did you know you were falling for me?
137. What does love look like to you in practice, not in theory?
138. What’s the moment you’d relive if you could only pick one?
139. What do you hope I never stop doing?
140. What did you think love would be like before you’d felt it?
141. What’s the most loved you’ve ever felt, by anyone?
142. How do you want to be looked after when you’re old?
143. What would our perfect ordinary Sunday be?
144. Where would you want to live together if nothing was stopping us?
145. What’s something small I do that you’d miss immediately?
146. What do you want to be true about us that isn’t yet?
147. What’s your favorite thing about the way we are together?
148. How do you know when you’re home?
149. What would you write on a note in my bag?
150. What’s the kindest thing anyone’s ever done for you?
151. What do you want our life to sound like on a normal weekday evening?
152. What have I taught you without meaning to?
153. What do you love that you’ve never told me you love?
154. What’s the version of us you look forward to most?
155. If you had to explain us to someone who’d never met either of us, what would you say?

Late-night questions

The 1am category. Something about the dark makes people answer these honestly.

156. What’s keeping you awake lately?
157. Do you think people fundamentally change, or just get better at hiding things?
158. What’s the strangest dream you remember?
159. If you could know the date, would you want to?
160. What do you think happens after?
161. What’s something you think about far more than you let on?
162. Do you believe in luck?
163. What would you do differently if nobody would ever find out?
164. What’s a memory you return to for no clear reason?
165. What’s the most alive you’ve ever felt?
166. Do you think you’d like yourself if you met yourself?
167. What’s something you’ve never told your parents?
168. What scares you about the future?
169. What’s the best decision you’ve ever made?
170. If tomorrow reset and only you remembered today, what would you do with it?

Serious questions worth asking before things get serious

Not romantic, and not meant to be. These are the ones people skip and then discover the answers to two years in.

171. Do you want children, and how certain are you?
172. What does your ideal financial setup look like as a couple?
173. How do you feel about debt?
174. Where do you see yourself living long-term, city or otherwise?
175. How important is religion or spirituality to you now?
176. What role do you want your family to play in our life?
177. How do you handle conflict when you’re genuinely hurt?
178. What’s a dealbreaker for you?
179. What did your last relationship teach you?
180. How much time alone do you need to be okay?
181. What are your ambitions for the next five years, professionally?
182. Would you move for someone else’s career?
183. How do you feel about therapy, individually or together?
184. What does cheating mean to you, exactly?
185. How do you want to divide the invisible work of a household?
186. What would make you end a relationship you otherwise loved?
187. How do you want to handle it if one of us earns significantly more?
188. What do you need to feel secure long-term?
189. What are you unwilling to compromise on?
190. What do you think makes a relationship last?

The 21 questions game: a ready-made set

21 questions is a turn-based game where neither person is allowed to skip. That last rule is the whole point. Here’s a set that’s deliberately front-loaded with easy ones so it warms up rather than ambushing.

191. What’s your comfort food?
192. Best concert you’ve been to?
193. What’s your most-used app, honestly?
194. Morning person or night person, and were you always?
195. What’s the best day you’ve had this year?
196. What’s the last thing you cried at?
197. Who’s your oldest friend?
198. What are you bad at that you wish you were good at?
199. What’s the nicest thing a stranger has done for you?
200. What’s your biggest fear?
201. What makes you feel loved?
202. What’s something you’re embarrassed to admit you enjoy?
203. Who do you envy?
204. What’s your worst habit?
205. What would you do with a completely free year?
206. What’s the hardest thing you’ve been through?
207. What do you want to be remembered for?
208. What’s something you’ve forgiven that you thought you couldn’t?
209. What do you want from the next ten years?
210. What’s something you want to ask me but haven’t?
211. What’s one thing you’d change about us?

Random questions to break autopilot

For when conversation has flattened into logistics and you need something with no obvious answer.

212. How would you survive a zombie apocalypse, realistically?
213. What’s the best thing you’ve ever bought for under twenty dollars?
214. If you had to sabotage a wedding without being caught, what’s the plan?
215. Which historical period would you least want to live in?
216. What’s a conspiracy theory you find entertaining but don’t believe?
217. What would your villain origin story be?
218. What’s the worst advice you’ve ever been given?
219. Would you rather always be slightly too hot or slightly too cold?
220. What’s your most controversial food opinion?
221. If you had to be famous for something, what would you pick?
222. What’s a job you’d be terrible at?
223. What’s something you’ve pretended to understand for years?
224. Who would play you in the film?
225. What’s the strangest compliment you’ve received?
226. What’s a rule at your school or first job you still can’t believe existed?
227. What would you do first if you woke up as me?
228. What’s a small superpower that would genuinely improve your life?
229. What’s the worst possible name for a restaurant?
230. What would you put on a billboard?
231. What’s a hill you’d die on that you know is stupid?

How to actually use these

Four things, and then get off the internet and go ask her something.

• Don’t read from a list in front of her. Skim, pick three, put the phone down. Reading questions off a screen turns a conversation into a survey.
• Follow up before moving on. “Why that one?” is doing most of the work here.
• Match the question to the setting. Number 42 is a bad question in a loud restaurant and a great one on a long drive.
• Answer them too. The list works as a two-way thing or not at all.

If you want the same idea in a different format, the would you rather questions for couples list turns this into a game with no wrong answers, and 100 questions for couples is sorted by mood for couples who are already well past the getting-to-know-you stage. There’s also a matching list of questions to ask your boyfriend if she wants to turn this around on you.