325 Questions to Ask Your Boyfriend For Every Situation (2023)

What do men want? Each guy is different! These questions will help you learn what is important to your boyfriend and what he needs from you.

Our 20 Favorite Questions to Ask Your Boyfriend

Asking your boyfriend good questions can:

• Help you get to know him better
• Identify red flags early on
• Strengthen the relationship
• Deepen intimacy
• Establish open communication
• Show you what he needs in the relationship

A guy needs to feel invested in the relationship and that you care about what he cares about. Once you know what he cares about, it will help you build a more genuine connection.

Ask follow-up questions, and be willing to learn about new things. At the same time, be genuine in your interest. Don’t fake it just to appear more appealing!

When you combine authenticity, warmth, and a healthy dose of attention, he’ll feel seen and heard by you. Not only that—he will probably find you more attractive as a result!

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Guidelines for Asking Questions

• Remember—you’re asking questions, not conducting an interrogation. When you ask a question, lean forward and make eye contact waiting for the answer. Listen and interact with the response the way you would with your best friend. Nod, smile when appropriate, and mirror his verbal and facial cues.
• Use the questions as a starting point. Ask follow-up questions, and share your answers.
• Grab our list of questions to ask girlfriends, so he can ask you his questions.
• Pay attention to nonverbal cues while he’s speaking. His cues might send you a different message than his words.
• Always listen to his serious answers without criticism or judgment. Just like you, he needs to feel safe in the relationship.
• When asking fun and weird questions, be playful with your responses.
• This isn’t a checklist! Choose the best questions that resonate with you, and naturally ask them during conversations.

1. Who are you closest to in your family?

This question can reveal much about his family dynamics and who he feels safest with. If he has a complex family or childhood, this question doesn’t feel as probing or complicated as questions like, “Tell me about your family.” or “Did you have a happy childhood?”

You might also learn what makes him feel accepted or loved. Is he closest to his aunt because she always listens? Closest to his sister because she makes him laugh? Closest to his mom because she never dismissed his feelings?

2. What’s your best quality?

You might already have an idea of what his character qualities are, but you might be surprised by what he selects to share. The character quality that people value in themselves is often what they hope to find in others as well. If he says he is genuine, honest, or kind, you can bet that he’s looking for a woman who is genuine, honest, or kind. If his favorite quality is being masculine, dig deeper and discover what that means to him and why he values it.

3. How Do You Most Feel Loved?

Learning how he feels loved will give you a foundation to connect more deeply and effectively. It will also remove much of the guesswork on what he needs from you.

You may think you’re showing him love, but if it’s in a way, he doesn’t value (or is even suspicious of) your relationship will have a hard time moving forward.

On the other hand, once you start showing him love the way he needs it, you can make him feel secure and respected.

4. What do you feel makes a healthy relationship?

Find out what he views as healthy and his expectations for the relationship. You can also ask him who in his life has modeled a relationship that he admires. Follow up by asking why he admires their relationship and if he sees that happening for the two of you.

5. What is your passion project?

Find out what matters to him and where he spends his time. When you learn what he’s passionate about, express interest in sharing that with him. Don’t forget to affirm his passion! He may have had girlfriends in the past who dismissed his ‘hobbies’ or belittled what he cared about. You have the opportunity to build him up and encourage him.

6. Who is the person in your life you can always count on?

Whether it’s his best friend from grade school or cool Uncle Pete, the person he can always count on holds an important place in his life. Ask him to tell you some stories of how this person was there for him, and as a result, you’ll learn some of his struggles, victories, and even regrets.

7. What’s something most people don’t know about you?

A fun question to ask allows him to share something personal about himself. He might give you a funny or a serious answer, but either way, this question can build intimacy in your relationship through self-disclosure.

8. What is a weakness in other people that bothers you?

What a person views as a weakness is the area he will be critical and judgmental about. This is a fascinating question as it reveals what he has little patience for in others (and himself!). You’ll get a glimpse of what he values most with this answer.

9. What makes you angry?

Honey, you don’t want an angry man. It’s just a toxic timebomb. Everyone gets mad about different things, but if he’s prone to getting angry, especially out of proportion with the situation, don’t mess with that.

10. What is your favorite thing to do after work?

Does he always go out with the guys after work? Does he prefer to head home and relax on the couch? Does he work out at the gym or take the dog for a nightly run?

Find out what he does to relax. This could indicate whether he is an extrovert who gains energy being around other people or is more introverted. You might also get a glimpse into how he deals with stress.

11. What are your annoying habits?

This is less about identifying his annoying habits and more about seeing how self-aware he is. Plus, you’ll get an idea of how serious his habits are. Leaving socks everywhere might be incredibly annoying, but it isn’t a deal-breaker. On the other hand, cursing or always joking in serious situations could be annoying habits that cause problems later in the relationship.

12. What do you love about your mom?

Is he overly attached to mom, or one of those guys who have trouble respecting women? Get an idea of what you’re dealing with by asking him about his relationship with his mom. Listen for any bitterness, hurt, or overreliance because these can be red flags.

Just because he has a mommy wound doesn’t mean you should dismiss him right out the gate! But be aware it could impact how he treats you, especially if this isn’t something he’s working to deal with.

13. What stresses you out?

Help him talk about his stress, and listen with empathy. If you don’t understand why something is a stressor to him, ask, “What stresses you most about that?” In the process, you’ll learn more about how he responds to his work and personal environment. Look for ways to encourage him when he’s feeling worn down.

14. What’s your perfect day?

While it’s usually the guys who plan the perfect date in movies, why not arrange the ideal date around his answer to this question? You’ll show him you were listening to what he said and that you don’t expect him always to be the one to make you happy.

15. How did your last relationship end?

If it was a toxic relationship or he’s still attached to his ex, you need to talk about it. Process these feelings openly and find out how you can both build a relationship that doesn’t repeat old mistakes.

16. Can we talk about our health histories?

We don’t like talking about this with other people, but it’s essential to be open about past or present health concerns. This includes STDs (you have a right to know this information before being sexually active), mental health struggles, and other health concerns that could impact your relationship.

17. Tell me about your best friend.

You might get the same answer to this question as #6, “Who can you always count on?” but it might be completely different. While you may be hoping you’ll be his best friend, it’s healthy for you to have other friends outside of your relationship.

You also need to know if he’s a lone wolf or if he’s capable of having healthy platonic relationships.

18. What do you feel is your most significant achievement?

Go on, give him a chance to brag a little! Plus, you’ll learn about what he values in life. Then, ask him how that accomplishment made him feel and what he’s working towards now. Whatever his goals, let him know you believe he can do it.

19. What are your political ideals?

This one can get heated. So, find out early what his stance is. If you don’t share those ideals, explore whether you are comfortable agreeing to disagree. A minor disagreement can be healthy, but you don’t want ongoing tension. Even if you disagree on a specific policy or party, see if you agree on the heart of the matter. You might have more in common than it seems on the surface.

20. I need your advice, can you help me with ____?

Guys usually like to fix things.

So surprise him by asking for his advice AND his help. Just make sure you ask for advice on something you want advice on!

When you ask someone for help, it kicks in the Franklin Effect. In short, The Franklin Effect happens when you ask for help or favor, and it causes others to feel favorably towards you. You can thank Ben Franklin and another Legislator for discovering this little technique, which could strengthen your relationship with your boyfriend.

Keep reading for 300 more questions to ask your boyfriend. Want the Short List? 36 Questions to Truly Know Your Significant Other

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Deep Questions to Ask Your Boyfriend

Ask your boyfriend deep questions to spark… deep conversations. You’ll learn a lot about his thoughts, who he is, and how he perceives himself.

21. What makes you the best version of yourself?
22. What are things you do even though you don’t want to?
23. What does love mean to you?
24. What’s your best quality?
25. What’s something you’ve always dreamed of doing but never have?
26. What’s something we could change about our relationship to make it stronger?
27. What makes us special or unique together?
28. What do I mean to you?
29. What can’t you live without?
30. How have you changed in the last several years?
31. What makes you feel accomplished?
32. What do you think a good man is?
33. What is something you’re afraid to lose?
34. How do you know if you’re successful?
35. What kind of dad do you want to be?
36. What do you want to be remembered for?
37. What would you do if you lost your job?
38. If your family or friends didn’t approve of me, what would you do?
39. Are you an introvert, extrovert, or ambivert? How has that been both an asset and a weakness in your life?
40. What do you think is one of the most significant issues in our country today?
41. What keeps you awake at night?
42. If you could make a playlist of your life in high school, what songs would you put on it?
43. Have you ever been disappointed by your religion? What did you do to work through it?
44. Can you remember seeing your dad cry when you were growing up? How did you feel?
45. What do you wish you’d had more of as a kid?
46. What do you think about X’s current event?
47. What would you change about the medical system in our country?
48. What would you change about the education system in our state?
49. If you were a politician for a day, what would you do?
50. If you could immigrate anywhere, what country would you choose? Why?
51. What is the best thing about our country?
52. Tell me about a time you had an opportunity you didn’t deserve?
53. What causes do you care about? Why?
54. Have you ever done NGO work? What was that experience like?
55. When was the first time you realized you needed a bigger perspective on the world? What changed for you?
56. What summer stands out the most in your memories?
57. What was your coming-of-age experience?
58. When did you first feel like a man?
59. What fictional character do you identify with?

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Fun Questions to Ask Your Boyfriend

Don’t limit yourself to only deep or serious questions! These fun questions will help him share stories and maybe even get you both laughing.

60. What’s the craziest thing you’ve ever done?
61. Tell me your favorite travel story.
62. How many places have you lived? What was your favorite place?
63. Tell me a funny story about your first car.
64. What do you always procrastinate doing?
65. What’s your favorite song? Sing it for me!
66. What’s your favorite way to relax?
67. Have you ever traveled outside of the country? Tell me about it!
68. What are your guilty pleasures?
69. If you could travel anywhere in the world right now, where would you go and why?
70. Where are you originally from?
71. What are some of your family traditions?
72. How did you spend your summer vacations?
73. What was your favorite subject in school? Did you have a favorite teacher?
74. Do you have a pet? If not, would you ever want one?
75. If you had a pet tiger, what would you name it?
76. What was the best sporting event you ever attended?
77. What was your proudest sporting moment? (If they play a sport)
78. Are you mentoring anyone? (e.g., coaching a team, teaching a skill, volunteering, etc.)
79. What was your best day?
80. Have you ever sung karaoke? How good or bad was it?
81. Who is your hero or someone you’ve admired for a long time?
82. What do you like to do on a rainy day?
83. Do you prefer to stay home or go out on the weekend?
84. What was your biggest adventure?
85. What was your biggest travel mishap?
86. What was the dumbest thing you said to a crush?
87. What is your favorite holiday?
88. What was the best or strangest gift you ever got?
89. If someone told a joke and no one laughed, what would you do?
90. What did you like to do during recess?
91. Did you love or hate P.E.?
92. Do you play an instrument or sing?
93. What’s your favorite city?
94. What extreme sport have you always wanted to try? (bungee jumping, parkour, paragliding, etc.)

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Cute Questions to Ask Your Boyfriend

Up the cute factor and focus on the warm and fuzzies. Help release the happy hormones by talking about good memories and positive emotions.

95. Will you teach me (insert passion or hobby)?
96. What can I do to make you feel better after a bad day?
97. What is your happiest memory?
98. What is the kindest thing you’ve ever done?
99. What is the kindest thing someone else has done for you?
100. Describe your dream house.
101. If you’re sick, do you want someone to care for you, or do you prefer to be left alone?
102. Will you promise to fix my hair if it gets messed up by the wind?
103. What stuffed animal did you sleep with as a kid? Do you still have it?
104. What is the cutest couple you’ve known?

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Serious Questions to Ask Your Boyfriend

Early in your relationship, start asking serious questions to learn what he values and believes. You don’t want to be 6 months into a relationship and suddenly discover alpha females threaten him or that you regularly do things that get on his nerves (he’s just never told you!).

105. What makes you the happiest?
106. How can I support your interests?
107. Do you hold grudges?
108. How would you describe your family?
109. Tell me about your relationship with your parents and siblings.
110. What do you want to improve or change about yourself?
111. Do you have any regrets? Would you go back and change those things if you could?
112. What terrible experience taught you a valuable lesson?
113. How do you deal with failure?
114. What are some things that offend you?
115. What gets on your nerves?
116. Do you love your job? If so, why? If not, why do you stay there?
117. What do you need when you’re upset? Space? Talking it out? Something else?
118. What’s something you’ve been scared to ask me?
119. Where do you see our relationship going?

120. What mistake have you made in a past relationship that you don’t want to repeat?
121. Where do you see yourself settling down? / Will you be here long?
122. Are there any strong women in your life? How do you feel about powerful/successful women?
123. Do you want children?
124. Does our age difference bother you? (If relevant)
125. What should never be joked about?
126. What does friendship mean to you?
127. How do you handle conflict?
128. Do you have children? If so, what does co-parenting look like for you?
129. Who do you live with?
130. What’s your relationship like with your dad?
131. Are you single? Is there anyone out there who thinks you’re their man?
132. Do you have any significant responsibilities?
133. What is something you’re working on to become a better person?
134. How are you? (Ask this question and mean it!)
135. What are the things you spend the most money on?
136. When you break up with someone, how do you do it?
137. If one of my friends flirted with you, would you tell me?
138. Have you ever broken the law?
139. Do you have a mentor? What is the most important lesson they taught you?
140. Do you believe people should only date within their socio-economic status?
141. Who do you think should pay for dates?
142. How do you feel about surprises? Do you like to be surprised?
143. Have you ever been married?
144. Have you ever been engaged?
145. What are you doing to care for the planet?
146. Do you have any serious allergies?
147. Have I ever made you feel cut down or belittled in front of people?

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Cultural Questions to Ask Your Boyfriend

Are you dating someone from a different culture? That could be either religious, ethnic, or even socio-economic. If so, you will have differing worldviews, values, customs, and expectations. Ask him questions, but also ask him to teach you, even when you don’t think to ask.

Some of these questions are more appropriate later in the relationship and may be more or less relevant depending on the differences between your two cultures.

148. Is there anything I should know about interacting with you in front of your family?
149. Does your culture have a hierarchy?
150. What values are most important in your culture?
151. What’s your favorite faith tradition or cultural tradition in your family?
152. What are the most critical parts of your culture that you want me to know about?
153. What expectations will your family have for us?
154. How should I interact with your parents? What should I call them?
155. How can I show respect to your family?
156. What things might I do unintentionally that would offend you?
157. Can you teach me to eat a traditional meal without causing offense or looking stupid?
158. Will I be expected to help prepare or clean up after a family meal?
159. Where should I stand/sit?
160. What should I do when I first meet your family?
161. What was it like growing up in your culture?
162. Is there hostility between our cultures? Do you ever feel that hostility/prejudice from my friends or family? Will your family feel hostility/prejudice towards me?
163. How do you want me to express when I disagree with you?
164. Are there parts of your culture that I shouldn’t try to assimilate because it would be offensive?
165. Are there prayers I should or shouldn’t expect to take part in?
166. How can I say no to your family without offending them (e.g., if they offer me food I don’t like, offer a gift that is offensive to my culture/religious belief, etc.)
167. Do you celebrate holidays common to my culture? Do you celebrate holidays common to your culture? Am I allowed to be a part of those celebrations?
168. Are there any foods or drinks I should know about that are restricted by your religion?
169. Can you teach me some basic phrases in your first language?
170. Can you teach me some basic phrases from the language your family speaks?
171. Can you teach me to make your favorite ethnic food?
172. What food does your family typically make for sick people in your culture? Can you teach me how to make it?
173. How can we make our traditions?

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Romantic Questions to Ask Your Boyfriend

Talk openly about your feelings, your needs, and your expectations. Regarding relational intimacy (physical or emotional), it’s essential to talk about it beforehand.

Be clear on:

• Expectations
• Boundaries
• Personal and religious beliefs

As well as what you both see as being healthy, respectful, and morally responsible. Get the conversation going with these important relationship questions.

174. What do I do that makes you feel loved?
175. How can I make you feel more appreciated?
176. What are you like as a boyfriend?
177. Why do you want to be in a relationship with me?
178. What do you think is most important to have in common with someone you’re dating?
179. Do you believe in monogamy? How would you define that?
180. Once you get married, if you weren’t happy in the relationship, would you break up or work through the difficulties?
181. What is your view on sex in long-term relationships?
182. What are your views and beliefs about physical intimacy?
183. How does your culture or religion view sex?
184. What makes you think your partner wants more physical intimacy?
185. How do you feel about public displays of affection?
186. What do you consider cheating?
187. Have you ever cheated?
188. Have you ever been cheated on?
189. I expect you to: ask first, stop if I say no, wait for verbal consent, let me lead, wait for me to meet you halfway, etc. (fill in the blank with what you need/want). Are you willing to respect that?
190. How do you like to show love?
191. How do you like to receive love?

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Flirty Questions to Ask Your Boyfriend

Try out these flirty questions to spark attraction.

192. Would you braid my hair?
193. Will you dance with me right now?
194. What sets me apart from other women?
195. What color best describes me?
196. How is your life different with me in it?
197. Will you help me pick an outfit for tonight?
198. How many times did you want to ask me out before you finally did?

199. What was our first kiss like for you?
200. Will you cook for me?
201. I want to cook for you. What would be your ideal meal?
202. What do you think about me during the day?
203. If I was sad, what would you do to cheer me up?

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Random Questions to Ask Your Boyfriend

From silly to serious, here are additional questions to keep the conversation going.

204. Are you a night owl or an early bird?
205. Books or movies?
206. What is your favorite book?
207. What is your favorite movie?
208. Do you have a favorite food?
209. Who is your favorite team? (basketball, football, soccer, etc.)
210. What are you like when you’re grumpy and tired?
211. What’s your favorite dessert?
212. Would you rather homestead or be a financial advisor?
213. What food do you always crave?
214. Who do you spend the most time with?
215. What is one place you never want to go again?
216. What is one place you’ve always wanted to go back to?
217. How long should people date before meeting their parents?
218. Do you have any irrational fears or phobias?
219. Who inspires you?
220. What’s something most men dislike that you love?
221. Tell me about your grandma.
222. Do you prefer to eat out or cook for yourself?
223. How would your friends describe you?
224. Would you rather be right or happy?
225. What was your most embarrassing moment?
226. What was your childhood nickname?
227. What is your silliest pet peeve?

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Weird Questions to Ask Your Boyfriend

These questions are suitable for a laugh and making fun icebreakers when you’re on a date.

228. What conspiracy theory are you tempted to believe?
229. What’s your nighttime ritual?
230. Have you ever slept in your shoes?
231. Do you sleep with your mouth open?
232. What was the weirdest place you ended up sleeping?
233. Do you snore?
234. Will you tell me if I have food or lipstick on my teeth?
235. Would you rather be a puppy or a kitten?
236. Would you rather own a baby elephant named Jeff or a fluffy bunny named Snookums?
237. Did you want to be an astronaut when you were a kid? What did you want to be?
238. What is the weirdest thing you’ve put on a sandwich?
239. What is the weirdest thing a coworker said to you?
240. What was the strangest wrong number text you’ve received?
241. What flavor of ice cream are you?
242. Do fish have necks?
243. Are chickens a bird since they don’t fly?

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Intimate Questions to Ask Your Boyfriend

Keep these more intimate questions for when you’re moving towards a committed long-term relationship. Some of these may be asked earlier, but most of these questions are very personal and will require closeness and trust.

Healthy relationships are ones where both people are willing to explore and understand the hurts and experiences of the other person. Instead of toxic behavior patterns, learn how to support each other emotionally and develop healthy communication.

If your boyfriend isn’t ready to talk about some of these things (such as adverse childhood experiences), respect their boundaries, but let them know these questions are essential and need discussion.

When you ask these questions, be prepared to listen without judgment or criticism; only ask questions you’re also willing to answer.

244. When was the last time you cried?
245. What are you afraid of?
246. What makes you feel sad?
247. Did you feel love and support from your parents growing up?
248. Have you ever been in therapy?
249. What did you learn about relationships in therapy?
250. How do you regulate your emotions?
251. What triggers you?
252. What are your coping mechanisms?
253. Is there a past relationship that you still feel hurt or angry about? Tell me about it?
254. What is your earliest memory?
255. What relationship causes you the most stress?
256. What is your worst memory?
257. What do you most regret not saying to someone?
258. What is something you wish you hadn’t done?
259. What is the best decision of your life?
260. What was the hardest decision of your life?
261. How do you approach finances? Do you have debt? What are your financial goals?
262. How would you feel if I earned more money than you?
263. Aside from parents/guardians, who shaped you the most growing up?
264. What signs are you getting stressed that others don’t pick up on?
265. How can we communicate when either of us needs space?
266. What makes you feel disconnected from me?
267. What was your relationship with your siblings growing up? Was there favoritism?
268. What are some terrible family traits you are working on so you don’t pass them down to your children?
269. How many sexual partners have you had?
270. What are your retirement plans?
271. What are your thoughts on how to raise/discipline children?
272. What do you think each person’s role is in marriage?
273. How will we spend our holidays?
274. How would we make decisions as a couple?
275. What role will your family play in our relationship?
276. If we get married, how much say will your parents expect to have in raising our kids?
277. Have you lost anyone close to you?
278. How can we both communicate more openly?
279. Who can I go to for help or advice about you?
280. What are you afraid people will think about you?

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Questions to Ask Your Boyfriend over Text

Texting is an excellent opportunity to talk about less serious things and engage in witty banter. Be playful when you respond to his answers and use emojis so he knows when you’re joking.

281. You can only rescue one thing from a 🔥. Your favorite 👞👞, this week’s groceries, or your work laptop. These are your only options. Which do you choose? 🤷🏾‍♀️
282. What emoji would you use to describe me?
283. Do you remember the first day we met?
284. Would you rather eat Mexican 🌮 or Korean 🍚??
285. Would you instead go to a ⚾ game or art museum?
286. If you could only eat 🌭 or 🍔 for the rest of your life, which would you choose?
287. This may be a deal-breaker, but what is your stance on the ever-controversial subject… Pineapple on pizza? Yes or no?
288. What do you think is my favorite food?
289. What do you think would be my ideal date night?
290. What’s your favorite movie that I would be surprised you like?
291. What’s your favorite movie of all time?
292. What movie did you watch every chance you got when you were a kid? 🧒
293. What makes you feel comfortable around someone?
294. Did anything weird or funny happen to you this week?

295. Tell me your worst dad joke!
296. I’m sorry your day was horrible. Is there anything I can do to improve it? 😙
297. Would you rather have stability or adventure?🤠
298. ⛰️ or 🌊?
299. 🛋️or a day in the city?
300. Can you teach me to 🎣?
301. Would you rather skip work or skip your gym workout? 💪💪
302. What’s your favorite magazine?
303. What’s your favorite 📕?
304. Dark, milk, or white chocolate? Do you like nuts in your chocolate? 🍫
305. What’s your favorite scent?
306. What’s your hidden talent? 👀
307. Do you have any plants? 🌱 What is the longest you’ve kept a plant alive?
308. What can your friends always count on from you?
309. What is the longest time you’ve gone without taking a shower? 🛀
310. Are you a foodie? 🥐 What were the best tacos you ever ate? What made them so unique?

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Questions to Ask Your Boyfriend about You

Curious what he thinks about you? Just come right out and ask him! He might not naturally offer this information, so help him express his feelings by asking specific questions.

311. When did you first realize you liked/loved me?
312. What was your very first impression of me?
313. What song makes you think of me?
314. What’s something I do that you love?
315. What do I do that makes you feel rejected or unloved?
316. What’s your favorite thing about me that’s not a physical feature?
317. How can I be a more supportive girlfriend?
318. If one of your friends flirted with me and I told you, what would you do?
319. What makes me beautiful to you?
320. Do you smile when you think about me? Why?
321. What’s your favorite outfit that I wear?
322. Do you like it when I wear my hair up?
323. How would you handle another guy hitting on me?
324. How have you seen me grow in the last several months?
325. Do you think I’m living up to my potential?

Does your boyfriend need a list of questions too? Check out 315 Questions to Ask Your Girlfriend.