1. Who are you closest to in your family?

2. What’s your best quality?

3. How Do You Most Feel Loved?
4. What do you feel makes a healthy relationship?
5. What is your passion project?
6. Who is the person in your life you can always count on?
7. What’s something most people don’t know about you?
8. What is a weakness in other people that bothers you?
9. What makes you angry?
10.What is your favorite thing to do after work?
11.What are your annoying habits?
12.What do you love about your mom?
13.What stresses you out?
14.What’s your perfect day?
15.How did your last relationship end?
16.Can we talk about our health histories?
17.Tell me about your best friend.
18.What do you feel is your most significant achievement?
19.What are your political ideals?

What makes you the best version of yourself?

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

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.)

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?
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?

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?

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?

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?

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?

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?

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?

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?

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?

Career and Ambition Questions to Ask Your Boyfriend

326. What inspired you to pursue your current career path?

327. Where do you see yourself in your career five years from now?
328. Are there any dream jobs or positions you’ve always wanted to
attain?
329. How do you maintain a healthy work-life balance?
330. What are your strategies for managing workplace stress?
331. Have you considered pursuing further education or certifications to
advance in your career?
332. Do you have any mentors or role models who have influenced your
career decisions?
333. What has been your proudest career achievement so far?
334. Have you faced any significant career challenges, and how did you
overcome them?
335. What values and principles are most important to you in your
workplace?
336. How do you handle conflicts or disagreements in a professional
setting?
337. Are there any ways you’d like to give back to your community or
make a positive impact through your career?