400+ Questions To Ask Your Parents For Deeper Connections

Image: Midjourney/ MomJunction Design Team

Exploring your family history by asking your parents the right questions can bring a deeper sense of purpose and fulfillment to your life. During your childhood, you tend to be more attached to your parents, but as you grow, you sometimes move apart from them. In addition, your busy lives affect your connection with them.

This distance and lost connection prevent you from learning more about their lives, experiences, and legacy. Thus, you must find a way to bridge this gap. You can do this by asking them open-ended questions. So, keep scrolling as we bring you some enlightening questions you can ask your parents to learn more about them and strengthen your relationship. These questions have been gathered from multiple online sources, offering you a diverse selection to foster meaningful conversations with your parents.

How Asking Reasons For Asking Your Parents Questions Helps

Studies show that family relations are key to shaping a person’s well-being throughout life (1). Researchers have also suggested that healthy family communication can help reduce anxiety and depression in adolescents (2). Hence, having healthy interactions with family and parents is crucial for any individual’s development.

One effective way to nurture such healthy interactions is through effective conversations. Meaningful questions can facilitate a healthy discussion. Research highlights that questions are crucial tools that help us communicate, gather information, and improve interactions (3).

When you converse with your parents, hoping to learn more about them and yourself, you open the doors of communication and gather information from them, which helps you better understand them. It enables you to strengthen your relationship and spend a memorable time with them.

Thought-Provoking Questions To Ask Your Parents

A fun question-answer session with parents can provide deeper insight into their lives and give you a great learning experience.

Amitt Mahajan, a blogger and serial technology entrepreneur, shares how interviewing his mother enlightened him and strengthened their relationship. He says, “My mom turned 65 recently, and I wanted to interview her and capture her life story. My goal was to spend time with her, listen (and practice being patient!), and create a family relic I could hopefully share with my kids and grandkids someday.

“The interview also filled in some gaps I had in my knowledge of my mother’s history and helped me understand her journey more completely, even though I had heard bits and pieces of her story over my lifetime. Some philosophical differences also were highlighted and articulated, which are interesting future topics of conversation (i).”

Here are a few thought-provoking questions to ask your parents about their experiences. You can follow up with more questions based on their answers, but avoid asking interrogatory questions, which might hurt them. These questions are best asked on a calm day when your parents are willing to revisit old memories and speak about their life experiences.

1. How and when did you know you were in love with each other?

Image: IStock

2. How would you describe your father?
3. How would you describe your mother?
4. Were you popular in high school?
5. What is your biggest regret in life?
6. Where did you go for your honeymoon?
7. Are you happy with the work you do?
8. Whom did you idolize growing up?
9. Have you ever admired a historical figure? If yes, why?
10. Did you play any sports in high school?
11. Has a sport taught you any valuable lessons in life?
12. How many countries have you traveled to?
13. What is the one piece of advice you would give your teenage self?
14. What is the happiest moment of your life?
15. When did you buy your first car? How was the experience?
16. What scares you the most?
17. How many people did you date?
18. What do you love the most about mom/dad?
19. Did you have a pet name when you were a child?
20. Were you closer to your mom or your dad?
21. What was your favorite subject in school?
22. Were you a part of any club in high school?
23. Have you ever played a prank on someone?
24. What was your favorite band growing up?
25. How was your college life different compared to mine?
26. What was the worst job you ever had?
27. Did you have a part-time job while studying?
28. Have you ever juggled multiple jobs?
29. Have you ever been rewarded for your hard work at a job?
30. What were your hobbies and interests when you were a child?

Quick tip

You may use the questions as an icebreaker if you need to talk about a serious issue but sense that your parents might not like talking about it.

31. What was your preferred toy as a child?
32. What subject were you terrible at in school?
33. Can you share a funny or memorable story from your school days?
34. Who was your closest friend growing up?
35. What was your first job, and how much were you paid?
36. What significant life lessons did you learn from your first job?
37. How was the financial situation at home when you were a child?
38. What did you do on your birthdays when you were growing up?
39. Did you own any pets when you were a child?
40. What is your proudest moment in life?
41. What quality of your partner do you love the most?
42. Were you close to your siblings?
43. How many times have you fallen in love?
44. How was dating during your time different compared to now?
45. What kind of student were you?
46. Describe your first meeting with your spouse?
47. What is one quality you have always wanted your partner to imbibe?
48. What is the most important lesson you have learned in life?

Did you know?

Asking questions can help you know your parents on a deeper level and find out how their experiences have molded their personality.

49. Describe the story of your proposal.
50. In what way was your upbringing different from mine?
51. What was your dream job when you were a child?
52. What is the one thing about me you would want to change?
53. How is your relationship with your in-laws?
54. Could you tell me your most special childhood memory with your parents?
55. Are you still in contact with any of your childhood friends?
56. Why did you choose this career option?
57. Were your parents strict or lenient?
58. What is the one technology or gadget you wish was available when you were younger?

Image: IStock

59. Where did you go on your first date?
60. Who was your favorite professor in high school? Why?
61. What was your favorite hangout spot in high school?
62. What is the one mistake you made that you never want me to make?
63. What did you do with your first paycheck?
64. How did you celebrate different festivals growing up?
65. Were you close to your grandparents?
66. How many long-term relationships have you had?
67. What is the one thing in life you always wanted to do but have not done it yet?
68. Who was your favorite actor growing up?
69. Did you dislike any of my school friends? Why?
70. Have you ever broken someone’s heart?
71. What is your worst habit?
72. Were you ever suspended from school?
73. Is there anything you always wanted to tell your parents but couldn’t?
74. How would your teachers from high school describe you?
75. Do you have a teacher who significantly influenced your academic performance?
76. Which was your favorite fantasy movie as a child?
77. What was the most difficult phase of your life in which you faced many challenges?
78. Which childhood memory do you cherish the most?
79. How were your high school days?
80. Did you have any favorite extracurricular activities?
81. Which is your most memorable field trip in school?
82. Have you ever won any academic or sports competition in school?
83. What is the most endearing thing you have ever done for your parents?
84. How did your parents handle the challenging times faced by your family?
85. What is the most memorable gift your parents have given you?
86. Do you want to change anything about your career?
87. Is there any member of your family you wish I had met?
88. How do you and your spouse resolve conflicts?
89. Which is your favorite book?
90. Was there a piece of literature that left a lasting impact on you during your school years?
91. What is the biggest life lesson your parents have taught you?
92. What are you most grateful for in life?
93. What is your biggest accomplishment?
94. How do you want the world to remember you?
95. What was your favorite breakfast when you were a child?
96. Do you believe in life after death?
97. What is your personal belief and motto in life?
98. What was your most memorable trip as a child?
99. Do you have any phobias?
100. How do you deal with your insecurities?
101. What was your go-to song when you were a teenager?
102. Which is your favorite childhood picture?
103. Did you have any serious health problems as a child?
104. What kind of neighborhood did you grow up in?
105. Did you have any bad break-ups? How did you cope with them?
106. What would you describe as a turning point in your life?
107. What is the biggest difference between teenagers today and teenagers during your time?
108. When was the last time you were emotional about something? What was it?
109. Are you happy with the person I am today?
110. What did your parents do for a living?
111. What did your grandparentsdo for a living?
112. Have you ever been disappointed in me? When was it?
113. Have you ever gotten in trouble with the law?
114. Which is your best investment decision?
115. Did you get any pocket money growing up? How much was it?
116. Were you close to anyone from your extended family?

Image: iStock

117. When did you first consume alcohol?
118. What is your favorite travel destination?
119. Has a travel experience changed your perspective on life?
120. Do you have a bucket list? How many wishes have you checked off the list?
121. What do you like the most about the city you currently live in?
122. What was the biggest disagreement you ever had with your parents?
123. If you had to choose a different career path, what would you want to be?
124. How did you generally spend your school vacations?
125. Do you believe that you and your partner are soulmates?
126. How did you realize you wanted to spend the rest of your life with your spouse?
127. If you could have dinner with any celebrity, dead or alive, who would you choose?
128. Have you ever suffered from severe anxiety or depression? How did you cope with it?
129. Have you ever faced bullying in school?
130. What was your favorite pastime when you were a child?
131. Who taught you to drive?
132. Did you ever become prom king or queen?
133. Which was your go-to store to shop for clothes when you were in high school?
134. When was the last time you were happy?
135. Were your parents openly affectionate?
136. What was the highlight of your wedding day?
137. Which family traditions or rituals do you enjoy the most?
138. Are there any family traditions that you want to be passed down to future generations?
139. What is the worst decision you have ever made?
140. What was that moment that made you realize you wanted to marry each other?
141. Did you play any musical instrument when you were a child?
142. What is your perspective on religion? How did it change now?
143. Have you ever bumped into any celebrity? How was your experience?
144. Have you ever tried to trace back your ancestry? What did you find?
145. Did your parents ever raise a hand on you?
146. What do you miss the most about your college days?
147. What is the best gift you have ever received?
148. What is the one hobby you wish you had pursued?
149. Have you ever kept a diary?
150. What games did you enjoy playing in childhood?
151. What are your earliest memories of your hometown?
152. What is your most special memory from your dating years?
153. What do you do to ensure personal well-being while being parents?
154. How important is a self-care routine to you?
155. What is the toughest decision you have made as parents?
156. What is the most rewarding thing about being parents?
157. What is the most valuable lesson you have learnt from your children?
158. What advice would you give to couples who are considering starting a family?
159. In retrospect, is there anything you wish you had done differently as parents?
160. How has parenthood changed you as a person?
161. What are your dreams and aspirations for your children?
162. How have your childhood experiences shaped you as a parent?
163. Have you ever had a life-changing encounter with a stranger? If yes, how did it affect you?
164. Have you ever gone on an unplanned or spontaneous journey?
165. If you could relive one day from your past, which day would it be? And why?
166. What are the good and bad changes you have noticed in the education system since you were a student?
167. What advice would you give your younger self as a student?
168. What is your most cherished memory from your college days?
169. What was your first impression of each other?
170. What is the most romantic gesture made by your partner that moved your heart?
171. What is the funniest topic you have ever discussed on a date?
172. How did you manage your finances and do your budgeting in the initial days of your career?
173. Have you ever made a sacrifice for someone else and regretted it later?
174. Were there any fashion trends or styles that were popular during your teenage years?
175. How did you handle academic pressure as a student?
176. Did your parents impose any strict rules on you when you were a teenager?
177. How was your relationship with your parents in your teens?
178. Who was your first friend in life?
179. What are you most scared of losing?
180. Did you and your best friend ever have a fight?
181. What do you think is the best thing about being a teenager?
182. What do you think is the worst thing about being a teenager?
183. How did you handle peer pressure as a child?
184. Describe your teen years.
185. How have you dealt with failure or setbacks in life?
186. What important life lessons have your failures taught you?
187. Has an act of kindness or generosity significantly impacted your life?
188. What tip would you like to give me about time management?
189. What is your biggest motivation to work hard in life?
190. What is the work ethic you never compromise on?
191. How do you handle competition at work?
192. Have you ever had to choose between work and personal life?
193. Which place in the world would you like to visit right now?
194. How have your dreams and ambitions changed over the years?
195. What relationship advice would you like to give me?
196. If you were my classmate, would you like to befriend me?
197. How do you manage work and family commitments?
198. Have you ever been on a trip with total strangers?
199. Which place makes you feel calm and comfortable?
200. Have you ever been to a rock concert?
201. What is the most thrilling sports moment you have ever experienced?
202. Have you ever had a real life encounter with a famous athlete?
203. What is your go-to comfort food when you are feeling low?
204. Have you ever tried a unique or exotic dish in another city or country and wish to try it again?
205. Which was the first dish you cooked by yourself?
206. What is the thing you like to do to destress yourself?
207. Did you ever try starting your own club or community in college?
208. Were you ever a teacher’s favorite student?
209. Did you have any teacher with a peculiar or unique style of teaching?
210. Can you remember a funny mishap at a family event or gathering?
211. Have you ever been a witness to a historical moment?
212. Did you ever take up a hobby or skill class just to impress someone?
213. Have you ever kept a funny or embarrassing nickname for your friend?
214. What is the most surprising way in which you have bumped into an old friend?
215. Has your friend ever tried to set you up with a weird date?
216. Has a friend of yours ever lied to your parents to save you from their scoldings?
217. Have you ever blanked out in an exam?
218. What is the most creative way someone you know has cheated in an exam? Have they been caught?
219. Have you ever misread an exam question and provided an unintentionally funny answer?
220. Have you ever followed a ritual before an exam?
221. Who do you like to share your secrets with?
222. What is your philosophy on money and career?
223. How do you adapt to changes in life?
224. Have you ever experienced a funny kitchen mishap while trying to cook alone?
225. Have you ever made a new dish that turned out surprisingly well?
226. How did it feel to be financially independent for the first time?
227. Were you scared when you first moved out of your parents home?
228. Can you give some tips on how to achieve work-life balance?
229. What is the biggest risk you have taken in life? Was it worth it?
230. How has your definition of success and happiness changed over the years?
231. How would you like your future generations to remember you?
232. Describe a moment when you felt proud of yourself for helping someone selflessly.
233. Did you ever get a bad haircut? If yes, what did you do about it?
234. Have you ever given someone a fake contact number to avoid them?
235. If you were a rule maker of the country, what taxes would you abolish and what new ones would you impose?
236. Have you ever participated in any movement or protest?
237. If you could turn your hobby into your profession, would you do it?
238. If you could go back in time and meet your spouse again, would you like to have met them sooner or later than you did in real life?
239. How do you escape an argument with your spouse?
240. Is there any fun activity you would like to undertake with your spouse?
241. When you feel lonely, who do you call first to feel better?
242. Have you ever denied owning a personal item to avoid sharing it with someone?
243. Have you ever danced spontaneously in a public place?
244. What is the biggest sacrifice your parents made for you?
245. When was the last time you laughed uncontrollably?

Funny Questions To Ask Your Parents

Lighten the mood with these funny questions to ask your family when the conversations get serious. Here are questions to ask your parents during family gatherings. Consider these questions to spark fun conversations and laughter.

246. What is the funniest prank you have played on someone?
247. What is the funniest thing I have ever done as a child?
248. What is the most annoying thing about your spouse?
249. Did your parents ever catch you smoking or drinking when you were a teen?
250. Have you ever acted sick to skip school?
251. Have you ever been caught sneaking out of the house after curfew? Where were you going?
252. Have you ever stolen money from your mother’s purse?
253. What was the most embarrassing thing your parents have ever said to you in front of your friends?
254. Who is the first one to say sorry when you and your spouse fight?
255. What is the most embarrassing moment of your life?
256. What is the most embarrassing thing you have done on social media?
257. When did you have your first kiss?
258. Have you ever done anything silly after getting drunk?
259. What is the most spontaneous thing you’ve ever done?
260. Did you ever make a date embarrassing? How?
261. Have you ever cried watching an animated movie?
262. What is the craziest fashion trend you have ever tried?
263. What was the naughtiest thing I had done as a child?
264. When did you start dating?
265. Have you ever flunked in a test or exam?
266. What is your pet name for your partner?
267. Till when did you believe in Santa Claus?

Image: IStock

268. Did I ever break something valuable as a child? How did you react?
269. What is the most absurd lie you have said at work for being late?
270. Is there a funny or memorable parenting moment that still makes you laugh?
271. Have you ever fake called someone just to check if they are at home or not?
272. What is the silliest thing you have done to impress your crush?
273. If you could swap lives with me, what is the first thing you would do?
274. If you were a celebrity, what would you like to be known for?
275. If you had a superpower, would you use it to gift me anything I ask for?
276. Which is the worst pickup line you have ever used on someone?
277. Can you imitate a cartoon character?
278. What is the most embarrassing nickname someone has ever given you?
279. Have you ever had a weird encounter with a stranger?
280. If you were a professional wrestler, what would be your ring name?
281. Describe the most bizarre dream you have ever had.
282. Have you ever accidentally sent a text or email to the wrong person? If yes, then what happened?
283. Have you ever been caught talking loudly to yourself in a public place?
284. When I was a child, did I do something that embarrassed you?
285. What is the most absurd item you have purchased online?
286. Have you ever secretly enjoyed seeing two people fight?
287. What is the funniest costume you have ever worn at a Halloween party?
288. What do you do when someone you don’t like hits on you?
289. What is the most weird and impossible new year’s resolution you’ve ever made?
290. Have you ever pretended to be on a fake call just to avoid speaking with someone near you?
291. Have you tried a DIY beauty treatment at home that failed epically?
292. In your childhood, have you ever broken a toy and blamed your sibling for it?
293. What is the funniest misunderstanding you have ever had with a parent or teacher?
294. As a child, did you have any peculiar habit or quirk that your family still teases you about?
295. Did you ever consider running away from home in your childhood?
296. Did you accidentally invent or discover something in your childhood?
297. Have you ever called a random number and tried to have a conversation with a stranger?
298. Have you ever hit on a friend’s girlfriend or boyfriend?
299. Can you share a funny incident involving your childhood friends and you that makes you laugh even today?
300. Have you ever enacted a scene from a movie in front of a mirror?
301. Has a romantic gesture for your spouse ever failed badly?
302. What’s the silliest relationship advice you received when you were younger?
303. What did you think of relationships and marriage as a child?
304. What’s the most hilarious autocorrect fail you have experienced while texting someone?
305. Have you ever faked an accent while talking to a stranger?
306. Have you ever had a funny conversation with a voice assistant imagining it was a real person?
307. Can you recall a funny interpretation by a voice assistant?
308. What is the most ridiculous excuse you ever came up with for not doing homework or assignments?
309. Have you ever played hooky from work?
310. Have you ever been caught imitating someone behind their back?
311. What is the weirdest rumor you have heard in school?
312. Have you and your bestie ever given a coworker a secret nickname or codename?
313. Have you ever eaten during a lecture in school?
314. Why don’t schools have a subject on how to play video games?
315. Have you ever fallen asleep during an official conference call?
316. Can you remember being a part of a group project that made a hilarious presentation?
317. Do you have secret nicknames for each other?
318. What’s the weirdest thing you have done when you thought no one was watching?
319. What is the funniest thing you have caught your parents or siblings doing when they thought they were alone?
320. Have you ever laughed at a serious moment?
321. Did you have any weird practices or habits that helped you study better?
322. Have you ever attended an official online call in your jammies?
323. Have you ever made a fake social media account just to stalk someone?
324. Have you ever had imaginary interviews in your mind?
325. If you could ask your favorite celebrity a question, who and what would you ask?
326. Have you ever drunk-dialed your partner?
327. Did you have a crush on your professor?
328. What is the weirdest way in which you proposed to someone?
329. Did you ever behave like a clown to impress your friends?
330. Have you ever eaten at a restaurant and left without paying the bill?
331. If you could be a bird or a fish, what would you be? Why?
332. Did you ever add salt to your food thinking it was sugar?
333. If you were the principal of a school, what subject would you remove from the syllabus?
334. Have you ever gatecrashed a party?
335. Have you ever used Algebra in your life after high school?

Questions To Ask Parents About Children

Are you curious about what your parents felt about you and your siblings when you were little? If so, consider asking them the following questions politely and respectfully, avoiding any interrogative expressions. Also, ask these questions when they are chatty, and be okay with revisiting their past to answer your questions.

336. What was your biggest belief about raising children that turned out to be untrue?
337. How would you describe the day I was born?

338. How many children did you want to have?
339. How did you react when you learned that you were going to have a baby?
340. How did you feel when you first held your baby in your hands?
341. If you could ask for one wish for your children, what would you ask?
342. How did you know you were ready to have children?
343. Did you face any complications when having children?
344. How did you change as a person after having children?
345. What do you miss the most about the time when you didn’t have any children?
346. How did your relationship with your spouse change after having children?
347. What is the one thing you want to give your children that your parents could not give you?
348. When are children the toughest to raise?
349. Were you ever guilty of comparing your children with those of others?
350. If you had a chance to change anything about the way you raised children, what would you change?
351. Did you plan to have children, or did it just happen?
352. Were there any disagreements between you and your partner about parenting styles for your children?
353. What parenting advice would you give to new parents?
354. What is the toughest thing about raising children?
355. Did the idea of having children ever scare you?
356. Did you ever wish for more children?
357. Did you read any parenting books or seek parenting advice from your elders?
358. How did you feel when your firstborn started school?
359. What is the most fulfilling thing about raising children?
360. How did you teach your children to pick up good habits?
361. What is the worst complaint you have received about me?
362. Was I a difficult baby to manage?
363. What did you feel when you first saw me after I was born?
364. What is your favorite memory about me?
365. What was the most annoying thing about me when I was little?
366. What did you crave the most when I was yet to arrive in the world?
367. Why did you decide to name me……?
368. According to you, whom do I resemble the most personality-wise?
369. How was I as a baby?
370. What qualities do you and I have in common?
371. What was the most challenging thing about being a parent to two/three/four children?
372. How would you describe me in three words?
373. Which is your most cherished photo of me?
374. Did I walk first or talk first?
375. What was the first word I uttered?
376. What is your favorite story about me as a child that you always used to tell in family gatherings?
377. Who used to pamper me the most as a child?
378. Who has changed my nappies the most?
379. Where was the first trip you took with me when I was still a baby?
380. What is the loveliest thing your children have ever done for you?
381. When I was a child, what scared me the most?
382. What do you love the most about me?
383. What kind of parent do you think I will be?
384. How did you celebrate my first birthday?

Image: IStock

385. When did I start walking?
386. When did I start talking?
387. What is the one thing you always wanted to ask me but have not done it yet?
388. What was my favorite bedtime story?
389. Can you recall the other name options you had for me in your mind?
390. What similar traits do I share with you?
391. What is that one thing I did that made you feel proud of me?
392. What is the most adorable thing I did or said as a child?
393. Did I ever surprise you with an unexpected act of kindness?
394. What is the best thing I have ever given you or done for you?
395. What surprises you most about me?
396. Have I ever asked you an embarrassing question in public?
397. Did I have any food aversion as a child?
398. Did I have a favorite song as a baby?
399. Who would sing me to sleep most of the time?
400. Can you recall any moment when I tested your patience?
401. Do you remember the first time I smiled?
402. What good qualities do you think I should develop in me?
403. How do you think I can improve myself as a person?
404. Did I dislike any relatives as a child?

How To Deepen Your Interaction With Parents?

Depending on the purpose of your interaction, prepare the relevant and follow-up questions that will give more insight into your parent’s life and personality.

For instance, if you intend to have a thought-provoking interaction regarding their career choices, “Are you happy with the work you do?” and based on their answer, you can then ask them more work-related questions like “What was your first job, and how much were you paid?” and “What significant life lessons did you learn from your first job?”

You can also ask them about their dream job to understand their real dreams and ambitions. Combine questions related to the same topic and ask them when discussing the particular topic with them.

Illustration: Fun Yet Meaningful Questions To Ask Your Parents

Image: Stable Diffusion/MomJunction Design Team

Infographic: Questions To Ask Your Parents

Establishing a strong bond with one’s parents is important. If you are having trouble doing it, we are sure that the right questions can help you get to know them better. The following infographic contains a list of such questions that you may ask your parents in the next family time moment.

Illustration: Momjunction Design Team

Community Experiences

Join the conversation and become a part of our nurturing community! Share your stories, experiences, and insights to connect with fellow parents.

Reviewer Author Editor Fact Checker

Dr. Holly SchiffPsy.D.

Dr. Holly Schiff is an experienced clinical psychologist with around nine years of experience in the field. She did her Doctorate of Psychology in School and Community Psychology from Hofstra University and graduated from Fordham University.

Read full bio of Dr. Holly Schiff

Shikha ThakurMBA

Shikha is a writer-turned-editor at MomJunction, with over seven years of experience in the field of content. Having done a certification in Relationship Coaching, her core interest lies in writing articles that guide couples through their courtship to marriage and parenthood.

Read full bio of Shikha Thakur

Akshay NairMA

Akshay is an associate editor and former journalist with more than four years of experience. A post graduate in Mass Communication and Journalism, he has strong professional and academic background in the field of content writing and editing.

Read full bio of Akshay Nair

Shinta Liz SunnyM.Tech

Shinta is a biotechnologist who is highly intrigued by science and technology. She holds a master's degree in Biotechnology from Karunya Institute of Technology and Sciences and a PG Diploma in cellular and molecular diagnostics from Manipal University.

Read full bio of Shinta Liz Sunny