80+ Questions to Ask Your Grandparents & Parents before it's too late

My grandparents were not forthcoming about their life stories. I'm not sure why. I imagine it may have had something to do with their personalities (they were private, soft-spoken people), my age (they may have assumed I was too young to be interested), avoidance (there may have been things they didn't want to remember - they lived through some hard times), or perhaps it merely had to do with the social "rules" of their generation, a generation that tended to be more reticent about sharing their memories with others. 

Since they passed, I've deeply regretted that I wasn't more proactive about asking them about their world, their lives, their memories. The conversations might have been a bit awkward - it's even possible that they might have declined to participate entirely - but I sure wish I'd tried.

Now that my parents are aging, I'm realizing I have another chance. To this end, I've crafted a list of questions that I plan to introduce over the course of the next year - not all at once, but in the course of ordinary conversation, as I can work the questions in. There are a lot of lists like this out on the internet, which I've consulted in the course of compiling this, but you'll probably notice mine is a deal longer, and a bit more detailed. Why? Because my list is designed to dig a level deeper than superficial "What are your happiest memories"-type questions to extract deeper levels of reflection and understanding. 

To anyone else out there in the same boat - use these questions, don't use these questions: just take the time, while you still have it, to think about the conversations you'd like to have, those questions about family you always meant to ask, those memories you'd always hoped to share.

QUESTIONS ABOUT YOUR RELATIVES

1. Tell me about your maternal grandparents. Where did they live over the course of their lives? Who were their siblings? What were their personalities  like (strengths & weaknesses)? What did they do for a living? What were their hobbies/interests/gifts? 

2. How did the maternal side of your family end up in the US? Where did they come from? Why did they leave? Where did they settle? 

3. What role did your maternal grandparents play in your life? 

4. Tell me about your paternal grandparents. Where did they live over the course of their lives? Who were their siblings? What were their personalities  like (strengths & weaknesses)? What did they do for a living? What were their hobbies/interests/gifts? 

5. How did the paternal side of your family end up in the US? Where did they come from? Why did they leave? Where did they settle? 

6. What role did your paternal grandparents play in your life? 

7. Tell me about your maternal aunts & uncles. Where did they live over the course of their lives? What were their jobs? What were their personalities  like (strengths & weaknesses)? What did they do for a living? What were their hobbies/interests/gifts? 

8. What role did your maternal aunts & uncles play in your life? 

9. Tell me about your paternal aunts & uncles. Where did they live over the course of their lives? What were their jobs? What were their personalities  like (strengths & weaknesses)? What did they do for a living? What were their hobbies/interests/gifts?

10. What role did your paternal aunts & uncles play in your life? 

11. Tell me about your mom/dad. Where did they live over the course of their lives? What were their jobs? What were their personalities like (strengths & weaknesses)? What did they do for a living? What were their hobbies/interests/gifts? 

12. Tell me about brothers/sisters. What were their personalities  like (strengths & weaknesses)? What were their interests? What were their jobs? Tell about your relationship with them. Who did they marry, and what do you remember most about their married lives? 

13. Tell me about your cousins. What do you remember about them, and what role did they play in your life? 

14. Did anyone in the family serve in the military? Tell what you know about their service. 

15. Did your family have any customs or traditions related to the country of their origin? 

16. Tell me about any people who were important in your family's life but weren't necessarily relatives

QUESTIONS ABOUT YOUR LIFE (BEFORE MARRIAGE)

1. Where were you born? What do you remember about your first house/town?

2. What other places did you live before you got married? What are your memories of each? (Do you have specific addresses?)

2. What is your earliest memory?

3. What were some of your hobbies/favorite things when you were a child? (toys, games, hobbies, foods, smells ....)

4. What was your parents' parenting philosophy? Were they easy on you? strict? Did they treat you differently from your bothers/sisters? 

5. What are your personal religious beliefs and traditions? The religious beliefs and traditions of your family? 

6. What values did your parents deliberately instill in you? What values did they inadvertently instill in you?

7. What did you want to be when you grew up?

8. Which "best friends" do you remember?  What did you get up to? What did you love about them? 

9. Tell about any especially beloved pets you had

10. How did your family celebrate Christmas? Easter? Halloween?

11. Who took care of you as a child? Did you go to kindergarten/preschool? What was your personality like back then? What memories do you have? 

12. Where did you go to elementary school? What was your personality like back then? What memories do you have? 

13. Where did you go to middle school? What was your personality like back then? What memories do you have?

14. Where did you go to high school? What was your personality like back then? What memories do you have? 

15. Where did you go to college? What was your personality like back then? What memories do you have? 

16. Where did you go to grad school? What was your personality like back then? What memories do you have? 

17. What vacations did your family take? What do you remember about them? 

18. What jobs did before you got married?

QUESTIONS ABOUT YOUR LOVE LIFE

1. Who was your first love?

2. Before getting married, did you have any other serious romantic relationships? What did you learn about love from these relationships?

3. How did you meet your spouse? 

4. What made you fall in love? What did you most admire about each other? 

5. Tell the story of how you got engaged

6. Tell me about your wedding - where? when? who was there? What are your favorite memories?

7. What marital challenges did you need to navigate early in your married life? (money? family? traditions? foods? housekeeping responsibilities?)

8. Any advice about love & relationships that you want to pass on? 

QUESTIONS ABOUT YOUR LIFE (BEFORE CHILDREN)

1. Where did you live? 

2. Would you characterize yourselves as poor, getting by, or wealthy?

3. What jobs did you have during your married life? What do you remember about each? 

4. What did you guys enjoy doing before you had children?

5. What vacations did you take before you had children? 

QUESTIONS ABOUT BEING PARENTS!

1. When did you find out you were pregnant with me? How did you handle the news?

2. What do you remember about your pregnancy?

3. Tell me about the day I was born (where, when, how ...)

4. What was your parenting philosophy?

5. What values did you feel like it was important for you to instill in your children? 

6. What were the hardest things about parenthood? The most unexpected things about parenthood? The coolest things about parenthood?

7. As parents, what did you do best? What did you get right? 

8. As parents, what do you wish you could go back in time and do differently? 

QUESTIONS ABOUT MY LIFE (BIRTH TO 18)

1. Where are all the places we lived before I turned 18? 

2. What was my personality as a baby? As a child? 

3. Who was my first best friends? 

4. What vacations did we take as a family?

5. What are some things about my childhood that I may not know? 

MEMORIES OF A LIFE WELL-LIVED

1. What world events do you remember witnessing? Where were you, and how did they impact you? 

2. How has technology changed since you were a child? Which technologies have changed your life most meaningfully? 

3. In what ways is the world a better place than when you were a child? What should current generations be celebrating? 

4. In what ways is the world a worse place than when you were a child? What could current generations be aspiring to? 

5. Did you have any "heroes" growing up? Who do you most admire, and why? 

6. What's the kindest thing anyone ever did for you? 

7. What's the best advice anyone ever gave you? 

8. What professional accomplishments are you most proud of? 

9. What personal accomplishments are you most proud of? 

10. What are some interesting things about you that people may not know?

11. What physical possessions are most important to you, and why? 

12. What's your happy place? 

REFLECTIONS/LIFE WISDOM

1. Compare what you wanted to be when you grew up with what you actually became when you grew up? How did things work out? 

2. How has your personality changed since you were a child? What would you characterize as your greatest strengths/weaknesses then vs. now?

3. Which relationships/experiences have had the most impact on shaping who you've become as a person? 

6: What are you most thankful for? What are the best decisions you ever made? 

8. What are the most important lessons you've learned about life? What wisdom/insights would you share with future generations? 

9. Let's talk about hard things: What has been the biggest source of stress in your life? 

10. What were some of the most difficult challenges you had to face, and how did you deal with them? What did you learn from them?  

11. What are some things that never happened for you? Things you wish you'd had the courage, or time, or opportunity to do? 

12. What are the hardest life lessons you ever learned?

13. Any secrets you've never told anyone? What are people going to learn about you after you've passed? 

14. What would you like to be remembered for? What do you want the mentioned in your obituary? 

15. What physical possessions would you like to be preserved by your heirs, and why?

Advice for Rising High Schoolers

All these posts about high school graduations set me thinking: what advice might I have benefited from back when I was transitioning from middle school to high school? Like many students, I look back on high school as an awkward time: I was socially clueless, immature, confused, anxious, and absolutely convinced that every other student in the school had the whole thing figured out. Would a list like this have made my journey less fraught? At the very least, feel like seeing so many of my anxieties acknowledged and expressed might have been reassuring, if not actually instructive. 

What advice do you wish someone had imparted to you before your high school career? 

MENTAL HEALTH

1. Get over yourself. While it's tempting to imagine that everyone's judging you by your every word and deed, the fact of the matter is that people are way too distracted and self-absorbed to spend time observing and judging others. Don't let an exaggerated sense of self-consciousness prevent you from doing you. 
2. Everyone else in high school will be as insecure as you are - they just may hiding it better. It's not you - it's an unpleasant but inescapable phase of human development.
3. Pretty much everything you're going to think matters - appearance, number of friends, dating, reputation - doesn't actually matter. You will come to realize this for yourself the day you graduate. Until then, just take our word for it. 
4. Envy is both pointless and poisonous. Over the long term, life has a way of evening things out. In the words of Elsa, "let it go." 
5. Every day is a new day, and a chance at a new start. No need to wait for a new year, a new quarter, a new teacher, a new group of friends, a new season: change starts happening the moment you let it start happening. 
6. Time heals all wounds, including broken friendships, betrayal, and heartache.
7. There *will* be stress. Your job is to develop healthy ways to deal with it. Sleep, exercise, laughter, family, pets, hobbies .... all of these will help you deal. 
8. Set boundaries and trust your instincts. Don't let your core values be corrupted by pop culture or peer pressure.  To quote Professor Dumbledore: "It takes a great deal of courage to stand up to our enemies, but just as much to stand up to our friends."
9. You may not be able to control what happens to you, but you can control how you react to it.  Practice meeting adversity with dignity.
10. When the temptation to go low is strongest, that's when it's most important to go high. Remember that forgiveness isn't about absolving the other person of guilt (it doesn't) - it's about protecting your own mental health. 
11. Pursue things that make you happy, not things you think *should* make you happy ... or that others tell you should make you happy. 
12. Changing your attitude can change your reality. Research has shown that if you pretend to more confidence than you actually feel, you'll start feeling more genuinely confident over time. 
13. Who you are now isn't who you're going to be forever.  Not feeling like you've achieved your best self? Don't worry, there's still plenty of time for that. 
14. Grades may be fine for measuring your performance on a specific task, but they don't measure your intelligence, your worth, or your future.
15. Don't punish yourself for mistakes, but do learn from them. If you aren't making mistakes, you're not learning - you're just treading water. The challenge is owning up to your mistakes and trying to avoid them the next time.   
16. It's okay if high school isn't "the best time of your life." Life is a long game; who wants to peak in high school?  

FRIENDS & EMPATHY

1. Practice empathy; don't judge others until you've walked in their shoes. (And, while you're at it, avoid killing mockingbirds.) 
2. Actions speak louder than words. It's what you *do* that matters, not what you wish you'd done, or what you intended to do. Gratitude, kindness, respect, and courage matter. 
3. Gossip isn't entertainment, it's bullying. Just don't.
4. The friends that matter are the ones who like you for who you are, not who you're pretending to be. 
5. Some friends are there for a season, some for a reason, some for a lifetime. Learn how to tell the difference
6. Relationships require effort. Take the time and effort to nurture the ones that matter. 
7. Surround yourself with people who challenge you. The best way to advance is to surround yourself with people who constantly push you forward. 

ACADEMICS & ACHIEVEMENT

1. Success in high school is, as in life, 90% effort, 10% luck.  Your success will depend almost wholly on the effort you put into it. However, some things will also require patience. 
2. Develop your critical thinking skills.  High school is when you need to learn how to start thinking for yourself instead of allowing other people (parents, teachers, friends, politicians, social media influencers) to think for you. The sooner you master this skill, the better. 
3. Venture beyond your comfort zone and seek out new experiences. Growth comes from exposing yourself to new ideas and experiences. Later in life, new experiences can be harder to come by, so take advantage of opportunities when they arise.
4. Maintain a healthy balance between academics and extracurriculars. Both are equally important in preparing you for life. 
5. You don't know as much as you think you know. Not even close. Be open to viewing things from different perspectives, changing your mind, and accepting constructive criticism graciously.
6. Never be afraid to ask questions. You're not expected to know all the answers - otherwise, you wouldn't need schooling
7. Teachers are there to help you, but they can't help you if you don't tell them what you need. 
8. You can do anything, but not everything. Don't expect to be good at everything you do, but also don't let not being great at something prevent you from doing it!  
9. Most of the things you think are limiting you are actually self-imposed. Practice replacing "I can't do that" with "I can't do that YET."
10. Perfection isn't attainable.  Stop trying, and never, ever use "I'm afraid it's not going to be perfect" as an excuse not to attempt something. You learn 0% of what you don't attempt. 
11. Academics is one path to success, but it isn't the only path.
12. Even if your future lies along another path, however, a high school degree can be critical to accessing all the other paths. Don't close doors that you may one day need to walk through.