Take the time to deepen your closest relationships
You spent your childhood with your parents and siblings—maybe even a cousin or grandparent—but can you honestly say you know who your relatives are as people? The truth is, you probably didn’t bother posing many probing questions for family when you were younger. But now, asking a few of your mom and dad, brothers and sisters, grandparents and extended family will allow you to forge stronger connections with them as you delve into some of their inner thoughts, hopes and dreams.
Remember, questions for family don’t have to be shot out of a canon, rapid-fire style. Nor do they need to be submitted to your sibling like a kind of test. Instead, pick a few at random during a quiet moment over coffee. Or suggest a family dinner where everyone gets a turn to ask some burning questions. Think of it as less of an interrogation and more of a get-to-know-you chat.
However you approach it, know that questions for family may lead to deep, thought-provoking conversations you never knew were possible. So choose your family member, set a date, then keep scrolling for prompts that will help you understand your family in new and exciting ways.
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Questions for your mom
- Who was your best friend growing up?
- What’s the smartest advice you ever received as a mom?
- What is your favorite memory of me?
- At what point in my childhood did you feel confident as a mother?
- Can you describe your childhood bedroom?
- Do you think you’re a good parent?
- Who was the biggest influence in your life?
- What was your relationship like with your mother?
- Did you feel ready to become a mom?
- What are you most looking forward to right now?
- What were you like as a teenager?
- Did you like school when you were growing up?
- Did you have pets as a child?
- What was your happiest childhood memory?
- Did you have a favorite job—or one you hated?
- What are you most grateful for?
- If you could relive a moment in your life, what would it be?
- Was I a difficult child?
- Did you have any hobbies when you were younger?
- What makes you laugh the most?
Questions for your dad
- Who was your hero as a child?
- What did you want to be when you were growing up?
- Did you feel confident as a young dad?
- What was your hometown like as a kid?
- What’s the biggest challenge you’ve faced?
- How has being a dad made you a better person?
- What advice would you offer for raising my own kids?
- Were you scared to become a parent?
- What has been your favorite job in your career?
- How do you want to be remembered?
- What was your relationship like with your dad?
- Which skill do you value the most?
- Does anything keep you up at night?
- Did you play or follow a sport as a child?
- What do you want to do in your retirement?
- Did you have a mentor when you first started out?
- What is your earliest memory?
- What was your most embarrassing moment?
- What do you remember about my birth?
- What are you most proud of?
Questions for your siblings
- What’s your favorite childhood memory?
- Was it hard being my sibling?
- Do you think Mom or Dad favored one of us?
- Were you ever bullied or teased?
- Which holiday was your favorite when we were kids?
- Were you jealous of me when we were growing up?
- Do you think it’s harder to be the older or younger sibling?
- Who was your first love?
- What is your hidden talent?
- What was your most rebellious moment?
- Would you say you’re good with money?
- If we could take a dream trip together, where would we go?
- What scares you the most?
- Do you worry about our parents getting older?
- Which family vacation did you love most?
- Is there a special tradition you plan to continue with your family?
- What legacy do you hope to leave behind?
- How do you define success?
- Is there a family secret or story I don’t know about?
- If you could master one skill, what would it be?
Questions for your grandparents
- What’s your most cherished memory?
- What’s the biggest difference between your generation and mine?
- If you could relive any year of your life, which would you pick—and why?
- What’s the best thing about being a grandparent?
- And what’s the worst or hardest thing?
- What’s your greatest wish for the next generation?
- Are you afraid of dying?
- What brings you the most joy right now?
- Are you looking forward to something special this year?
- What has been the biggest challenge you’ve faced?
- Which historic moment stands out from your lifetime?
- What do you wish you had more time for?
- What were my parents like when they were younger?
- How has your relationship with money changed as you’ve aged?
- Which humanitarian causes mean the most to you?
- What do you miss most about your own parents?
- Which habit do you wish you’d kicked sooner?
- What would you tell your younger self, if you could?
- Did you have a cherished teacher while growing up? Can you tell me about them?
- What was your biggest failure?
Questions for your extended family
- Which family tradition do you look forward to the most?
- What was the best or happiest time in your life?
- Which quality do you wish you had more of?
- Are you closest to a particular aunt, cousin or other family member? What makes them special?
- What is your biggest goal for the coming year?
- How did you meet your spouse?
- Were you an introvert or an extrovert as a child?
- If you could go anywhere in the world, where would you travel?
- Who did you feel unconditional love from growing up?
- What was the greatest invention in your lifetime?
- Have you ever stolen something or cheated in school?
- What is your favorite memory of me?
- What has been your biggest disappointment?
- What was your worst financial mistake?
- What career advice would you give to a young colleague?
- What was your best memory from high school or college?
- How did you decide upon your life path or career?
- What is your life philosophy?
- What’s the best part about being together as a family?
- What do you value most in a personal relationship?
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For over 100 years, Reader’s Digest has explored the nuances of relationships, working with such luminaries as Dr. Ruth Westheimer, John Gottman, PhD, and Leo Buscaglia (“Dr. Love”). We ran a decade-long relationships column and have published a compendium of features, Love and Marriage: The Reader’s Digest Guide to Intimate Relationships. We support this information with credentialed experts and primary sources such as government and professional organizations, peer-reviewed journals and our writers’ personal experiences where it enhances the topic. We verify all facts and data and revisit them over time to ensure they remain accurate and up to date. Read more about our team, our contributors and our editorial policies.
