Questions to Ask Your Brother: A Guide

Brothers know things about you that nobody else does. They remember the stuff you'd rather forget. But unless you ask the right questions, most conversations stay on the surface. These questions go deeper: childhood memories, goals, lessons learned, and the weird hypotheticals that make conversations interesting.

For more family conversation starters, visit our questions to ask family members guide with 350+ questions organized by relationship and life theme.

Article Snapshot

• Questions covering childhood memories, goals, life lessons, hobbies, success, adventures, and superpowers.
• Childhood questions bring up shared games, family trips, arguments, and shows you watched together.
• Aspirations questions explore past dreams, current goals, and what happened to the plans that didn't work out.
• Life lessons questions surface pivotal moments and advice worth remembering.
• Hobbies questions find common interests or activities to try together.
• Success questions reveal what your brother actually values.
• Adventure questions bring out stories of risks taken and bucket list items.
• Superpower questions add some fun and reveal personality quirks.

Brotherhood Bonds: Questions Worth Asking

Your brother is one of the few people who remembers your childhood from the inside. Asking good questions turns a regular conversation into something more interesting. Here are questions that actually work.

Childhood Chronicles: Shared Memories

You lived through the same years, but you probably remember them differently. These questions bring out stories you might not have heard or thought about in years.

• Which childhood game or prank do you remember most clearly?
• Is there a family trip that stands out in your memory?
• What was the dumbest thing we ever argued about as kids?
• Can you remember a time when we got in trouble together?
• What's the funniest thing that happened during school?
• Did we have any secret codes or languages?
• Was there a snack or meal we always begged for?
• Which cartoon or TV show were we obsessed with?

Aspirations: Then and Now

Dreams change. The things you wanted at 10 probably aren't the things you want now. These questions compare past ambitions with current goals.

• What did you want to be when you were a kid, and how has that changed?
• What's one dream you've held onto over the years?
• Is there something you're working toward right now that gets you excited?
• How do you balance your goals with everything else you have to do?
• Did any of our childhood games influence what you do now?
• How do your current goals compare to what you imagined as a kid?
• What's a dream you had to give up, and why?
• How do you stay motivated when progress feels slow?

Hindsight Wisdom: Lessons Learned

Experience teaches things you can't learn any other way. These questions surface the moments that changed how your brother sees the world.

• What moment changed your outlook on life?
• Have you ever taken a risk that paid off in an unexpected way?
• What's a piece of advice you actually use?
• How has a failure or setback shaped where you are now?
• Can you share a lesson from something that seemed small at the time?
• How have your values changed over the years?
• What do you wish you knew earlier?
• Is there a book or movie that changed how you think about something?

Passions and Pastimes: The Pursuit of Joy

Hobbies reveal what people care about when nobody's telling them what to do. These questions might surface shared interests or activities to try together.

• What hobby helps you relax after a hard day?
• Have you picked up any new interests that surprised you?
• Is there a skill you're working on getting better at?
• What's something we could do together that you'd enjoy?
• How did you get into your main hobby?
• Is there a childhood activity you wish we could do again?
• Is there a hobby you want to try but haven't yet?
• What's the most unusual hobby you've heard of or tried?

Defining Success: A Personal Perspective

People define success differently. These questions show what your brother actually values, which might be different from what you assume.

• What does a good life look like to you?
• What's an achievement you're genuinely proud of?
• How do you measure success outside of work?
• How do you balance ambition with being okay with where you are?
• Who do you think of as successful, and why?
• How does your idea of success differ from our parents' or friends'?
• Can you describe a time you felt successful without anyone else noticing?
• How do you handle feeling like you're falling short?

Adventurous Tales: Thrills and Spills

Adventures make good stories. These questions bring out the risks, challenges, and spontaneous decisions that shaped who your brother is.

• What's an adventure that pushed you outside your comfort zone?
• Do you have a good story about overcoming something hard?
• What's on your bucket list?
• How do you approach new experiences or challenges?
• What's the most spontaneous thing you've ever done?
• Have you ever faced a fear directly during an adventure?
• Can you share an adventure that went wrong but taught you something?
• What's a local adventure you'd recommend?

Imagining the Impossible: Superpower Dreams

These questions are just for fun. They reveal personality quirks and creative thinking without any pressure.

• If you could have any superpower for a day, what would you pick?
• How would your superpower choice reflect what you actually want?
• In a world of superheroes, what kind would you be?
• What fictional world would you want to visit?
• Which superpower would be the most fun to use?
• If we both had superpowers, what trouble could we get into together?
• How do you think having a superpower would change how you see everyday life?
• If you could give a superpower to someone else, who would get it and what would it be?

Brothers share history that nobody else has. These questions help you learn things about someone you've known your whole life. Try a few next time you're together. The answers are usually better than you expect. Learn more about recording family stories with Telloom.