Questions to Ask Your Little Brother
Meaningful questions to ask your younger brother to build connection, understand his world, offer support, and strengthen your sibling bond across different ages.
1What's the best part of your week so far?
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What's the best part of your week so far?
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Why this works
Positive opener that invites sharing and highlights what matters to him.
2Is there anything you're worried about or stressed about?
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Is there anything you're worried about or stressed about?
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Why this works
Opens space for vulnerability and shows you're safe to confide in.
3What are you most proud of recently?
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What are you most proud of recently?
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Why this works
Celebrates achievements and builds his confidence.
4Who are your closest friends, and what do you like about them?
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Who are your closest friends, and what do you like about them?
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Why this works
Understands his social world and peer influences.
5What's something you wish our family understood better about you?
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What's something you wish our family understood better about you?
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Why this works
Validates his perspective and identifies unmet needs.
6What do you want to be when you grow up, or what are you interested in right now?
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What do you want to be when you grow up, or what are you interested in right now?
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Why this works
Shows interest in his dreams and aspirations.
7Is there anything I can help you with or teach you?
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Is there anything I can help you with or teach you?
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Why this works
Positions you as supportive resource, not just authority figure.
8What's your favorite thing to do when you have free time?
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What's your favorite thing to do when you have free time?
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Why this works
Reveals interests and potential bonding activities.
9What's something you wish you could do but haven't tried yet?
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What's something you wish you could do but haven't tried yet?
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Why this works
Uncovers hidden interests and potential opportunities you could facilitate.
10How do you feel about school, and what's your favorite/least favorite subject?
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How do you feel about school, and what's your favorite/least favorite subject?
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Why this works
Understands academic experience and where he might need support.
11What makes you feel happy and confident?
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What makes you feel happy and confident?
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Why this works
Identifies what lifts him up and how you can encourage him.
12Is anyone giving you a hard time, and how are you handling it?
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Is anyone giving you a hard time, and how are you handling it?
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Why this works
Screens for bullying or conflict and offers guidance.
13What's something you think I don't know about you?
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What's something you think I don't know about you?
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Why this works
Invites sharing something personal and deepens understanding.
14What do you like most about being brothers/siblings?
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What do you like most about being brothers/siblings?
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Why this works
Affirms relationship and highlights positive aspects.
15What's a dream or goal you have that maybe feels too big to say out loud?
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What's a dream or goal you have that maybe feels too big to say out loud?
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Why this works
Encourages ambition and shows you believe in his potential.
16What advice would you give me about something?
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What advice would you give me about something?
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Why this works
Empowers him by valuing his perspective and wisdom.
17What's the funniest thing that happened to you recently?
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What's the funniest thing that happened to you recently?
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Why this works
Keeps conversation light and builds shared joy.
18If you could change one thing about your life right now, what would it be?
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If you could change one thing about your life right now, what would it be?
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Why this works
Reveals dissatisfaction or struggles you can help address.
19What do you want to do together sometime soon?
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What do you want to do together sometime soon?
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Why this works
Actively plans quality time and shows you prioritize the relationship.
20Is there anything you want to ask me?
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Is there anything you want to ask me?
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Why this works
Opens reciprocal conversation and gives him space to lead.
Building Strong Sibling Relationships
Expert tips and techniques for getting the most out of these questions.
Best Practices
Meet Him Where He Is
Adapt questions to his age and maturity—younger kids need simpler, more concrete questions.
Listen Without Lecturing
Resist the urge to immediately give advice—sometimes he just needs to be heard.
Share Your Own Stories
Reciprocity builds trust—tell him about your own struggles and wins at his age.
Questions by Age Group
Young Kids (5-10)
Tweens (11-13)
Teens (14+)
Common Pitfalls
Being Too Preachy
Big brother advice is valuable, but constant lectures push him away—balance guidance with listening.
Comparing Him to Yourself
Avoid 'when I was your age'—he's his own person on his own timeline.