Deep questions to ask your friends

Friendships can run for years on logistics and gossip. These go under that — what they're genuinely worried about, what they'd change, the thing they've somehow never told you.

50 deep questions to ask your friends

The big questions worth sitting with. Showing 30 of 50.

• What three hours of your life would you relive exactly as they happened?
• What's the first thing you'd look for in a box of everything you've ever lost?
• What would you do right now if you knew it couldn't hurt you emotionally?
• What one thing about your future would you lock in if you could guarantee it?
• What conversation about you would you want to secretly overhear?
• What question would you ask at the pearly gates?
• What year of your life would you live in forever if you had to pick?
• What would your younger self be most surprised by about your life today?
• What chapter title would you give this current period of your life?
• When's the last time you felt completely like yourself?
• What's something you're scared to want because you might not get it?
• What door did you close that you still think about sometimes?
• Where do you go in your head when you need to feel calm?
• How would people remember you if you disappeared tomorrow?
• What's something you've outgrown but haven't fully let go of?
• Who do you wish you could talk to one more time?
• What's a truth about yourself you've only recently accepted?
• What would you do with your life if money and fear weren't factors?
• What part of yourself do you feel like most people never see?
• What's something you believe now that you didn't believe five years ago?
• What's a skill you've always wanted to learn but felt too late to start?
• What do you think is the most misunderstood part of your personality?
• If you could be an expert in one random, specific thing, what would it be?
• What's a truth about yourself that took you until this year to accept?
• If you could see a stat for your life, which one would you check?
• What's a hobby you lost that you wish you could get back into?
• How has your definition of success changed since you were 18?
• What part of your daily routine do you feel most 'you' in?
• If you could live in any fictional world for a month, where would you go?
• What's something you've outgrown recently that you're glad to leave behind?

+ 20 more in the app.

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