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Deep Questions to Ask
Curated by Ellie “The Player of Games” Lusk
Every friendship has a surface — and a trapdoor. Deep questions are the trapdoor: one honest “what are you actually afraid of?” at the right moment and suddenly it’s 2 a.m., the tea is cold, and you know someone properly.
These 90 deep questions work with a partner, a close friend, a road-trip passenger or a journal. The only rule: whoever asks also answers.
Ready? Tap the button and let the game begin. 🎉
👇 All 90 questions below — steal freely, no sign-up needed.
About Life
- What do you think your life is about, this year specifically?
- What’s the best decision you’ve ever made — and did it feel like it at the time?
- If you could relive one ordinary day — not a milestone, just a Tuesday — which one?
- What’s something you know now that you couldn’t have been told — you had to live it?
- What would you regret not doing if everything stayed exactly as it is?
- What season of life are you in — and what is it asking of you?
- What’s a risk you didn’t take that still visits you?
- What does “enough” look like for you — money, success, recognition?
- Whose life do you quietly envy, and what does that tell you?
- What’s the most alive you’ve ever felt?
- What are you building right now — even if it doesn’t look like building?
- What would you do differently if nobody would ever find out?
- What’s a chapter of your life that deserved a better ending?
- What do you hope is very different about your life in ten years — and what do you hope is exactly the same?
- What’s the hardest thing you’ve survived that you rarely mention?
- When did you last change your mind about something that mattered?
- What’s your relationship with time lately — friend, enemy or stranger?
- What tiny decision turned out to be a hinge your life swung on?
- What are you waiting for — literally, right now, in life?
- If your life so far were a book, would you keep reading — and why?
About Love & People
- What has loving someone taught you that nothing else could?
- What do you need in a relationship that you’ve had to learn to ask for?
- Who loved you well, and what did they do differently?
- What’s the difference, for you, between being wanted and being known?
- What heartbreak shaped you the most — romantic or not?
- What do you find hardest to forgive?
- Who do you miss — and have you told them?
- What’s a relationship you outgrew, and how did you know?
- What role do you usually play in the lives of people you love — and is it by choice?
- What does loyalty look like when it’s hard?
- What’s the kindest thing anyone has ever done for you?
- What do people misread about the way you love?
- What conversation do you owe someone?
- When have you been wrong about a person — in a good way?
- What does home feel like — and who’s in it?
- What’s something you’ve never thanked someone for properly?
- How has your definition of love changed in the last ten years?
- What do you want the people you love to feel around you?
- Whose approval are you still working for — and would they even want that?
- What’s the most love you’ve ever felt in a single moment?
About Yourself
- What do you like about yourself that took years to appreciate?
- What’s a compliment you deflect that you should probably accept?
- What part of you is still the kid you were at eight?
- What are you afraid people would think if they really knew you?
- What’s a pattern you keep repeating — and what’s it protecting you from?
- When are you hardest on yourself, and whose voice is that really?
- What have you outgrown this year?
- What do you do when nobody’s watching that’s the most “you” thing ever?
- What’s something you pretend not to care about — but do?
- What’s the bravest thing you’ve done that nobody clapped for?
- What emotion do you have the hardest time letting yourself feel?
- What would your younger self be shocked you tolerate — and proud you overcame?
- What are you still proving, and to whom?
- What’s your favorite thing about your own mind?
- What healing have you done that nobody gave you credit for?
- What’s a truth about you that took you long to say out loud?
- Where does your confidence come from, on the days you have it?
- What do you need to hear right now, from anyone?
- What are you learning to let go of?
- If you met yourself at a party, what would you think — honestly?
The Big Stuff
- What do you think happens after we die — and how does the answer change how you live?
- What do you believe that you can’t prove?
- Is a good life more about meaning, pleasure or peace — pick and defend?
- What’s something humanity gets badly wrong that seems obvious to you?
- If consciousness could be copied, would the copy be you?
- What’s worth suffering for?
- Do you think people can fundamentally change — or just reorganize?
- What would you sacrifice everything for — is there something?
- Is it better to be fully known or fully free — if you had to overweight one?
- What does “a life well lived” mean, in one sentence, yours?
- What’s the most useful thing you believe, regardless of whether it’s true?
- If you could know the full truth about one thing — the universe, yourself, someone else — what would you pick?
- What do you think future generations will find unforgivable about our time?
- Are we the stories we tell about ourselves, or what’s left when the stories stop?
- What’s sacred to you — religious or not?
- Would you want to know the date of your death — and what would you do differently?
- What’s a question you hope you never stop asking?
- If everything you own and achieved disappeared, what would be left of you?
- What do you owe strangers — where does your responsibility end?
- What’s your answer to “why get up in the morning” — the real one?
Rapid Deep (One-Breath Answers)
- What are you most grateful for, right now, this minute?
- One word for what you need more of?
- What’s your biggest fear, in five words or less?
- Who would you call at 3 a.m.?
- What’s one thing you know for sure?
- Peace or passion — which do you choose today?
- What are you avoiding?
- What’s your favorite feeling?
- What deserves more of your time?
- What would you tell your younger self, one sentence?
FAQ
What are good deep questions to ask?
Ones that ask about experience rather than opinion: “what’s the hardest thing you’ve survived that you rarely mention?” goes further than “what’s your biggest fear?”. Specificity gives people a door to walk through instead of a spotlight.
How do I start a deep conversation without it being awkward?
Timing does most of the work: late evening, a walk, a drive — moments with no eye-contact pressure. Answer first yourself if the question is heavy; going first buys the other person safety.
Can I use these questions for journaling?
Absolutely — every question here works solo. Pick one with the random button each morning or night and write for five minutes without stopping. The “About Yourself” section is essentially a therapy warm-up.