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154 thoughtful picks · long talks, journaling & deep dives

Deep Would You Rather Questions

Would you rather relive your best day or see one day of your future? These deep would you rather questions are about life, love, memory and what matters most: choices with no right answer that make you stop and think about yourself. There are 154 of them on this page, grouped by theme, and you can play them right here for free, with no sign-up and nothing to download. Pick a side, see how your pick compares, and then talk about why.

They’re written for slow conversations: a long drive, a second date, a late night with an old friend, or a quiet half hour with a notebook. Thoughtful, warm and sometimes a little bittersweet, but never heavy.

How to play

  1. Read it slowlyRead both options out loud, then pause. A deep question needs a few seconds of quiet before anyone answers.
  2. Pick what you’d really chooseTap your option or press ← or →. Go with your honest answer, not the one that sounds wiser.
  3. Compare, then talkSee how your pick compares, then share the reason behind it. Use the theme filter to stay with love, memory or family for a while.

Would you rather questions about memories and the past

  1. Relive your best day or See one day of your future?
  2. Relive the first day of summer break when you were 10 or Relive your first night in a place of your own?
  3. Remember every day of your childhood clearly or Remember every day of the last five years clearly?
  4. Erase your most embarrassing memory or Erase the memory of your worst heartbreak?
  5. Own a photo from every day of your life or Own a diary entry for every day of your life?
  6. Bring back one toy you loved as a kid or Bring back one ordinary afternoon from when you were a kid?
  7. Spend an afternoon with yourself at age 7 or Spend an afternoon with yourself at age 17?
  8. Recall the name of everyone who was ever kind to you or Recall every place you’ve ever called home in perfect detail?
  9. Get a song that takes you back to your happiest summer or Get a scent that takes you back to your happiest summer?
  10. Reread every note you passed in school or Reread every message you sent as a teenager?
  11. Keep your childhood bedroom exactly as it was or Keep one small box of ten things from your childhood bedroom?
  12. Find a box of letters your grandparents wrote when they were young or Find a box of home videos from before you were born?
  13. Keep one beautiful memory forever but never talk about it or Share a beautiful memory with everyone and slowly lose its details?
  14. Remember your first day at every new place or Remember your last day at every place you left?
  15. Watch a video of your parents on their first date or Watch a video of your own first steps?
  16. Visit the place where your best memory happened or Go somewhere new to make an even better memory?
  17. Find out which day so far was your happiest or Never find out, so it might still be ahead of you?
  18. Record every moment of your life to rewatch later or Rely only on what you remember, with no recordings?
  19. Recall every birthday you’ve ever had or Recall every trip you’ve ever taken?
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Deep would you rather questions about love

  1. Fall deeply in love once, for life or Fall in love several times, each one different?
  2. End up with someone who understands you without words or End up with someone who always talks things through with you?
  3. Give a little more love than you get or Get a little more love than you give?
  4. Meet the love of your life at 22 or Meet the love of your life at 42?
  5. Have a love that feels like an adventure or Have a love that feels like coming home?
  6. Hear “I love you” every single day or See love in small, quiet actions every day?
  7. Build a life with someone who feels like your best friend or Build a life with someone who still gives you butterflies?
  8. Remember the exact moment you fell in love or Find out the exact moment your partner fell for you?
  9. Hear every story from your partner’s past or Start fresh, knowing nothing about your partner’s past?
  10. Choose a calm relationship with a little less passion or Choose a fiery relationship with big highs and loud arguments?
  11. Hear your partner say “I’m proud of you” more often or Hear your partner say “I’m sorry” more easily?
  12. Fall for a friend slowly over many years or Fall for someone the moment you meet?
  13. Be someone’s first love or Be someone’s last love?
  14. Share a tiny apartment with someone you love or Own a big, beautiful home all to yourself?
  15. Fall for someone very different from you or Fall for someone a lot like you?
  16. Win someone over with how you think or Win someone over with how you care?
  17. Always say what you feel, even when it’s awkward or Always keep the peace, even if you hold some things in?
  18. Know your partner would choose you again in every lifetime or Know you’d choose your partner again in every lifetime?
  19. Start a love story with a grand romantic gesture or Start a love story with a long, easy conversation?
  20. Grow and change together over the years or Stay just the way you both were when you met?
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Deep would you rather questions about life choices

  1. Excel at work that bores you a little or Do just okay at work that thrills you?
  2. Be brave in love or Be brave in your career?
  3. Build your whole life in the town you grew up in or Build your whole life somewhere nobody knows your name?
  4. Make one huge leap you can’t take back or Make a hundred small changes over ten years?
  5. Try your dream at 20 and fail or Try your dream at 50 and succeed?
  6. Live with one big mistake you made or Live with one big chance you never took?
  7. Take a big opportunity that scares you or Turn down a big opportunity to protect the life you’ve built?
  8. Get a second try at your teenage years or Get a second try at your twenties?
  9. Follow the path your family hoped for you or Follow a path your family never pictured for you?
  10. Get a map of the choices that lead to a happy life or Find your own way with no hints at all?
  11. Travel for a year after school or Work and save for a year after school?
  12. Find out which of your choices you’ll regret at 80 or Never find out and choose freely?
  13. Spend a year learning from a master of your craft or Spend a year teaching what you know best?
  14. Settle down early and explore later or Explore early and settle down later?
  15. Change the world a little with one choice or Change your own life a lot with one choice?
  16. Spend your 30s building a career or Spend your 30s seeing the world?
  17. Make every big decision in one minute or Take a whole year over every big decision?
  18. Live a life full of firsts or Live a life full of traditions?
  19. Look back at 80 on a life of bold choices or Look back at 80 on a life of wise ones?
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Would you rather questions about values and character

  1. Come across as kind but a little naive or Come across as sharp but a little guarded?
  2. Never tell a white lie again or Never hear a hard truth again?
  3. Do a good deed that nobody ever finds out about or Do a smaller good deed that inspires others to do the same?
  4. Forgive people easily, even when it costs you or Rarely need anyone’s forgiveness?
  5. Stand up for a stranger and look a little foolish or Stay quiet and wonder about it for years?
  6. Give your money freely or Give your time freely?
  7. Keep a promise that no longer makes sense or Break the promise and explain why?
  8. Say what everyone else is thinking or Hold back when it’s better left unsaid?
  9. Show courage in the big moments or Show patience in the small ones?
  10. Live by a strict personal code or Decide what’s right case by case?
  11. Be remembered for your kindness or Be remembered for your courage?
  12. Be truly good but often misunderstood or Be just okay but admired by everyone?
  13. Always admit when you’re wrong or Always stay gracious when you’re right?
  14. Stay loyal to a friend even when they’re wrong or Stay fair to everyone even if it costs you a friend?
  15. Lead from the front or Quietly hold everything together behind the scenes?
  16. Keep a friend’s secret that’s heavy to carry or Tell your friend it’s too much for you to hold?
  17. Live simply and give a lot away or Live comfortably and give a little?
  18. Never judge anyone too quickly or Never be judged too quickly yourself?
  19. Speak up even when your voice shakes or Pick your battles and stay calm?
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Deep would you rather questions about family and friends

  1. Give the best advice in your friend group or Give the best hugs in your friend group?
  2. Show up every single time someone needs you or Know exactly what to say every time someone needs you?
  3. Click with new people instantly but drift apart easily or Take years to open up but keep friends for life?
  4. Stay close to your family with a call every day or See your family in person twice a year for a whole week?
  5. Learn what your family really thinks of you or Learn what your friends really think of you?
  6. Spend a week with your family with no phones or Spend a week with your best friends with no phones?
  7. Share a meal with your great-grandparents when they were your age or Share a meal with your great-grandkids when they’re your age?
  8. Remember every little thing your friends tell you or Make every group plan actually happen?
  9. Grow up in a family that’s loud and close or Grow up in a family that’s calm and private?
  10. Always make your friends laugh or Always make your friends feel understood?
  11. Make one new close friend every decade or Keep the same close friends your whole life?
  12. Call your sibling your best friend or Call your best friend your sibling?
  13. Teach a younger relative everything you know about one thing or Learn everything an older relative knows about one thing?
  14. Throw one huge reunion for everyone you’ve ever been close to or Steal a quiet weekend with your three oldest friends?
  15. Hear first when a friend needs help or Hear first when a friend has big news?
  16. Protect a family tradition exactly as it’s always been or Begin a brand-new tradition your family will keep for years?
  17. Read a letter written about you on the day you were born or Read a letter your best friend wrote the day you met?
  18. Forgive an old friend and start over or Let the friendship go and keep the good memories?
  19. Surround yourself with friends who challenge you or Surround yourself with friends who comfort you?
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Would you rather questions about happiness and meaning

  1. Get your sense of purpose from your work or Get your sense of purpose from life outside work?
  2. Collect a lifetime of great stories or Collect a lifetime of quiet, easy days?
  3. Do work that matters to the world or Do work that leaves you lots of time with people you love?
  4. Feel deeply content but rarely thrilled or Feel thrilled often but rarely content?
  5. Become famous for one great thing or Become quietly great at many things?
  6. Have a perfect Sunday morning every week or Have one perfect week every year?
  7. Feel at home anywhere you go or Have one place that will always feel like home?
  8. Make a small difference to many people or Make a huge difference to one person?
  9. Feel sure of what you want, even if you never get it or Get what you want, even if you’re never sure of it?
  10. Live a life you’re proud of or Live a life you enjoy every day?
  11. Wake up excited every morning or Fall asleep at peace every night?
  12. Find joy in small, everyday things or Achieve one big lifelong dream?
  13. Pour your free time into a hobby you love that pays nothing or Pour your free time into a side job you like that pays well?
  14. Feel one moment of pure, total happiness or Feel a steady, gentle happiness most days?
  15. Make a stranger’s day or Have a stranger make your day?
  16. Create something that outlasts you or Experience as much as you can while you’re here?
  17. Tend one garden for 40 years or Fill a passport with stamps?
  18. Slow down and enjoy more or Speed up and achieve more?
  19. Laugh until you cry once a week or Learn something that amazes you once a week?
  20. Find out what you’re truly meant to do or Find out who you’re truly meant to be with?
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Deep would you rather questions about growing older

  1. Grow old in a home full of noise and people or Grow old in a home full of quiet and books?
  2. Get wiser every year but a little slower or Stay quick and sharp but never get wiser?
  3. Turn into the grandparent everyone wants to visit or Turn into the grandparent with the wildest stories?
  4. Start something new at 60 as a total beginner or Master one thing completely by 40?
  5. Spend your 70s traveling the world or Spend your 70s close to home with family around?
  6. Know the world will be kinder in 100 years or Know your own family will be happy in 100 years?
  7. Pass down a family home or Pass down a book of family stories and recipes?
  8. Become more patient as you get older or Become more adventurous as you get older?
  9. Have your best years still ahead of you or Know your best years so far were truly great?
  10. Age into the wise one people come to for advice or Age into the curious one who’s always trying something new?
  11. Hear your life story told at 80 by your best friend or Hear it told at 80 by your family?
  12. Celebrate your 80th birthday with 100 people or Celebrate your 80th birthday with the five people closest to you?
  13. Feel more confident with every year or Feel more at peace with every year?
  14. Have the energy of a 25-year-old at 75 or Have the calm of a 75-year-old at 25?
  15. Keep your sense of humor all your life or Keep your sense of wonder all your life?
  16. Make your future self proud or Make your younger self proud?
  17. Grow old with a big circle of friends nearby or Grow old with one person who knows you completely?
  18. Settle in for good where you live now or Move somewhere brand new for your later years?
  19. Still be learning new things at 90 or Still be working on something you love at 90?
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Would you rather questions about how you see yourself

  1. See yourself the way your best friend sees you or See yourself the way a stranger sees you?
  2. Discover your biggest strength or Discover your biggest blind spot?
  3. Feel completely confident in how you look or Feel completely confident in how you think?
  4. Be called the calm one or Be called the fun one?
  5. Hear what your 90-year-old self would tell you today or Hear what your 10-year-old self would think of you now?
  6. Change one thing about your personality or Change one thing about your past?
  7. Always be underestimated or Always be overestimated?
  8. Understand yourself completely or Understand other people completely?
  9. Hear an honest review of yourself from your closest friend or Write an honest review of yourself and read it out loud?
  10. Stay exactly who you are now or Become who you hoped to be at 15?
  11. Carry a quiet confidence or Carry a loud, contagious energy?
  12. Feel everything deeply or Stay steady no matter what happens?
  13. Lose one fear for good or Gain one talent for good?
  14. Be the main character of your own life or Be the best supporting character in other people’s lives?
  15. Understand exactly why you do the things you do or Understand exactly why the people who love you love you?
  16. Go one whole day without fear or Go one whole day being completely honest with yourself?
  17. Discover a hidden talent at 40 or Spot your talent at 10 and spend your life growing it?
  18. Act the way you do around your best friend, everywhere or Act the way you do on your best day at work, everywhere?
  19. Like yourself a little more or Be liked a little more by everyone else?
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What makes a would you rather question deep?

A deep question asks about your values, not your trivia. Pizza or tacos tells someone what you’d order. Would you rather give a little more love than you get, or get a little more love than you give? tells them how you think about relationships, and maybe something you hadn’t put into words before.

The best deep questions share three things:

  • Both sides are good. There’s no obvious winner, so the answer depends on what you care about, not on which option is less bad.
  • The answer has a reason behind it. “Make your future self proud or your younger self proud?” is quick to answer and slow to explain. The explaining is the good part.
  • Your answer can change. Ask the same question at 20, 35 and 60 and you might get three different picks. That’s what makes them worth coming back to.

That’s also how they differ from tough dilemmas. A hard question tests what you’d sacrifice. A deep one shows who you are, so it tends to start a conversation instead of an argument.

When to use deep would you rather questions

  • Long drives. A passenger reads from the phone and the driver just listens and answers, eyes on the road. Not having to look at each other makes it easier to be honest, and the miles give every answer room to breathe.
  • A second date. You’ve covered jobs and hometowns, and now you want to know what the other person is really like. Ask two or three questions, not twenty, and start with the gentler themes like happiness or growing older. For more playful questions with a partner, try the would you rather questions for couples.
  • Catching up with an old friend. The questions about memories and family work beautifully here, because you share a past. Try asking which pick they’d have made ten years ago. If you live far apart, vote on a question, press Copy link and send it with a “what would you pick?”
  • Late-night talks. Sleepovers, the last two people at a party, a quiet porch. Let the conversation wander away from the question. That usually means it’s working.
  • Getting to know yourself. Play alone and answer honestly. The questions about how you see yourself are a gentle mirror.

Deep would you rather questions as journal prompts

Every question on this page is a ready-made journal prompt. The choice is already there, so you skip the blank-page feeling and go straight to the thinking.

  1. Pick one question a day. Work through the list in order or choose a theme that fits your week.
  2. Write your pick at the top of the page before you think too hard about it.
  3. Write why. Then write one thing you’d miss about the option you didn’t choose.
  4. End with one sentence about what the answer says about you right now.

Date every entry. Come back to the same questions in a year and see whether your picks have changed. It’s one of the simplest ways to notice how you’re growing.

How to listen and ask good follow-up questions

The pick takes a second. The conversation lives in what comes after, and that depends on how well you listen. Don’t argue to win, don’t rush to share your own answer, and let a pause sit for a moment. People often say the most interesting thing right after a silence.

Follow-up questions that open people up:

  • What made you pick that one so fast?
  • Was there a time in your life when you’d have picked the other side?
  • What would you miss most about the option you didn’t choose?
  • Who do you know who would choose the opposite?
  • Is that what you want, or what you think you should want?

Then answer the same question yourself. Deep conversations work best when both people take the same risk.

Keeping deep conversations comfortable

A deep question should feel like an invitation, never a test. A few simple rules keep it that way:

  • Anyone can pass. Say “pass” and the next question comes up, no explanation needed. On a phone, swipe left to skip a question without voting.
  • A pick is enough. Some people want to talk for ten minutes; others just want to choose. Both are fine.
  • What’s said here stays here. Don’t bring an answer back later as a joke.
  • Match the theme to the company. The love questions suit a partner or a close friend, not a coworker.

These questions are written to be thoughtful, not painful. You won’t find questions about illness, loss or hard family history here. If the mood gets too serious, switch to something lighter. The funny would you rather questions are a good way to end the night on a laugh.

Our favorite deep would you rather questions

If you only have time for a few, start with these. Would you rather…

  • relive your best day, or see one day of your future?
  • hear what your 90-year-old self would tell you today, or what your 10-year-old self would think of you now?
  • relive the first day of summer break when you were 10, or your first night in a place of your own?
  • be the main character of your own life, or the best supporting character in other people’s lives?
  • feel deeply content but rarely thrilled, or feel thrilled often but rarely content?
  • be someone’s first love, or someone’s last love?
  • find out which day so far was your happiest, or never find out, so it might still be ahead of you?

Every one of the 154 questions is in the list below, grouped by theme, so you can read them aloud or keep them for later.

Questions people ask

What are some good deep would you rather questions?

Good deep questions ask about values, with two options that are both worth choosing. Would you rather relive your best day or see one day of your future? Have a love that feels like an adventure or one that feels like coming home? Make a small difference to many people or a huge difference to one person? The best ones take a second to answer and ten minutes to explain.

What’s the difference between deep and hard would you rather questions?

Hard questions are tough trade-offs where every option costs you something, and they often turn into lively debates. Deep questions are gentler. Both options are usually good, and the answer says something about who you are. For real brain-twisters, try the hard would you rather questions.

Are these questions good for couples?

Yes. The love theme is written with partners in mind, and the questions about growing older and happiness make great talks for two. They work just as well on a second date as on a long-married evening on the couch. Answer each one yourself too, so it feels like a conversation and not an interview.

How many deep questions should we ask in one sitting?

Fewer than you think. Five to ten questions can easily fill an hour if people are really talking. On a date or a drive, stop while the conversation is still good instead of rushing through the list. For journaling, one question a day is plenty.

What if a question feels too personal?

Pass, with no explanation needed. On a phone you can swipe left to skip a question without voting. The questions were written to stay thoughtful rather than painful, but everyone has their own tender spots, and nobody should feel pushed to answer.

Can I play deep would you rather on my own?

Yes. Playing alone is a calm way to think about what you value. Tap your pick, see how it compares, and notice which questions you find hard to answer. Those are usually the ones worth writing about.

Do I need an app or an account?

No. The game runs in your browser on any phone, tablet or laptop. There’s nothing to install and no sign-up, and your votes are anonymous. For a broader mix of questions, play the full Would You Rather game.

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