Deep would you rather questions

A deep would you rather question works because it makes a big, abstract topic concrete. Asking "What do you value?" gets a shrug. Asking "Would you rather be loved by many or deeply understood by one?" gets a real answer, and usually a story.

Try one or two deep questions after a round of funny ones, once people are relaxed. Couples should also look at the deep section of our couples questions.

Looking for every category in one place? See the full list of would you rather questions.

Tap an option to make your pick. Then ask the group what they'd choose.

Philosophical questions for long talks, journaling and real connection.

• Would you rather be loved by many or be deeply understood by one?
• Would you rather be remembered for something great or be happy but forgotten?
• Would you rather live a life of adventure or a life of comfort?
• Would you rather always follow your heart or always follow your head?
• Would you rather live in the present with no memories or live in the past with no future?
• Would you rather find true love or find your life's purpose?
• Would you rather have a life full of experiences or a life full of possessions?
• Would you rather change the world or change one person's world completely?
• Would you rather have a life with no regrets or a life with no mistakes?
• Would you rather live a simple life or an extraordinary one?
• Would you rather be wise or be happy?
• Would you rather know the meaning of life or know the secret to happiness?
• Would you rather have unlimited knowledge or unlimited creativity?
• Would you rather start your life over or fast forward to the best part?

Questions about love, friendship and the people who shape us.

• Would you rather be loved for everything you're not or liked for everything you are?
• Would you rather have one soulmate or many deep friendships?
• Would you rather always forgive or always be forgiven?
• Would you rather say everything you feel or keep everything inside?
• Would you rather have your heart broken or break someone else's?
• Would you rather reconnect with an old friend or make a new best friend?
• Would you rather know what people really think of you or never know?
• Would you rather be the one who loves more or the one who is loved more?
• Would you rather have honest friends or loyal friends?
• Would you rather lose touch with someone slowly or have one clean goodbye?
• Would you rather be understood without explaining or explain everything and be understood?
• Would you rather tell your younger self one thing or hear one thing from your older self?

Self-reflection questions for journaling and personal growth.

• Would you rather be recognized for your intelligence or for your kindness?
• Would you rather always feel understood or always feel appreciated?
• Would you rather never be able to show emotions or never be able to hide them?
• Would you rather be more confident or be more disciplined?
• Would you rather fix your biggest flaw or double your biggest strength?
• Would you rather be braver or be calmer?
• Would you rather have a voice people listen to or ears that always understand?
• Would you rather be known for what you do or who you are?
• Would you rather achieve your goals alone or with help and share the credit?
• Would you rather be good at many things or great at one thing?
• Would you rather change how you look or change how you think?
• Would you rather know your purpose now or discover it slowly?

Time, memory and the choices that stay with us.

• Would you rather have a pause button for your life or a rewind button?
• Would you rather relive your happiest day or erase your worst day?
• Would you rather know the happiest day of your life in advance or know the worst?
• Would you rather have more time or have more energy?
• Would you rather live in the past or live in the future?
• Would you rather give up all your memories from this year or all the money you made this year?
• Would you rather remember every day of your life or forget everything that hurt?
• Would you rather live to 100 in average health or to 70 in perfect health?
• Would you rather spend one more day with someone you've lost or know they're at peace?
• Would you rather see one moment from your future or revisit one moment from your past?
• Would you rather have your childhood back for a week or your twenties back for a year?

Bigger-picture debates for thoughtful groups and classrooms.

• Would you rather live in a world without money or a world without borders?
• Would you rather end poverty or end loneliness?
• Would you rather have everyone tell the truth or have everyone be kind?
• Would you rather live in a society with perfect equality or perfect freedom?
• Would you rather have the internet disappear or have cars disappear?
• Would you rather be a great leader or a great teacher?
• Would you rather solve climate change or solve world hunger?
• Would you rather have every person speak one language or keep every language alive?
• Would you rather live in a world without art or without science?
• Would you rather make one law everyone must follow or abolish one law forever?

For close friends who want to go beyond small talk.

• Would you rather have a friendship that lasts forever but is never close or one that is close but short?
• Would you rather know your friend's darkest secret or have them know yours?
• Would you rather always be there for your friends or always have your friends be there for you?
• Would you rather have friends who challenge you or friends who comfort you?
• Would you rather share every big moment with a friend or keep some for yourself?
• Would you rather repair a broken friendship or start fresh with someone new?

Take one a day. Write your answer, then write why.

• Would you rather face your biggest fear or achieve your biggest dream?
• Would you rather forgive yourself for one thing or be forgiven by someone else for one thing?
• Would you rather have closure or have a second chance?
• Would you rather be proud of who you are or be proud of what you've done?
• Would you rather live by your values and struggle or compromise and thrive?
• Would you rather slow your life down to half speed or speed it up to double?
• Would you rather be at peace or be excited?
• Would you rather have one great passion or many small joys?
• Would you rather learn from failure or never fail at all?
• Would you rather let go of the past or worry less about the future?
• Would you rather be known for your courage or for your compassion?
• Would you rather spend more time alone or more time with people?

Big ideas for young people figuring out who they are.

• Would you rather be confident or be humble?
• Would you rather be a leader or be a loyal friend?
• Would you rather have a clear path or have freedom to explore?
• Would you rather be accepted or be admired?
• Would you rather be true to yourself or make everyone happy?
• Would you rather chase success or chase happiness?
• Would you rather learn from your parents or learn from your own mistakes?
• Would you rather make your family proud or make yourself proud?

How to use these questions

• Ask follow-up questions: "Why?" and "Has that always been true for you?"
• Use one question a day as a journal prompt. Write your answer, then why.
• Don't rush. With deep questions, one good conversation beats ten quick answers.
• Respect passes. Some questions touch on loss or regret, and that's personal.

Frequently asked questions

What are deep would you rather questions?

Deep would you rather questions ask about values, relationships and meaning, like "Would you rather be loved by many or deeply understood by one?"

What are good deep would you rather questions for friends?

Try "Would you rather have friends who challenge you or friends who comfort you?" or "Would you rather repair a broken friendship or start fresh with someone new?"

Can I use these as journal prompts?

Yes. The journaling and self-reflection section is designed for it. Write your answer, then write why.

Are there deep would you rather questions for teens?

Yes. See the deep questions for teens section, with questions like "Would you rather be popular or be respected?"