40 Deep Would You Rather Questions That Make You Think

Some Would You Rather questions stay with you long after the conversation ends. These questions don't have easy answers - they reveal what we truly value.

Why Deep Questions Matter

In a world of small talk and surface-level conversations, deep Would You Rather questions create space for genuine connection. They force us to examine our priorities and often surprise us with our own answers.

Questions About Success & Happiness

1. Would you rather achieve all your dreams but have no one to share them with, or never reach your dreams but always have a strong support system?
2. Would you rather have universal respect, or unlimited power?
3. Would you rather be extraordinarily intelligent but lonely, or average intelligence but surrounded by loved ones?
4. Would you rather work your dream job for average pay, or work a boring job for incredible pay?
5. Would you rather be famous but constantly scrutinized, or unknown but free?

Questions About Time

1. Would you rather have a rewind button in life, or a pause button?
2. Would you rather know how the world began, or how it will end?
3. Would you rather live 100 years in the past, or 100 years in the future?
4. Would you rather meet your ancestors from 500 years ago, or your descendants from 500 years in the future?
5. Would you rather relive the same perfect day forever, or experience new days that are never quite as good?

Questions About Truth

1. Would you rather always know when someone is lying, or always get away with lying?
2. Would you rather know all the world's secrets, or be blissfully ignorant?
3. Would you rather have all your thoughts be public, or never be able to speak again?
4. Would you rather always have to tell the truth, or always have to lie?
5. Would you rather know what everyone thinks of you, or never know?

Questions About Legacy

1. Would you rather be forgotten after you die but remembered fondly while alive, or be remembered forever but hated while alive?
2. Would you rather make a small difference in many lives, or a huge difference in one life?
3. Would you rather be remembered for one great thing, or many good things?
4. Would you rather live a short life full of adventure, or a long life of safety?
5. Would you rather change the past, or see the future?

How to Have Deep Conversations

Create the right environment: No phones, no distractions, comfortable setting.

Listen actively: The answer matters less than the reasoning.

Share vulnerability: Go first with honest answers to set the tone.

Avoid judgment: There are no wrong answers to philosophical questions.

Follow up: "That's interesting - what made you choose that?"

The Value of Uncomfortable Questions

The best deep questions create a moment of genuine uncertainty. If you immediately know your answer, the question isn't deep enough. The pause before answering - that's where the magic happens.

Play Deep Questions →