Would You Rather?
20 dilemmas
Deep
Deep would you rather questions don't have funny answers — they have revealing ones. These 20 weigh time against money, kindness against achievement and a quiet life against an exciting one, which makes them good for road trips, first dates and late-night talks with old friends.
All the questions
- Relive your favorite day once a year or See one day of your future
- Do a job you love that pays little or Do a job you don't mind that pays a lot
- Be remembered for your kindness or Be remembered for your achievements
- Live in a big city or Live in a small village
- Have a few very close friends or Have many good friends
- Speak every language or Play every instrument
- Travel the world for a year or Have your dream home right now
- Always say exactly what you think or Never say anything you'd regret
- Change one past decision or See how it would have turned out, without changing it
- Be ten years older with everything you've learned or Be ten years younger and start again
- Have more time or Have more money
- Be the best in the world at one thing or Be good at many things
- Read minds or Have everyone always tell you the truth
- Have a quiet, peaceful life or Have an exciting, unpredictable life
- Learn something new every day or Teach someone something every day
- Meet your younger self or Meet your older self
- Never feel embarrassed again or Never feel bored again
- Lose all your photos or Lose all your messages
- Have a perfect memory or Be able to forget anything you choose
- Know what everyone thinks of you or Never know what anyone thinks of you
Frequently asked questions
What makes a would you rather question deep?
Both options are reasonable choices people really make, so the answer shows what someone values — like a job you love that pays little or one you don't mind that pays a lot.
Are deep would you rather questions good for couples?
Yes, and for friends. They're gentle ways into bigger topics — family, work, regrets — without anyone feeling interviewed.
Is there a right answer?
No. The point is the reason behind each choice, and people often surprise themselves.