Deep Questions to Ask
Small talk is easy; real conversations need better questions. These deep questions go past "what do you do?" into values, regrets, dreams and the big philosophical ones, the kind that make people stop and think before answering.
Use them with a friend or partner, or answer them alone: Twenty1 solo mode keeps your answers in a private journal on your device.
45 deep questions
- 1What do you need more of in your life right now?
- 2Is it better to have loved and lost or never loved?
- 3What's something you pretend not to care about?
- 4Are people born good?
- 5When was the last time you felt really proud of yourself?
- 6Should we colonise other planets?
- 7What's something you've never told anyone?
- 8What makes something beautiful?
- 9What do you think your purpose is?
- 10Is it better to be happy or to be good?
- 11What's a belief you held strongly that you later changed?
- 12What does it mean to be a good person?
- 13What recharges you when you're exhausted?
- 14Do you think animals have feelings like we do?
- 15What's a moment that changed the direction of your life?
- 16What's a truth most people don't want to hear?
- 17Which fear has held you back the most?
- 18What's more important: freedom or security?
- 19How do you want to be remembered?
- 20What's a rule society follows that makes no sense?
- 21What's the best decision you've made in the last year?
- 22What would a perfect society look like?
- 23What do you hope people feel after spending time with you?
- 24What do you owe to strangers?
- 25What are you most afraid of losing?
- 26What do you think dreams are for?
- 27What's the bravest thing you've ever done?
- 28What does time mean to you?
- 29What's a question you're afraid to ask yourself?
- 30Should you judge the art separately from the artist?
- 31What's something you've outgrown?
- 32Is boredom good for us?
- 33What's something you've learned from a difficult person?
- 34What is love, really?
- 35What's a small thing that instantly makes your day better?
- 36Should animals have the same rights as humans?
- 37Which version of you do your parents know best?
- 38Is happiness a choice?
- 39What do you think you'll regret not doing?
- 40Is there such a thing as a selfless act?
- 41How do you usually handle sadness?
- 42Is it possible to be completely objective?
- 43What would you tell your 15-year-old self?
- 44Would you rather know everything or feel everything?
- 45What does a perfect ordinary day look like for you?
How to use these questions
Pick a quiet moment, ask one question and really listen to the answer before moving on. Follow-up questions are where the good stuff is. In Twenty1, choose Solo to reflect on your own, or play online with a room code to answer together and reveal at the same time.