100 deep questions to ask friends, or someone new

Deep questions turn a pleasant chat into a memorable one. They are not about prying; they are about giving someone a chance to talk about what matters to them.

These 100 questions are grouped by theme. They work with close friends, for a late-night conversation, or with someone new once the chat is clearly going well.

How to ask deep conversation questions well

• Earn it first. Start light. Deep questions land better after some easy conversation.
• Go first sometimes. Share your own answer to show it is safe to be honest.
• Listen more than you talk. Follow up on what they say rather than moving to the next question.
• Let people pass. “I would rather not answer that” is always fine.
• With strangers, keep it about ideas, not identity. Values and experiences are great; names, places and personal details are not needed.

Deep questions about life

1. What does a meaningful life look like to you?
2. What is something you believed as a child that you no longer believe?
3. What would you do if you knew you could not fail?
4. What is the best decision you have ever made?
5. What is a lesson you had to learn more than once?
6. What does success mean to you now, compared with ten years ago?
7. What are you most curious about in life?
8. If you could live one year of your life again, which would it be?
9. What is something you are still figuring out?
10. What small moment from your past do you think about more than you expected?
11. What would you like to be doing in ten years?
12. What is a risk you would still like to take?
13. What makes a day feel well spent?
14. What is the most important thing you have learned from a mistake?
15. When have you felt most alive?
16. What do you wish you had started earlier?
17. What is something you have outgrown?
18. What is a question you are still trying to answer for yourself?
19. What habit has changed your life the most?
20. What would your perfect ordinary day look like?

Deep questions about values and beliefs

1. What is one value you would never compromise on?
2. What do you think makes someone a good person?
3. Is it better to be kind or to be honest, when you cannot be both?
4. What is something most people believe that you disagree with?
5. What cause would you give your time to for free?
6. Do you think people can really change?
7. What does fairness mean to you?
8. What is a rule you follow that nobody taught you?
9. What do you think is overrated?
10. What do you think is underrated?
11. What would you stand up for, even if you were alone?
12. What does freedom mean to you?
13. What do you think the world needs more of?
14. Where do you find hope when things are hard?
15. Is there something you are sure about that others find hard to believe?
16. What have you changed your mind about in the last few years?
17. What makes you trust someone?
18. What do you think happens when we stop learning?
19. What is the most generous thing someone has done for you?
20. What does courage look like in everyday life?

Deep questions to ask friends

1. What is a memory of us that always makes you smile?
2. What is something about you that you think I do not know?
3. When have you felt most supported by a friend?
4. What makes a friendship last, in your opinion?
5. What is something you have always wanted to tell me?
6. How have you changed since we first met?
7. What is something you are proud of that you rarely mention?
8. What do you need more of from the people around you?
9. What is a goal you would like me to hold you to?
10. What would you like us to do together in the next year?
11. What is the best advice you have ever given someone?
12. What is a fear you have not told many people about?
13. What is something that has been on your mind lately?
14. What do you appreciate most in the people you are close to?
15. Which of your friendships surprised you the most?
16. What do you wish people asked you about more often?
17. What is a moment when you felt really understood?
18. What do you think you will always be grateful for?
19. How do you like to be cheered up?
20. What is something you would like to get better at, and how can I help?

Deep late-night conversation topics

1. Do you think there is life on other planets?
2. If you could know one truth about the universe, what would you ask?
3. What do you think dreams are for?
4. Would you want to know the future if you could?
5. What do you think people will think of our time in 200 years?
6. If you could relive one conversation, which would it be?
7. What would you do with a year where nothing you did had consequences?
8. Do you believe in fate or chance?
9. What is something that fascinates you but you do not understand?
10. What would you want your last meal to be, and who would be at the table?
11. Is it better to have loved and lost, or never loved at all?
12. What does home mean to you?
13. What would you ask your future self?
14. If memories could be deleted, would you delete any?
15. What is the most beautiful thing you have ever seen?
16. Do you think we are the same person we were as children?
17. What is a sound or smell that takes you straight back in time?
18. What would you do if you woke up tomorrow with no fear?
19. What song describes your life right now?
20. What do you hope never changes?

Deep questions for someone you have just met

Gentler questions that still go beyond small talk, and do not ask for personal details.

1. What is something you are looking forward to this year?
2. What is a book, film or song that changed how you see things?
3. What is something you are really good at that you rarely get to show?
4. What is the best piece of advice you have been given?
5. What is a skill you would love to learn?
6. What made you smile today?
7. What is a place that feels like peace to you?
8. What is something you have changed your mind about recently?
9. What is a small thing that makes a big difference to your day?
10. What is a question you enjoy being asked?
11. What is something you are grateful for right now?
12. What would you do with a completely free week?
13. What kind of conversations do you enjoy most?
14. What is a tradition you would like to start?
15. What is something you would like to understand better?
16. What is the most interesting thing you have learned this year?
17. What would your younger self be surprised to know about you now?
18. Who is someone you admire, and why?
19. What is a small act of kindness you still remember?
20. What would you like more of in your life?

Start with lighter questions

Deep questions work best once a conversation has warmed up. Begin with icebreaker questions or this or that questions, then go deeper when it feels right. You can practise in a random text chat or a random video chat.