Conversation Starters Deep Questions

Deep questions can help you get to know someone better or get a better understanding of their life perspectives. Here are 20 conversation starters that inspire deeper thinking and meaningful conversations:

1. If you could ask one person, living or dead, one question, who would it be and what would you ask?
Explanation: This question allows you to get a sense of who they admire and what they would like to understand more about.

2. What is something you are passionate about?
Explanation: This conversational starter reveals the values and interests that they feel strongly about.

3. What would you do if you weren’t afraid?
Explanation: This question can spark a conversation about limiting beliefs and identify areas of personal growth.

4. What makes you laugh?
Explanation: Knowing what they find funny can help bring laughter and lightheartedness to the conversation.

5. What is your definition of success?
Explanation: Everyone is unique in their definition of success and this question allows you to better understand theirs.

6. What is one thing you want to accomplish before you die?
Explanation: This question can bring up interesting conversations about how they want to live their life and what legacy they want to leave behind.

7. What does true love mean to you?
Explanation: This question can help to learn more about their beliefs on love and how they want to be treated and loved.

8. Do you have any unhelpful thinking patterns?
Explanation: This question can lead to a conversation about how they identify and challenge their limiting beliefs.

9. What do you appreciate most in your life?
Explanation: Acknowledge and be grateful for what you have in life is a powerful practice and this conversation starter can help show what they appreciate the most.

10. What is something you wish you knew when you were younger?
Explanation: This question gives insight into what was difficult for them in the past and how they think they could have handled things better.

11. What are you most proud of?
Explanation: This question shows what accomplishments or experiences they value most, and how they define success.

12. How do you think you can use your talents to make a difference in the world?
Explanation: This question opens a conversation about how they can use their unique strengths and abilities for a greater purpose.

13. What does it mean to be courageous?
Explanation: This question allows you both to reflect on how one could be courageous in different situations.

14. What is the most important lesson you have learned in life?
Explanation: This conversation starter can help gain insight into their life experiences, values, and wisdom.

15. What do you love most about yourself?
Explanation: This question can help foster positive self-esteem and encourage appreciation for the self.

16. What would you do differently if you could go back in time?
Explanation: This question can start a meaningful conversation about regrets and lessons learned.

17. How do you handle stress?
Explanation: This conversation allows you to share strategies used to manage stress and difficult moments.

18. What has been your biggest challenge, and how did you overcome it?
Explanation: This question can help gain insight into how they have dealt with difficulties and the strength needed to overcome them.

19. What does a perfect day look like for you?
Explanation: This question helps you learn more about what brings them joy and how they find happiness.

20. What do you want to be remembered for?
Explanation: This thought-provoking conversation starter reveals their hopes and dreams for their legacy.