wikiHow Questions to Start a Deep Conversation Here are 20 questions to bring about a deep conversation with your crush: 1. What are your core values and beliefs? 2. What motivates and inspires you in life? 3. What are your goals and aspirations for the future? 4. What are some experiences that have shaped who you are today? 5. What is a personal challenge you have faced and how did you overcome it? 6. What is a passion or interest of yours that you'd like to pursue more? 7. What are your thoughts on love and relationships? 8. What is something you believe in strongly and why? 9. What are your fears and insecurities? 10. What is your idea of happiness and how do you strive to achieve it? 11. What is a memorable experience from your childhood? 12. What is a difficult decision you have had to make and how did you handle it? 13. What is something you would like to learn in the future? 14. What is your idea of a perfect day? 15. What is a cause you are passionate about and why? 16. What is a personal accomplishment you are proud of and why? 17. What is a place you'd like to visit and why? 18. What is a favorite book, movie, or song that has had an impact on you? 19. What is a tradition or ritual that is important to you? 20. What is a lesson you have learned that you'd like to pass on to others? Page