### Intimate Questions To Ask Friends ### **Serious:** 1. For what in your life do you feel most grateful? 2. If you could change anything about the way you were raised, what would it be? 3. What is one of your most terrible memories? 4. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why? 5. What’s something people wrongly assume about you before they get to know you more? 6. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet? 7. How would your friends describe you? 8. Of all the people in your family, whose death would you find most disturbing? Why? 9. When did you last cry in front of another person? By yourself? 10. Complete this sentence: “I wish I had someone with whom I could share…” 11. Alternate sharing something you consider a positive characteristic of the person you are with. Share a total of 3 items. 12. How do you handle stress like loneliness and anxiety? 13. What's a value or belief that you hold strongly, even if others might disagree? ### **Playful:** 1. Given the choice of anyone in the world, whom would you want as a dinner guest? 2. If you could have anything written on a massive billboard where you live, what would it be? 3. What does a perfect day look like to you? 4. If you had Scrooge McDuck levels of wealth and no societal obligations to do a certain thing, would you live your life any differently? 5. If you could eat only one dish for the rest of your life, what would it be? 6. If your life had a theme song, what would it be? 7. What fictional character would you want to be friends with? 8. Which board game do you believe reveals the most about a person's character? 9. Imagine you're in a karaoke competition; what song do you sing? 10. If you could add any word to the dictionary, what would it be and what would be its definition? ### **Interesting:** 1. Before making a telephone call, do you ever rehearse what you are going to say? Why? 2. What do you value most in a friendship? 3. What are three of your shiny dimes that you come back to again and again in life? 4. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it? 5. What is one of your most treasured memories? 6. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any three items. What would it be and why? You can’t replace anything? 7. Who is a person who has deeply impacted your life? Why? 8. What is one of the books or movies that has most impacted your life? 9. What's a book or movie you think we should watch together that has deeply impacted you? 10. What is a culture that fascinates you? 11. If you could witness any event in history, which one would you choose and why? 12. If you could live in any historical period and as any person what would it be and why? 13. If you had the chance to relive a day from your past, which one would it be and why? 14. Which historical figure do you find the most intriguing and why? 15. If you could spend a day living in any era of history, when and where would it be? 16. What's a myth, legend, or folklore that fascinates you? 17. What's the most interesting thing you've read or watched lately? 18. What's the story behind one of your most unique possessions or skills? 19. Pick one bad habit and ask yourself, what can I do today to break that habit? 20. What are your greatest weaknesses/habits/attitudes/grudges that will take you there? 21. What does ultimate failure mean to you? Define your version of personal hell? 22. What can I do this week to help with with that one step?/get there? 23. What are the most important decisions you've ever made? (Most import people, events...?) What have been your greatest dreams and goals? 24. What are you most afraid of losing? Your biggest fear? What is something that if you lost it today, life wouldn't be worth living (If it's a person, what does that person give you? How do you define ultimate success? 25. Be as specific as you can What are the steps you would need to take to get there (to ultimate success) 26. What's the most memorable conversation or moment we've shared over the past year? 27. Can you name a specific piece of advice or insight you've gained from our discussions that has made a difference in your life? 28. Have you noticed any common themes or topics that we've consistently discussed or evolved on throughout the year? 29. What's something new and exciting you'd like to explore or discuss in the upcoming year of our friendship? ### Intimate Questions To Ask Romantic Relationships ### **Serious:** 1. How do you define love in a romantic relationship, and how do you know when you're truly in love? 2. What lessons from past romantic relationships do you bring into our current one? 3. How do you envision our future together? What are our biggest dreams and challenges? 4. What qualities do you value most in a potential partner? 5. What can I do to make you feel most loved and cherished in our relationship? 6. Is there something you've never shared in a romantic context due to fear of judgment? 7. What do you think are the most important elements for maintaining passion and intimacy over the long term? 8. How do you feel about our differences, and how can we best navigate them? 9. What boundaries are essential to you in our relationship, and how can we respect and uphold them? 10. What's one of your most cherished memory from our relationship? ### **Playful:** 1. If we could go on any fantasy date, anywhere in the world or even in a fictional universe, where and what would it be? 2. If we had to role-play characters from any film or book for a date night, who would they be? 3. What's a fun or flirty secret you've never told me? 4. What's the most playful or daring thing you'd want to do with me? 5. If we had to cook a romantic meal together, but only using three ingredients, what would they be? 6. Do you believe in love at first sight, or should I walk by again? (A playful, flirty question!) ### **Interesting:** 1. If we could relive any moment in our relationship, which one would you choose? 2. What's an unconventional date idea you've always wanted to try with me? 3. If we had to survive a zombie apocalypse together, what would be our strategy? 4. What's a book or movie you think we should watch together that has deeply impacted you? 5. How do you feel about love languages, and which one do you think you most resonate with? 6. What's a song that makes you think of our relationship and why? 7. What's the most interesting thing you've read or watched lately?