Deep Questions to Ask Your Partner

1. If you could change one core personality trait, what would it be?
2. What is your deepest regret?
3. What makes you truly happy?
4. What one thing would you change about the world?
5. Who do you trust completely?
6. When was the last time you felt lost?
7. What is an absolute relationship deal breaker for you?
8. If you could participate in one historical event, what would it be?
9. What is your biggest, best green flag?
10. What do you think about when you’re alone?
11. What is a secret about yourself you’ve never shared with anyone?
12. What takes your breath away?
13. Have you ever had one of your worst fears happen?
14. What would you do if you knew you would not fail?
15. What’s the most important lesson you took from a past relationship?
16. Who in your life do you wish you could make amends with?
17. What’s your earliest memory?
18. What have you learned about yourself this year?
19. What negative self-talk do you struggle with?
20. What’s your definition of manhood?
21. What’s your love language?
22. How would you define or describe commitment?
23. What scares you the most?
24. What was your happiest moment so far?
25. Why do you think people cheat on their partners?
26. What are the keys to a happy relationship?
27. What makes you anxious?
28. When did you feel like you were living life to the fullest?
29. How do you actively try to achieve personal growth?
30. Do you ever feel like a failure?

Deep Questions to Ask a Friend

1. If you could time travel, what is the one piece of advice you would give younger you?
2. What quality do you value most in a friend?
3. What is holding you back?
4. What was the best era of your life?
5. Did you have a happy childhood?
6. What is the one thing people misunderstand about you?
7. When was the last time you cried and why?
8. What’s the last surprising thing you learned about yourself?
9. What do you find unforgivable, if anything?
10. How do you comfort yourself when you’re upset?
11. Do you like to be alone?
12. What’s your biggest insecurity?
13. Do you believe in soulmates or twin flames?
14. What’s your favorite thing about being a woman?
15. What’s the worst thing about being a woman?
16. What are your biggest challenges right now?
17. What’s more difficult: saying you’re sorry, or someone saying they’re sorry to you?
18. What’s the most important relationship in your life?
19. What’s your definition of healthy?
20. If you could have every bad memory erased, would you?
21. Do you think you’re brave?
22. What’s your least favorite emotion?
23. How do you deal with conflict?
24. Do you like yourself?
25. What’s the most difficult thing you’ve ever had to tell someone?
26. If you could choose between living a long, ordinary life, or a short life filled with distinction, which would you choose?
27. What has made you feel ashamed?
28. How much personal space do you need in a relationship?
29. What makes you feel vulnerable?
30. Do you have an easy or difficult time letting go of the past?

Deep Questions to Ask an Acquaintance

1. Who has been your biggest influence?
2. How long has your oldest friend been in your life?
3. What’s the best decision you’ve ever made?
4. Are you an introvert or an extrovert?
5. What is your most treasured memory?
6. Is the glass half-full or half-empty?
7. Is there anything too serious to be joked about?
8. Are you more like your mother or father? How so?
9. Do you embrace change or fight it?
10. What does a great day look like to you?
11. If you had more time in the day, how would you spend it?
12. Do you think you’re tough on yourself?
13. What impresses you?
14. What’s your favorite way to relax?
15. Where is your favorite place in the world?
16. If you could live a totally different life, what would it look like?
17. How important is family to you?
18. What did you want to be when you grew up?
19. Have you ever been so happy you cried?
20. What’s your definition of beauty?
21. Surprises: yay or nay? Why?
22. Are you good with finances?
23. What’s one thing that totally blows your mind?
24. Do you express your emotions or suppress them?
25. Do you daydream a lot, or tend to stay present in the moment?
26. What’s something you are choosing to ignore?
27. How do you respond to criticism?
28. Have you ever been in a toxic relationship?
29. How do you practice self-care?
30. If you could live forever, would you want to?

Deep Questions to Ask at a Party

1. If you could choose one person, living or dead, to have dinner with, who would it be and why?
2. What’s the top item on your bucket list?
3. Why is art important?
4. What is your favorite quote?
5. What book changed your life?
6. What are you proudest of?
7. What’s your biggest guilty pleasure?
8. What’s the biggest lie you’ve ever told?
9. What’s the nuttiest thing you’ve done for love?
10. Have you ever had a moment of clarity or an epiphany?
11. If past you could see present you, what would they say?
12. What big dream do you have yet to realize?
13. What’s the best advice you’ve ever been given?
14. What was the last big spontaneous thing you did?
15. What was the most intense experience of your life?
16. What do you miss most about being a child?
17. Do you love your job?
18. What’s your biggest quirk?
19. What are you looking forward to?
20. If you could step into another person’s shoes for a day, who would it be and why?
21. What’s your “walk-up” or theme song?
22. Have you ever seen or experienced something uncanny that you can’t explain?
23. Has social media improved or impaired society?
24. If you had a free pass to do one thing without suffering the consequences for it, what would you do?
25. What’s your favorite conspiracy theory?
26. What is the most unsettling dream you’ve ever had?
27. What is your oddest habit?
28. If you could, would you choose to be incredibly famous?
29. If you had all the money you could ever need, what would you do with it?
30. What’s your spirit animal?

Deep Questions to Ask About Life

1. What philosophy gets you through life’s challenges?
2. Do you believe in an afterlife, and if so, what is it?
3. What one thing are you most grateful for in life?
4. Do you believe a person can be born evil?
5. If you knew you were going to die in one year, what would you change about how you’re living your life?
6. What do you want to be remembered for?
7. When do you feel most alive?
8. Of all the people you’ve lost, which death shook you hardest and why?
9. What does spirituality mean to you?
10. What do you have faith in?
11. In ten years, how would you like to be living your life?
12. What’s one thing you hope you’re wrong about?
13. How do you define success?
14. If you could solve any one of the world’s problems, which one would it be?
15. When do you feel most free?
16. What’s worth killing or dying for, if anything?
17. Do you think everyone has a purpose in this life?
18. Do you believe in fate?
19. What defines your identity, or who you are?
20. Do you believe there is life on other planets?
21. Do you think about death often?
22. Are you afraid to die?
23. What’s something society has lost that you wish we still had?
24. Can people ever really change?
25. Is it important to forgive people who have wronged you?
26. What does “home” feel like to you?
27. If you could live your entire life free from any emotional pain, would you choose to do it?
28. What is emotional intimacy and why is it important?
29. If you could only love or be loved, which would you choose?
30. What philosophical question keeps you up at night?