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299 Deep Questions To Ask Your Date, Partner, Family Members & More

Sarah Regan
June 15, 2023
Sarah Regan
mbg Spirituality & Relationships Editor
By Sarah Regan
mbg Spirituality & Relationships Editor
Sarah Regan is a Spirituality & Relationships Editor, and a registered yoga instructor. She received her bachelor's in broadcasting and mass communication from SUNY Oswego, and lives in Buffalo, New York.

Amidst all the small talk and day-to-day bustling, we don't always take the time to dig deep and ask people (ourselves included) deeper, more thought-provoking questions.

But it's often those deeper questions that help us really get to know someone and learn more about the people in our lives. Plus, they can lead to some pretty interesting conversations. So, we rounded up a huge list of deep questions you can ask anyone and everyone in your life.

Deep questions for getting to know someone

  1. What are you excited about right now?
  2. Is there anything you're worried about?
  3. How connected are you feeling to the world?
  4. What are you passionate about?
  5. What do you value most in a friend?
  6. What consistently brings you joy?
  7. What feels hard in your life right now?
  8. Is there a decision you're contemplating that would be helpful to talk through together?
  9. What's bringing you pleasure right now?
  10. What's something difficult you're working on?
  11. Where are you finding the most meaning in life?
  12. What do you imagine your legacy will be?
  13. How long do you think you'll be remembered?
  14. What do you feel has been the most important thing you've done in life so far?
  15. What lasting impact do you know you've made in the world?
  16. What's the most important quality a person can have?
  17. What does the world need more of?
  18. What does the world need less of?
  19. Do you think organized religion have a bigger or smaller place in society going forward?
  20. What is the meaning of happiness?
  21. Do you place a bigger value on helping yourself, your family, or the world? How so?
  22. Do you feel like the world is changing for the better or changing for the worse? How so?
  23. Is there a motto or principle you live by? 
  24. What from the past is worth preserving?
  25. In what ways has society changed during your lifetime? What do you think caused these changes?
  26. Is it better to be realistic or optimistic?
  27. Are you a city person or a country person?
  28. What element do you resonate most with: fire, water, earth, or air?
  29. What were you like as a child?
  30. What were you like as a teenager?
  31. What were you like in college, if you went?
  32. Are you a risk-taker?
  33. Do you have any routines that you stick to religiously? 
  34. Have you had any major turning points in your life so far?
  35. What's something you're proud of?
  36. Do you have any beliefs or values that have changed over the years?
  37. What role would you play in the group of people trying to survive a zombie apocalypse?
  38. Are you a good gift-giver?
  39. What's the best gift you've ever received?
  40. Where is the next place you'd like to travel?
  41. Have you ever done anything illegal?
  42. What do you want to do in retirement?
  43. What's your favorite part of your typical day?
  44. What does self-care look like for you?
  45. What's a question you wish more people asked you?
  46. What does your ideal day look like?
  47. What's something random that you're extremely into?
  48. What's your astrology sign, and do you think it's accurate?
  49. What's the most interesting thing you've read recently?
  50. What's your latest controversial hot take?

Deep questions to ask a girl

  1. Why do you think you are the way you are in relationships?
  2. What does an ideal relationship look like to you?
  3. What do you think about the concept of marriage?
  4. What does commitment mean to you?
  5. What do you think you would be like as a mother?
  6. What scares you about becoming a parent?
  7. Do you feel like you've found your life purpose?
  8. What are the values you hold dearest to you?
  9. What is your greatest fear?
  10. When did you last cry in front of another person?
  11. When is the last time you felt truly, exuberantly happy?
  12. Are you close with your family?
  13. Do you think your family knows the real you?
  14. What is your relationship with your parents like?
  15. Has it always been that way?
  16. What was your childhood like?
  17. Would you change anything about the way you grew up?
  18. Do you feel like money affected the way you grew up? How so?
  19. Do you feel like race has affected your life? How so?
  20. What do you think your younger self would think about who you are today?
  21. If money wasn't an issue, how would you spend your days?
  22. What are you most proud of in your life?
  23. Is there anything from your past that you're ashamed about?
  24. In what ways do you think you have grown as a person? 
  25. What is one part of yourself that you think still needs work?
  26. What is the most difficult thing you've ever had to go through?
  27. Do you love yourself?
  28. How do you feel about your gender?
  29. What feels hard in your life right now?
  30. When do you feel most alive?
  31. What is the meaning of life?
  32. Do you think humans are inherently good or inherently evil?
  33. Do you think our society is progressing or regressing these days?
  34. When is the right time to say "I love you" to someone?
  35. What little things make you feel loved in relationships?
  36. Do you enjoy compliments?
  37. Do you believe in soul mates?
  38. How about twin flames?
  39. When was your first kiss?
  40. What kind of proposal would you want?
  41. What's your favorite thing about me?
  42. What's your favorite thing about yourself?
  43. What's your favorite thing about our relationship?
  44. What makes you feel loved?
  45. What makes you feel beautiful?
  46. How do you like to celebrate your birthday?
  47. What are some things you think we have in common?
  48. Do you believe in astrology?
  49. Do you relate to your astrological sign?
  50. Who is a music artist that you love that you think other people don't get?

Deep questions to ask a guy

  1. What does it mean when you say "I love you" to someone?
  2. Do you believe in the concept of soul mates?
  3. Is jealousy healthy in a relationship?
  4. Is lying ever OK?
  5. Is cheating ever OK?
  6. Have you ever cheated on someone before? Why did you do it—and do you regret it?
  7. Do you want to be more or less like your parents?
  8. What do you wish you had more of in your life right now?
  9. What do you wish you had less of in your life right now?
  10. When was the last time you cried?
  11. Do you talk about your feelings often? Why or why not?
  12. Who do you feel most comfortable talking about your feelings with in your life? Who do you feel least comfortable doing that with?
  13. What would you be doing if money wasn't a concern?
  14. What are your thoughts on pornography?
  15. What do you want to be remembered for after you die?
  16. What's more important: science or art?
  17. What's your relationship to your gender?
  18. What does masculinity or being a man mean to you?
  19. What gender stereotype do you wish the world would let go of?
  20. What does friendship mean to you?
  21. What's the meaning of life?
  22. Cat person or dog person?
  23. Would you survive a zombie apocalypse?
  24. Would you survive being stranded on a deserted island?
  25. What's your favorite conspiracy theory?
  26. What reality TV show would you be on?
  27. What's your most annoying habit?
  28. What's the most embarrassing thing in your search history?
  29. How would you feel if your partner made more money than you?
  30. What was your last relationship like?
  31. What's your usual approach to conflict?
  32. Have you ever been cheated on?
  33. Have you ever been to therapy?
  34. Have you ever been in love?
  35. What initially attracted you to me?
  36. Morning sex or sex at night?
  37. What's your relationship with your parents?
  38. What were you like in high school?
  39. What's your relationship to religion?
  40. Are you a spiritual person?
  41. How long does it take you to open up to someone?
  42. What's your attachment style?
  43. What parts of yourself are you working on right now?
  44. Do you want kids? Why or why not?
  45. How do you deal with conflict in relationships?
  46. What was your last big fight about?
  47. Do you have any big regrets in life?
  48. What's your favorite type of music?
  49. Best concert you've ever been to?
  50. Worst concert you've ever been to?

Deep questions to ask yourself

  1. What am I most happy about in my life right now? Why is that?
  2. Where do I want to be in five years?
  3. What's one quality I have that I'm proud of?
  4. What are my core values?
  5. Am I a good listener?
  6. What's my relationship to money, and where did it come from?
  7. Who are my closest friends?
  8. Which friends or family members do I wish I had a stronger connection with? What can I do to nurture that connection?
  9. What do I value most in a friendship?
  10. What do I value most in a romantic partnership?
  11. How do I feel about the idea of getting married, and why?
  12. Which family member has most shaped who I am today?
  13. What is my attachment style?
  14. How can I better own my past?
  15. Do I like who I am?
  16. Do I like who I'm becoming?
  17. What is my intention?
  18. What are my core values?
  19. Which of my deep inner longings have I been ignoring?
  20. Who lights me up when I'm around them?
  21. Who drains my energy when I'm around them?
  22. When do I feel most alive?
  23. What am I feeling—nervous, anxious, trepidatious, excited, eager—and what is making me feel that way?
  24. How do I honor myself? Neglect myself?
  25. How have I grown as a person?

Deep questions to ask your partner

  1. What feeling have you been experiencing the most lately?
  2. How connected are you feeling in our relationship?
  3. Are you sexually fulfilled?
  4. What could make our relationship even better?
  5. What makes you feel most loved?
  6. Is there something you care about for which you would be willing to risk your life?
  7. How can I be a better partner to you?
  8. What were you like as a child? As a teen?
  9. Tell me about the last time you felt lonely when you were with me.
  10. What are your dreams for your future?
  11. What makes you feel closest to me?
  12. Is there anything you are grappling with where I can help?
  13. What is your vision for a great relationship
  14. How have your parents affected the way you show up in relationships?
  15. Is there anything in our relationship that you’re hoping will change in the future?
  16. What does healthy love feel like for you?
  17. What’s one positive thing you’ve learned from me since we’ve been together?
  18. What’s something you think I could learn from you?
  19. In what ways do you still feel like a kid inside?
  20. Is there anything you haven’t told me because you’re afraid I’d judge you?
  21. How can I better support you in your personal or professional life?
  22. What is something you've always wanted to try in the bedroom?
  23. What is something you've always wanted to experience together?
  24. What is one dream you’d like to see come true this week/month/year?
  25. What do you fear about our relationship?
  26. How can I contribute to your needs being met today?
  27. What’s something your parents have taught you about love that you now realize is wrong?
  28. What do you think the 16-year-old you would think about our relationship?
  29. What are your long-term goals for our relationship?
  30. Everyone loves differently. What do you think we can learn from the different ways you and I show love?
  31. How much jealousy is too much jealousy?
  32. How do you define unconditional love?
  33. What is your favorite thing about our relationship?

Deep questions to ask friends

  1. What qualities do you admire most in your parents?
  2. What's one of your most cherished memories?
  3. What's something you used to believe in that you don't anymore, and what changed?
  4. Are you a religious or spiritual person? If so, what does that mean to you? If not, why not?
  5. What is your favorite childhood memory?
  6. Do you often find yourself worrying about the things you have no control over? 
  7. How do you calm yourself down when you're feeling stressed?
  8. How do you like to be comforted when you're sad?
  9. When is the last time you felt deeply inspired, and why?
  10. How do you want to be remembered/what would you want your eulogy to say?
  11. Do you have a harsh inner critic?
  12. How can I be a better friend to you?
  13. What areas of your life would you like to grow in, and how can I help support that growth?
  14. Who's an older person in your life that you really look up to?
  15. What's the deepest desire of your heart?
  16. Is there anything you consider unforgivable, if so what is it?
  17. Have you ever hurt someone and deeply regretted it? Did you ever make amends?
  18. Do you enjoy discussing politics?
  19. What kind of conversations make you uncomfortable?
  20. Have I ever said or done anything that's offended you without realizing it?

Deep questions to ask family

  1. What excited you today?
  2. What are you feeling grateful for today?
  3. What was missing from your life this week?
  4. About what have you been proud of yourself for this week?
  5. What are you eager to feel more confident about in the next few weeks?
  6. What word would you use to describe our family?
  7. Do you identify with our family, or do you feel more like an outsider, and why?
  8. What family traditions do you carry on?
  9. Tell me about a time you did something you "weren't supposed to" but it was worth it.
  10. Tell me about a family member of ours who I never had the chance to meet.
  11. What are our strengths as a family?
  12. What is your favorite present you've ever received?
  13. What are our values as a family?
  14. Any traditions that you were happy to say goodbye to?
  15. What do you think our family will look like in 50 years?
  16. If you could wake up with any skill tomorrow, what would you choose?
  17. Do you identify as an introvert, extrovert, or ambivert?
  18. What's one thing the family probably doesn't know about you?
  19. What's one thing you wish you could tell your younger self?
  20. If you could do it all over, what career would you choose?
  21. What's one thing you like about yourself?
  22. What's one thing you like about me?
  23. What's one of your core values?
  24. Have your values changed at all from the past to what they are today?
  25. What's one thing that's been bringing you pleasure lately?
  26. Tell us about one of the happiest moments of your life.
  27. What's one thing you love about being in your (30s/40s/50s/etc.)?

Deep questions to ask on the first date

  1. Do you like your job?
  2. How did you end up in your current line of work?
  3. What personal goals are you working toward right now?
  4. Do you enjoy dating? 
  5. What are you looking for from dating right now?
  6. What do you look for in a partner?
  7. For you, what does it mean to be in a relationship?
  8. Why did your last relationship end?
  9. What's your love language?
  10. What are your relationship deal-breakers?
  11. What's a topic or hobby you're randomly passionate about?
  12. What's a social issue you're very passionate about?
  13. Are you engaged with politics?
  14. Are you religious?
  15. How has the pandemic affected you personally?
  16. Video dates: yes or no?
  17. What do you prefer: texting or phone calls?
  18. Which word describes you better: carefree or intense?
  19. Which would you rather be: normal or weird?
  20. Is astrological sign at all important in a match?
  21. Could you date someone who does drugs?
  22. Choose the better romantic activity: kissing in Paris or kissing in a tent in the woods.
  23. Is jealousy healthy in a relationship?
  24. Are you ready to settle down and get married right now?
  25. About how long do you want your next relationship to last?
  26. Do you like scary movies?
  27. Do you often find yourself worrying about the things you have no control over?
  28. Which of the following types of intelligence do you value most: logical/mathematical, social/interpersonal, or visual/artistic?
  29. Regardless of future plans, what's most interesting to you right now: sex or love?

Deep questions about sex & intimacy

  1. What's an unusual thing that turns you on?
  2. How do you define good sex?
  3. What's your dirtiest fantasy?
  4. Wildest sex story?
  5. What do you find to be the sexiest part of a man/woman/person's body?
  6. Do you prefer to make the first move?
  7. When did you first have sex? How did it go?
  8. What's on your sexual bucket list?
  9. Lights on or off?
  10. Favorite sex position?
  11. What does sexual chemistry mean to you?
  12. What do you like better: oral or intercourse?
  13. What’s the kinkiest thing you've ever done in bed?
  14. What's the hottest memory you have of us?
  15. Do you consider yourself a particularly sexual person?


How do you ask deep emotional questions?

First, check if you can ask them a personal question to make sure they're in a space to share. If they say yes, phrase your question openly and non-judgmentally and use a gentle tone. As they respond, practice active listening.

What questions build intimacy?

The 36 questions to fall in love, developed by psychologists Arthur Aron, Ph.D., Elaine Aron, Ph.D., and other researchers, are believed to help people build connection and intimacy.

The takeaway

From being a good friend or partner to knowing how to keep a good conversation going, having some go-to deep questions to ask is always helpful. Not only can you exchange your thoughts and ideas, but you learn more about the people in your life, they learn more about you, and you're able to deepen and strengthen your relationships.

Sarah Regan author page.
Sarah Regan
mbg Spirituality & Relationships Editor

Sarah Regan is a Spirituality & Relationships Editor, a registered yoga instructor, and an avid astrologer and tarot reader. She received her bachelor's in broadcasting and mass communication from State University of New York at Oswego, and lives in Buffalo, New York.