Questions to ask Your Partner to deepen your connection.



On life:

  1. What’s something you’re glad you’ll never have to do again?

  2. What’s one thing you always procrastinate on?

  3. What would you do with your life if you were suddenly awarded a billion dollars?

  4. What should a healthy relationship provide for the people in it?

  5. Do you believe everything happens for a reason, or do we just find reasons after things happen?

  6. Is there anything you consider absolutely unforgivable?

  7. If you woke up tomorrow with no fear, what would you do first?

  8. In your life, what has been the biggest blessing in disguise?

  9. If you could pick one year of your life to do-over, which would it be and why?

  10. What is one behavior that you never tolerate?

  11. If you could write a note to your younger self, what would you say in only three words?

  12. What is the one thing that makes you feel alive?

  13. What would your perfect day look like?

  14. Do you usually follow your head or your heart when making decisions?

  15. What is something that never ends well?

  16. If you could change anything about the way you were raised, what would it be?

  17. Given the choice of anyone in the world, whom would you want as a dinner guest?

  18. Would you like to be famous? In what way?

  19. Before making a phone call, do you ever rehearse what you’re going to say? Why?

  20. What would constitute a perfect day for you?

  21. When did you last sing to yourself? To someone else?

  22. If you were able to live to the age of 90 and retain either the mind or body of a 30-year old for the last 60 years of your life, which would you choose?

  23. Do you have a secret hunch about how you will die?

  24. Name three things you and your partner appear to have in common.

  25. For what in your life do you feel most grateful?

  26. If you could change anything about the way you were raised, what would it be?

  27. Take four minutes and tell your partner your life story in as much detail as possible.

  28. If you could wake up tomorrow having gained one quality or ability, what would it be?

  29. If you had one day left to live, how would you spend it?

  30. If you were offered a place in the first colony to be established on Mars, would you take it?

  31. If you had three wishes, how would you use them?

  32. What’s the most daring thing you’ve ever done?

  33. When you were a child, what was the craziest job you imagined your grown-up self doing?

  34. What extreme sports would you love to try one day?

  35. Have you ever broken the law?

  36. If you could have one superpower, what would it be and why?

  37. Would you rather be the funniest person out there, or the most attractive

  38. .What are three things that you could never live without?

  39. If you could only eat three foods for the rest of your life, what would they be?

  40. What would be the holiday of your dreams?

  41. What’s the most embarrassing thing that has ever happened to you?

  42. What’s the weirdest thing you’ve ever bought?

  43. What were you like when you were a teenager?

  44. What’s your favorite thing about being an adult?

  45. And your least favorite thing about being an adult?

  46. If you could inhabit any fictional universe, what would it be?

  47. If money was no object, what would your dream house be like?

  48. If you could choose to have been born in a different decade, which one would you go for?

  49. How important is religion or spirituality to you?

  50. How do you feel about gay rights?



On your relationship:

  1. What did you think when you first met me?

  2. What about our relationship makes you really happy?

  3. If you had one word to describe our relationship what would it be?

  4. What’s your biggest fear for this relationship?

  5. What’s one difference between us that you absolutely love?

  6. What’s one similarity between us that you absolutely love?

  7. What about me made you fall in love?

  8. What’s your favorite memory of us?

  9. What’s one thing you want to do together that we’ve never done before?

  10. Where is your favorite place to be with me?

  11. What’s one thing you’re scared to ask me, but really want to know the answer to?

  12. What’s one thing you feel our relationship is lacking?

  13. What’s your favorite non-physical quality about me?

  14. If our relationship ended, what’s the one thing about it you’d miss the most?

  15. What do you think was your most vulnerable moment in our relationship?

  16. What’s one secret you’ve wanted to tell me, but haven’t?

  17. What’s your favorite way to receive affection?

  18. What’s one thing you think makes our relationship unique from everyone else’s?

  19. If you could change one thing about our relationship what would it be?

  20. What do you think is your biggest strength in this relationship?

  21. What’s one thing about your life you would never change for someone else, including me?

  22. What about us do you think works well together? How do we balance each other out?

  23. What does love mean to you?

  24. What do I mean to you?

  25. What can I do to show you how much I love you?

  26. Do you believe in soul mates? What about love at first sight?

  27. Have you ever been hurt in the past and questioned the possibility of love?

  28. When did you realize you were in love with me?

  29. Do you see our love lasting? Do you ever have any doubts?

  30. If you had to choose, would you rather receive a gift or have someone do something nice or helpful for you?

  31. Do you like sentimental gifts or do you always want a gift to have a practical purpose and be something you need?

  32. How do you think you best express love?

  33. What types of compliments do you like to hear?

  34. What do you think we need to work on most in our relationship?

  35. Do you think we spend enough time together? Or too little, or too much?

  36. Is there a question about our relationship that you’ve never asked me?

  37. What do you consider to be cheating?

  38. Were you looking for love when we met?

  39. What do I do to make you feel appreciated?

  40. Is there anything I could do to make you feel more loved?

  41. Do you think I make enough effort with your family and friends?

  42. Do you enjoy spending time with my family and friends?

  43. How can I support you more?

  44. Do you think we’ve changed each other in positive ways?

  45. Do you think we encourage each other’s bad habits?

  46. Do we communicate well when we’re not together?

  47. What’s your happiest memory from our relationship so far?

  48. If we could recreate one day from our relationship, what would it be?

About Intimacy

  1. Is our relationship physical enough for you? What would make it better in your eyes?

  2. How and where do you like to be touched?

  3. Do you have any fantasies you would like fulfilled?

  4. What are your thoughts on toys?

  5. Is there anything we haven't tried that you'd like to?

  6. Ideally (and a bit realistically, too), how often would you like for us to be intimate?

  7. What are some things I can do outside of the bedroom to keep the feelings of intimacy going all day?

  8. What do you miss most about me right now?

  9. What's something you've always wanted to say to me but couldn't?

  10. What would you like me to do the next time we're together?

  11. Where would you like me to kiss you?

  12. What is the closest you've ever felt to me?

  13. What one word would you like to be the theme of our relationship?

  14. How can I be a better partner to you?

  15. What do you think makes me smile?

  16. What’s your idea of the perfect romantic date?

  17. What’s the most romantic thing I’ve ever done for you?

  18. What do you remember most about our first date?

  19. What’s your favorite love song?

  20. Do we have a song?

  21. What’s the first thing you thought when you met me?

  22. When did you realize that you were in love with me?

  23. Who is your role model in love?

  24. Who was your first crush?

  25. What’s your definition of intimacy?

  26. What is the one thing I do that turns you on the most?

  27. What’s the first thing you noticed about my appearance?

  28. How did it feel the first time we kissed?

  29. What was your first kiss like?

  30. Is there a sexual fantasy of yours that we could play out together?

  31. How do you feel about sex toys?

  32. Is there anything that we haven’t tried sexually that you’d like to?

  33. What’s your favorite part of your body?

  34. What’s your favorite part of my body?

  35. In an ideal world, how many times would you want to have sex in a week?

  36. Have you ever had a threesome? Would you want to?

  37. How did you lose your virginity?

  38. Have you ever had sex in a public place?

  39. Are there any words or phrases that really turn you on?


Sexual Questions

What’s your dirtiest sexual fantasy?

How many people have you slept with?

Where’s the weirdest place you’ve had sex?

What’s your favourite part of my body?

Have you ever had anal sex?

If you could choose what I was wearing right now, what would you choose?

Where on your body is your favourite place to be touched?

When was the last time you had a dirty dream?

If you could have sex anywhere in the world, where would it be?

When did you first have sex?

What’s the best sex you’ve ever had?

What’s your favourite position?

Have you ever been caught having sex?

Do you watch porn?

What kind of porn do you watch?

How often do you masturbate?

Name a sex position you’d like to try

Do you prefer to give or receive?

What was your best orgasm ever?

Have you ever been skinny dipping?

Have you ever slept with someone you work with?

If we were out for dinner and I said I wanted to have sex right now, what would you do?

Have you ever sent nudes of yourself?

If you could sleep with any celebrity, who would it be?

Would you/have you had group sex?

What’s the most sex you’ve had in a day?

Are you loud or quiet during sex?

Have you ever tried using food during foreplay?

Have you ever made a sex tape?

What’s the first thing that sexually attracts you to someone?

Would you say you have any fetishes?

When it comes to BDSM, how far have you gone/would go?

What’s your favourite toy?

Do you ever read erotic fiction?

Have you joined the mile high club?

Do you think you could take off my underwear with no hands?

Would you say you’re kinky?

Do you enjoy shower sex?

Where’s the weirdest place you’ve ever masturbated?

Do you like to be spanked?

What was your most embarrassing sexual experience?

Have you ever fantasised about someone else during sex?

If I ever caught you masturbating, would you stop or would you finish?

Have you ever had an inappropriate crush?

Have you ever cried or fallen asleep during sex?

Do you prefer eye contact or not during sex?

Do you like to kiss during sex?

Do you get tired after sex?

How many positions do you think you’ve tried?

What’s the longest you’ve ever gone without sex?

How high is your sex drive?

What’s a surefire way to turn you on?

Sex with lights on or lights off?

Do you like dirty talk?

Have you had sex in a car?

Do you prefer to take control or be submissive?

Do you prefer one night stands or longer-term sexual partners?

Do you prefer to be on top or bottom?

What would you like to do more of in bed?

What’s your favourite time of day to have sex?

Rough or romantic?

Quickie or marathon session?

What’s your favourite part of foreplay?

Would you dress up for me in bed?

What’s your favourite place to be kissed?

Do you like sexting?

What’s the best thing about our sex life?

What’s the shortest time it’s ever taken for you to have an orgasm?

And the longest?

How would you make me have an orgasm?

On the future

  1. Where do you see yourself in 5 years?

  2. How do you see our future together? Where do you see it headed?

  3. What are your goals in the relationship?

  4. What are your thoughts on having a family?

  5. Where do you see yourself living when you retire?

  6. What are your financial priorities and goals?

  7. What is on your bucket list that we can do together this year?

  8. What’s the one thing you want to achieve the most before you die?

  9. Do you have any habits you want to change?

  10. What do you most look forward to about getting old?

  11. What are you hoping to learn in the coming year?

  12. If you could see into the future, what’s one thing you want to see?

  13. How do you want to be remembered?

  14. Where do you see this relationship headed in the next year? What about the next five years?

  15. What is your opinion on marriage and children?

  16. Would you stay with me if you found out I was unable to bear children?

  17. What are your occupational goals and how could they affect our relationship?

  18. Where do you see yourself living when you retire?

  19. I want to be a good lover, and I want to be there for you. What can I do for you to be that woman or man?

  20. How do you imagine a day in the life of us, married with kids? What about a week in the life?

  21. What are your thoughts on having our elderly parents live with us if they can't live on their own one day?

  22. How do you plan to save for retirement? What are your goals?


On the past:

  1. When’s the last time you felt vulnerable? How did you cope?

  2. What have you accomplished in the past year that you are most proud of?

  3. What were the major turning points in your life?

  4. When’s the last time you pushed out of your comfort zone? How did it make you feel?

  5. What is your happiest memory?

  6. How have you changed in the past 5 years?

  7. When was the last time you cried and why?

  8. What is an important life lesson you’ve learned?

  9. What’s the most daring thing you’ve ever done?

  10. What is the biggest lesson you’ve learned from previous relationships?

  11. What’s the most challenging setback you’ve ever experienced? How did you overcome it?

  12. If you could change one thing in history, what would it be?

  13. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

  14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

  15. What is the greatest accomplishment of your life?

  16. What do you value most in a friendship?

  17. What is your most treasured memory?

  18. What is your most terrible memory?

  19. If you knew that in one year you would die suddenly, would you change anything about the way you are living now? Why?

  20. What does friendship mean to you?

  21. What roles do love and affection play in your life?

  22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

  23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

  24. How do you feel about your relationship with your mother?

  25. Read more at: https://www.scienceofpeople.com/deep-questions/

  26. Have you ever cheated on a partner? If not, have you considered it but changed your mind?

  27. How many past partners have you had?

  28. Did you debate whether or not to ask me out? Why would you have chosen not to?

  29. What were you thinking on our first date?

  30. Have you ever been in love before me?

  31. Who is your role model in life? Who is your role model in love?

  32. What did it feel like when you realized you were in love with me?

  33. Do you think we were so destined to be together, that if we hadn't decided to date when we did and lost touch, we'd run into each other again?

  34. What were you looking for when you found me? Were you looking for love at all?

  35. What’s the biggest success you’ve had in your life?

  36. And the biggest failure?

  37. If you could change anything about your past, what would it be?

  38. How many times have you been in love?

  39. How long was your longest relationship? Why did it end?

  40. Are you friends with any of your exes?

  41. Have you ever cheated on someone?

  42. What did you learn from your last relationship?

  43. Have you ever done anything you’re really ashamed of?

  44. Do you have any regrets?

  45. What’s the one thing in your life that you’re most proud of?

  46. If you could go back to any moment in your life and change it, would you do it?

  47. What moment would that be?

  48. What’s your happiest childhood memory?

  49. Would you change anything about your childhood?

Just plain fun ones:

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?

  2. Would you like to be famous? In what way?

  3. If you were able to live to the age of 90 and retain either the mind or body of a 30-year old for the last 60 years of your life, which would you choose?

  4. Do you have a secret hunch about how you will die?

  5. If you could wake up tomorrow having gained one quality or ability, what would it be?

  6. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

  7. Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?

  8. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

  9. Share with your partner an embarrassing moment in your life.

  10. 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 one item. What would it be? Why?



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