511 Deep Questions to Ask to Strengthen Your Connection

If you’re feeling disconnected from a loved one, consider deep questions to ask to help enhance your connection. Even if you’re not feeling distant, these are wonderful relationship-building questions that can strengthen your connection.

Communication in a relationship might suffer if you’re too preoccupied with other duties, or if you’re so wrapped up in the day-to-day events of life that you lose sight of each other and who you’re both becoming.

When this happens, there are a few deep questions for friends to help repair their friendship. With that goal in mind, here are some deep questions to ask that will help you give your relationships with friends and family a much-needed boost.

Super Deep Questions to Ask

You and your spouse may set up a date night or a virtual session to sit down and take turns asking and answering each other’s super deep questions to ask. Here are some thought-provoking questions to get you started.

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. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

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

6. 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 want?

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

8. What do you want people to remember about you after you’re gone?

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

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

11. What is your star sign? And do you believe in astrology?

12. If you could wake up tomorrow having gained any one quality or ability, 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 now living? Why?

20. What does friendship mean to you?

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

22. Share something you consider to be 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. If you could have three wishes, what would they be?

26. Who was your favorite cartoon character when you were a kid?

27. What does spirituality mean to you?

28. Do you believe in giving people second chances, and why?

29. How would you describe your first crush?

30. What are your favorite hobbies?

Very Deep Questions to Ask

You might want to ask more than the conventional “how are you?” and close-ended inquiries to assist create this knowledge — instead, inquire about their history, present, and future, their recollections, thoughts, and affinities. This is why, we have developed some very deep questions to ask.

1. What was the most important lesson you’ve learned from a past relationship?

2. What are some of your favorite books?

3. Have you ever had an epiphany? If so what was it like for you?

4. What is the most intense experience you’ve had in your life?

5. When you dream big, what would you do with your life?

6. Are you a morning or a night person?

7. Do you think anyone has the capacity to cheat or do you think only cheaters cheat?

8. Have you ever shoplifted anything?

9. Have you ever told a lie that you regretted?

10. Have you ever done something you regretted?

11. Do you ever make excuses for your bad behavior? (e.g., I punched him because he was a jerk.)

12. What do you think of A.I. (Artificial Intelligence)? Scary or amazing?

13. What do you think of Elon Musk?

14. What do you think of Steve Jobs? Hero or Villain?

15. What do you think the solution is to climate change?

16. Do you think psychics are actually psychic?

17. What is your favorite workout?

18. How do you think you’d be different if you were raised in a different family?

19. What is the most important lesson you’ve learned this year?

20. What is your dream vacation?

21. What superpowers did you wish you had when you were a kid?

22. What did you want to be when you grew up?

23. Are you a mountain or a beach person?

24. What is your spirit animal?

25. Are you very close to anyone in your family? Why?

26. What are your top three strengths?

27. What are your top three positive qualities?

28. If you could live anywhere in the world, where would you live?

29. What are your passions in life?

30. Have you ever had your heart broken? What did it feel like to you?

31. What type of music energizes you?

32. Are you still friends with anyone from high school?

Really Deep Questions to Ask

Deep, open-ended questions can assist both partners in seeing and validating one another. It allows you to express your thoughts and feelings in a secure environment where you can be yourself. Here are some really deep questions to ask.

1. What was your favorite subject or class in high school?

2. What was the most memorable experience from your childhood?

3. How do you relax when you’re stressed out?

4. What is a skill that you want to build?

5. If you could change one decision you made when you were younger what would it be and why?

6. If you could change one thing about your childhood what would it be and why?

7. Do you know how to play any musical instruments?

8. Who or what inspires you?

9. What is your place in the whole world?

10. Who is your doppelganger?

11. Have you ever been camping? Did you like it?

12. What is one accomplishment that you’re proud of?

13. What three non-electric or non-automatic items would you take on a deserted island?

14. If “hello” were to be replaced by another word as a greeting, what word would that be?

15. When you see your family, what do you do together?

16. What is your Achilles heel (your weak spot)?

17. What is your favorite (least favorite) emotion?

18. What do you think makes a meaningful life?

19. Is there anything from the 1980s that you wish would come back?

20. Do you believe in good and evil?

21. What do you think prevents people from manifesting their dreams?

22. Do you get déjà vu? What does it feel like for you?

23. What makes you feel nostalgic?

24. What would you do if you found out you had a year to live?

25. If you redesigned society, what would you change?

26. What would be a perfect day for you?

27. What impresses you?

28. If you had to eat only one meal for the rest of your life what would it be?

29. What’s your least favorite food?

30. What’s one thing I don’t already know about you?

Deep Questions to Ask Your Boyfriend

Let us now go through some deep questions to ask your boyfriend. You can skip questions and offer yes/no responses if you wish, but you’ll have the most fun and learn the most if you commit to answering every question as thoroughly as possible. Go ahead and share your innermost ideas with one another!

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

2. Have you ever been engaged or married? Do you ever want to get married?

3. Have you ever lived with a partner?

4. How important is religion or spirituality to you?

5. How do you feel about gay rights?

6. Do you think money can buy happiness?

7. What is your dream job?

8. What one thing do you want to accomplish in your life?

9. Is there anything from your past that you regret?

10. What are you afraid of? When was the last time you voted?

11. How would you describe your relationship with your family?

12. Do you have a best friend?

13. What is your love language?

14. Are you an introvert (those who recharge by being alone) or an extrovert (those who feel energized from being around other people)?

15. Do you hold grudges?

16. Have you ever struggled with addiction?

17. Have you ever been in an emotionally or physically abusive relationship?

18. Do you think a relationship can come back from cheating?

19. What makes you the best version of yourself?

20. What are things you do even though you don’t want to?

21. What does love mean to you?

22. What’s your best quality?

23. What’s something you’ve always dreamed of doing but never have?

24. What’s something we could change about our relationship to make it stronger?

25. What makes us special or unique together?

26. What do I mean to you?

27. What can’t you live without?

28. How have you changed in the last several years?

29. What makes you feel accomplished?

30. What do you think a good man is?

31. What is something you’re afraid to lose?

32. How do you know if you’re successful?

33. What kind of dad do you want to be?

34. What do you want to be remembered for?

Deep Questions to Ask Your Girlfriend

If you’re feeling distant or simply want to get to know your girlfriend better, taking the time to communicate, actively listen, and establish intimacy may strengthen your relationship. And for that closeness, you’ll need these deep questions to ask your girlfriend.

1. Do you want to get married someday?

2. Do you want children? If you couldn’t have them, what other options would you consider?

3. Do you believe in God?

4. What social causes do you feel passionately about?

5. What makes you smile when you’re having a bad day?

6. Who have you been friends with the longest?

7. How long was your longest relationship?

8. Are you close with your family?

9. If you got pregnant today, what would you do?

10. What challenging experiences have made you stronger?

11. What inspires you?

12. What are your life goals?

13. Who do you look up to?

14. What do you consider cheating? (Kissing, sexting, webcam girls, etc.)

15. What one change do you wish you could make in the world?

16. What would most people be surprised to learn about you?

17. Have you ever been discriminated against?

18. Is honesty always the best policy?

19. What is your biggest fear?

20. When are you the happiest?

21. What scares you most about our relationship?

22. Can you remember the last time you cried and what the reason was?

23. Do you think we could parent well together if we had children?

24. Who do you want our children to take after?

25. Do you think you are misunderstood?

26. What are you most ashamed of?

27. What did you learn from your last relationship?

28. What was the hardest thing that you ever had to get through as a kid?

29. Have you ever felt like giving up in the past?

30. What is an innocent mistake you made that had dramatic consequences?

31. Has anyone ever broken your trust beyond repair?

32. Why did your last relationship end?

33. Is there someone you haven’t spoken to in a long time that you miss?

34. How do you measure success?

35. If our relationship ended, what is the one thing about it you would miss the most?

Deep Questions to Ask Your Friends

When you’re open enough to communicate your ideas and feelings in a friendly relationship, it can enhance your bond. To strengthen your bond, you may use these deep questions to ask friends.

1. If you could magically change one thing in your life, what would it be?

2. What do you think of mindfulness?

3. Do you think we’d be better off without social media?

4. What do you think it means to be healthy?

5. What do you love the most in life?

6. Do you vote?

7. Do you believe in karma?

8. What do you think about freedom of speech?

9. Do you think there is an afterlife of any kind?

10. What do you think about veganism?

11. What do you think about the current younger generation?

12. Do you think bullies see themselves as bullies?

13. Do you tend to trust people?

14. Do you feel like men and women are equal?

15. Do you think people can change?

16. What’s your favorite activity to do with friends?

17. What’s one thing you believe in that’s kinda weird?

18. Where is your favorite place to go eat?

19. What was one of your funniest moments?

20. If I asked you, “Who are you?” How would you answer?

21. What do you like about me?

22. What are my best qualities?

23. What are my worst qualities?

24. What aspects of myself do I need to work on to be a better friend?

25. What makes you feel comfortable around me?

26. What do you think it is about us that made us such good friends?

27. Do you have any secrets that you need to get off your chest? If so, I promise to hold them with you.

28. Do you think we’ll still be friends when we die?

29. What do you think your life would be like without me?

30. What’s one thing you’d like to do together that we haven’t yet done?

Deep Questions to Ask Your Partner

How well do you know your companion? Certain inquiries might help you connect with them on a deeper level. When was the last time you and your partner had a meaningful conversation? Intimate dialogues may help partnerships create trust and compassion, enhancing your connection. Here are some deep questions to ask your partner you may make use of.

1. What do you look for in a relationship?

2. What personal qualities do you love?

3. Do you believe in marriage? If so, what age do you think is the best for marriage?

4. Do you believe in soul mates?

5. Do you have any love language for your partner?

6. What is your idea of a perfect date?

7. Are you able to fight in a loving way?

8. How do you describe commitment? How do you describe freedom?

9. Do you want to have kids?

10. How do you imagine your life in 10 years? 20 years? 50 years?

11. If you had all the money you needed, what would you do with your life?

12. Where would you put yourself on the workaholic to relaxaholic spectrum?

13. How do you react when you’re upset?

14. If you had a partner who gained a lot of weight, would you stay with them?

15. What do you think leads people to cheat in relationships?

16. If you were having relationship troubles, would you ever go see a relationship counselor?

17. What’s one time when you had to compromise? How did that feel to you?

18. What would be the perfect amount of time each day that you’d spend with your partner?

19. What’s a deal-breaker for you in a relationship?

20. What is a healthy relationship to you?

21. What is your most irrational fear? What’s your most rational fear?

22. What’s the biggest risk you’ve ever taken that didn’t pay off?

23. What’s one risk you took that did pay off? 

24. How do you think you will die?

25. Do you wish you were raised differently? Why?

26. What quality do you wish you had? What’s one thing you wish you were really good at?

27. Would you rather spend a day with your kindergarten self or your elderly self? Why?

28. What’s your favorite childhood memory?

29. What’s your favorite early adulthood memory?

30. If today were your last day to live, and your life suddenly flashed before your eyes, would you be proud and satisfied with how you lived?

31. What has been your greatest accomplishment in life?

32. What memory keeps you up at night? What mistake you’ve made keeps you up at night?

33. What are your favorite characteristics of each other?

34. Is your family warm and affectionate?

Deep Questions to Ask Your Crush

When you have a crush on someone, one of the worst mistakes you can make is not asking enough of the correct questions. You may learn what your crush needs and wants from you and your time together by making use of the deep questions to ask your crush.

1. What is one thing you wish you never did?

2. Would you rather be incredibly intelligent or incredibly happy?

3. What’s something you believe that most people don’t?

4. If you could have one superpower for a day, what would it be?

5. When in life have you been most nervous?

6. What celebrity do you have the biggest crush on?

7. What city has been the best city you’ve ever lived in or travelled to?

8. What are you doing when you’re at your happiest?

9. What’s something about your past that most people don’t know about?

10. Where is the one place in the world that you want to travel to and why?

11. What is your most bizarre habit?

12. What was your favourite movie ever?

13. What was the last book you read?

14. What’s the best piece of advice that you received from your parents?

15. What TV show could you just binge watch all day?

16. What age has been your best so far?

17. If you could go back in time and talk to yourself, what advice would you give?

18. What’s the biggest regret you have?

19. Would you rather be in love or have a lot of money?

20. Are you a mountain or beach person?

21. If you knew you would die in one month, what would you do?

22. What’s your favorite type of music and why?

23. If you could be incredibly skilled at one thing, what would you choose?

24. If you won the lottery, what would be the first thing you would do?

25. Would you rather be rich and famous or rich without the fame?

26. If you could contact the whole world and they would listen, what message would you give?

27. If you were an incredibly talented rapper, what would you want to rap about?

28. What’s something you did in your past that your friends still tease you about?

29. Do you prefer big parties or small gatherings?

30. What was the worst age you’ve been so far?

31. What’s your most common deal-breaker?

32. If you could be a fictional superhero, who would you be?

Deep Questions to Ask to Get to Know Someone

It is not always simple to open up to people. As a result, asking questions allows both participants to feel seen and heard, reducing the possibility that the sharing feels one-sided. Here are some questions to get to know someone deeply.

1. Do you respect yourself?

2. Are you confident? Why or why not?

3. Do you like who you are?

4. How do you express your emotions?

5. What makes you happy?

6. What are your strengths and weaknesses?

7. Do you forgive those who have hurt you? How?

8. Do you think you’re brave? Why or why not?

9. How do you engage in self-care?

10. Do you try to grow and improve your abilities?

11. Are you proud of yourself?

12. Do you know what you want in life?

13. In what ways do you think positively? negatively?

14. What’s your personal mission statement?

15. Do you believe you can manifest your dreams?

16. What are your long-term goals?

17. What are you thankful for?

18. Do you love yourself?

19. What are your core values?

20. Do you consider yourself an introvert, extrovert, or somewhere in the middle?

21. What motivates you?

22. How do you respond to rejection?

23. Do you ever feel shame or guilt? What causes it?

24. Do you suppress or express your emotions? Why and how?

25. Are you generally present in the moment or do you spend a lot of time in your head?

26. Do you have a healthy relationship with your smartphone?

27. What makes you feel vulnerable?

28. What are your good habits and bad habits?

29. What is your true calling?

30. What makes you feel empowered? Disempowered?

31. What anti-stress strategies help you most?

32. Do you ever have FOMO (Fear of Missing Out)?    

Deep Questions to Ask a Guy

According to some experts, “reciprocal self-disclosure” – giving personal information in the same context as another person — might improve emotions in a relationship. Here are some deep questions to ask a guy that you may utilize to achieve that outcome.

1. What are some qualities that you wish you had?

2. How important is your health to you?

3. Are you close with your parents?

4. What is more important to you, love or money?

5. What’s on your bucket list this year?

6. How would you describe your best friend?

7. What do you think of best friends of the opposite s#x?

8. Are you aware of the ways that you self-sabotage?

9. How do you feel about sharing your password with your partner?

10. Is there anyone you feel jealous of?

11. Would you still love your spouse if they were diagnosed with a terminal disease?

12. What qualities do you admire about your parents?

13. What are some of your favorite songs?

14. Is it ever okay to lie?

15. What’s the biggest sacrifice you’ve made for your partner?

16. If a genie granted you 3 wishes right now, what would you wish for?

17. Does your job make you happy?

18. What are the things you would like to change?

19. Would you ever take back someone who cheated?

20. What is a relationship deal breaker for you?

21. Are you more into looks or brains?

22. When do you think a person is ready for marriage?

23. Is what you’re doing now what you always wanted to do growing up?

24. What do you fantasize about?

25. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

26. What’s the one thing that people always misunderstand about you?

27. What is your relationship like with your father?

28. When was the last time you broke someone’s heart?

29. Would you relocate for love?

30. What did you want to be when you were younger?

31. What kind of parent do you think you will be?

32. Do you judge a book by its cover?

Deep Questions to Ask a Girl

There are a million questions you might ask a girl, and this list of deep questions to ask a girl is only a starting point. Does that make sense? Great. Have fun with the questions.

1. What’s your “and then it got worse” story?

2. What’s the best piece of advice someone has given you?

3. What’s something you learned recently that you really should have already known?

4. What was something you ate regularly as a child but now cringe at the thought of eating?

5. If you were an action figure, what accessories would you be sold with?

6. What’s the craziest thing you’ve ever done for love?

7. Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?

8. What snack can you just not get enough of?

9. Is flirting cheating?

10. If you were given $15,000 to give the most amount of happiness to the most amount of people, what would you do?

11. What piece of culture or trend has died out, but you would like to see it make a comeback?

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

13. What kinds of things are normal now but will be highly valued antiques a century later?

14. What’s the best practical joke you’ve pulled or seen pulled?

15. What weird smell do you really enjoy?

16. If you inherited a private jet from a stranger, what would you do with it?

17. What do you wish you could re-live in your lifetime?

18. What’s an innocent mistake you made that had dramatic consequences?

19. Have you ever trusted your boyfriend to buy clothes for you?

20. What’s something weird that you recommend everyone trying at least once?

21. What country can you name but besides the name you know almost nothing else about it?

22. What are you most grateful for?

23. What would be the worst thing to put into a piñata?

24. Would you go through a boyfriend’s phone if you could?

25. What’s something horrible that we as humans have accepted, because that’s just how things are; but actually things don’t have to be that way at all?

26. If you could hear every time someone said something good about you or something negative about you, which would you choose?

27. What do you think people automatically assume about you when they look at you?


29. What’s the best gag gift you’ve ever seen or gotten?

30. When was the last time you laughed so hard you cried?

31. What would you do if your parents didn’t like your partner?

32. If you were forced to create a new dance move, what would it be and what?

Deep Questions to Ask on Instagram Story

If you’re looking for some fascinating questions to utilize as Instagram stories, your wish has been granted. These are some of the most fascinating and deep questions to ask on Instagram story.

1. What unnecessary products or services do you consider necessary?

2. Which fictional villain made you feel real hatred towards them?

3. What habit do you have that you think not many other people have?

4. How often is your brain on autopilot?

5. What’s the grossest thing you’ve drunk?

6. If colors had a taste, what would each color taste like?

7. What names were ruined for you because you knew someone terrible with that name?

8. What’s the best conspiracy theory you can make up on the spot?

9. How often do you feel utterly worn down?

10. What gross and unhygienic things do people do that bothers you?

11. What was the best thing about how your parents raised you?

12. Where is the craziest place you have danced?

13. If when you died, you got put into a room for eternity with people who died the same way, how would you want to die?

14. What would an amusement park filled with your biggest fears be like? What rides would it have?

15. If jobs/careers had slogans what would be some of their slogans?

16. What do people really need to chill out about?

17. What are the two biggest lessons you’ve learned from previous relationships?

18. Why do you think we dream?

19. If you could switch genders for a length of time of your choosing, would you? And if so, how long?

20. What inedible thing do you wish you could eat?

21. Which hairstyles fit with which personalities?

22. If you could choose the next president of the United States, who would it be?

23. What’s the most stress relieving thing you can get/do for less than 20$?

24. What’s something you wish you had never learned how it was made or how it works?

25. What do most people overestimate or underestimate about you?

26. What silly thing do you take a lot of pride in?

27. What crazy things will you do if you ever become rich?

28. If you were forced into a dance competition, what song would you choose to dance to?

29. How often do you go into a room and forget why you went into the room?

30. How would the world change if health potions existed?

31. How do you feel about God?

32. What scrambles your brain every time you think about it?

Deep Questions to Ask Your Significant Other

Developing emotional intimacy with your significant other entails going beyond the simple “yes” and “no” transactional issues of our daily lives and forming a personal relationship. Here are some deep questions to ask your significant other that may help.

1. What is your bucket list of life?

2. Is there anything new that you want to try in bed?

3. Have you ever stayed in a relationship that you knew was toxic? If yes, why?

4. What is the craziest thing you’ve ever done and would you do it again?

5. What is your greatest fear in a relationship?

6. What’s your biggest regret in life?

7. What jobs exist because people are selfish?

8. What do you think about when you’re by yourself?

9. What is one dream you have yet to accomplish?

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

11. What does your perfect relationship look like?

12. What’s your worst habit?

13. If you could change one thing about yourself what would it be?

14. Is self-improvement important to you?

15. Do you love what you do enough to want to do it for the rest of your life?

16. What is your greatest fear?

17. Who was your favorite teacher and why?

18. What was the worst phase in your life?

19. What is one thing you think I could work on?

20. What’s your philosophy in life?

21. If you had to go back to school, what would you study?

22. What accomplishment are you most proud of?

23. What’s your favorite hobby to do alone?

24. Did you ever write a journal?

25. Do you feel like we communicate well?

26. What did your past relationship teach you?

27. What are your thoughts on online dating or tinder?

28. Which parent are you closer to and why?

29. What was the best phase in your life?

30. What are three things you value most about a person?

31. Who are five people you are closest with?

Deep Questions to Ask on a Date

Remember your first dates, when you were both looking at each other across the restaurant table, dreamily imagining and chatting about your life’s commonalities, aspirations, and visions? Well, you won’t have to deal with it anymore. Here are some deep questions to ask on a date for your convenience.

1. What was the thing that ruined your last relationship?

2. What’s the one thing you would like to change about yourself?

3. Are you religious or spiritual?

4. Do you consider yourself an introvert or an extrovert?

5. Do you have a good work-life balance?

6. What was the most difficult time of your life?

7. What is more important in a relationship: a physical or emotional connection?

8. Is there any way we can support each other better?

9. Do you know what your attachment type is?

10. What’s your favorite book/movie of all time and why did it speak to you so much?

11. In what way do you mostly easily receive love?

12. What is the best advice someone has ever given you?

13. When you have a problem do you want me to help you find a solution or just comfort you?

14. If you’re having a hard day, how can I show up for you to make it better?

15. When do you think someone is ready for marriage?

16. What is one way that I could try to be more understanding?

17. When was the last time you got rejected?

18. Who is that one person you can talk to about just anything?

19. Do you usually stay friends with your exes?

20. Have you ever lost someone close to you?

21. What challenging life experiences have made you stronger?

22. What’s an ideal weekend for you?

23. What do you think of best friends of the opposite sex?

24. Do you feel safe in our connection?

25. Are you confrontational?

26. What would a perfect day spent together look like?

27. What are your biggest fears in our relationship?

28. When you look into the past, what do you miss the most?

29. What are you most thankful for?

30. Do you believe in second chances?

31. Do you feel more loved when I compliment you or cuddle you?

32. What is your idea of a perfect vacation?

Deep Questions to Ask about Love

You just started to know each other’s inner worlds intimately, and your eager and loving inquiry, discovery, and curiosity generated a powerful sense of emotional closeness between you two, didn’t it? And now you’re not sure if it’s functioning. You need some answers and for that you can use these deep questions about love.

1. How did you feel saying ‘I love you’ and meaning it for the first time?

2. What is the biggest dealbreaker for you in a relationship?

3. How do you feel about letting your partner have full access to your phone?

4. When do you know you’re in love?

5. How do you know when you’ve found the one?

6. What bad habits would you be willing to give up for a relationship?

7. Kiss on the first date?

8. Is there such a thing as soul mates?

9. Have you ever doubted you’ll find your forever love?

10. Where was the weirdest place you made love?

11. What is your biggest fear about a relationship?

12. How would you spend a date if you could only use $30?

13. Are you confrontational in relationships?

14. Do you have a movie-worthy kiss memory?

15. Would you date your ex again?

16. How do you feel about dating someone who is still close with their ex?

17. Have you ever regretted leaving a relationship?

18. What’s your biggest non-physical turn on?

19. Do you think there has to be a sacrifice in true love?

20. How old were you when you first experienced romantic love?

21. When was the first time you said “I love you” to someone in your life other than family?

22. When and where did you go on your first date ever?

23. Do you remember our first date?

24. Were you nervous during our first kiss?

25. When did you know you loved me?

26. What is your ideal night?

27. What is your favorite thing about me?

28. Do you believe in true love or love at first sight?

29. Do you think people are made for each other?

30. Where is the perfect honeymoon locale?

31. Would you rather a night in a fancy penthouse suite or a private beach house?

32. Describe the most romantic date you can think of — spare no expense!

33. If you were on a dating game show, what questions would you ask?

34. What is your favorite memory with me?

35. What do you look forward to experiencing with me?

Deep Questions to Ask about Life

It is a sense of trust and closeness that contributes to the longevity of your relationship. Consider having a “no-filter” sort of authenticity, where someone sees and accepts you for who you are. You may use these deep questions about life to learn more about your perspectives on life.

1. What is the biggest thing you want to achieve in your life?

2. Where do you want to be 10 years from now?

3. What’s one thing you look forward to about getting old?

4. Where is one place you want to take someone else, where would it be, and who would you take?

5. Do you believe in fortune tellers?

6. Who in your family do you view as a role model?

7. Are you inspired by any celebrities dead or alive?

8. What thought or object gets you through the day?

9. Do you find praise or criticism to be more motivating?

10. What inspires you to better yourself?

11. What advice would you give to your children to stay determined?

12. What is the best way to motivate each other?

13. What is your greatest success to date?

14. What do you hope to achieve in the short-term?

15. If you could know one thing about your future now, what would it be?

16. Is there anything that scares you about the future?

17. Have you ever predicted something significant about your future that came true?

18. Would you prefer to retain a young body, or a young mind, until you die?

19. What is an awesome invention you think will be created in your lifetime?

20. Do you think we can change our future, or that it is already predestined?

21. What is one thing you want your future self to remember?

22. Would you rather acquire material items or experiences?

23. If it cost the same, would you live in a mansion or a mid-sized house with a lot of land?

24. In what scenario, if any, is it okay to lie?

25. When, if ever, is it okay to break the law?

26. What is the most important lesson to teach a child?

27. How often do you go out of your way to help someone?

28. If you could pick a new “golden rule,” what would it be?

5 Tips for Choosing Deep Questions to Ask

If you’re not sure how to pick questions to get to know someone deeply while playing this game, here are some pointers.

1. Find a Partner

Find your significant other, friend, parent, brother, sister, travel companion, internet stranger… Really, anyone you want to get to know better! Make sure they want to answer these deep conversation questions with you.

2. Find Your Personal Space

Find a secluded and comfy place where you will not be troubled for at least 45 minutes to an hour. You don’t want to be bothered by a phone call from your landlord!

3. Do Not Use All of Them at Once

You do not have to do all of these in one sitting—in fact, I advise against it. Sometimes it takes time to develop effective communication skills. Begin with one every supper or one per car journey. Take your time with them, relish them, build on them, and see where they lead you.

4. Concentrate on the Process, Not the Answers

The questions are divided into several different groups, with each set of questions being somewhat different from the last. You and your significant other will take turns asking these questions and answering the deep personal questions.

Even if you know the answers to the questions, you should not skip them. Remember that vulnerability draws people closer together.

The aim of these questions is to boost continuous, rising, and reciprocal self-disclosure. Allow time for both parties to respond to the questions and fully listen to their responses without judgement.

5. Staring Is Not Respectful

When you’ve completed asking the questions, the original experiment offers one further step: For four minutes, look your lover in the eyes. This step is entirely optional, but according to a 2019 study by Japanese experts, eye contact activates the regions of our brain that are responsible for empathy.

It will be a unique ending to your round of questions if you truly stare into your partner’s eyes! Just remember to blink… Otherwise, that’s just a tad disturbing.

Final Thoughts on Deep Questions to Ask

Make it a habit to use one or two of these deep questions to ask on a consistent basis to keep the communication going and to help you develop or restore the sort of relationship you want.

The aim isn’t to know the solutions to these good deep questions. What counts are the talks that follow, as well as the time spent listening to and focusing on one another.

These deep questions to get to know someone will reveal facts and tales you didn’t know existed! We recommend asking a few questions over dinner each night and taking turns answering them.

Before you know it, you’ll be talking about childhood experiences, your future plans, and exchanging insights on would-you-ever ideas… something you’ve probably never thought of before.

When we’ve been together for a long time, we often believe we know all there is to know about our ‘better half,’ but there’s always more to discover! Go over this list of deep questions to ask your partner or friend to get to know them even better.

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