562 Deep Questions to Ask Your Boyfriend to Create Intimacy

Continue reading for the hundreds of deep questions to ask your boyfriend, ranging from serious and romantic to lighthearted and charming.

These questions are ideal for opening up dialogue, creating intimacy, and getting to know your boyfriend better whether you’ve been together for six weeks or six years.

Your boyfriend had a life before you, full with embarrassing incidents, tremendous accomplishments, and unsuccessful relationships. You must know certain deep questions to ask your boyfriend if you want to learn more about his past and what makes him going.

If your relationship is becoming more serious, it’s critical to determine whether you and your boyfriend share the same values, want the same sort of life, and want the same type of relationship.

Understanding his past issues and how he like to be treated in a relationship is also helpful. The answers to the following crucial deep relationship questions can help you get to know him on a deeper level.

Super Deep Questions to Ask Your Boyfriend

It doesn’t have to be that grave to get to know your new boyfriend. These deep questions to ask him will give insight on his early exploits, treasured experiences, and personal preferences.

1. What is one thing that can destroy a relationship and never be forgiven?

2. Do you want to have kids someday when you meet the right person?

3. What is the one thing you learned a little too late?

4. Has there ever been a time when you were too hard on yourself?

5. Do you think it’s more important to work or spend time with family?

6. What do you look for most in a spouse?

7. How often do you feel yourself wearing down?

8. What is your go-to choice, mind or body?

9. What religious/spiritual views do you have and why?

10. How important do you think s#x is in a marriage?

11. Do you think one can have too many favorite memories?

12. What has been the lowest point in your life?

13. What are three key elements in every successful relationship?

14. If one of us had to move far away, would you be able to handle a long-distance relationship?

15. How important is it for you to save money?

16. Would you consider yourself proud to live in this country?

17. Is there anything too serious to be joked about?

18. Do you believe in the concept of fate?

19. What is the most significant sacrifice you’ve ever made for the sake of a relationship?

20. What do you think happens after death, if anything?

21. Do you think people can or should be friends with their exes?

22. Do you believe in soulmates?

23. Do you forgive and forget or forgive and remember?

24. If you had kids, what would be your biggest hope and biggest fear for them?

25. Do you believe emotional ‘cheating’ is just as bad as real cheating?

26. What do you think of open relationships?

27. Who are three people in your life that you would risk dying for?

28. If I was giving birth to our child and complications arose that meant only one of us would make it, who would you save?

29. Do you think we have the power to control our own destinies?

30. What is your life story?

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

32. Where does true happiness come from? And how would you describe it?

33. Complete this sentence: “I wish I had someone with whom I could share ______.”

34. If you could fix one world problem, what would it be?

35. Which has been your biggest achievement to date?

36. What do you think is the best part of human nature?

37. If you could have chosen your name, what would it be?

38. What’s your favorite thing about yourself?

39. What is your one memorable life miracle?

40. Do you believe in heaven?

Very Deep Questions to Ask Your Boyfriend

When you’ve been in a love bond for a long time, it might be difficult to come up with new topics to discuss. These deep personal questions to ask your boyfriend are a terrific way to keep things interesting between the two of you.

1. How do you think would people remember you?

2. What’s the most vulnerable you’ve ever been?

3. Have someone broken your trust that it became irreparable?

4. Have you ever broken someone else’s heart?

5. If you could make five rules before going into a serious relationship, what would they be?

6. Are there any conversations you wish we would stop having?

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

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

9. 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?

10. What’s something that you are most ashamed to admit?

11. Do you think happiness is permanent?

12. What’s something about you that changed the most in the last ten years?

13. How would you want to spend the next ten years of your life?

14. Is there anything that you absolutely refuse to forgive?

15. What does your ideal day necessarily involve?

16. Do you follow your mind or hear while making any important decisions in your life?

17. What are some of your excellent qualities that you admire you the most?

18. What do you think will never end well?

19. What would you do first if you wake tomorrow without fear?

20. What is the worst thing that would cause you to escape and go on a road trip alone?

21. Does one earn happiness or it simply happens?

22. How would you know if you have lived a good life?

23. What is your definition of intimacy?

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

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

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

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

28. What’s a problem you’re dealing with right now?

29. What’s the biggest struggle that you’ve ever faced?

30. Why do you think the divorce rate is so high nowadays?

31. Would you let me help you with your biggest problems?

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

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

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

35. Is there anything you consider absolutely unforgivable?

36. When you’re having a bad day, what makes you feel better?

37. Do you think crime can ever be erased?

38. What is something you think to be real that no one else believes to be true?

39. What is the most emotional scene you have watched in a movie that made you cry?

40. Do you love being around kids?

Really Deep Questions to Ask Your Boyfriend

Intimacy is one of the most vital aspects of a relationship, although we might feel disconnected from our partners at times. Reconnect with these really deep questions to ask your boyfriend.

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

2. What has been your greatest accomplishment in life?

3. If you ever had a remote control for a machine, which machine would it be?

4. Which is the most idiotic thing that you love doing?

5. Is there anything you’ve been too afraid to say out loud to someone?

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

7. What are your favorite characteristics of each other?

8. What was surprisingly the best mistake you made?

9. If you had a chance to go on a road trip right now, where would you go?

10. When have you had a lot of fun at work?

11. Which invention do you think is useless for humans?

12. Have you ever dreamed of owning a zoo?

13. What is the kindest thing you have ever done?

14. If you could have a time machine for a week, what three eras would you visit and who would you be? Why?

15. How do you feel about scientifically grown food?

16. Do you ever want to try gardening?

17. When you were little, what did you want to be when you grew up?

18. What is the worst injury you have ever had?

19. Have you ever taken a shortcut in life and regretted it?

20. When do you always agree to splurge on yourself?

22. Do you let people fight their own battles or always jump in?

23. Do you think emotional abuse exists?

24. Have you ever been scared of commitment?

25. If your life were a novel or a movie, would you be entertained? Would you admire your own character and the decisions they’ve made?

26. What are your simple pleasures in life?

27. Which movie was so upsetting that you’ll never watch it again?

28. Is there a sound that scares you?

29. What is the one thing you always hide from your parents?

30. When was the last time you laughed until you cried?

31. Have you ever had a friend with benefits?

32. Would your younger self be proud of who you are today?

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

34. What do you think the hallmark of a good relationship is?

35. Do you like sneaking in cute pictures of your friends and family?

36. What is the one food which can give you a million calories but you’ll still have it?

37. What is the meanest thing you have ever done to someone?

38. Have you ever felt like you did a less manly thing in your personal life?

Good Deep Questions to Ask Your Boyfriend

Knowing what question to ask your boyfriend might help you bring romance to your relationship. Rekindle your passion by using these good deep questions to ask your boyfriend.

1. Do you believe there is good in everyone?

2. Do you believe in ghosts? If yes, have you ever seen one?

3. Did you ever have a crush on anyone I know?

4. What would the title of your autobiography be?

5. Do you judge people too quickly? How often are you right about your judgment?

6. What is the worst yet most expensive purchase you have ever made?

7. Does it make you smile when I send you a text message?

8. Are you scared to love someone wholeheartedly? If yes, why?

9. Were you nervous when we had our first kiss? Were you expecting it to happen?

10. If (God forbid) our relationship came to an end, what is the one thing you would miss about me the most?

11. Do you think about me during the day?

12. If animals were as intelligent as humans, what types of jobs would certain animals be uniquely qualified for?

13. What names would you never give your own child? Name at least three.

14. Who do you think is the vulnerable one in our relationship?

15. Do you like watching romantic movies? What is the most romantic movie you have ever watched?

16. What about both of us is exactly the same since we first got into this relationship?

17. What is the most relaxing thing you can get done or do for less than 500 rupees?

18. What do you visualize when you are kissing me?

19. Would you be embarrassed to hold my hand in public?

20. If I was really sad, what would you do to cheer me up?

21. Did you ever think that I looked completely crazy in an outfit of mine? If yes, which one?

22. What silly things are you capable of doing that you take a lot of pride in?

23. Do I make you want a future with me?

24. Who has been your strangest celebrity crush that others don’t like but you have a soft corner for? Why do you like him/her?

25. If you were a fruit, which one would you be and why?

26. If I was scared, would you hold me?

27. What kind of trip would you like to take? Traveling to Maui for an all-inclusive resort, London for sightseeing, or Yosemite National Park for camping?

28. What has been the strangest conversation you have ever overheard? Do you remember the details?

29. If you were a girl, would you date Batman or Superman? Why?

30. Has someone ever confessed their secrets to you while being drunk? What did they say?

Random Deep Questions to Ask Your Boyfriend

Your partner most likely has fantastic stories that you haven’t heard since they haven’t come up in any conversation. These deep random questions to ask your boyfriend will prompt him to recall his most amazing experiences.

1. Would you rather have a life full of love or a life full of money?

2. Do you like to spend your time alone? What do you like to do when you are alone?

3. When do you have the feeling of being most alive? Can you tell me something about this?

4. What do you think I’d say is your most attractive quality?

5. What’s your favorite way to show affection?

6. Do you think your friends would describe you as a loyal person?

7. What’s one thing that would make your personal life stronger?

8. Can a positive outlook make any situation better?

9. If we could go anywhere together right now, where would you want to go?

10. What is the most romantic movie you enjoy?

11. What did you expect your actual first kiss to feel like?

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

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

14. Do you think children are more of a blessing or a burden?

15. What’s a lame joke you use on a regular basis?

16. What’s the weirdest wrong number text or phone call you’ve gotten?

17. Do you believe in the phrase “opposites attract”?

18. Do you measure yourself against others and their successes?

19. What keeps you up at night?

20. What event from the past do you most want to see a recording of?

21. What are you a non-military veteran of?

22. Do you believe anyone should be able to get married?

23. What are your thoughts on equal rights?

24. How do you define success for yourself?

25. What chore do you dread most?

26. What product are you shocked that no one has made a better version of?

27. What’s one of the biggest issues in our society?

28. What are your political views?

29. If you could make a candle with any scent, what type of scented candle would you make?

30. If wars were abolished, what would be the most interesting way for countries to settle their differences?

31. What’s legal but still feels illegal?

32. Do you think money makes people happy?

33. What is God to you?

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

35. What’s one of the biggest failures in your life?

36. Who helped craft and define who you are?

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

38. Do you hold grudges against those who have wronged you?

39. When do you want to retire?

40. What’s the last thing you Googled?

Fun Deep Questions to Ask Your Boyfriend

Don’t restrict yourself to simply serious or meaningful questions! These fun deep questions to ask your boyfriend will encourage him to tell you tales and may maybe make you both chuckle.

1. What’s the craziest thing you’ve ever done to impress someone?

2. How often is your brain on autopilot?

4. Which moments of your life do you cherish the most?

5. What is your favorite ride at an amusement park?

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

7. Where is the craziest place you have danced?

8. Which is your favorite travel music song?

9. If you were a part of a cult, what would it be?

10. What do you think aliens would actually look/be like?

11. What’s the spiciest thing you’ve eaten?

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

13. Have you ever kissed someone who was kissing you beneath the mistletoe?

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

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

16. Do you have any hidden talents?

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

18. Which hairstyles fit with which personalities?

19. If you could meet one celebrity, who would it be?

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

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

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

23. What’s the most embarrassing thing you would willingly do for a million dollars?

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

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

26. What’s the lamest thing you did to make your first crush notice you?

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

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

29. Did you pull on her pigtails in the playground? Savage.

30. If you could get the first kiss with your celebrity crush in a movie, who would you do the kissing scene with?

31. If you could have a remote control that controls any one type of machine, what would you have a remote for?

32. Were you ever guilty of peeing in the swimming pool and acting like you didn’t when someone asked about it?

33. What’s the funniest / strangest thing that someone has drunkenly confessed to you?

34. Can you tell me the biggest lie you’ve ever told a girl to get her to like you?

35. What are some non-traditional toppings for ice cream that you think would be pretty awesome?

36. If you could relive one day in your life, what day would you choose?

37. What is the craziest thing you ever googled?

38. What’s your most awkward first kiss story?

39. Which is your dream name to have?

40. If you could switch genders, what will you do first after the switch?

41. What’s the weirdest thing a girl has ever done for or told you?

Deep Questions to Ask Your Boyfriend Over Text

Texting is a great way to converse about lighter topics and participate in clever banter. Respond to his responses with levity and emoticons so he understands you’re kidding. Here are some interesting and deep questions to ask your boyfriend over text.

1. Do you prefer me with makeup or looking natural?

2. When was the last time you honestly felt appreciated or loved?

3. In your opinion, what makes humanity successful?

4. What’s the best advice that anyone has ever given you?

5. What qualities do you look for in a future partner?

6. What is your all-time favorite movie quote?

7. What’s the nicest thing that anyone could ever say about you?

8. What’s something that makes you anxious?

9. Who do you look up to as an inspiration?

10. How did you get me to fall for you?

11. What’s the most beautiful place you have been and wished to go to again?

12. What is your preference: Money or Love?

13. What’s the worst text you’ve ever sent by accident?

14. Who is your number one fan/ supporter?

15. What is a fact that you’re shocked more people aren’t aware of?

16. What happens in real life that is rarely shown in films?

17. Did you imagine then… we would be where we are today?

18. What is your relationship with your parents like?

19. Who is the one person who knows you better than anyone else?

20. Do you think people underestimate you/ take you for granted?

21. On a scale of 1 to 10, how much do you love me?

22. What do people underrate about you?

23. What is that one thing people don’t know about you?

24. What is it about people that drive you crazy?

25. What makes our love different to all the rest?

26. What do you try to do to yourself when you are angry?

27. What do you do when you are in a happy mood?

28. What do you do when you are mad at someone?

29. Do you believe in karma?

30. What is it that makes us work the most do you think?

31. What do you believe most in?

32. What is something you’ve never told someone?

33. What is the best pickup line you’ve ever heard?

34. If you have a superpower to eliminate any world problem, what would that be?

35. If you could dedicate your life to solving one problem, what problem would you choose?

36. If there’s one thing you could do for me, or I could do for you what would it be?

37. What is your worst behavior that you strongly wish to change?

38. What would you ask for if you could talk to someone who is no longer alive?

39. Who do you feel if you hadn’t met them before, your life would be different?

40. What is your take on s#x before marriage?

Deep Questions to Ask Your Boyfriend in Person

If you want to excite things up in your relationship, you will need deep questions to ask your boyfriend in person. These questions will set you two off to a terrific start.

1. How do you cope with stress?

2. What do you get overly emotional about?

3. What event made you mature as a person the most?

4. What would it look like if you fully lived up to your potential?

5. How curious are you?

6. How would you handle it if I lost my job, and we were living together and sharing expenses?

7. Are you able to keep your anger under control?

8. What’s the best way to earn somebody’s respect?

9. How do you handle disagreements?

10. What makes life worth living to you?

11. What is something you do which might cause me to question your loyalty?

12. If you had to leave your house, what is the one thing you would take with you?

13. What tv show could you binge-watch all day?

14. What would you do if money and work were not factors?

15. Who is one person you wish you could be?

16. What’s the hardest truth you’ve come to grips with?

17. Would you ever quit your job to travel the world?

18. What word describes you better than any other word?

19. What are you really obsessed about?

20. What are some of your ideas for how to keep a relationship strong over time?

21. Do you think men and women can be platonic friends?

22. How often do you get into arguments with people on the internet?

23. What do you want to get out of life?

24. How adventurous are you?

25. Are you comfortable talking about where our relationship is going?

26. If one of my friends flirted with you, would you tell me?

27. How would you deal with a disagreement with one of my family members or friends?

28. How much time do you think we should each spend with our family/friends outside of gatherings that require us both to be there?

29. If one of your friends or family members told you to break up with me because he/she didn’t like me, would you?

30. How do you feel about my family and/or friends?

31. If I were offered a promotion and had to move away, would you move with me?

32. When you break up with someone, how do you do it?

33. What’s the worst breakup you’ve ever experienced? Why was it so bad?

34. What are your thoughts on marriage?

35. Do you believe there’s one person you’re ‘meant’ to be with?

36. If money were no object, what would you have for breakfast every day?

37. If you could have dinner with three people in the world, who would they be?

38. Do you think it’s OK for men and women who are in separate relationships to go have coffee or lunch together?

39. Do you like to travel or would you rather stay home?

40. What has been the best phase in your life thus far?

Deep Questions to Ask Your Boyfriend about Your Relationship

Communication is a compulsory factor of any relationship. Problems may arise if you do not discuss your relationship and where it is headed. These deep relationship questions to ask your boyfriend can assist you in developing the connection that you desire.

1. What is your favorite thing about us as a couple?

2. What do you think when you look into my eyes?

3. Would you ever like it if I write a song about you?

4. Do you find saying ‘I love you’ difficult?

5. How would you describe the feeling of being in a relationship with me?

6. Would you ever want to go on a picnic with me?

7. What makes you super happy in our relationship?

8. How long did you think our relationship would last when we first started dating?

9. Do we communicate enough when we’re not together?

10. Which habit of yours do you think annoys me the most?

11. What song do you think best fits our relationship?

12. What famous real or fictional couple reminds you the most of us?

13. Do you think you act like a snob at times?

14. If we had children, what features would you want them to get from you and which from me?

15. Which day from our relationship would you choose if we could relive it?

16. Are you a pro-choice or a pro-life individual?

17. What are your expectations for our relationship?

18. Do you think you are nurturing enough?

19. What is your favorite memory from our time together?

20. If you could bring me to a place you absolutely love, where would it be?

21. What do you think you bring to our relationship? What about what I bring in our relationship?

22. What’s something I can do that will instantly make your mouth drop open and make you speechless?

23. What’s something about us, or me, that you miss the most whenever we’re not together?

24. What kind of journey do you want to do together?

25. What is your favorite aspect of our friendship?

26. What is one thing I can do to improve our relationship?

27. What is a pastime or talent that you would like to learn as a couple?

28. Do you believe we fight in a fair manner?

29. What do you think are three things we have in common?

30. What’s something you could never compromise about?

31. What are the biggest differences between us?

32. Is there anything in our relationship that you think we need to work on?

33. Is there anything that you always wanted to tell but never got the guts to talk about?

34. What am I doing that makes you feel valued?

35. What’s your favorite thing about our relationship?

36. What is one difference between us that you think makes our relationship quirky and adorable?

37. Would reading a love note that I wrote for you give you butterflies?

38. What would you do if I got distraught to make me smile?

39. What is the basic recipe for a healthy long-term relationship?

40. What is the most important thing in a relationship?

41. Do you think fights and jealousy are healthy components of a romantic relationship? Or do you think it should be avoided?

42. Are you content with the emotional closeness we share?

43. What can we do to help each other out more?

44. What’s the best and worst relationship advice you’ve ever gotten from someone? And from whom was it?

45. What’s something you’ve done but will never do again, no matter what?

46. Are we positively influencing each other?

47. Is it possible that we’re enabling each other’s unhealthy habits?

48. What goes in your mind whenever you close your eyes when kissing me?

49. Before we even got together, have you thought about what it will be like to kiss me?

50. If I look into the photos on your phone right now, what pictures would surprise me the most?

51. What would be the worst thing I can do to make you want to end the relationship right away?

Deep Questions to Ask Your Boyfriend about Love

There’s a lot to learn when you start dating someone new, from how he likes to be treated to what he dreams about. These are the deep love questions to ask your boyfriend to get to know his views about love.

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

2. When was the first time you were in love?

3. Who was your first love interest?

4. Do you think it’s possible to fall in love at first sight?

5. What do you enjoy most about dating?

6. What is your ideal night?

7. When did you first find out that I liked you?

8. Is there a song that you think of when you think about me?

9. What is your favorite thing about me?

10. If you could travel anywhere in the world with me with no monetary restrictions, where would we go?

12. What is the best compliment you have ever received from me?

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

14. Where is the perfect honeymoon locale?

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

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

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

18. Do you remember our first date?

19. Were you nervous during our first kiss?

20. What is your favorite memory with me?

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

22. When did you know you loved me?

23. What is your favorite song about love?

24. If you could describe me in only one word, what would it be?

25. What was the first thing that you noticed about me that made you feel attracted?

26. When are you the happiest with me?

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

Deep Questions to Ask Your Boyfriend to Get to Know Him

Every relationship, no matter how long you’ve been together, requires time and work. These deep questions to ask boyfriend can warm up any date and bring you closer together.

1. What is the weirdest thing you want to do with me?

2. Do you think the best way to move on is to wait for a long time?

3. What do you observe as the biggest sign of weakness in a person?

4. Do you fear the future and what it holds?

5. What motivates you to work hard?

6. Is it more necessary to have an emotional or physical connection in a relationship?

7. Whose relationship do you admire the most among your friends and family?

8. What can make you angry, easily and quickly?

9. What’s your best quality? 

10. What are your secret and most useful stress buster activity?

11. What will you write on your tombstone if given a chance?

12. What will you be like if you were given a chance to change your appearance?

13. Do you prefer materialistic gifts or emotional gestures?

14. If you could have a pet, any animal you like, what would you pick and why?

15. What will the job description be like if you can create your ultimate dream job?

16. Have you ever been in a toxic relationship?

17. What makes you feel the most loved?

18. Do you consider yourself a jealous person often?

19. Are you a laid-back person or an adventurous soul?

20. How fascinated are you by nature?

21. How often do you talk to yourself about yourself?

22. What makes you excited whenever you think of tomorrow? How about the biggest fear about tomorrow?

23. Who is the one person that makes you highly uncomfortable?

24. Who do you value the most in your life?

25. If your life was a movie or a song, what would it be?

26. If you can be brutally honest, what truth about yourself can you share with me?

27. Which three words would you choose to describe yourself?

28. When do you say was the most defining moment of your life?

29. Do you have adamant opinions?

30. What do you want out of life after five years?

31. If you could be the first person to achieve something, what will you achieve?

32. When have you felt the loneliest?

33. What is your temperament?

34. What do you believe makes you unique from other guys?

35. Have you ever been obsessed with something for a long time?

36. What is something that most people underestimate or overestimate about you?

37. Have you ever sneaked out of your house for a date?

38. If I could, would you like me to read your mind?

39. Do you think romantic comedy movies are underrated?

40. What are the habits in others that annoy you the most?

Deep Questions to Ask Your Boyfriend about You

Are you curious what he thinks of you? Just go ahead and ask him! He may not automatically share this information, therefore assist him in expressing his sentiments by asking deep questions to ask your boyfriend about you.

1. What is your favorite thing that I do for you?

2. When did you realize you’re falling in love with me?

3. What do you like the most about spending time with me?

4. What do I mean to you?

5. When did you realize I was the one for you?

6. When did you first realize that you wanted to pursue me?

7. Would you surprise me with an expensive gift, or would you consult me before spending the money on it?

8. Do you like us holding hands or me holding close to your arm while walking?

9. What’s your favorite part of my body that you want to touch the most?

10. What do you think made me fall in love with you?

11. Would you rather I be good in the kitchen or good in the bedroom?

12. What is the one quirk that you love about me?

13. What kind of clothing do you think I look the best in?

14. Would you rather take a bullet or kiss me all day?

15. What’s your favorite photo of me?

16. What’s one thing you’re scared to ask me but really want the answer too?

17. Would you love it if I kissed you in public?

18. Where do I fit in in the next five years of your life?

19. What’s one thing that you wish I did more?

20. Would you still think I’m cute when I look like a mess?

21. If I get scared watching horror movies, would you hold me?

22. Can you tell me something that I texted you that made you smile?

23. If I were a dessert, what do you think I would be and why?

24. What should I focus on more? What should I cut back on?

25. Do I make an appearance in your dreams or fantasies?

26. What is something you appreciate about me?

27. What does it make you feel whenever you hold my hand?

28. What was something about me that attracted you at first sight?

Deep Questions to Ask Your Boyfriend about His Past

Begin asking important questions early in your relationship to uncover what he values and believes. You don’t want to be 6 months into a relationship and learn that dominant ladies are threatening him or that you consistently do things that irritate him. Make use of these deep questions to ask your boyfriend about his past.

1. What is a tradition you did as a child that you want to do with your kids someday?

2. Have you ever had your heart broken?

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

4. Do you have any dreams from childhood that you can vividly recall?

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

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

7. How long was your last relationship and what was the reason for ending it?

8. Have you ever gotten married or engaged so far? If not, then do you ever want to get married?

9. What were your childhood aspirations, and how have they changed?

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

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

12. Have you ever loved a partner and how was your experience with this?

13. Have you ever struggled with addiction? If so, then what was that addiction?

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

15. How do you picture your life when you’re 60?

16. What’s the best gift you’ve ever received?

17. If you had to listen to just one of the songs you loved as a kid for the rest of your life, which song would it be?

18. Did you have any pets growing up?

19. Have you ever done something that you deeply regret?

20. What is your most terrible memory?

21. Who was your role model while growing up?

22. When you were a kid, what career did you want to opt for and why?

23. In what areas do you want to change the most?

24. Have you ever lost a friend? If so, what happened?

25. Is there any book that changed your life?

26. What did you and your friend usually do in middle school for having some fun?

27. What is one of the toys that you always wanted as a child but no one ever bought for you?

28. What do you admire most about your parents?

29. What is your biggest insecurity?

30. Is there anything you’re ashamed of?

31. What were some lessons in life that you had to learn the hard way?

32. Is there anything you wouldn’t want your family to know?

33. If you could change anything about the past, what would it be?

34. Is there a book or movie that completely changed your life?

35. Have you ever emotionally hurt someone before? What did you do?

36. What is your happiest memory?

37. Were you close to your family when growing up?

38. How did your parents meet?

39. How have you changed the most since you were younger?

40. What was your childhood dream, and have they changed?

41. Have you ever cried tears of joy?

42. What was the most painful experience you ever had to go through?

43. Who do you think influenced you the most throughout your childhood?

44. What has been the biggest change you ever made that made you proud of yourself?

Deep Questions to Ask Your Boyfriend about the Future

It’s natural to run out of topics to discuss in a relationship after spending so much time together. With these deep questions to ask your boyfriend about the future, you can restart the conversation.

1. What do you look forward to about being a parent?

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

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

4. What’s the future plan you have done till now for us together?

5. What advice would you give your son when he starts dating a girl?

6. What would be our kids’ names?

7. What are your financial priorities and goals?

8. If you were told you had a terminal illness, what would be three things you’d want to do?

9. What are your goals in the relationship?

10. What are your thoughts on having a family?

11. How do you see our future together: do you envision a 2-income household, or a different arrangement?

12. If you could live to 90 and have either the mind or body of a 30-year-old, what would you choose?

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

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

15. What is a tradition you did with your family that you want to continue on with your kids?

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

17. If we had a chance, would you plan a baby for the 29th of February?

18. When we fight during the day we can’t sleep together at night, is this ok for you? Or will you come and say sorry?

19. What’s one thing you hope happens in the future of our relationship?

20. What’s the best advice you’ve ever received in your whole life?

21. f your friends flirt with me, would you be angry at them or me for having some fun with them?

22. What will you do when your kid comes after the first fight?

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

24. If you don’t want to be a parent, why?

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

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

27. Where do you see yourself in five years?

28. How do you want to be remembered?

29. If we saw our relationship together, how happy would you be after three years?

30. If I tell you to leave a bad habit, would you leave it or do that again alone?

31. What place can we use for a perfect date for years?

32. Which school do you think would be perfect for our kids?

33. If you see me in one piece when you come after work, what would you do first?

34. Do you think a proposal should be a grand public display or a private intimate moment?

35. Do you want to live near or far from relatives?

36. What are your future goals, or have you made some savings for your future?

37. How do you react to my guy friends talking to me after marriage, or do you have a girl just friends with you?

38. Will you stay with your family even after marriage?

39. What special treat would you give me on my next birthday?

40. Where would you plan your honeymoon?

41. If we ever have a live-in-relationship with me, how much would you like to pay, and what would you expect me to pay?

42. If you have to plan something for our future now, what would you prepare?

43. When your parents get old, how do you plan on taking care of them?

44. Do you still have a bond between your parents and keep it after marriage?

45. What could be the factor for our distance?

Deep Questions to Ask Your Boyfriend about Values

Do you have a date from another culture? This might be religious, ethnic, or even socioeconomic in nature. If this is the scenario, you will have opposing worldviews, beliefs, customs, and expectations. For such scenarios, here are some deep questions to ask your boyfriend about values.

1. Would you rather acquire material items or experiences?

2. What do you see as your best character trait?

3. If you could change one thing about your character, what would it be?

4. Would you consider yourself a pessimist or an optimist?

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

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

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

8. What are important societal values? (ex. Democracy, fundamental rights, etc.)

9. How have your values changed from ten years ago?

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

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

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

13. When were you the most disappointed in yourself?

14. If you could change one thing about the way you look, what would it be?

15. Do you put as much effort and emphasis on inner beauty as outer beauty?

16. When were you the most proud of yourself?

17. Generally speaking, do you like the way you look?

5 Tips for Choosing Deep Questions to Ask Your Boyfriend

If you don’t know how to choose deep questions to ask boyfriend, here are some tips that might come in handy.

1. Keep this thing in mind that you are not conducting an interrogation, but rather deep relationship questions. Lean forward and make eye contact while waiting for a response when you pose a question.

Listen to the reaction and communicate with it as you would with a best friend. Nod, grin when needed, and replicate his verbal and facial gestures.

2. Begin by answering the questions. Pose follow-up questions and share your responses.

3. Print out our list of deep questions for boyfriend so he may ask you his. While he’s speaking, pay attention to nonverbal signs. His nonverbal clues may convey a different meaning than his words.

Always listen to his sincere responses without judgement or criticism. He, like you, requires safety in the connection. Be humorous with your replies when asked amusing and unusual questions.

4. This is not a to-do list! Choose the greatest questions that speak to you and ask them spontaneously throughout talks.

Asking the correct question at the right moment may help us achieve breakthroughs in many aspects of our lives, from determining what we want to accomplish with our lives to strengthening personal relationships.

5. As much as I enjoy asking my partner probing questions to find out what he’s truly thinking, a long list of probing questions may be exhausting, so I strongly recommend throwing in some lighter ones to keep things light and the discussion moving!

When you and your lover are ready to lighten the atmosphere, go through our lists for additional entertaining question/answer sessions!

Final Thoughts on Deep Questions to Ask Your Boyfriend

Thank you for taking the time to ask these deep questions for boyfriend. How well do you know your boyfriend? We don’t just mean knowing their desired color or show, but actually getting to know them.

Have you ever asked them about their deep relationship questions, such as their likes, dislikes, trauma, regrets, interests, dreams, and biggest wants?

These deep questions to ask your boyfriend aren’t meant to kill your connection; rather, they’re meant to bring attention to a weakness that has to be fixed if you want to make it through both the good and the bad moments.

Luckily, there is a rather unpretentious method to enhance your relationship. And, fortunately, it’s a lot of fun. Consider the last time you had a meaningful chat with your lover.

Through the development of trust, empathy, and compassion between partners, an honest and open talk may aid in the union of two people. Communication leads to comprehension, and comprehension leads to happy mutual relationships, which can lead to peace and stability.

Knowledge is the doorway to compassion and love, and questions assist us get that degree of understanding, allowing us to learn why our boyfriends behave or think the way they do. You can create that understanding using these deep questions to ask your boyfriend.

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