150 Deep Questions To Ask Your Boyfriend To Get Closer To Him

Know your lover better and deepen your relationship with these meaningful questions.

Reviewed by Joy Nwokoro, Relationship Coach
Written by Sneha Tete, Certified Relationship Coach
Edited by Subhrojyoti Mukherjee  • 

Got bored of casual conversations with your boyfriend like what’s up or how’s your day, and searching for deep questions to ask your boyfriend?

This article is for you! It is essential to know your partner at a truly intimate level regardless of when your relationship has started. The partners should be aware of each others’ dreams, likes, and dislikes.

This will only happen when your bond is connected at a deeper level. Communication plays a key role in any relationship. So, what are you waiting for? Check out the article to get an idea about meaningful conversations and things to ask your boyfriend.

150 Deep Questions To Ask Your Boyfriend To Strengthen Your Relationship

Questions To Get To Know More About Him

Questions to ask your boyfriend to get to know more about him
Image: Shutterstock
  1. Do you want to have children?
  2. How long was your longest relationship?
  3. Do you ever want to get married?
  4. Have you ever lived together with someone? How was the experience?
  5. How important is religion or spirituality to you?
  6. What are your thoughts on gay rights?
  7. Do you think money can buy happiness?
  8. What is your dream job?
  9. What is the primary goal you want to accomplish in your life?
  10. What accomplishment are you most proud of?
  11. What makes you feel vulnerable?
  12. How would you describe your relationship with your family?
  13. Do you have a best friend?
  14. What is your love language?
  15. Are you an introvert (those who recharge by being alone) or an extrovert (those who feel energized when around other people)?
  16. Do you hold any grudges?
  17. Have you ever struggled with addiction?
  18. Have you ever been in an emotionally or physically abusive relationship?
  19. If you could have any skill without having to work for it, what would it be?
  20. What is your favorite city?
  21. How do you like to be treated when you are sick? Do you like to be waited on hand and foot or left alone?
  22. Do you have any phobias?
  23. What is your biggest pet peeve?
  24. What cause have you volunteered for that you feel passionate about?
  25. If you were going to start a charity, what would it be for?
  26. Do you watch, read, or listen to the news?

protip_icon Quick Tip
Since these are questions about deeply rooted ideologies, there are chances that you both might disagree. Be prepared to hear them out and be calm as you express your disagreement.

Once you have an idea about him, you would like to know about his childhood days to know how he was as a kid. You can ask him these questions.

Questions To Know More About His Younger Days

Questions to ask your boyfriend to get to know more about his younger days
Image: Shutterstock
  1. Who was your role model growing up?
  2. When you were a kid, what career did you want to have?
  3. Did you go to a summer camp?
  4. What is your idea of a perfect Sunday afternoon?
  5. What is your favorite holiday destination?
  6. What is the best present you’ve ever received?
  7. What did you and your friends do for fun in middle school?
  8. Did you have any pets while growing up?
  9. What is your happiest childhood memory?
  10. If you could cook any dish perfectly, what would you choose?
  11. When you’re having a bad day, what makes you feel better?
  12. At an amusement park, what ride do you prefer to try and why?
  13. What toy did you always want as a kid, but no one ever bought for you?
  14. Have you ever slept with stuffed animals?
  15. What sound do you love?
  16. What are your favorite scents?
  17. What candy do you hate?
  18. What is your favorite karaoke song?
  19. What was your favorite thing to do during recess?

protip_icon Quick Tip
Be open-minded about being asked the same questions. Keep in mind that your answers need not be impressive, only honest. Here’s where you can tell them how you missed out on certain things in childhood and wouldn’t mind experiencing them with your partner now.

Knowing about your boyfriend’s likes and dislikes will help you understand their preferences and views on various things like what type of activities or sports they usually enjoy. You can also find out if you both have anything in common. Keep scrolling to check out related questions for your boyfriend.

Questions To Know More About His Likes And Dislikes

Questions to ask your boyfriend to know his likes and dislikes
Image: Shutterstock
  1. What is your favorite thing to do on a rainy day?
  2. What is the weirdest reason you ever broke up with someone?
  3. When was the time you laughed the hardest?
  4. If you could listen to only one song for the rest of your life, what song would you choose?
  5. What celebrities have you met?
  6. What word do you hate?
  7. What is your pop culture guilty pleasure?
  8. What is the most embarrassing thing that has ever happened to you?
  9. What is the weirdest thing you’ve ever bought?
  10. Have you ever been to a palm reader or a tarot reader?
  11. Who would you rather hire: a personal trainer, a personal chef, or a housekeeper?
  12. What would you do if you could be a woman for a day?
  13. What is the one movie you’ve seen more times than you can count?
  14. If a movie was being made about your life, what actor would play you?
  15. What were you like in high school?
  16. What fictional character do you relate to the most?
  17. Would you rather be hot or cold?
  18. If you could be born in a different decade, what decade would you choose?
  19. What is your favorite part about being an adult?
  20. Have you ever played Truth or Dare? What was the most memorable dare that you accepted?
  21. Where is your ideal place to live – a farm in the middle of nowhere, an elegant house on the water, or in a hip, downtown condo?
  22. What do you want to do when you retire?

While the questions mentioned above may help you connect emotionally, building physical intimacy is also crucial. And both of you should be on the same page in this regard. You may ask him the following questions to understand his views on intimacy and sexual compatibility.

Questions To Get Him Talking About Intimacy

Questions to ask your boyfriend to get him talking about intimacy
Image: Shutterstock
  1. Which sense is the most sensual to you?
  2. What is something you’ve always wanted to try with your partner?
  3. What is the closest you have felt to me?
  4. Have you ever been attracted to a man?
  5. Would you be willing to go out of your comfort zone for me?
  6. How do you like to show love?
  7. Do you have any fantasies you want to fulfill in real life?
  8. Where is your favorite place to be intimate with someone outside of the bedroom?
  9. How do you want me to show you love?
  10. What do you think is the best way to show someone that they care about their partner?
  11. What makes you attracted to a person physically?
  12. How often would you like to be intimate with me?
  13. How do you think we can keep the romance alive in our relationship?
  14. What is your favorite part about intimacy?
  15. If we were going to role-play, who would you want me to dress up as?
  16. Which movie would you choose to describe our relationship?
  17. What do you like the most about me?
  18. What words or phrases make you think of me?
  19. What is the weirdest thing that you have heard about being intimate with someone?

protip_icon Quick Tip
Here’s your opportunity to set physical boundaries. If there is anything you are not open-minded about trying, let them know. You do not want a pleasurable experience to get disturbed because of certain inhibitions.

If you are in a relationship that just feels right, you would also like to know if your boyfriend feels the same about it. And the only way to find out is with these serious questions to ask your boyfriend regarding relationships.

Questions To Understand How He Feels About Relationships

Questions to ask your boyfriend to understand how he feels about relationships
Image: Shutterstock
  1. When we’re not together, do we communicate enough?
  2. What is your happiest memory from our relationship?
  3. What trip would you like us to take together?
  4. What hobby or skill would you like to learn together?
  5. Do you think we fight fair?
  6. Do you think it’s possible for men and women just to be friends?
  7. Do you think a relationship can recover from cheating?
  8. What is the best advice anyone ever gave you?
  9. Do you like talking on the phone?
  10. What are your relationship deal breakers?
  11. What relationship cliché do you think is true?
  12. What is the most important quality you look for in a partner?
  13. What is the first thing you noticed about me?
  14. What is the sexiest thing a partner can wear?
  15. Describe your ideal date.
  16. Have you ever gotten anyone pregnant? How did you handle it?
  17. What is one thing you wish you could change about yourself?
  18. Have you ever cheated on anyone? Have you ever been cheated on?
  19. What are your biggest regrets in life?
  20. Who are you jealous of?
  21. What is your favorite thing about our relationship?
  22. What one thing can I do to make our relationship better?
  23. Do you like spending time with my family and friends?
  24. Are you happy with the physical intimacy we share?
  25. What do I do that makes you feel appreciated?
  26. Are you satisfied with the emotional intimacy that we share?
  27. Do we spend enough time together?
  28. What have you always wanted to teach me?
  29. Is there anything you always wanted to tell me but never had the guts to?

It’s quite common for most of us to judge a book by the cover. However, it will be rewarding if you go beyond the cover and take a peek at what’s inside. Ask your boyfriend these questions to know him inside out.

Questions To Find Out What He Is Like On The Inside

Questions to ask your boyfriend to find out what he is like on the inside
Image: Shutterstock
  1. What is the biggest misconception people have about you?
  2. Have you ever spent the night in jail?
  3. Have you ever been to therapy?
  4. Have you ever had to break up with a friend?
  5. Are you friends with any of your exes?
  6. Do you have any bad habits that you would like to change?
  7. Have you ever snooped on a partner?
  8. When was the last time you cried?
  9. Have you ever had your heart broken?
  10. What was the most difficult time in your life?
  11. Do you think it is okay to lie?
  12. What do you like most about yourself?
  13. What is the biggest risk you’ve ever taken?
  14. What is the hardest decision you’ve ever made?
  15. If a genie grants you three wishes, what would they be?
  16. Who was your first crush?
  17. What was your first kiss like?
  18. What is more important in a relationship: an emotional connection or a physical connection?
  19. If you had only a week to live, what are the things you would like to do?
  20. If you ever want to adopt a dog, would you go for a purebred or get a rescue dog?
  21. Would you move to a new city for your partner?
  22. Do you keep mementos from past relationships? (Cards, notes, photos, gifts)
  23. What is a ridiculous thing you’ve ever done to impress someone?
  24. Have you ever kissed someone under the mistletoe?
  25. Do you believe in love at first sight?
  26. What is your favorite part about dating?
  27. Do you believe in fate?
  28. What is the biggest sacrifice you’ve ever made for a relationship?
  29. What is your favorite love song?
  30. What are your thoughts on getting older? Is there anything you fear about aging?
  31. If you had to go back to school, what would you study?
  32. What is your favorite time of year?
  33. What motivates you?
  34. What has been the best year of your life so far?
  35. What would you change about your childhood?

Infographic: Deep Questions To Ask Your Boyfriend Over Text

Asking your boyfriend deep and personal questions allows you to understand them better. Additionally, it will improve the communication between both partners and deepen the relationship. Check out the infographic below for a list of deep questions you can ask your boyfriend over text. Scroll down!

deep questions to ask your boyfriend over text (infographic)

Illustration: StyleCraze Design Team

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Casual conversations can only take your relationship to a certain level. Knowing the right deep questions to ask your boyfriend can take your relationship to the next level. Asking him about his life goals, hobbies, and principles can help you understand what they enjoy and their views on life. While emotional intimacy is important, so is physical intimacy. That is why knowing his preferences can give you a deeper idea about his views on intimacy. Lastly, understanding his fears, motivations, and behaviors will help you build a deep and meaningful relationship with him. Come back to the list when you think, “ I wish I have a few questions to ask my boyfriend to know more about him”.

Frequently Asked Questions

How can deep questions be used to build trust and intimacy in a relationship?

Deep questions help you know your significant other well. When you both know each other well, you will be able to trust each other. Trust and vulnerability are two important pillars to build intimacy. Thus once you have trust and intimacy in check, the relationship strengthens.

How can you handle it if your partner does not want to answer certain questions or is uncomfortable with deep conversations?

Everyone requires time. Give them time and do not dominate or force them. If he is not encouraging the particular question or is not ready to have ‘the deep conversation’, take a step back and give him the required space and time.

How can deep questions help a couple work through conflicts and challenges in their relationship?

When we know about each other’s past, present, and future plans, no third person can be a barrier. You both will be in a safe space where we both will trust each other and thereby fight the odds together. Deep conversations strengthen relationships.

How can you avoid asking questions that might be triggering or hurtful to your partner?

Discuss before embarking on a relationship or journey or conversation, that way you both will know the limits. Those limits might not be very explicit thus understand your partner’s body language.

How can deep questions be used to promote growth and self-discovery in both partners?

When two people know each other and their strengths, they can work together to achieve bigger goals in life. They can encourage each other to achieve personal growth and discover the strengths and traits that help them in their life.

Key Takeaways

  • If you want to get to know your boyfriend a little more intimately, there are some deep questions you can ask him.
  • You can ask him questions about him, his younger days, his likes and dislikes, intimacy, relationships, and the true inner self that he keeps hidden from everyone.
  • With these questions, you can learn his thought process and characteristics better.

Discover the depths of your relationship with your partner from the video below that features 50 deep questions. Get to know each other better and strengthen your bond.

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