150 Deep Questions To Ask Your Boyfriend

Written by Harini Natarajan

Let us begin by asking a simple question: How well do you know your partner at a truly intimate level? Irrespective of the time you have been with each other, how well are you aware of his dreams, passions, likes, dislikes, traumas, tragedies, and regrets?

Connecting with your boyfriend at a deeper level strengthens the bond and helps you both discover all aspects of each other. And communication is the best way to do that. So, get beyond the casual ‘what’s up?’ or ‘how was your day?’ and strike a meaningful conversation with these deep and intimate questions. Keep scrolling.

150 Deep Questions To Ask Your Boyfriend To Strengthen Your Relationship

Questions To Get To Know More About Him

Questions To Get To Know More About Him

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  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?

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 Know More About His Younger Days

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  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?

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 the questions.

Questions To Know More About His Likes And Dislikes

Questions To Know More About His Likes And Dislikes

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  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.

Questions To Get Him Talking About Intimacy

Questions To Get Him Talking About Intimacy

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  1. In an ideal world, how many times would you have sex in a week?
  2. What is something you’ve always wanted to try in bed?
  3. Have you ever tried a threesome?
  4. Have you ever been attracted to a man?
  5. How did you lose your virginity?
  6. When was the first time you ever masturbated?
  7. What is your number one sexual fantasy? Would you ever do it in real life?
  8. Where is your favorite place to have sex outside of the bedroom?
  9. Have you ever been walked in on during sex? Have you ever walked in on someone else?
  10. What is the craziest thing you’ve ever been asked to do in bed? Did you do it?
  11. Do you watch porn, or would you like to watch one?  If yes, what would be your preference?
  12. What is your favorite sexual position? What is your least favorite sexual position?
  13. What are your most sensitive erogenous zones?
  14. What is your favorite part about sex? (Foreplay, teasing, penetration, oral sex, pillow talk, etc.)
  15. If we were going to role play, who would you want me to dress up as?
  16. Would you ever go to a dominatrix or like to try BDSM activities?
  17. What sex toy have you been dying to try?
  18. What words or phrases turn you on?
  19. What is the weirdest thing that turns you on?

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 that out is by asking these questions.

Questions To Understand How He Feels About Relationships

Questions To Understand How He Feels About Relationships

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  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. Do we have enough sex?
  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 Find Out What He Is Like On The Inside

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  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?

All the questions listed in the article will help you learn more about your boyfriend and reveal much about your compatibility. These questions will allow you to understand your boyfriend in a better way, learn his thought process and behavior, and establish a deeper connection.

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As Chief Editor, Harini sets the tone and editorial direction for StyleCraze to deliver engaging, interesting, and authentic content revolving around women's health, wellness, and beauty. She has over 14 years of experience in content writing and editing for online media. She specializes in the areas of Beauty, Lifestyle, and Health & Wellness and is proficient in Medical Sciences (Biology, Human Anatomy and Physiology, and Biochemistry). Her background in Biomedical Engineering helps her decode and interpret the finer nuances of scientific research for her team. Harini is a certified bibliophile and a closet poet. She also loves dancing and traveling to offbeat destinations.