What Are The Deep Questions To Ask Your Boyfriend? This Is The List You Need!

What Are The Deep Questions To Ask Your Boyfriend? Let Him Reveal Himself To You. Love is the food for our soul. Without love, one cannot survive. So, if you have a boyfriend and wish to know him better, then there are a few things you should know. But then again, it is not possible for someone to know a person completely, even for a whole lifetime. However, you should still know some basic things about him which will help you take the relationship forward.

This is why we have a few questions in here which can help you know him better. These questions are funny, silly, and interesting yet deep enough to give you a glimpse of how he thinks about life and his overall outlook.

So, without any further ado, let’s get started.

Why Do You Need To Ask Deep Questions to Your Boyfriend?

Men are a bit different from women, and they don’t communicate the way women do. Everything about them is quite different from women. So, no matter how good-looking he is or how charming he might appear, there is still something he might keep to himself. So, if you wish to know him better, you must simply figure out a way to go deeper into his thinking.

what deep questions to ask your boyfriend list know
What deep questions to ask your boyfriend list know

This is where these questions will help you. With these questions, you can communicate with him better, and as you know, communication is the key to a healthy relationship.

Plus, they can perfectly work as a conversation starter, and you can use them to break the ice whenever things seem a bit monotonous. So, let’s look at them one by one.

Also Read: My Boyfriend Doesn’s Respect Me

Some Deep yet Interesting Questions to Ask Your Boyfriend

In the Beginning, it’s fine. But when you are ready to take it to the next step, then you need to be absolutely sure about him. This is where these questions will come to help you. They reveal the way he was in the past and how he deals with things at present. Also, you get to know him on a much personal level. So, here are some deep questions

  1. What are your plans for the future?
  2. Are you planning to have kids in future?
  3. Tell me about the longest relationship you had with someone and also why did it end?
  4. Have you ever been in a loving relationship?
  5. What is your take on religion, spirituality and God?
  6. What is your view on LGBTQ?
  7. Do you believe that money can buy you all kinds of happiness?
  8. Tell me about your dream job.
  9. Tell me about that one thing you wish to accomplish in your life the most.
  10. What is that one thing about which you are really proud?
  11. Are you afraid of anything in particular?
  12. Do you use your voting rights every year?
  13. What are the dynamics of your relationship with your family?
  14. Tell me about the best friend you have.
  15. Do you have a specific love language?
  16. Would you call yourself a total introvert or extrovert?
  17. Do you have the habit of holding grudges against somebody?
  18. Have you ever had any kind of addiction in your life?
  19. What is your take on emotionally or physically abusive relationships? Have you been in a relationship like this?
  20. What is your take on cheating in a relationship? Would you forgive your partner if she cheats?

Also Read: Guy Stops Talking to you

Some Deep yet Cute Questions to Ask Your Boyfriend

Who on earth likes to be serious all the time? After all, he is your boyfriend and not your boss. So, why don’t you be a bit cute and cheeky with him! Trust me, he would love that! Here are some cute questions which may reveal some fun things about him and his childhood, his favorite memories and also perhaps about things very dear to him. Yet they are deep enough to let you know about his outlook. Here are some questions for you.

  1. Have you ever had a role model while growing up?
  2. While growing up, have you ever had any ambition?
  3. Have you ever been to summer camp?
  4. Describe to me your perfect Sunday afternoon.
  5. What according to you can be the best holiday?
  6. Tell me about the best present you have ever received.
  7. Have you ever had any pets while growing up? If yes, what is that?
  8. What was your most favorite thing to do when you were in school with your friends?
  9. Tell me about the happiest childhood memory you have.
  10. Do you know how to cook? Will you cook me a dish someday?
  11. How do you manage or handle depression and stress? 
  12. Suppose you had a bad day; what do you do to feel better again?
  13. What is your favorite ride in some amusement park?
  14. Is there a toy you had always wanted as a kid?
  15. Do you love playing with stuffed animal toys?
  16. What is your favorite sound?
  17. Tell me about your favorite scent.
  18. Is there a candy in particular that you absolutely hate?
  19. Do you love Karaoke? What is your favorite song in that?
  20. What do you use to do during recess back in school?
  21. Do you love rainy days? If yes, then what is the most favorite thing you like to do?

Also Read: How to tackle relationship issues

Some Deep Yet Fun Questions to Ask Your Boyfriend

We know how most of the couples get confused as to which question to ask to get to know their partner better. But as I said, nothing can be better than having a good hearty laugh. So, if you are not sure as to which question you can ask, you can ask these funny questions and have a good time laughing with each other. They can reveal the fun side of him, and you can strengthen the connection. Let’s get started.

  1. Tell me the most bizarre excuse you have ever heard while breaking up with someone.
  2. What made you laugh the hardest in your life?
  3. Do you have any favorite songs that you can listen to over and over again?
  4. Have you met any celebrities in your life?
  5. Is there a particular word that you really hate?
  6. Do you have any pop culture guilty pleasure?
  7. Tell me about the most embarrassing thing that has ever happened to you.
  8. The weirdest gift you have ever received.
  9. The most bizarre thing you have ever bought.
  10. Do you believe in Astrology? Have you ever been to a palm reader?
  11. Between a personal trainer, a good housekeeper and a personal chef, whom would you choose to hire?
  12. What would you likely do if you became a woman for one day?
  13. Is there a particular movie that you have seen more than once?
  14. Suppose a biopic is happening based on your life; whom would you like to play your role?
  15. Which famous Hollywood actress would you want to play the female lead?
  16. Were you a good student back in high school?
  17. Is there any fictional character that you related to the most?
  18. Between being hot and cold, which one would you prefer?
  19. If you were allowed to be born at a different time, which time period would you choose?
  20. What, according to you, is the best part of being an adult?
  21. Have you ever played the game of Truth or Dare? 
  22. Do you have any unforgettable memory related to that game?

Also Read: Are you emotionally needy?

How About Some Deep Questions to Ask Your Boyfriend about You?

Well, you have been asking all kinds of questions to your boyfriend. But how about you ask something regarding you? How about you ask him some questions to understand what he thinks about you? But are you wondering what kind of questions you can ask? Well, here are a few questions you can surely ask. Now, it is time for you to get into your partner’s head. 

  1. Did you find me this much more interesting right from the start?
  2. Do you think that I have all the nice traits one must have to be a perfect girlfriend?
  3. Is there anything special that you wish you could change about me?
  4. Tell me some of my qualities that you absolutely admire.
  5. How was your “the first” impression of me?
  6. Do you think that I can be a very good parent?
  7. Were you feeling a bit nervous when we first kissed each other?
  8. Tell me the most important reason for which you love spending time with me.
  9. Do you often feel very nervous around me?
  10. What is the one thing that you find the best or nicest about me?
  11. Do you ever feel that I am the one for you?
  12. The single best thing about dating me?
  13. Is there any bad side to dating me?
  14. Tell me about the biggest lesson you have learned from our relationship.
  15. Tell me the moment you realized that you loved me.
  16. Have you felt like ending this relationship with me and going for someone else?
  17. The one lovely or bitter thing you can never forget about me?
  18. Do you have any memorable moments after meeting me for the first time?
  19. Have I shaped your life for good?
  20. Do I ever inspire you?
  21. Can you describe me in three words?
  22. Is there anything that you have learned from me?
  23. Do you have any favorite memory with me?
  24. How long can you stay angry with me if we have a fight?

Also Read: Are you emotionally needy?

Some A Bit Dirty Questions to Ask Your Boyfriend

Who doesn’t want some intimacy in the relationship? And if you wish to make the most of it, then why not spice things up a bit? Those same boring questions will not make your relationship too special. If you want to spice up your sex life or intimate life with him, then you should ask these questions. After all, our sexual preferences and desire reveal a lot about ourselves. 

  1. If you are allowed, and the conditions stay ideal, how many times would you like to be intimate in a week?
  2. Is there something mischievous you wish to try in bed?
  3. Do you have any such fantasy as committing a threesome?
  4. Have you ever found a man sexually attractive?
  5. At what age and where did you lose your virginity?
  6. What is your view on masturbation?
  7. Tell me about your biggest sexual fantasy and how you would like to do it.
  8. If you are to make love somewhere outside your bedroom, which place would you prefer?
  9. Have you ever got caught while being intimate with someone?
  10. Is there something crazy that you have done on bed or would like to do?
  11. What is your view on porn? Do you watch it often?
  12. Do you have any preferred sexual position? Does something in particular turn you on?
  13. What is the most sensitive erogenous zone in your body?
  14. What is your most favorite part of intercourse with your partner? Is foreplay very important to you?
  15. Are you into role plays while being intimate? If yes, what do you want me to be?
  16. Would you ever prefer to go to a dominatrix?
  17. What is your view on sex toys? Do you have any preference that you wish to try?
  18. Does dirty talk in bed turn you on?
  19. Is there anything really weird that turns you on?

Also Read: Relationship Goals

Good Deep Questions to Ask Your Boyfriend

Now, we are going to look at some basics. Maybe you have been in a relationship for a while, and now suddenly you don’t have anything new things to talk about. But this is where these questions can help you get over the problem. They will ensure that you will not have any dull moments with your boyfriend. These are some good questions, some questions that will offer you some insight about him and also keep the conversation going. 

  1. Tell me about your best place to live the rest of your life.
  2. Would you prefer a farm in the middle of nowhere or some elegant penthouse in the middle of a crowded city?
  3. Do you have any kind of retirement plans?
  4. What is your ideal vacation? Do you have any place in mind, like Andaman, Maui or some other exotic place?
  5. Tell me the name of your favorite city
  6. If God grants you one skill without you doing any kind of training, then what would that be?
  7. Do you think that a guy and girl can be just good friends?
  8. Would you like me to treat you when you are sick? 
  9. Would you prefer me to wait for you on hand and foot, or should I just leave you alone?
  10. Do you have any kind of phobias? 
  11. Is there any pet peeve you have?
  12. Have you ever opted for anything voluntarily in your life, like some good cause or something?
  13. Do you wish to start a charity? If yes, then what would be the cause?
  14. Do you watch, read, or listen to the news on a daily basis?
  15. Tell me the best advice you have ever received and who was the person who gave you that?
  16. Do you love talking on the phone?
  17. Do you have any specific relationship deal breakers?
  18. Is there any relationship cliché present in your mind? 
  19. If you are allowed to go back to school, what would you study?
  20. Tell me your most favorite time of year.
  21. What is that one thing that never fails to motivate you?
  22. Tell me about the best year of your life so far.

Also Read: How to flirt with guys

Some Deep Questions to Ask Your Boyfriend about His Past

Past is history; tomorrow is a mystery because the time you are in is most important, and that’s why it is called a present. Now, I know that most people think that their partner’s past is not relevant to their future with you. But still, his past can help you understand him better. Maybe there are things you need to know about his past behavior. So these questions will reveal all these information to you.

  1. Who is that one special thing or a moment you miss the most in your life?
  2. Tell me about the biggest success you had in your life
  3. Tell me when you were the happiest in your life.
  4. What are the qualities that you absolutely admire in your parents?
  5. Tell me the unhappy memory of your life
  6. Tell me about the single most embarrassing thing that happened with you.
  7. Have you ever lost someone very close to you?
  8. When you were younger, what was that one thing you had always wanted?
  9. Would you still be friends with your ex?
  10. What is your political belief, and what has shaped that?
  11. Tell me about the biggest regret you have in your life. 
  12. What is the greatest passion you have in your life?
  13. Tell me about the best birthday gift you’ve ever received.
  14. How many countries have you visited so far in your life?
  15. Did you ever want to get back with your ex?
  16. What are the lessons that you have learned the hard way?
  17. What is that one thing you wish you had never done?
  18. Tell me about the three events that had the biggest impact on who you are today.
  19. What is that one thing you did accomplish but you still cannot imagine?
  20. Tell me about the best memory of one of your exes.
  21. Tell me the scariest thing that ever happened when you were a kid.
  22. Is there any decision that can be considered the worst decision of your life?

Also Read: Dating with Married woman

Some More Funny Yet Deep Questions to Ask Your Boyfriend

Now again, some questions to light up the mood. This can also portray your sense of humor as well. So, ready to show your funny bones? Well, these questions can help you explore his funny bones as well. Check them out.

  1. Suppose you have a genie in front of you; what are the three wishes you would ask?
  2. If you become a woman somehow, would you still date me?
  3. If you are stranded in a desert, what would you look for first? Me or water?
  4. Tell me that one movie that influenced you the most.
  5. Between your dream car and your dream house, which one would you choose?
  6. What is that one feature you wish your phone had?
  7. What can you do to me if someone gives you a million dollars?
  8. Tell me the craziest thing you have done for love.
  9. Who do you resemble the most from your immediate family members?
  10. How would you compose the soundtrack to your life?
  11. Tell me your go-to phrase.
  12. Have you kept any of your favorite childhood toys?
  13. Tell me the worst thing you have purchased for a lot of money
  14. Tell me, what, according to you, is the biggest mistake made in history by human beings?

Questions that a Girl can Ask Her Boyfriend to Get Him in the Mood

These are some more kinky questions to get into the mood of love, and they can uplift his mood if he has had a bad day.

  1. What would you do with me if no one was watching?
  2. What is the most favorite body part of me?
  3. What do you think when you kiss me?
  4. Tell me about your guilty pleasure thing to do with me.

What Remains?

So, these are the deep questions you can ask when you are in a relationship. I hope next time you meet a guy, you can use these questions. If you have any such personal experience, then do feel free to share that with us in the comments section. Your experience can help our readers a lot.

Refer to our a few articles.

Long distance relationship

Healthy relationship

20 signs She is Losing Interest in you

How to get a man to commit

Reference Articles


Hello Friends! We are really happy to present to you the various articles to get a lot of concepts for various relationships

Recent Posts

You cannot copy content of this page