20 Deep Questions to Ask Your Boyfriend


It would be difficult to decipher what exactly is running through the mind of your boyfriend or anybody.  How is it possible to find out what is the inner layer of current running through his mind?  The best way to dig out something from the deep inner thought of a person is asking some intelligent questions.  For people who are in a deep relationship and confused to know about the hidden trait, it is better to ask these 20 deep questions.

deep questions to ask your boyfriend

  1. What is the most disturbing thing in your life that you regret always?

The question has an emotional attachment when you ask this question to your boyfriend he will feel secured to open his mind.  He may tell you those top guarded secret in his life and share those feeling with you.  If he opens his mind and tells you all about his life, it is a good indication to make you understand, why he regrets that incident.  You can relate those events with any of the current incidents and plan your relationship with your boyfriend.

  1. How do you define about yourself?

This is an open question allowing him to explain about himself.  So people have a good assessment about their positive and negative drawbacks. This will also give you a chance to understand whether he want to hide something deliberately from you.

  1. Have been into a relationship before?

You may feel it is an embarrassing question.  It is better to know about his past relationship or relationships.  If he had many relationships and you are also one among them, then it will give you a good understanding of the person.

  1. Do you believe in marriage?

There is no ill feeling asking a direct question straight to point if you are thinking of a wedding life with your boyfriend and he is not yet proposed to you.  As the common adage say, ladies always first.  So take the chance and force him to open his mind.

  1. What is the good thing about me that attract you the most?

This question let you focus on what is the best thing that attracted him to you.  It could be your eyes, hair, lips, your skin, your body posture, your talking style, your manners or anything.  This will let you more refine in those areas and make him very comfortable.

  1. Tell me what do you think about beauty?

Are you serious in asking this question?  You can certainly find out from him what he is thinking about beauty.  If he is the person with exceptional qualities, he will let you know the difference between the inner beauty and physical beauty.  Beauty is always in the beholders eyes.

  1. What do you do if you lose somebody in a terrible accident?

If you want to know your boyfriend, how deep is he emotionally attached to his close friends and relatives.  People with strong emotional attachments are trustworthy guys.   It is a good question.  Listen to him carefully.

  1. What is your future plan?

When having a relationship for a long time and yet you are unsure about the future plans, it is time for you to ask this question to your boyfriend.  This will, or it will force him to open his mind and discuss about his future plans.  Who knows, maybe the answer what you are looking for all these days, you can hear from his mouth.

  1. Do you like to be loved or respected?

If you are confused about the character of your boyfriend and you cannot identify whether he want to be respected or loved, you can certainly through this question.  People who are very much serious in character would say that want to get respected rather than loved.  It is good, let whatever be the answer.  You can take the cues to nourish the relationship.

  1. What is your favorite color?

Is there anything special in the color sense?  Yes, people who life soft colors will be soft in thoughts than people who opt for violent colors.

  1. What is your best food?

Food habits and food choices are always imperative in any relationship.  It is better to have common food habits to have a sustainable long-standing relationship.  If your boyfriend is a non-veg and you are a veggie, then it will always be a conflicting situation when you select the menu, whether at a restaurant or be at home.

  1. What is your professional ambition?

Organized people will have professional goals.  They have precise calculations about their life.  They will have better plans to achieve their career objectives.  It is better to maintain a relationship with somebody who is better organized in their life.

  1. Do you like gambling?

This is a simple question to know the gambling tendency of the person.  Gambling for fun is good, but gambling for life is very dangerous.

  1. Do you like to hang around?

In the early stages of your courtship, it will be a delightful experience to hang around with your boyfriend.  If he is shy in nature, you can take the initiative by asking this question. He will certainly like to hang around with you.

  1. If your house was on fire, what would be your first thoughts?

It is an easy question to know his priorities when engulfed in an emergency situation.  If he is only interested save his personal effects, he is indeed a selfish person.  Instead if he gives priority to save human life, pet animals then it shows the right side of his personality.

  1. If you win a lottery what you would do with the money?

An easy going person will find ways to spend all the money for luxury.  A serious person with good objectives in life will have calculated movements on how to spend the cash.  This is a hypothec question but good one to know him clearly.

  1. Do you love doing charity activities?

People with a kind heart will love to do charity services.  If you boyfriend is socially committed, he will love this question.

  1. Do you like traveling?

Most of the people like to travel around the world.  But there are different type of travel plans.  Some with adventure, some are only interested in visiting historically important places and yet others interested in visiting countries with beautiful beaches.   It is a good question indeed to know if his interest is matching with yours.

  1. What do you hate something about yourself?

It is a valuable question to evaluate his personality and confirm that he is also aware of his negative elements in his character.  He may regret with you his inability to manage the situation.  But it is better to know from your boyfriend so that you can vouch for the situation.

  1. In life if you get a second chance, what would be your preference?

Almost everybody at some stages of their life would have sincerely wished to have a second chance in their life, if they failed to take a right decision at a crucial moment that had just slipped away between cup and lips.  It can let you understand how well prepared to grab the next opportunity in life.

These 20 questions may seem to be silly, but each of these questions can help you to analyze the person.  His personal plus and negative traits can be easily extracted they way how is responding to these questions.  However, make sure to ask these questions very carefully without letting him know that you are asking something very deliberately to evaluate his personality.  You can take calculated intervals to put these questions over a period of time and consolidate your opinion about your boyfriend.  You may also put a conscious effort by putting you also in the same situation and ask these questions to yourself and get an unbiased answer.   You don’t have to leave everything to the fate.  Calculated movements can bring you long lasting healthy friendship.  So make a bold effort to find out the best boyfriend with whom you can have a successful long lasting life.