45 Hard Questions To Ask Your Boyfriend When Getting Serious In A Relationship

Before your relationship can evolve to become something serious, there are a few questions you need to ask your boyfriend to have a good understanding of where things lie. Even if he is always showering you with gifts and giving you the best fun of life, there is more to it all. You have to ensure that you have a deep knowledge of what his plans are towards the relationship as well as what his real personality is. Being romantic and getting all loved up is cute but having a relationship that has a deep understanding will help it to last.

The questions listed below are examples of the type of questions you need to ask your boyfriend. They help check compatibility, level of maturity, understanding, and many other things. This shouldn’t be done in an interrogative way, rather during your fun time to avoid being boring or scaring him away.

What Are Some Deep Questions To Ask Your Boyfriend?

You have to know your boyfriend to a reasonable extent before taking further steps with him. Most times, when you don’t know deep things about your boyfriend, the relationship ends in tears. Having deep knowledge about your boyfriend helps with compatibility which goes a long way in ensuring that you make the right choice. The following deep questions to ask your boyfriend will go a long way in making the relationship sweet.

1. Do You Have Regrets That Stick With You?

Regret comes as an action or decision which resulted in a very bad result. This question gets to bring back your boyfriend’s past and give an edge into knowing the very worst thing he regrets most. For him to open up and tell you his regrets means that he sees the future in you and can trust you with his secrets. It is difficult to get this kind of conversation out of a guy because they tend to keep it to themselves.

2. What Are Your Future Plans?

The very worst thing that will happen to a young girl is dating a guy without dreams and aspirations. This is one of the deep questions to ask your boyfriend to know if he has ambitions and a future that he is pursuing. It enables you to know the dreams he possesses and the time frame he plans to get them achieved. This will help you evaluate his dreams and his plans in getting it to actualization with what he is currently doing for a living.

3. Who Was Your First Girlfriend and Why Did You Break Up?

If you are not his first sweetheart, this question fits in perfectly and answers to this question serve as a guide in staying away from things that will get the relationship into thorny paths. It also gives you an insight into how he relates to his lovers as well as what to expect if changes are not made.

4. What Can’t You Begin Your Day Without?

Moving into the early morning private life of a guy is always necessary for any girl because that is exactly what you will eventually find yourself doing in the long run. It also determines how a guy gets to jump into his day. Getting an answer to this question from your boyfriend will prevent unnecessary surprises that might come up in no distant time if the relationship is to progress.

5. How Do You React To Failures?

Failure is part of a man’s development, but the important part of the development process is how he keeps pushing after failing. The question has a way of exposing more of his personality, whether he is target-driven or reluctant when it comes to achieving his goals.

6. What Are The Basic Qualities You Expect From A Girl?

A guy will always have qualities he is looking out for from a girl he intends to go into a serious relationship with. The main aim of asking the question is to evaluate yourself and know if you possess those expected qualities. It also helps you to evaluate the extent of his expectations, to know if he is a perfectionist or has an accommodating heart.

7. How Often Do You Experience Mood Swings?

Mood swings are unexpected changes in the mood of a person. It affects your relationship negatively and might eventually send everyone in a different direction. This is one of the questions to ask your boyfriend to help you draw out how often he experiences mood swings and equally help you decide between staying or walking away.

8. How Will You React If Someone Should Insult Your Wife Unnecessarily In The Public?

Most times you have to know how your boyfriend holds the special people in his life. This question is targeted at knowing how he will value his wife and how crazy he can be wearing his furious garments. It is expected that a man should protect his girl against any external attack whatsoever. His reaction can depict being a coward or even not being matured enough.

9. What Is Your Take About Gay Rights?

Always be very inquisitive before venturing into a relationship with a guy. His opinion on matters that relates to gay rights should tell you if your future with him may be shared with a gay or not. Some guys get into ladies just to have children and then throw them off to then cling to their gay partners. Always be a step ahead of what will come into your relationship.

10. Have You Lived With Your Ex and What Was It Like?

Be well informed that your boyfriend has a life before you came around. Knowing about his stay with his previous girlfriend can give you a clue of whether to moving with him or to stay separate from each other for a while. Some guys lose the love and affection that have for a girl if she should quickly accept moving in with him, while some see it as a means of stirring up the love.

11. Can I Meet Your Best Friend?

Being smart with questions most times saves us the negative reaction that might come up. Knowing your boyfriend’s best friend helps you know the kind of company he keeps and how his social life is. There is a strong likelihood that he will be highly influenced by his friend. It is then your duty to find out if he is having a negative influence on him and the best possible way of correcting the problem.

12. What Do We Do To Make The Best Out Of Our Relationship?

This question comes in handy in knowing the feelings of your partner in the relationship; if they are tired, unhappy, or feel choked in the relationship. This question shouldn’t stop at your boyfriend, you should also air your opinion concerning before moving on. This question should come in randomly to ensure a sweet relationship.

13. How Do You See Religion?

Before venturing into any relationship with a guy try and know what his religious background stands for and the religion he really chooses to be with. This is one of the questions you ask your boyfriend to know if his religious beliefs contradict yours. If so get to understand if he takes his religion in the direction that may be of threat to you. By knowing all these you get to know if the relationship will work or not.

14. What Unnatural Thing Turns You On?

Talking deep cannot just flow without getting to know the triggering point of your boyfriend. Everyone has a very funny area that resurrects weak bones and your boyfriend is not an exception. This is very important to know because it is to your advantage sooner or later. No external body will teach you this except you and your partner. The question brings you and your boyfriend to romance and sex which is very important in a relationship.

15. How Do You Imagine Your Old Age To Look like?

Every man has a good imagination for his retirement and this answer explores his ability to embark on long-term plans. You don’t just date, marry and grow old, without knowing how your downward slope of life will look like. This is mostly the period he relaxes more with his wife, moving from one tourist center to another. As a young girl, try and know if you fit into your guy’s retirement plans if he even has plans that involve you, and how you can relate it to your plans towards your old age. If his plans are not so suitable, you can propose a suggestion that might be of help.

16. Can You Cope With A Career Woman?

This is also a question targeted towards knowing your stand as a career woman in your new relationship. His reply tells you if the relationship will negatively affect your personal ambitions in life or not. Some guys still hold onto the old-fashioned way that puts the job of providing for the family as the business of the man alone.

17. How Do You Handle Stress?

As far as life is concerned, stress is inevitable especially for couples who are at the foundation of their lives. When responsibilities are not clearly defined, it can result in excessive stress to one partner. Putting this to rest when things are getting so serious gives you a clear picture of how calculative your boyfriend can be in handling stress, how much stress he can handle, and when to come in.

18. Have You Attempted Hurting Yourself Or Others Before?

The answer to this question comes in handy in helping solve some psychological problems.  Most times asking your boyfriend this type of question is to know if has attempted suicide or murder – it helps you know if to stay and fight with him to correct what led him to that or use the door. So if you get a negative answer, you must take the necessary action to save your relationship.

19. How Often Do You Think About Your Ex?

This is a question that should be taken seriously especially when he talks about her or sees her often. If the two parties in this relationship should be serious with each other, they should be true to each other and let their past relationships not affect the present relationship. The more you think about the good days of your past relationship the likelihood of finding yourself back into it or even cheating.

20. What Are Your Fears About Marriage?

When a relationship gets serious, it is likely to end up in marriage. This question helps in pointing out his readiness, if he is excited about it, if he is skeptical about it or if he is going to run out of love. You have to help in sorting out his fears to avoid being disappointed in the long run.

21. What Impression Did You Have About Me When You First Saw Me?

This question reflects what drew him close to you the first time he met you. In talking about this, you get what attracted them to you and try your best to maintain it. Most times when you lose that attraction, you lose the man totally.

22. What Is Your Take In Our Relationship?

This can be regarded as the climax of deep questions to ask your boyfriend in a relationship. The question helps you to know your stand in the relationship, if he thinks it’s not working out perfectly as he expected, or if he wishes to fire on with it. This is the opportunity you have to get your answer. Also, don’t find it difficult to call it quits when his replies go against your plans for a relationship.

Good Questions To Ask Your Boyfriend

Most times, people don’t have to be totally compatible before being in a sweet relationship. What fuels an issue in a relationship is when both parties lack common things that they share, as well as other numerous things that can cause issues. The test for compatibility by asking good questions to your boyfriend and making findings through them helps in curbing the lengthy time that you put into loving a person who does not suit your personality.

23. How Many Times Did You Imagine Kissing Me Before Our First Kiss?

Every relationship had an imagery time when one party nurtured the other in their heart before becoming a couple. At the first stage when he was still crushing on her, he keeps on building imaginations on the relationship, and trust me he kissed you several times in an imaginary world before the very first real kiss. The only time he gets to let you know the extent he crushed on you is when he finally achieved his desires and is still in love with what he got.

24. Who Are Your Worst Friends?

Everybody has this friend that is not behaving as expected and yet you cannot just send them out of your life. This is one of the good questions to ask your boyfriend and serves as a test to know if he is the type that hoards up things against people in his mind. It is also a typical mind linking test especially when you hoard up the same hatred for people.

25. If You Are Buoyant Enough, Where Would You Love To Live?

This is a question that is aimed at knowing if you share the same choice of environment with your boyfriend. He may love an environment with many trees, cool as well as quiet, but you prefer an environment with lots of people, lots of buildings, and recreational centers. This is a problem that needs immediate attention and has to be sorted before things get deeper.

26. What Is Your Definition Of Infidelity and How Do You Tackle It

The term infidelity which is mostly seen as betrayal has been the reason for many crashed marriages. Most times, it happens so quickly before you realize it which makes most people that have cheated confused because it was not their initial plan. Infidelity is defined in so many ways by different people, some define it as having sex with someone else while some define it as having a deep conversation or flirting with someone else. The answer to this question will help you in knowing the boundaries that your boyfriend has set for his partner in relating to the opposite gender.

27. Have You Ever Been Heartbroken?

This is one of the good questions to ask your boyfriend that makes him see you as someone who cares about his past life. He will loosen up and let out things that would help you in making decisions concerning taking the relationship to the next level. Most times, some guys find it difficult getting over their exes and no one would wish to go into that kind of relationship.

28. What Do People Tend To Overrate Or Underrate About You?

Whether you are overrated or underrated, it all depends on your coordination and the level of respect you command in relating to people. Within you, you know that you are not up to a certain standard people rate you, but due to your contributions and your intellectual capabilities, they tend to overrate your abilities. Knowing those aspects about your boyfriend gives a clear definition of his intellectual capabilities and contributions to people.

29. What Unique Qualities Do You Possess Most People Don’t Have?

Unique qualities are those special skills that are not so common in everyone. Some possess adorable voices, while others can display enviable skills in football. This is your boyfriend’s special selling point that may even have attracted you to him. You must keep admiring them and keep them special. You have to avoid comparing him to other people whose skills are better than him, rather encourage him.

30. What are the Unique Steps Your Parents Trained You With?

Every parent has a very special way of getting their children to adulthood which defers from other families. To avoid questioning his home training directly which may sound so rude, you can go with this. The behavior of a man will let you know the basic principles that were instilled in him growing up as a child by his parents. If your boyfriend can tell you these unique steps employed, then you are on a smooth sail to a good deep relationship that will last.

31. What Are The Obvious Signs Of Fear In A Person?

There is an existence of fear in everybody but what makes the difference is control over fear. When you get to have control over what scares you a lot, you are gradually eliminating fear. This question gives you signs you need to watch out for any time you think he is afraid of venturing into something big with you. You must find a way of working things out with him to subdue the fear.

32. Do You Like Pets?

One thing about pets is the lovely attitudes they display. Do not forget the fact that not everyone likes having pets around them especially if you are a lover of pets. If you intend to move in with your boyfriend, you should know if he is the type that likes pets around him or not.

33. What Is Your Most Preferred Dressing Style?

Your outlook goes to an extent in describing your real personality and can even attract respect and value. It is necessary to know his preferred style of dressing to know more about his personality. You don’t need explanations when you see a gangster, neither do you need to be taught that bankers go on corporate dressings. Also, know his dressing style that is restricted by the nature of his work.

34. What Chore Do You Like Most?

Guys normally don’t like doing home cleaning; they prefer doing the harder part like clearing the garage, disposing of old house appliances, repairing the sink, and some minor electrical aspects. But still, there are some guys that love doing house chores and a girl with this kind of boyfriend is lucky and has lesser troubles in home cleaning.

35. What Offends You Most In A Girl?

Getting to know what offends or turns your boyfriend off in a girl, is like having the answer to one of the most difficult questions of life. If he can open up to you on what he hates most in a woman, it means he wants you to be the best for him. You should strive to avoid that particular thing and embrace what will keep the joy flowing in the relationship.

36. What Did You Do Unknowingly That Finally Gave Positive Result?

The Life of every man is like an adventure, most of his decisions are not just planned or even reasoned. But it gets funny that sometimes the unplanned decisions pay more than the critically planned ones. That doesn’t mean that he should be taking uncalculated risks, but it always occurs in the life of any man that takes risks.

37. Which Music Always Comes To Your Mind When The Thought Of Me Comes?

This is almost an abnormal thing that is normal in the mind of many. Whenever they remember that special person, a particular song automatically gets inside their head as they swim in deep thoughts. To spice up your conversation with your boyfriend get to know if he has this same abnormal normalcy. Find out the song and then get to know what the song also means to him.

38. Why Do You Always Kiss My Forehead?

The forehead is always a good place to kiss a girl whenever you want to kiss randomly or you are in a hurry. Making it your regular kiss spot brings in suspicious questions. Certain reasons can make a guy get used to kissing a lady’s forehead as height differences can result in constant kissing of the forehead, bad breath can get a guy busy with your forehead. Find out his reasons and work strictly on getting things right.

39. What Do I Smell Like?

The truth is that everyone has a smell that he or she is known with; some are nice while others are awful. From the very first day you meet your love, their scent gets registered somewhere within their mind. Even if you are blindfolded, they can detect their lovers with a particular scent that they are known for. The answer helps you in working towards your body scent if it is bad or improving if it is great.

40. If I Am Angry How Can You Make Me Smile?

Relationship comes with a lot of issues – happy and sad moments. It is left for the two involved to know how to get this bad moment covered. This is one of the good questions to ask your boyfriend to know how he will cheer you up in your sad moments, this will definitely take a long discussion because it cannot in any way have one method of doing this.

41. Do I Still Look Beautiful?

No matter how constantly your boyfriend sings your praise as the most beautiful woman he has ever seen, as the relationship is getting deeper, you will want to know if he still holds your beauty in that way. The question helps you to know if you are to work more on yourself to reach his desired taste.

42. What Will Be Your Reaction If Your Friends Should Suggest You Quit The Relationship?

Asking your man this particular question means that you believe he is influenced by his friends. If he is really in love with you, nobody can talk him into quitting his relationship. As a matter of fact, none of his friends should even interfere in his relationship. If you find yourself breaking up because a friend suggested to your boyfriend, allow him to go because he never had any love existing in the first place. You have to sort out the limits of the opinion of his friends in your relationship before things get deep.

43. Which Movie Made You Cry?

This is a casual question that is aimed at knowing how your man handles his emotions. A man should be emotionally balanced else things will go the wrong way. He shouldn’t be shedding tears no matter the emotional effects that the movie projects. Working on this helps him fall to his track as a man.

44. How Do You Feel When I Express My Love For You?

A guy deserves to be also admired in a relationship. Sometimes, tell your boyfriend how much you are still in love with him. This triggers excess expression of love and awakens his love. This question will make him go dumb for some seconds before unleashing his feelings on such an expression.

45. Who Understands You Better?

Before asking this question, you already know what his reply is. The answer to this question is mostly used to bring out smiles in a conversation. But if he is not so comfortable with you, you may get a shocking reply that can even crash the relationship.

When Is The Right Time To Ask Your Boyfriend Intimate Questions?

Relationships work perfectly with good communication from both parties. Good and deep questions are to be asked before things get deeper mostly at the right time. As soon as it involves intimate things that will involve his past or having knowledge of a certain aspect of his private life, you must wait for a perfect time to ask such questions. If you just met for the first time, give him some time before you start throwing deep and intimate questions. If the both of you have been together for a long time, you can ask these questions to your boyfriend when he is happy, relaxed, and ready to have a conversation with you.

You start with questions concerning his personal life, before proceeding to deep questions and then to intimate questions. Share an experience which he never knew about, which will encourage him to freely share his own experiences. With time, he will freely answer most of the questions you ask, giving you answers that you did not know about.


The reason for asking the aforementioned questions to your boyfriend is not to judge but rather to make decisions regarding your future with him as well getting things right. Taking words out of his mouth will result in half-answers which will not be enough to make choices.

Being a mental test, questions should be asked smartly to avoid being fed with lies or nothing at all. Going deep with him has a lot attached to it which should be sorted out to avoid issues that might arise in the future due to negligence.


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