30 Really Deep Personal Questions to Ask a Guy

Except you have a mind-reading superpower, it is impossible to know what a guy is thinking about or what his intentions are towards you and this is why you need to ask him really deep personal questions. However, you need to ask the right type of questions at the right time in order to get your expected results. Whether you are trying to improve an existing relationship, trying to find out the intentions of a guy towards you, or getting to know him, there are questions that need to be asked at appropriate times.

Some deep personal questions are suitable for the very first few days of a prospective relationship, while some other questions are best reserved during an ongoing relationship. You may be confused about what type of deep personal questions to ask and the right time to ask them; not to worry, we have curated an extensive list of 30 really deep personal questions to ask a guy.

Questions To Ask A Guy To Know His Intentions

Figuring out the intentions of a guy may not be an easy task, especially when you are just getting to know him. However, it is also very important to find out the intentions of your love interest or a guy that is asking you out. Since making assumptions about the intentions of a prospective partner is not advisable and could lead to serious disappointments, here are some honest questions to ask a guy to know his intentions that will not have you sounding desperate or pushy.

These questions are best asked as soon as you notice he is making a move toward a prospective romantic relationship with you, which is usually after the first date.

1. What are the top five things on your plans for the next two years?

Asking about nearest future plans like the next two years makes it easier for you to figure out his intentions for you. That way, you will be able to get an idea of where the both of you will be in the next two years. Plus it is more realistic to hear what a guy plans to do in the next two years than what he intends to do in the next ten years. Chances are, he is already working on his goals for the next two years and so it will be easier for him to tell you the top five things he has planned for the next two years, and that way, you can figure out his plans or intentions for you.

2. What do you consider to be the appropriate duration for courtship before marriage?

This is a smart way to ask him how long he intends to be in a relationship before proceeding to seal it in matrimony. It also gives you a chance to know if you are on the same page with him on that, as well as plan yourself and decide if that is what you want. For example, if he believes the appropriate time for courtship is 5 years, then you can as well have it at the back of your mind that you both might have to be in a courtship for five years and you can now base your decisions on that. This question is a stylish way to figure out a guy’s intention without sounding desperate about it.

3.  What aspect of your future are you most concerned about?

Everyone has concerns about certain aspects of their future, however, a particular aspect that usually stands out. This is a deep personal question to ask a guy to find out his intentions. If he is most concerned about his future family, then you can deduce that he plans on being a family man. But if he is most concerned with things unrelated to family or his relationship, then you can decide not to have too many expectations when it comes to being in a relationship with him.

4.  What do you think about being friends with benefits?

Not only is this a deep personal question to ask a guy, but it is also a brave one and that is because, for guys who are scared of commitments, being friends with benefits is their ideal choice. However, they may not know how best to say it and may end up leading you on, and as such this question gives him a chance to tell you the truth about his choices while you also get a chance to find out what his intentions towards you are. You can ask him this question as soon as you sense that he is making moves towards a sexual relationship with you.

5.  If you had a blank check to fulfill your top three desires, what will they be?

Everyone has their desires even if they are not open to talking about them. A guy’s intentions are usually embedded in their desires, asking him this question gives you a chance to know his top three desires and find out if you are in any of them. If one of his desires is getting married in no distant time, then maybe that’s his intention towards you.

6. At what age do you plan to stop having kids?

This is a really deep personal question to ask a guy, because, it is usually easier to say when you want to start having kids, especially when you don’t have any kids yet. However, asking when a guy intends to stop having kids gives you an idea of how he is planning his future and family. This also gives you an idea of the timeline of your relationship with him and if it is going to work out.

7.  Where do you see our relationship in the next year?

This is a great way to rephrase the “what do you want from me” question. This is a very important question, because it prevents assumptions as well as stops you from being led on, if you both are not on the same page. This question gives him the chance to lay his cards on the table and you get to make a choice on what you want.

8.  What is the ideal age you think a woman should get married?

A lot of guys have strong opinions on the age they think a woman should get married. His answer to this question will let you figure out the age he thinks his future or prospective wife should be. For example, if he says the ideal age for a woman to get married is around 25-31, you should know that he intends to marry a woman who is within that age range. This also helps you figure out his intentions towards you.

9. Do you fancy being in an open relationship?

Open relationships are becoming increasingly popular, especially for people who do not believe in monogamy. This is an important question because it helps you know the type of guy you are dealing with. And as such, if he is strongly in support of an open relationship, you can guess that it could be a part of his intentions.

10. How would you describe your ideal future?

Most guys have an idea of what they want their ideal future to be like. This is a simple yet deep personal question to ask a guy, because you will see a clearer picture of the kind of guy he is when he paints a picture of his ideal future.

Questions To Ask To Get To Know A Guy

Getting to know a guy may be labyrinthine, especially if you are trying to be sure of your options before making a conclusive decision. Also, many times, it may be difficult to keep a healthy track of his personality, especially if you are just getting to know each other and as such, one of the best ways to know a guy apart from observing him, is to ask pertinent questions that can point you to the right direction of who he truly is.

11. What kind of person will you describe yourself to be?

Taking lessons from the words of Maya Angelou, “When people show you who they are, believe them the first time.” Asking a guy to describe the kind of person he is, helps you figure out the kind of person he is. A person is more often than not, who they say they are. This is one of the deep personal questions you should ask a guy, to enable you to figure out who he really is. Although, he is most likely to say all the good things he can think of, if you listen actively, and read between the lines, you will pick up some strong points.

12. What is the best thing about your childhood?

A person’s childhood and experiences growing up play a huge role in how they turn out as adults. Finding out what he considers the best parts of his childhood, will give you an insight into his experiences and how they must have shaped him.

13. If you could change three things about your past, what will they be?

The past reflects the future, and there are things people wish they can change about their past in order to be able to fix some things about their present and the future. The three things he mentions about his past will give you an idea of who he is, and the experiences that contributed to that. For example, an insecure guy must have had a past filled with trust issues.

14. What is the worst thing you have ever done out of anger?

Before you can say you know a person, you must have seen them in their angriest form. If he will be truthful about his response, this question will definitely show you the kind of person you are dealing with and if it is something you can put up with or handle because chances are, it may be his habit.

15. What superpower do you wish you have?

Most people wish they had superpowers that reflect what is most important to them. This question helps you figure out what he considers most important to him.

16. How do you think your friends would describe you?

His response to this question will tell you how he is or who he is to his friends. If two or three of his friends say the same thing about him, then, that is probably the kind of guy he is. This is a really deep personal question to ask a guy because it will make him sit back and think before giving you a response.

17. What is that one thing nobody knows about you?

Who a person is when nobody is watching is who they really are. He may or may not give you an entirely honest response, but this question will definitely give you an idea about the kind of person he really is.

30 Really Deep Personal Questions to Ask a Guy
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Relationship Questions To Ask A Guy

Whether it is a fresh relationship of a few days old or a long-term affair that has spanned years, there are certain questions that you need to ask your partner from time to time in order to figure out the trajectory of the relationship. Change is constant and to be able to stay abreast with important evolving aspects of your relationship, there are important relationship questions you need to ask a guy.

18. What aspect of our relationship excites you the most?

In order to improve your relationship, you need regular reviews about the relationship from your significant other. Finding out what he considers to be the most exciting aspects of your relationship with him, will help you know what he values or enjoys more and what to improve upon.

19. What aspect of our relationship upsets you the most?

Finding out what he considers to be the most exciting aspect of your relationship will not be complete without equally finding out the aspects he considers to be most upsetting. This is a very important deep personal question because his response may be something you have hitherto thought to be insignificant. This question is a step in the right direction of improving the health of your relationship.

20. Is there anything you wish can improve in our relationship?

After figuring out what excites him and what upsets him the most, the next important question to ask a guy you are in a relationship with is the aspects he wishes can automatically improve. His response will let you know what needs to be worked on and improved as soon as possible.

21. What are your regrets about our relationship?

Most couples have things they wish never happened in their relationship. This question is a very healthy personal question because it affords you the opportunity to know the things he regrets most about your relationship; which is something some guys try to shy away from admitting.

22. Is our sexual life satisfactory?

This is a very serious question. As long as your relationship involves sexual intimacy, this is one of the really deep personal questions to ask a guy that cannot be overlooked. This question gives room for improvement and growth.

23. What are the things you consider unforgivable in a relationship?

Relationships require a lot of love, understanding, and forgiveness, however, there are things that can be considered unforgivable by certain people that they may not talk about. You can also ask him if there are things he is still holding a grudge over and finding it hard to forgive. If you plan to have a working long-term relationship, this question should be asked at the very beginning of the relationship.

30 Really Deep Personal Questions to Ask a Guy
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Questions To Ask A Guy Before Dating

Before you accept to get into a romantic relationship, there are certain questions to ask a guy before dating him. Relations are dynamic and are usually not a walk in the park, and as such, before you take the important walk into commitment, here are some deep questions you need to ask.

24.  What are your top three deal breakers?

Everyone has a deal-breaker or what they consider deal-breakers in their relationship. Before dating a guy, you need to ask him his top deal-breaker in order to help you figure out the kind of person you are dealing with and also find out if it is something you can handle, before going into the relationship. Some deal breakers may be too extreme, so it is best for you to know, before getting into the relationship.

25. Do you have any boundaries that should not be crossed?

Discussing boundaries before dating a guy is very important. He may be too carried away to tell you about them and it may become a source of conflict later on. To avoid such situations, it’s best to find out his boundaries and figure out if it is something you can handle. For example, if he considers showing up at his work unannounced as a boundary you shouldn’t cross, you will remember to not pay him any unannounced visits at his workplace in the future.

26. What is your plan for the both of us?

Before accepting to date a guy, it is very necessary to ask him the plans he has for the both of you. This is an important question because it gives you an idea of what to expect and his plans for the relationship if you decide to date him.

27. What are your toxic traits?

Everyone has a toxic trait or a trait of theirs that they consider to be the toxic one. This is one of the really deep personal questions to ask a guy before dating him. You need to be able to know what he considers to be his toxic trait and if that is something you want to put up with.

28. How important do you think sex is in a relationship?

This question is top on the list of deep personal questions to ask a guy before dating him. For some guys, sexual intimacy is an integral part of a romantic relationship that cannot be compromised. If you plan on being celibate, and he tells you that sex is as important as the relationship, then you will have to make a decision to compromise or walk away from the relationship.

29. What are the things you consider cheating?

Apart from the popular notions of what cheating is in a relationship, certain people consider some other things to be cheating. Before you agree to date a guy, you need to find out the things he considers to be cheating. This is because you may think going on a harmless date with a childhood friend means nothing, meanwhile, your boyfriend considers that to be cheating. To avoid friction, conflicts, and trust issues, this question needs to be asked before you proceed with the relationship.

30. Do you believe in splitting bills?

Finances and how they are handled should be decided before you start dating a guy.  You need to know if he supports splitting of bills, plans to foot all the bills, or prefers individual independence.

Deep Personal Questions To Never Ask A Guy

Just like there are deep personal questions that you need to ask a guy, there are certain questions that should be avoided because they may give off the wrong signals or put you in a bad position. Here are some examples:

Am I the prettiest lady you have been with?

This question is more of a disadvantage to you than it is to him. It puts your self-esteem/confidence in question. This question is highly unnecessary.

Can you choose between me and your family?

No guy wants to be asked this type of question. It will create friction. Never ask this question.

Am I better than your ex?

There is absolutely no need for this question. It is as unhealthy as it is unnecessary.

Would you still be in love with me if…?

This is a cliché question. You may not even get an honest response and he may be blunt about his reply and your feelings will get hurt.

In conclusion, always remember that asking the right questions is very important. Do not be afraid to ask, for it is better to ask than make assumptions or jump to conclusions that may end up being detrimental to you and the relationship. Asking the right questions also proves that you know your worth and you are aware of what you want out of a relationship with a guy.

Princess is a writer and an enlightened being.


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