84 Deep Questions To Ask A Guy You Like To Get To Know Him or His Intentions

When love grows sour, hate gets tasty and comes with a lot of drama and heartache that are avoidable. Unless you have a thing for being in toxic situations, there are deep questions to ask a guy before you go about proclaiming them as your soulmate. It hardly matters if he is crazy about you as much as you sing his songs, it is necessary to ask these questions to get important pieces of information about his intentions, values, and who he is.

Is he interested in being in a committed relationship, does he want you to be the only woman in his life or just looking for a casual relationship; what are his thoughts about marriage, would he want to have kids, what does he expect from a partner, is he someone that would want an open relationship, what is important to him, and so on. You have to have answers to these questions before you further invest your heart, else you might find yourself in a mess that would define your life for the rest of your days.

What Are The Kind of Questions To Ask a Guy?

There are many deep questions to ask a guy and their essence are glaring: apart from the fact that you get to know if you are compatible with him or just driven by emotions, you learn about his plans for the future and decide if you want to be a part of it. You might not get any sincere answer if you ask these questions from the perspective of someone who wants to know the intentions of his/her boyfriend.

While it is alright to be upfront with some questions to establish and acknowledge the feelings you have for each other, you should subtly find answers to most of the following questions while spending time with him. If he’s a player and realizes you are asking these questions to know his intentions, he will surely tell you the things you want to hear.

21 Personal Questions to Ask a Guy

The benefits of asking your guy personal questions are not limited to the fact that it can spark meaningful conversation. Such questions are known to make people share insightful details about their lives that they probably would never have mentioned. When your boyfriend shares such information with you, he would likely feel closer and more comfortable around you. This would in turn facilitate a deeper level of intimacy. While you can’t force intimacy, the following personal and deep questions to ask a guy will bring you close to that.

1. Are you introverted or extroverted?

One of the most important questions to ask, this goes a long way in helping you understand who he is and what to expect from him; as much as it determines compatibility.

2. What are the things most people don’t realize about you?

Most times, there is more to people, more than who we think they are. With this question, you might get to find out some details about him that leave you better informed about him and how he sees things.

3. When was the last time you called yourself a fool?

It is natural for people to reprimand themselves from time to time. If he admits to this, it tells a lot about him: that he doesn’t mind being vulnerable with you, and that he is not ignorant of his flaws.

4. What do you think are your hidden talents?

This is an important personal question to ask anyone you are interested in knowing better. Among other things, it presents the avenue to access people’s opinions of themselves.

5. What memory from your childhood do you cherish most?

Our childhood experiences shape our character and attitude to life in no small manner. By asking this question, you get to connect with these experiences and explore the foundations upon which some of his nature was developed.

6. What are the things you wish you knew when you are younger?

Like the previous question, this takes you back to the development stage of his life. More than that, it provides useful insights into what he knows about himself and how/if he has been striving to become a better version of himself.

7.  If you could live anywhere you want, where would you make your home?

This might seem to be trivia but it is one of the deep questions to ask a guy you want to know better. His answer should provide some useful information regarding what he wants for his future and if he has been thinking about it.

8. Do you believe there is a God?

No one should be told how this is an important question to ask a potential partner. People have different beliefs and value systems, you have to know if you can cope with whatever he believes in or if they are a dealbreaker for you.

9. What do you think of the most?

The things we think of the most are the things that are important to us, and what is important to us is what we want to live for. What does he want to live for?

10. What would you never forgive?

People are wired differently, so what he might consider as unpardonable might be something you do not consider a big deal. You need to know what lines one shouldn’t cross with and if it is something you are okay with.

11. What is the one thing you wish you can change?

Someone who is dissatisfied with his life, or someone who is forward-looking should have a thing or two he would want to change and it says a lot about who he is.

12. If you have to use only one word, what word describes you most?

This is one of the most effective ways to get someone you want to know better to tell you what’s at the core of their personality. But it only counts if the person answers truthfully.

13. What is the most meaningful gift you have ever received?

The essence of this question isn’t to rate the value of the gifts he has received but to gain insight into his value system: the things that are meaningful to him and why they are meaningful to him.

14. If you don’t have to work, what would you be doing?

What we do says a lot about who we are, especially when one considers why we are involved in that particular endeavor. There is so much to know from finding out if he would rather be doing something else other than what he does for a living.

15. What do you think is the weirdest thing about you?

We are all weird in some ways and it’s probably okay to have some odd attributes. If he offers a sincere answer to this question, you might just learn something very rewarding about who he is.

16. Are you doing what you wanted to do as a child?

Most of us have been pushed to a career path we didn’t aspire but nothing is wrong with that as long as you are happy with what you are doing. Nonetheless, it takes someone with a tenacious character to hold on to a childhood dream.

17. What is the happiest moment of your life so far?

This is a deep, personal question to ask anyone; it helps you connect to the happiest moment of the person’s life through which you can learn many other things about their life.

18. What is the biggest disappointment you have faced?

We often carry around our biggest disappointment and it has a way of manifesting in our relationships with people: how much we are willing to trust people and how much we can commit in a relationship.

19. If you win a lottery, what’s the first thing you’d buy?

The only way this is a personal question to ask is the fact that it provides the chance to evaluate his relationship with money. How you spend your money says a lot about who you are.

20. What is the worst thing you have ever said to a person?

This is one of the questions that seem innocent but can expose a lot about an individual. Almost everyone has said nasty things to people, it takes a strong character to acknowledge this.

21. What do people think you like doing that you hate?

Amongst other deep questions to ask a guy, this allows him to relate secrets about who he is that most people might never get to know. It can strengthen the bond between you and him.

21 Questions to Ask a Guy Over Text

Asking a guy random personal questions through text messages can deepen the bond between you and him. Such questions can make him see you as an interesting person and you can learn a lot about him through them. Below are some examples.

22. Who would you describe as a lucky person?

The purpose of this question revolves around getting a better picture of his perspectives about life. From his response, you can ask follow-up questions that would help you get to know him better.

23. What is the funniest meme you have on your phone?

This may not seem to be one of the deep questions to ask a guy but it grants one access to access his emotional intelligence, how sensitive he is, and things of that sort.

24. What is the silliest thing you have admired?

As much as it might not be obvious, almost everyone has a silly nature that can unveil some interesting facts about who we are, the things we like, and how real we are.

25. Do you ever feel insecure?

Psychologists would agree it is pretty normal to feel insecure at some point, but not everyone would agree to this. So if he does, don’t take whatever you learn from that for granted.

26. What food do you never get tired of eating?

A good question to ask a guy over a text, this indicates your interest in knowing more about him and would go a long way in making him comfortable around you.

27. What is your fondest memory of high school?

Many wouldn’t consider this a serious question to ask anyone until it leads to a series of revelations about the person and the experiences that have shaped their identity.

28. Who is your childhood best friend?

If the friends we keep can tell a lot about who we are; our childhood friends, and how we were with them, mirror our character development, especially when it comes to how we relate with people.

29. What is the strangest thing that happened to you this week?

It is important to stay connected with someone you are interested in dating and questions like this enable that; it reinforces your interest in the person and creates room for intimacy.

30. Do you have a favorite sibling?

For reasons that are not farfetched, our siblings are some of our most favorite people. The way we are with them can offer useful insights into who we are.

31. Do you have a favorite parent?

Oftentimes, it has been said that children who received unconditional love and support from their parents are emotionally stable as adults. So his relationship with his parents isn’t something you should overlook.

32. What are the things that make you nervous?

If he answers this truthfully, he is bound to feel closer to you and see you as someone he can trust. There is no doubt that this is one of the deep questions to ask a guy you like.

33. Do you have a celebrity crush?

A fun question to ask anyone, this can expose useful details about the things that capture his fancy.

34. What makes you laugh?

While some people can tolerate anything in the name of laughter, dark humor is frowned upon by many who regard it as insensitive. So this question can offer clues about his temperament.

35. Do you have a role model?

You don’t need to be told that someone who considers Adolf Hitler a role model is messed up in the head, so this is a meaningful question to ask a guy you like.

36. What are the things on your bucket list?

This has always been a good question to ask anyone you want to know better. When people share the things they want to do before they die with you, they begin to see you as someone special.

37. What kind of songs do you listen to?

People’s taste in music reflects their personality in no small manner. If you can connect to him from his brand of music, don’t be surprised to discover you can do the same in other areas.

38. What kind of movies do you like?

Some researchers have used movie preferences to determine personality types. So there is more to this question other than the fact that it is fun and interesting to ask.

39. What is your favorite quote?

As it is with music and movie, one can make an inference about a person’s core attributes from their favorite quotes. It is definitely a question that would help you get closer to anyone.

40. What do you do when you are angry?

For someone you are considering to have as a romantic partner, you don’t need to be told why you should ask this question.

41. What fictional character would you want to be in real life?

More than being a fascinating question to ask anyone, this question can trigger a meaningful conversation through which you get to gather useful information about the guy.

42. Who was your first crush?

There are reasons why we crush on people, and these reasons, no matter how trivial they seem, are products of our innate identity.

21 Questions to Ask to Get to Know a Guy

Some of the deep questions to ask a guy should focus on getting to know him better. No matter how much of a decent person a potential partner seems to be, one shouldn’t forsake devoting time to learn more about them as it is the prime way to evaluate compatibility. These are some examples of the questions to ask.

43. What is the pettiest thing you have done to get back at someone?

While this is one of the deep questions to ask a guy you want to know better, people ignore it based on the assumption that guys are not petty, this is not true.

44. What dead person would you talk to if you could?

Sometimes, the key to getting closer to someone lies in their pains. With this question, you might find that you have attained a level of bond you are not ready to deal with.

45. What experience is most valuable to you?

Life is all about experiences, anyone that stands out for whatever reason often influences us in ways that are unique and define our personality in no small manner.

46. What is the worst lie you have told?

An engaging question to ask anyone, this might lead to an interesting tale that would expose peculiar facts about him; who he was and how much he has changed.

47. Would you rather be successful or happy?

What this question intends to find out are what happiness means to him and how he defines success. If he is career-driven, he might only be happy when he is successful in his career.

48. How would you want to die?

It is a weird question to ask and some people are not comfortable discussing death, so you be certain the time is right for this question. It should be asked when you have already established some measure of connection with him.

49. What do you think people think of you?

No matter how much we assert that we don’t care about people’s opinions, it is something that says a lot about who we are and how we relate to those around us.

50. What do you admire most in people?

The purpose of this question is not farfetched, when you know what he admires in people, you know what attracts him to people, the things he wants to be associated with, and whatnot.

51. When was the last time you were involved in a physical altercation?

You need to know not only when but why he was involved in it; did he start the altercation or was he attacked and defending himself? In a nutshell, you have to know if he is prone to violence.

52. What about you irritates most of the people around you?

Someone aware of his flaws is closer to dealing with them than someone who doesn’t know that there is something about him people can’t stand. Don’t be upfront with this question if you want to get a sincere answer.

53. Would you rather be loved or respected?

It is probably good to be loved as much as it is good to be respected. But someone who prefers the latter to the former might prioritize building a successful career over building a family. So this is one of the deep questions to ask a guy you like.

54. How do you deal with people who disagree with you?

People must not agree with everything you say, no matter how sure you are about some issue, someone would find reasons to not agree with you. This is okay, what’s not is the inability to stand it.

55. Have you ever struggled with your mental health?

This is an important question to ask as someone with mental health issues might be difficult to deal with; knowing what they are struggling with makes it easier to do so.

56. What do you like most about who you are?

A deep question to ask a guy and indeed anyone you want to know better, this question would help you assess the person’s self-worth. If he doesn’t think much of himself, it might constitute some serious troubles like insecurity in a relationship.

57. What have you accomplished that you are most proud of?

This is also similar to the preceding question. Through it, you can determine the measure of self-respect he accords himself and how satisfied he is with his life.

58. What do you do to deal with stress?

Stress can make a monster out of any decent human, especially when the person doesn’t know how to manage it. This can degenerate into a problem with far-reaching consequences in a relationship.

59. What do you consider as your worst habit?

Hardly is there anyone perfect, we all have our flaws. What makes the difference is how conscious we are about them which goes a long way in determining how well we manage them.

60. What would you say is your biggest fear?

We all have something we are afraid of and it is part of being human. The only problem here lies in our inability to live beyond it. Do his fears motivate him or does it hold him back from living?

61. What do you wish for people to care more about?

Undoubtedly one of the deep questions to ask anyone, this would validate or debunk any view you had held about how he sees the world and the things that are important to him.

62. What are the things that inspire you?

Our inspiration comes from various things and these things ultimately define what we have embraced as our essence in life, so this is a good question to ask anyone you want to know better.

63. How would you want to be remembered?

You can regard this as a raw alternative to the question: what is your life purpose. His answer to this, if sincere, should tell you most of the things you need to know about how he wants to live his life.

21 Serious Questions to Ask a Guy Before Dating

Many people have rushed out of relationships as quickly as they rushed into it because they failed to get answers to some pertinent questions before entering the relationship. Here are some deep questions to ask a guy before dating him.

64. What is your plan for the future?

Our plans for the future are different, just as our faces are. If you don’t want to find yourself stuck in the future you didn’t want, then this is a question you shouldn’t forget to ask.

65. What are the qualities you look for in a partner?

You have to know if what attracted him to your have substance: are they things that would endure in years to come or would they be less relevant in years to come, think about that.

66. What happened to your last relationship?

There are so many reasons why you need to know this and you will realize them as soon as he begins to answer this. Do not ignore any red flag that emanates from his response, take it seriously.

67. Have you ever been heartbroken?

Many people try to get over heartbreak by falling in love again. Oftentimes, it amounts to a big disaster as their hearts are yet to be freed from the hurt they suffered in the previous relationship.

68. What attracted you to me; how and when did you realize you are in love with me?

The things that attract people to us often spell out what they expect from us. Explore his expectations and find out if they are who you are or if he would be asking for the impossible when you date him. Do not be carried away with the sweet things he might say while responding to this, focus on how real they are: are they consistent with your personality or just a bunch of nice expressions of feelings?

69. What do you think of people getting married?

Not everyone wants to get married and start a family. Some people are okay with just being romantic partners and nothing more. Do not date anyone based on the assumption that they would want to get married someday.

70. What do we have to prioritize as a couple?

The best of couples are those with a common sense of purpose. If your relationship goals are different, your expectations would be different and so also your priorities. This can be very frustrating for both of you.

71. Have you ever attempted to hurt yourself?

Also one of the deep questions to ask a guy you intend to date, this question should serve as an avenue for you to estimate how emotionally stable or unstable he is.

72. What is the one thing you won’t tolerate from your partner?

We all have our limits and for some people, some lines must not be crossed. You must know what these lines are and decide for yourself if you are okay with it or not.

73. How do you know you are loved?

There are different love languages and you should find out what his’ is. Is it someone who feels loved when he is supported or one of those who needs words of affirmation to feel loved?

74. Who would you describe as a cheater?

Cheating doesn’t always mean the same thing to people. Everyone might agree it includes sexual infidelity and some regard sharing an emotional connection with someone else as cheating.

75. How often do you need to be alone?

Being in a relationship, for most people, doesn’t mean they want to give up every sense of individuality. So you have to know what level of individuality he would want to maintain as your partner.

76. What are the things you can’t compromise on?

Some things are non-negotiable for some people, it might be their political views, religion, or opinions on sensitive matters like abortion and sexuality. You have to know what it is and if it’s something you can deal with.

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

As silly as it might sound, people have entered into relationships because they want to be having decent regular sex. Sex-related issues have ruined a lot of otherwise healthy relationships, it would be unwise to not check if you are on the same page with him on that.

78. How do you feel about relationship counseling?

Almost every relationship has been troubled at some point, some of these issues which can be addressed with a few hours of counseling sessions have ruined many relationships because one or both of the partners weren’t up for counseling.

79. How do you express yourself when you are upset?

It is difficult to imagine you will never upset your partner; it is quite natural to do so: no matter how much you love them, you are bound to upset them. So it is important to know how they would deal with that.

80. What do you consider as the role of your partner in a relationship?

Again, people enter into a relationship with expectations. It is the disappointment of not having these expectations met that leads to nasty breakups and toxic situations. You just have to know what he would be expecting from you.

81. What did you learn from your first relationship?

It is quite easy to see how this is one of the deep questions to ask a guy you are considering to have as a boyfriend. It presents the opportunity to see how much he has improved himself to be a better partner, or if he is even ready to date again.

82. How do you deal with jealousy?

Jealousy is natural to humans but it is never okay for one to be jealous of his/her partner. If nothing is done about it, it can amount to a huge disaster that would leave both parties scared for life.

83. Who would you describe as a supportive partner?

For some people, a supportive partner offers encouraging words, for others, you have to proffer useful solutions to difficult circumstances. Most people would agree it entails both but essentially, you need to know how he appreciates being supported

84. Are you open to having kids someday?

If you have hopes of having kids, you should know that some people are not up for that, so ask him first. And don’t get into the relationship hoping he would change his mind about it if he says he doesn’t want to.

Final Words

There are probably hundreds of deep questions to ask a guy and you shouldn’t hesitate to ask these questions. However, for deep, personal/intimate questions, you have to ensure the time is right for asking them. For instance, it might be too forward to begin asking questions about his sex life when you are only getting to know him.

Such questions and others that can make anyone uncomfortable should be asked when he has become quite close and comfortable around you. Nevertheless, if he is someone who has been your friend for a while before dating came into the picture, you can go straight into asking deep personal/intimate questions. Otherwise, focus on getting to know more about him. Ask personal questions you could ask anyone and then gradually proceed to the deep and intimate ones.


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