100 Deep Personal Questions To Ask A Guy Or Your Boyfriend

Eager to get close to your guy? Try asking him some of these deep personal questions, and you could get him to open up some hidden secrets about himself. At first, the questions might sound funny or uncomfortable, but by the time he starts answering, many mysteries will be unraveled, and you will get to know him better. Here we have a huge list of such questions.

Questions To Help You Find Out About A Guy’s Personality

Knowing the personality of a guy you just met will go a long way in informing you of the type of person he is. You will also be properly informed to decide and determine what will be become of your acquaintance with him. Of course, it’s not every question you can ask him but the questions below, though basic, are deep enough to reveal some personal things about him.

  1. What is your temperament?

The very first thing you might want to find out in a guy is his temperament. He can be any of sanguine (enthusiastic, active, and social), choleric (short-tempered, fast, or irritable), melancholic (analytical, wise, and quiet), and phlegmatic (relaxed and peaceful) or a mix of two temperaments. Bear in mind, though, that some guys don’t know their temperament, so you can explain these temperaments’ characteristics and explain which best defines them.

2. What is your zodiac sign?

Besides knowing someone’s temperament, you can get ahead by asking about which Zodiac sign they were born under. People born under a particular Zodiac sign tend to have certain characteristics associated with them. Moreso, certain Zodiac signs are compatible with the other, while some aren’t

3. How often do you exercise daily?

Though it is recommended for an adult to exercise at least 30 minutes every day, some guys simply don’t see the reason for this, while others go above this minimum recommendation. One’s exercise habit has a lot of input on his/her overall health status. So knowing what your boyfriend’s attitude is to exercise can help you gauge how serious he takes his physical wellbeing.

4. How important is religion or spirituality to you?

Before you ask him, ask yourself how important religion or spirituality is to you and how welcoming you will be to someone who has a contrary religious or spiritual view to yours. If you have answered this already, then your boyfriend’s response to you will probably start a long discussion on the subject matter if you both have divergent views and hold on sternly to them. On the other hand, you may both just laugh over his response and move on to other things.

5. What’s an ideal weekend for you?

Weekend to many people is for relaxation and socialization. For others, they might not be at liberty to relax and socialize as much you do. Knowing what a guy’s weekend is like, especially when you are both getting to know each other, is a step in the right direction for having compatible social lives.

6. Do you have any phobias?

Arachnophobia, ophidiophobia, aerophobia, trypanophobia are some of the phobias people have. Many guys will hardly ever admit they have a phobia for something, but you won’t know till you ask. Perhaps, your boyfriend has a phobia for something you won’t even flinch about.

7. What makes you angry?

With this question, you can quickly find out if he is a hot-tempered person or someone that is easily irritable.

8. What is your goal in life?

Not only will you have an idea of where he is headed in life, but you will also find out how serious he is with attaining such a goal when you ask him what he is currently doing to achieve the goal.

9. Are you confrontational?

One of the good qualities of a confrontational person is that such a person is not shy. Their opinion will hardly ever be surprised without being heard. However, if your boyfriend admits to being too confrontational, then he should probably get psychological help.

10. Are you an early or late person?

This question might seem odd for someone who is usually a late person because perhaps he might have been asked this before. Nevertheless, you need to know that you will be there right on schedule, at least in your next meeting.

11. Do you look forward to having children?

It is the norm to plan and expect to have children once your relationship matures to the point you consider spending your lives together. But time has changed, and people now want different things in life. Instead of having children, some couples would rather have none, others will prefer to adopt from foster homes, and still, some would rather be content having a pet or pets as the case may be. Whatever your boyfriend’s response will be, make sure he knows yours and what you both want will it align with each other. You can still reach compromises and be better with your decisions.

12. What’s the biggest struggle that you’ve ever faced?

Don’t judge his response to this question based on your perception of how serious or trivial the problem is. People face different problems in life, which also get compounded by certain conditions around them. Rather, judge him, try to offer a solution where you can, or encourage him to persevere.

13. Did you ever sleep with stuffed animals?

Sleeping with stuffed animals is something most kids do, but some adults still cling to the habit. Studies have shown that adults who still do this do it to combat loneliness, anxiety, and other negative feelings. Though this is often associated with kids, it’s not harmful to adults who still cling to this habit.

14. What skills do you want to master?

This question is forward-looking and will also result in another question: what are you currently doing to master that skill. Overall, it seeks to understand what your boyfriend is into or what he is seeking to go into.

15. What are some of the morals you live by?

It could be truthfulness, honesty, kindness, perseverance, keeping to a promise, dependability, etc. Someone who lives a moral life commands lots of respect.

16. What’s your favorite book/movie of all time, and why did it speak to you so much?

This is sure to get your boyfriend talking about the book or movie he loves so much. He might even get to convince you to try reading the book or see the movie.

17. Do you consider yourself an introvert or an extrovert?

Before now, you might already have an answer ready before he gives you his. It is often not difficult to tell whether someone has an introverted personality or is an extrovert.

18. What is your strangest habit?

From smelling books to counting steps while walking to nose picking, people have so many strange habits, and you can never tell which one has until you ask or observe closely.

19. What’s your favorite drink?

If you plan on buying him a drink someday, find out what his favorite drink is now. It might be an alcoholic or a nonalcoholic drink.

20. What website do you visit most often?

Check out the content of that website and get to know the kind of things that interest him. If you can, brush up on your knowledge and engage him in a discussion. He will be impressed with you.

21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

Different people handle bad moods differently; for some, being in other people’s companies might make them feel better, while others prefer being alone. Once you find out what he has to say about things, you will be better informed on what to do if you see him in a bad mood.

22. What is the most frightening thing you have ever done?

If it is not frightening to you, it does not make it something trivial because people have different perceptions about what they encounter in life.

23. How would you describe your relationship with your family?

Sometimes, this might describe how he will value his relationship with you if he is from a closely-knit family; otherwise, it might be totally different from you.

24. Do you hold grudges?

One question that indirectly answers this question is whether holding a grudge against someone is good or not. Perhaps, your boyfriend might hold a grudge against someone for reasons best known to him. Find out why if he is willing to talk. In the end, we are better off relating with people who don’t hold grudges compared to people who do.

25. How many girls have you been with?

If he had dated a good number of girls before you too became an item, the chances are that he has been with a good number of girls. Perhaps, he might have even lost count and might not necessarily tell you the truth. Well, just ask this question jokingly and hope you won’t get a shocker!

26. How do you deal with failure?

People see failure differently; to some, it is an opportunity to start afresh and succeeded at what they failed in previously. To others, failing at something marks the end of all their attempts at doing something. Obviously, the former is preferable to the latter, so which are you, and which category does your boyfriend fall under?

27. What’s your claim to fame?

This question presents an opportunity for him to talk about himself, and oh yes, people like talking about themselves, especially when they have done something good.

28. Which one fits you better? “Live for the moment” or “Save the best for last”?

It is also important to direct this question to yourself and give an answer before getting an answer from your boyfriend. Are you both alike, or are you his opposite?

29. What is one thing that you cannot start your day without?

Many people these days can’t start their day without having a hot cup of coffee; to others, it could be exercising or as simple as reading the news.

30. What do you like most about yourself?

Again, in general, people like it when they have an opportunity to talk about themselves, especially their good qualities, their most notable achievement, and how they came about it.

Deep Questions To Unravel Your Boyfriend’s Opinion About Love And Relationship

Some questions can reveal your boyfriend’s thoughts without putting yourself directly as the object of the question. He will answer such questions as innocently as you would want him to without any pretense. However, you should be careful with questions like this because you might find the answers he will give you very troubling. But should he have put you in perspective while answering the question, he would have responded differently.

31. How long do you think a couple should date before getting married?

There’s no rule on how long a couple should date before getting married. Some couples date and get married in a matter of weeks, while others might have their’s stretching into months. However, in a study titled the PAIR Project conducted by Penn State University, Professor Ted L. Huston found that couples who dated 25 months on average were mostly happy in their union.

32. What is a relationship deal-breaker for you?

Relationship deal breakers are the ultimate things that can cause you to call a relationship off. Apparently, people want different things in life. In a relationship where two people will be spending their lives together, you both must understand the limitations of what your partner can tolerate.

33. What is your love language?

There are so far 5 main love languages which various persons use to express love to their loved ones. These love languages include physical touch, gifts, service acts, spending quality time together, and words of affirmation.

34. Are you still friends with your ex?

Another way to ask this question if you don’t want to put him in the picture is to say, ‘do you think people should still be friends with their ex?’ His response will be based on the value he attached or still attaches to his ex and what made them split.

35. What role do you think religion and spirituality play in relationships?

The basis of this question is whether or not he is a religious/spiritual person before you can then think of how important he might consider it in a relationship. But if he is neither, there’s apparently no need to ask.

36. Can you handle being in a long-distance relationship?

Some many electronic tools couples are far apart from each other can use to keep in touch. The options are simply limitless, but there has to be a willingness first before he can make the best use of what is available.

37. Have you ever caused a couple to break up?

This is not something to be proud of, except he has his reasons. Well, maybe his reason/s could be justifiable but again, find out if causing the couple’s break up was the only option. But if he hasn’t done any of such, lucky you.

38. Do your friends share their relationship problems with you?

It tells how trusting his friends can be with him about matters that are otherwise personal to him, and just maybe he is good at keeping people’s secrete.

39. What do you think about same-sex marriage?

Most people these days accept same-sex couples the way they would of couples of different sex. So there’s no point discriminating against others.

40. Do you consider emotional cheating as serious as real cheating?

Emotional cheating is a form of cheating where someone in a relationship engages in a secretive closeness with someone who is not your partner over a long time. However, the relationship might be nonsexual.

41. What do you think of your parent’s relationship?

Different people from different homes will say absolutely different things about their parents. So whatever his answer will be, take it as an assessment of how he perceives his home.

42. What do you think could make our relationship break?

He is most likely going to say things he has noticed you do, which he doesn’t like when you ask him this question. So it’s a good thing you asked now so you can work on them.

43. Where do you see us in 5 years?

Your relationship ought to have grown probably into marriage if you are both adults of marriageable age. But if he says the two of you will still be partners but not married, you should find out the reason and see if it is okay with you.

44. What is your stance on divorce?

Don’t look too serious when you ask this question, so he won’t take it to be you considering opt-out if your union doesn’t work.

45.  What does being in love mean to you?

Love is a beautiful thing understood and described by different people with words they understand best.

46. What does it mean to be in love with you?

It should be better than what his last relationship was like if you are not his first.

47. Do you see doing house chores as demeaning?

Well, this is simply a mind thing. There’s absolutely not demeaning about your boyfriend doing house chores with or without you. But if he feels it is, you should probably talk it through with him.

48. Who was your first love?

This question most times bring back fun memories for your ex, especially if they had their first love at a very young age.

49. What ended your last relationship?

The blame game typically rares up here. Allow him to say all that he wants to say and make few comments afterward. It might also be a wise thing to avoid mentioning his ex often in your new relationship.

50. How would you feel and react if someone told you something bad I did in the past?

When you ask this question, there’s no escaping telling him what you did in the past. In fact, you should tell him yourself if at all you have something up your sleeves than to leave him wondering. He will simply not stop thinking about it.

To Know If He Really Likes You Or Not, Ask These Questions

Sometimes, you find guys in a relationship with a lady but don’t really like the lady or don’t have long-term plans for her. At the slightest provocation, that relationship will come crumbling because it has no foundation; there’s no defined purpose why the couple is together. And while this can be catastrophic when it happens, it could simply be avoided by finding it if your boo likes you by asking him these carefully worded questions.

51. Do you think there is someone more perfect for you than me?

As blunt as it is, this question can be answered with a one-word (yes or no) answer, which can make or mar your relationship. It is best not to ask this question when you fight with each other. Instead, ask it playfully when all is well between the two of you.

52. What would you do if your ex-girlfriend suddenly wanted to get back together?

From the top of his head, he might tell you he wouldn’t want her back, but his facial expression while answering this question will probably tell you more about his thought than the literal answer he will give you.

53. When do you think a person is ready for marriage?

It is currently on record that many young people in the United States of America tie the nuptial cord with their better-half between the age of 25 and 30. Within this age bracket, men get married at a much older age than women.

54. What about me made you fall in love?

It could be something that could throw you off because believe it; cupid’s arrow strikes in ways we can’t understand sometimes. But whatever reason it is he genuinely loves you, let it be worth loving you for.

55. What did you think when you first met me?

Some guys admitted knowing the lady they just met would be their life partner, while to others, they first became friends before it dawned on them that their life partner is right beside them. So his response might just tell you where your relationship is headed.

56. What does love mean to you?

Listen carefully to his response because love means different things to different people. It is all about what they spend on their partner; to others, it is more of the sex, while still to others, love goes beyond all these and is only explainable based on how they express it at a particular time.

57. What’s one secret you’ve wanted to tell me but haven’t?

Can you be able to keep his secrete, because if you tell it to someone else, then it is no longer a secret, but with you, he still considers it a secret being that he trusts you enough.

58. What, according to you, is a perfect life, and how would you try to make it for yourself and me?

The answer to this question is dependent on what his aspirations in life are and how you fit into it. What a perfect life might mean to someone passionate about agriculture will be entirely different from that of another person who is passionate about space science. So at the center of it all, who well do you fit into the picture with him.

59. Would you relocate for love?

If he loves you enough, why not? Relocating to be closer to a loved one is one of the sacrifices couples make so the other can be happier. However, it is not a decision you both should hastily make, but you should evaluate the implications and burden it might pose to the relocating partner.

60. How do you feel about sharing your password with your partner?

Sharing of passwords and PINs between partners seems to be the new norm going by the findings of Kaspersky Lab. It was reported that about 70% of people in relationships willingly share their passwords and PINS with their partners and even exchange fingerprints for accessing each other’s devices. So are you and your partner part of this 70?

61. What do you hope never changes about me?

Maybe it is the very thing that attracted him to you, and somewhere in his mind, he believes it’s too good to be true. Well, if you didn’t fake it, just be yourself and assure him nothing will change about it.

62. What would you do if I get embarrassed in public?

He should come running to save the day for you, except if the embarrassment is undeniably amusing to both of you.

63. Do you think we spend enough time together?

There’s no universally accepted amount of time couples should spend together. But if he feels you both don’t spend enough time together, it is something to be happy about because it’s a way to say he misses you.

64. Do you think we spend too much time together?

If he thinks you spend too much time together, then you should take a proper assessment of your relationship because he might be getting tired of you already.

65. Will you cheat on me, and for what reason?

Seeing that the two of you are in a relationship, there’s no excuse for either party to cheat. However, if he has a reason he thinks he would cheat on you for, then it’s a good thing you found out now.

66. Do you think our relationship can recover from a cheating scandal?

There’s no better time to ask this question than now, but despite the response he gives you, it is best to avoid cheating.

67. When did you first realize you wanted to be with me?

It could be spontaneous or even after deep thought. No matter what his response is, the most important thing is that he has made you know.

68. What trip would you like us to take together?

Couples love spending time together; it could be up his sleeves to propose to you on that trip too.

69. Are we changing each other in positive ways?

No one is perfect, so we improve and learn from each other daily. There must be visible proof that you are both improving each other.

70. What will you rather do when missing me?

He might call you, look through the pictures you have together, or even take time to send you a card. It also shows how much he values your love and his love for you when you aren’t together.

71. What are the things we have in common?

It could be your penchant for similar music or movie genres; it could be the college you both attended your favorite things, places, food, etc. The more he lists romantic things you both have in common, the better it is for your relationship.

73. What makes me different from your ex?

No two people are the same, and also, so are our capabilities different from each other.

74. What do I look best in?

Some guys have better fashion sense than ladies; they know what best fits an occasion or how to look simple yet catchy.

75. Which hairstyle fits me best?

Your boyfriend will probably tell you the hairstyle he thinks people admire you most with in response to this question.

76. Can you make the first move for peace after we quarrel?

Avoid quarrels by all means as much you can. But when it happens, and your boyfriend happens to make the first move for reconciliation, then you should know you have got a man, unlike many others.

77. What do you see as my biggest mistake?

Now, it’s not just about the constructive criticism, but the bigger question is, what are you doing to overcome this weakness. Also, you can ask him how best he can help you overcome the weakness.

78. Do you imagine hitting me?

He shouldn’t, as domestic violence is not condoned in any quarters. Rather, both of you should cultivate a habit of always talking through your problems rather than having them degenerate into a quarrel.

79. How would you feel if you found out I lied to you?

By all means possible, avoid lying to your boyfriend no matter how trivial the issue might be. But even if you had in the past lied to him, this is the moment of truth!

80. Would you ever consider telling someone about our problems?

It is often better for couples to settle whatever issues they have within themselves rather than involve a third party. But if it comes down to involving someone for the issue to be resolved, then you both should go about it maturely and don’t wash your dirty linen in public.

These Romantic/Sex-Related Questions Will Reveal Your Boyfriend’s True Sexual Personality

It is not just enough to know the basics about your boyfriend when your friendship with him has gone beyond the friend zone. Knowing what his perspective is on certain sex-related topics will further broaden your understanding of who he is, what his sexual experiences have been, and if you can stay with him for the long haul.

81. What is your position on premarital sex?

In many young relationships, this question rarely comes up as premarital sex seems to be the norm. However, some guys have a contrary stand to the popular expectation and are determined to abstain from sex till marriage.

Well, it should interest you to know that a study reported that couples who abstain from premarital sex are happier and more stable in marriage, unlike their counterparts who don’t.

82. Are you a virgin?

It’s okay to ask your boyfriend this question, especially if you two are just beginning to date. However, if you already assume what his response will be, don’t judge him too sternly if he was a randy boy while growing up.

83. Do you like porn, and do you also watch it?

Watching pornography is something many guys do in their closets, and the introverted types will hardly ever make this publicly known. Perhaps your boyfriend has a craving for pornography, and you don’t know yet. Ask him and find out even the category of porn he likes. His response will be suggestive of what his sexual fantasies and preferences are. Make them a reality to him.

84. What sexual fetish do you have?

Most sexual fetishes are termed dirty and naughty by people who don’t have them. But to the person with such fetish, they aren’t and are, in fact, important for a fulfilled sexual experience. The type of fetish your boyfriend has can be foot fetish, voyeurism, bondage, role-playing, and impact play. An understanding of these fetishes will help you and your partner have a fulfilled sexual life.

85. What do you think about sex dolls, and have you ever used one?

This question scratches the surface of what will uncover many other questions if you prod further. But you must find out, especially in a time like ours when many guys prefer to acquire and date sex toys instead of a human being.

86. What is your favorite body part on a female?

Just as different ladies have their favorite body parts in guys, different guys will also have divergent preferences on what turns them on the most in a lady. It’s a lady’s breast; for others, it might be the nether regions. If your boyfriend’s response happens to be for a body part you are not endowed with. It’s a good thing you found out because he might have been attracted to you for another reason.

87. What do you like most about me?

Just maybe you thought he got attracted to you for one reason, but his response seems to be for another. Don’t feel bad; simply find out why he values it more than any other thing.

88. What is your biggest turn-on in a woman?

This question will make him give you answers about what he admires in other women, which might make you feel jealous. So are you really sure you want to ask him this question?

89. What is your biggest turn-off in a woman?

Similar to what turns him on in a woman, you can use the response he gives to this question to your advantage. This is so especially if the turn-offs are flaws you already have; perhaps he knows you have them, perhaps not. Whatever response you get, find a way to use it to your advantage and keep your boyfriend.

90. Where is your favorite place to have sex outside of the bedroom?

It could be on the all too popular couch, in the kitchen, car, or even on the lawn (under cover of darkness). His favorite sex place will be a bit of a pointer to how weird or adventurous his sex life is. Well, if his response left you gaped, you’re just getting to know your boyfriend, and it’s a good thing you asked.

91. Have you ever made a sex tape?

Can it get weirder than this? Of course, it’s not strange; many guys make sex tapes with their girlfriends for reasons they both agree to. So if he has in the past, find out his reasons for doing so because he will probably want to make a sex tape with you someday. Will you agree to it?

92. What is your biggest sexual fantasy?

Again, just like fetish, someone’s sexual fantasy mike seem repulsive or even offensive to another person. Knowing your boyfriend’s sexual fantasy could help you both have a better sex life. If perhaps you both share some sexual fantasies, then you shouldn’t be taken aback because a study by The Journal of Sexual Medicine reported that many men and women share the same sexual fantasies.

93. Does the thought or sight of two or more men having sex turn you on?

This is a dicey one because it can raise more questions than answers you will get from him. This is a deep and personal question that might push him to reveal deeper things about him that you never knew. If his response is in the affirmative, you should discuss further and understand the implications for your heterogenous relationship. It’s also not out of place if he asks whether you get turned on by two or more women having sex.

94. What is your favorite part during sexual intercourse?

Pillow talk, foreplay, teasing, oral sex all culminate into a pleasant sexual experience for most couples. But for some, the climax of copulation could be somewhere before where many of us are used to. So you must find out from your boyfriend what his favorite part of sex is and make the best of the moment.

95. Do you like to be dominated? Or do you prefer to be the dominant one?

It’s not atypical to see some guys prefer to be dominant during sex than to be dominated. However, if your boyfriend happens to be an exception, then his one unique person some type of ladies might be lucky to have. Different sex positions are best suited for his type of person.

96. What’s your favorite sex position?

Studies have shown that different sex positions give different levels of sexual pleasure to different people for divergent reasons. The particular sex position that gives a guy the most sexual pleasure apparently will be his favorite sex position. Knowing this will help both of you understand what works best for each other to have a rich sexual life.

97. Have you ever contracted an STD?

This is something most guys will hardly ever be proud of admitting. It is so deep and troubling a question to answer because STDs can be avoided in many ways. However, if he has, you both should talk it over and do everything possible to keep your sexual life healthy.

98. How many girls have you slept with?

This can make or mar your relationship, especially if you ask deeper questions on who he has slept with. His exes might come up too, and his response will be even more troubling if you both live close to each other.

99. What do you think of open relationships?

In an open relationship, both partners have other love interest who they are romantically involved with. If your boyfriend is considering being in an open relationship with you while you think or want otherwise, you both must reconsider your decision of going into a relationship and be sure you clearly understand what you want.

100. How often do you think couples should have sex?

Though studies have shown that women want more sex in a relationship when compared to their male partners, it has also been revealed that the frequency of sex couples have to decrease over time. Apparently, in the long run, women have more sex drive in relationships than men.

Guide To Asking Your Boyfriend These Personal Questions

For your relationship to thrive, you should ask questions and communicate and be open with each other. As a guide, you should take these steps when asking your boyfriend these thought-provoking questions.

  • Be conversational when asking questions.
  • Ask the questions in a friendly tone and tease him where necessary.
  • In case he asks you a question in the process, answer it to keep the conversation going.
  • Avoid questions that may lead to an argument or remembering hurtful events.
  • Don’t censure him for the mistakes he made in the past.
  • If he gets emotional while answering a question, comfort him.
Fact Check: We strive for accuracy and fairness, if you've found a possible error, be it factual, editorial or something that needs updating, please contact us
Adeola Seun
Adeola Seun
An avid writer for over 8 years with a purpose in mind – I express my thoughts so that others can be inspired to leave their dead weights behind, and forge ahead without holding back. Other than writing, I like to also spend my time playing video video games, watching movies, and maintaining a love/hate relationship with Arsenal.

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