94 Seriously Deep, Revealing Questions to Ask a Guy & Get to Know Him ASAP

It’s important to have deep chats with your boyfriend, but what do you ask? Here are some serious questions to ask a guy and understand him better. 

Deep Questions to Ask Your Boyfriend

There are many things we keep hidden at the beginning of a relationship. But if you hide the crazy for too long and then let it all out at once, it rarely ends well. You need to be constantly getting to know each other. Luckily, we have compiled a list of serious questions to ask your guy to help you do that while getting some clarity at the same time.

Being yourself is the key to any successful union, and that includes being honest and asking uncomfortable questions. With that said, you shouldn’t make your man sit down and fire deep questions at him one after the other. But a few here and there can help you get to know him much better.

After all, the things you don’t assume to be a big deal can become a major roadblock in the relationship if not addressed early on. [Read: 42 secrets to communicate better in a relationship and ways to fix a lack of it]

The importance of asking your guy serious questions and timing

While you should definitely go with the flow if you’ve only just met this guy, once you realize that it’s possibly going somewhere, you need to know that you’re on the same page.

Not all questions are the same, but things like whether you both want to be married or have children at some point are important topics to agree on.

The problem is that many people avoid serious questions like these because they worry that it’s going to make the guy run a mile.

Of course, it will if you ask him on the first date, but if he’s not open to answering questions like this after a while, do you really want to be in a long-term relationship with him?

Communication is vital, and if he’s not up for it, your relationship is going to be nothing but confusing all the way. For that reason, these serious questions to ask a guy are vital. [Read: Communication techniques to finally get them to open up to you]

Deep questions to ask a guy and get to know him better

These are the best serious questions to ask a guy to get to know him better and keep the conversation going.

Uncomfortable? Yes, but it is necessary to take things to the next level by being open and honest with each other. In turn, this will spark meaningful conversations that will bring you closer together.

1. Are there things you have done in the past that I should know about?

The last thing you want to do is to run into someone from their past to find out that they were the biggest player that ever lived or that they spent time in juvie for something very serious.

Giving them the floor to make any confessions about their past ensures that you never get blindsided. This is probably one of the most serious questions to ask a guy. [Read: 18 ways to get to know a guy before you decide to date him]

2. What type of guy were you before you met me?

Is he a serial monogamist or a sleep-with-anything type of guy? You may have changed him, but it is nice to know who he was before you turned his eye.

It’s one of the deep questions to ask a guy that you should always attempt to ask if you want to get to know your partner better. [Read: 46 good ad bad types of guys in the dating world and secrets to read them]

3. What were your old girlfriends like?

This is an important question to ask your boyfriend that you’re sure to be curious about! Are you his type? Knowing what his other girlfriends were like might give you a perspective about what he looks for in a girl.

You’ll also learn what it was about the other relationships that didn’t work. This could help you avoid making the same mistakes, and it’s therefore one of the key questions to ask a guy. [Read: How to talk about a past relationship and not piss your partner off]

4. What broke up your previous relationships?

Sometimes, there are things a guy won’t come right out and tell you about. By learning what broke up his old relationships, you’re given an insight into what he has been through before.

While you shouldn’t expect him to spill all, it’s one of the serious questions to ask a guy that will give you plenty of insights. [Read: 16 warning signs your boyfriend is not over his ex and still attached to her]

5. Have you been in love before?

Knowing whether or not he thinks he has been in love before will tell you whether he has the emotional maturity to get in touch with his feelings.

You have to have something to compare your feelings to. If he has never been in love, then how does he know what love is or when to recognize it? [Read: Immature men – 53 man-child signs, why he’s a pain to date, and ways to help him]

6. Who was the first girl to break your heart, and how did she do it?

We all have baggage from our past. Knowing what’s in his suitcase can help you navigate difficult times with him.

By asking this deep question, you can even reassure him that you aren’t his ex, nor would you ever do what she did. [Read: Broken heart syndrome – the truth to know if you can die from heartbreak]

7. What is your five-year plan?

If a crystal ball could tell you the truth, you wouldn’t have to ask your boyfriend serious questions like this. But unfortunately, it can’t.

Does his five-year plan involve a family and a wife, or is it all about his career?

Guys with plans rarely veer from those plans, so knowing what his intentions are upfront is the best way to find out how you will fit into them… or if you will at all. [Read: What age does a man emotionally mature? 19 signs of maturity in a guy]

8. Do you like children, and do you want to have them?

Regardless of what your stance is on having children, this serious question to ask a guy is one that you just can’t sweep under the rug.

We understand if you want to put off this question because you’re worried about scaring the guy off and making them think your biological clock is ticking.

But the truth is that no relationship is going to be healthy if you want different things out of life. Children are about the biggest change a relationship goes through. So just bite the bullet and ask.

You don’t want to waste years of your life dating someone who wants different things out of life. [Read: Emotionally unavailable man – 52 signs, causes, and ways to make him love you]

9. What is your biggest pet peeve?

Those little things we do that irritate each other at the start don’t seem that big, but they can become deal-breakers. Learn what makes him tick so you know if it is something inherent in you or something you are capable of avoiding.

This is one of the deep questions to ask a guy that may look playful on the surface but actually gives you great information for the future. Like if you even have one at all.

10. What is a deal-breaker to you?

What is it that he simply can’t stand in a relationship? You need to know this to make sure that your needs and values are aligned. If they’re not, it’s simply not going to work out. [Read: 27 most common relationship deal-breakers that push many couples apart]

11. Do you think divorce is okay?

When a couple gets married, they never think they will get divorced. But sometimes, the love dies or we just grow too far apart from the person we once loved.

There are some with a greater commitment to seeing it through, while others think that divorce is a way out if it isn’t going so well.

It is important that you’re both on the same level of commitment, which makes this one of the most serious questions to ask a guy. [Read: 59 signs it’s time to break up and give up instead of trying to fix a relationship]

12. If you do have children, is it important in what religion they are raised?

Even if he isn’t actively religious, the faith in which he raises his children may be very important to him. If you aren’t the same, that could pose some serious problems not just for you two but for your families as well.

13. What are your political beliefs?

Politics is a topic that people avoid because it tells a lot about who someone is. If he is ultra-conservative and you are a super-liberal, being together is going to be pretty difficult without strife.

This is one of those deep questions to ask your boyfriend that can help you see the world through a very different lens. [Read: 250 fun, deep relationship questions for couples to feel closer and more loved]

14. What do you think about prejudice?

We all hide our prejudice when we start dating someone for fear of judgment, but if he has some serious prejudices against some group or religion, you may want to know that before you hear the ugly later on.

In terms of serious questions to ask your boyfriend, they don’t get more serious than this.

15. Do you believe that family is important?

How important is his family to his life? Is it family or the peripheral family that guides his decisions? [Read: Family orientated – the meaning and what it means to be this person]

16. Who comes first, your wife or your mother?

Mothers can ruin even the most excellent relationships. Know where he would stand and whose side he would take before she becomes your biggest nightmare.

While you can’t really do a lot about it, knowing the information beforehand is key.

17. Would you rather have your wife stay home or go to work?

Does he believe in traditional roles, or does he want you to share in the financial responsibility?

In terms of serious questions to ask your boyfriend, this is vital. If he doesn’t see things the same way you do now, it’s not going to improve in the future.

18. Would you want to keep your finances separate?

He shares his bed but not his finances. That says a lot about the level of intimacy and closeness he wants to have with his significant other. [Read: Sharing expenses in a relationship – the golden must-follow rules]

19. If you were in trouble, would you hide it from your wife?

This is one of the questions to ask your boyfriend that’ll give you an insight into your future together and allow you to get to know him on a deeper level.

Is his wife his confidant or just an accessory? If you want to marry someone with whom you share everything, but he wants to keep things to himself, it will create issues, and you’ll feel like he hides things.

It is a very complex road to go down. It’s better to know about it now, while you still have time to walk away.

20. Would you choose your job or your family life?

Is he into raising his kids, or is it business at all costs? If you don’t want to be sitting on the bench alone forever, it is important to know whether he is going to want to take part in it all. [Read: Love or career – how to choose and make sure you’re not left feeling bitter]

21. Are you a spender or a saver?

If you are a saver, but he has out-of-control credit card debt, it can create huge problems. Asking this question checks your spending compatibility. Make sure you are on the same financial page to avoid potential drama in the future.

While talking about money is quite uncomfortable, it’s one of the most serious questions to ask a guy. [Read: How to make a relationship last – 25 rules of love you can’t ignore]

22. How strict were your parents?

We tend to either parent the way we were parented or go the complete opposite route. How did his parents raise him, and does he think that it was the right way or the wrong way?

23. Do you believe major decisions should be made together?

This is another of those deep questions to inform you of what may be to come.

Is he going to come home with a Porsche one day, having drained your savings account just because he felt like he needed an impulse buy? Or does he think he should discuss it with you? [Read: Decisions you should never let your partner make for you]

24. Would you be honest, even if you knew it would hurt my feelings?

If his feelings changed or something serious was going on, would he be honest if it wasn’t comfortable or something he didn’t want to talk about?

25. Would you ever look at my phone or go through my personal things?

If he starts spying, you will, too. Then, the trust will slowly chip away until there’s nothing left. As you can see, boundaries need to be set up pretty early on if you want love to work.

26. What do you remember your parents fighting about?

Were his parents disconnected fighters or good communicators? You tend to mirror what you grew up with *or the exact opposite of it*.

Knowing how his parents related is a good indicator of how he might communicate with you, and that makes it one of the serious questions to ask a guy for extra insights.

27. What type of relationship did your parents have?

Is he from a broken home or a perfect one? This gives you an idea of his perspective of what a family is supposed to be. [Read: Interfering parents – all the ways they can affect your love life]

28. Would you say you were closer with your mom or your dad?

Did he hang out with his dad in the garage or stick by his mom’s side? If it was his mom, be careful. He may just be a momma’s boy.

29. What is a tradition in your family that you absolutely have to keep?

If going skiing every Christmas is what he does, then those are the things you need to know. You will be doing them forever if things last. [Read: 150+ personal questions to ask a guy to get him to open up to you]

30. Would you be okay if your wife was more financially successful than you?

This is one of those deep questions to ask a guy that highlights his character. How comfortable is he with letting you shine, even if it makes his star not so bright all the time? [Read: What to do if your partner makes more money than you]

31. Have you ever been in trouble with the police?

He might have had some problems when he was younger. You can’t judge him by his past, but you should ask if you want to be sure that he’s really changed.

32. Do you have any crazy exes I should know about?

It might sound funny to ask, but this has a serious side. This is one of the deep questions to ask your boyfriend that could yield some very useful information.

If he just has one nightmare ex story to share, you two might be able to have a laugh at the absurdity of it all.

But if he says that all of his exes are “crazy, jealous bitches,” you have to wonder what the common denominator is. If a guy says that all his exes are crazy, that’s usually a glaring red flag.

33. Do you believe in having children outside of marriage?

Some people are dead against it, while others don’t mind. It’s important to know where he stands so that you can be sure your views align. [Read: Marital traditions – their not-so-sweet origins and our modern choices]

34. Would you drop everything for your friend?

This one might sound harsh, but some guys are all about their friends. If he’s happy to drop everything for a friend, even if it’s not something serious, that might tell you about the state of your relationship in a few months or years to come.

35. Did your parents have a favorite child?

As much as we all want to believe that parents love their children equally, this isn’t the case in all families. It could be that your boyfriend had to put up with their sibling being the favorite.

This can change his outlook on life, so asking about one’s childhood is one of the serious questions to ask a guy that will help you get to know him better. [Read: Toxic family members – 15 signs and reasons to cut them off for good]

36. Would you tolerate cheating in a relationship if it was a mistake?

Be careful with this one. You don’t want to freak him out, but it will tell you about what he considers cheating and what he doesn’t.

We all have a different take on this. It’s one of the deep questions to ask your boyfriend that will be quite enlightening.

37. What’s the one thing you can’t live without in a relationship?

This is a question that can help you choose whether to stay or go. You’ll get to know what he expects in a relationship, and that will help you decide whether you want to stick around or not!

38. Is love or money more important to you?

Some guys are all about the cash. If that’s the case, you’ll always come second to whatever materialistic gains he’s got going on. It’s better to know now rather than stick around and face constant disappointment.

39. Do you see a future with me?

Ah, the most awkward of them all, but one that we all secretly want to ask! It’s one of the deep questions to ask your boyfriend that will probably be a make-or-break one, so proceed with caution.

40. What’s the biggest lesson you’ve learned from past relationships?

Every relationship comes with a lesson. What has he gone through that has shaped his outlook and made him change his approach? It might be a tough conversation to have, but it’s one of the serious questions to ask a guy to get him to open up voluntarily.

41. What do you think about our sex life?

It can be awkward to come right out and ask his opinion on this. You also might not like the answer too much, but it’s one of the serious questions to ask your boyfriend that could bring real change.

If things aren’t that hot and heavy between the sheets right now, maybe you need to talk about your sex life! [Read: How to talk about sex without sounding like a pervert]

42. What are you hard on yourself for?

This question will teach you about how he sees himself and what he deems as important in life and in other people.

It could be that he’s too hard on himself entirely, and you can reassure him about it. Asking your partner this question will help to strengthen your connection.

43. How do you describe me to other people?

Hopefully, with good words!

44. Do you have any regrets?

Everyone has regrets. Though he may not share his deepest regrets, this question will open up the topic, making it one of the serious must-ask questions. [Read: 33 truths to overcome regret, deal with our bad choices, and learn from it]

45. Is there something I should do for you that I’m not doing now?

Maybe he wants more cuddles or kisses. Who knows? The truth is that we all need things in a relationship, and we have to open up and talk about them. We can’t expect our partners to be mind-readers.

That doesn’t mean you should be at your partner’s beck and call, but if your love languages are a little different, this is an important subject to discuss to keep things even. [Read: Words of affirmation – how to use them and 56 signs, tips, and examples to say it right]

46. What does love mean to you?

Do you two have the same definition? Love means something a little different to everyone.

Some people think it means that you’re a team in life. Other people think that it’s not always romantic. If you want to enjoy a long life together, you need to be on the same page about what love actually means! [Read: Love vs. in love – what makes them so different and yet so similar?]

47. What are the qualities you love about me?

It’s time to hear the compliments. Of course, these types of questions require a reciprocated response, so be prepared to tell him what you love about him, too!

48. Who is your role model in life?

Is it his father? Mother? Who does he look up to? What are the traits that he finds ideal in others?

49. If you could live anywhere, where would it be?

If you’re asking a series of deep questions in succession, you might want to use this one to lighten the mood.

Let’s see where he dreams of going. Perhaps in the future, you can plan the perfect way to move there if it’s a place that you and your partner both like. [Read: 15 reasons why you should travel at least once a year]

50. Are there any fantasies you want to try?

Oh, we all know this answer. Maybe you’ll be willing to try out his fantasies.

This is a good and sexy question to ask to get the sex talk rolling. Not everyone finds it easy to talk about sex, but when you open up this way, he’s more likely to feel comfortable enough. [Read: Arousing sexual fantasies to try in real life]

51. If you lived to be 90, would you choose to have the body or the mind of a 30-year-old for the last 60 years of your life?

This sounds like a funny question to ask, but it’s going to give you an idea of the core values of your partner.

52. Do you feel that you’ve been vulnerable in our relationship?

Is there room for growth? This is a good question to ask your boyfriend if you feel like he needs to open up a little more. It could be the prompt he needs to start communicating more openly with you. [Read: How to be vulnerable in a relationship, open up, and 28 secrets to grow closer]

53. Have I ever hurt you?

Sometimes, the small things we say or do hurt our partners, but we don’t realize it at the time. They might not bother to open up and tell you but internalize their hurt instead.

By asking your boyfriend this question, you can learn lessons from the past and avoid repeating them in the future.

54. What is your biggest fear for our relationship?

This might sound like a negative question, but this type of conversation can actually turn out positively. Fears are nothing more than thoughts. They’re usually not rooted in anything real.

By talking about your fears, you can overcome them and look forward to a more positive future. [Read: How to be fearless – 18 ways to set aside fear and live like a champion]

55. How can I be a better partner?

There’s always room for improvement. However, remember not to take what he tells you super personally or as an attack on you as a partner. You asked so you have to be able to take the answer!

56. What is your favorite memory of us?

Oh, he has at least one. It’ll be interesting to see what he keeps in his memory of your relationship.

This can also help you learn more about his love language because it shows what he deems important and sentimental. Perhaps you can do more of it!

57. What is something you’ve always wanted to tell me but never felt comfortable with?

Hopefully, he’s comfortable enough to tell you now. [Read: 60 deep fun questions to get to know someone romantically as a match]

58. How many children do you want to have?

A little earlier in our list of serious questions to ask your boyfriend, we mentioned asking if he actually wanted children. If he does, you’ll want to know the number he has in mind.

If you’re considering just one or two, but he’s thinking about a soccer team, you might want to think about a compromise!

59. How long was your longest relationship?

This question is useful because it helps you understand whether he’s a guy who likes long relationships or someone who struggles with commitment and tends to have short unions.

That doesn’t mean it’s going to be the same for the two of you, but it could give you some insight. [Read: Is he afraid of commitment? 30 signs he’s scared of a real relationship]

60. Have you ever lived with a partner?

If you’re thinking about moving in together soon, it’s useful to know whether he’s done any of this before. If he hasn’t, you’ll need to cut him some slack while he adjusts to living with a partner for the first time.

61. Have you ever been cheated on or cheated on anyone?

We’ve already mentioned that everyone has a different definition of what cheating actually is. You need to be sure that you both see things clearly and are on the same page. Otherwise, you may end up with murky waters later on.

If he’s been cheated on before, it may explain some of his ways in the present. If he’s cheated on someone in the past, it might not be pleasant to hear, but you’ll understand whether he’s remorseful or not. [Read: Should you forgive a cheater? How and 21 must-knows to make a choice]

62. Have you ever got anyone pregnant?

If so, what happened? How did he deal with it? This is one of the serious questions to ask your boyfriend that may cause him to feel a little awkward, so proceed carefully.

63. What do you think is the best thing about our relationship?

What is he going to choose? The fun vacations or the sex? See if you both have the same answer to this question, but if not, don’t worry.

Having different views of what is so great about your relationship can help you to open up to new possibilities and connect on a deeper level! [Read: 38 signs and traits of a happy, healthy relationship and what it should look like]

64. Do you like spending time with my family and friends?

This one is a tricky question. He’s not likely to say that he doesn’t, but he might hint at one particular person who makes him uncomfortable.

If so, you can use this feedback to try and make life easier for everyone.

65. What makes you the best version of yourself?

What does he think makes him the best version of who he is? That information can help you to understand how he views himself and what he considers to be his strengths and weaknesses. [Read: How to be chill and learn to live a happier life as a result]

66. When was the last time you cried?

Not all guys are comfortable opening up about their emotional side, but this question could be the prompt he needs. You’ll get to learn about the things that make him feel emotional, hurt, or happy.

Not all tears have to be sad tears!

67. What qualities do you admire about yourself?

Does he like blowing his own trumpet? This interesting question will tell you!

68. Were you attracted to me right away?

Don’t take it personally if he says he wasn’t. Maybe it was a slow burn for him. In some ways, that’s often a better situation. It means that he fell for your personality rather than just settling for looks. [Read: The science and rules of attraction and 29 traits that are far sexier than looks]

69. What do you miss most in your life?

Can you bring some of it back into his life? Out of all the serious questions to ask your boyfriend, this could make him feel better about his life and improve your relationship. This question is a really good one, as it helps you get to know someone better on an intimate level.

70. What do you need to feel loved and appreciated?

Again, this one comes down to understanding his love language and how he gives and receives affection. It’s also a good question to learn how to make him feel more loved and appreciated.

Whatever he tells you, simply do more of it! When you ask this question, make sure to make eye contact so he knows you’re intently listening. [Read: 19 ways to be a much better listener in a relationship and read their mind]

71. What do you look for in a partner?

This is one of the best deep questions to ask a guy to get to know what he’s looking for, and if what you both want can be found in each other.

Do they want someone who will be a homemaker, or are they looking for a partner who’s also working? What do they need from their partner? And what do they wish to bring to the relationship themselves? Can you provide these needs for them? [Read: What to look for in a relationship – 23 traits of a happy romance]

72. What are your goals in life?

It’s important to know what a person’s goals are as it gives you a sense of who they are and what keeps them motivated.

Is he interested in getting married? In having children? Does he want to finish university? How does he envision his life? Do some of his goals match with yours?

When you want to pursue a relationship with him, it’s important that your significant goals match. Otherwise, this can cause some form of conflict.

73. What does the perfect day look like for you?

Your lifestyle is another crucial aspect at play when you’re looking to see if you’re compatible. So if a perfect day for him consists of playing video games all day and that isn’t what you have in mind or you’re not comfortable with it, this will be an issue.

We’re not saying you need to find a guy who has the same interests as you, but you need to find at least some form of common ground to spend time together. [Read: Perfect date – 36 secrets to be a good date, plan an ideal one, and impress them]

74. Have you ever struggled with substance abuse?

This is important to ask your partner. Of course, this doesn’t mean that he’s a bad person if he has had substance abuse issues. However, it can be destructive to you if they’re currently dealing with substance abuse as it will cause damage to your relationship, one way or another.

This question allows you to be aware of any or all destructive tendencies when the time comes. 

75. What’s your biggest fear?

Everyone has their own fears, so what are his?

Knowing what those fears are will help you build intimacy and connection. Revealing fears is a vulnerable thing and that vulnerability can help you connect with each other. [Read: 20 downright strange but true phobias about love]

76. Where’s your happy place?

Where is that one place he goes to when he just wants to be alone by himself and reconnect with his thoughts?

We all have a place like that of our own. When he’s having a bad day or he’s anxious, what does he do or where does he go to collect his thoughts and calm himself down?

77. What are you thankful for?

Gratitude is such an important emotion as it helps counter all the negatives in the world. This is one of the deep questions to ask a guy to know what things or people he’s grateful for in his life.

It’s always interesting to see what people value in their lives. Is it money? Their valuables? Or friends and family? [Read: How to be grateful – 20 authentic ways to appreciate and express it]

78. Dogs or cats?

Okay, while this doesn’t exactly classify as a deep question, it can still help him open up more. What if you’re allergic to cats, and he has three cats of his own? You need to know this! 

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

Your personalities are essential when testing your compatibility. If your partner is an introvert and their ideal way to spend time is to watch a movie at home, this could be a problem when your ideal is attending a party and socializing.

Even if you’re polar opposites, ask yourself if you can both find a middle ground. It’s definitely one of the deep questions to ask a guy to spark a real conversation. [Read: Introverts vs. extroverts – why it’s fluid and what splits them apart]

80. What’s your proudest accomplishment?

We all have our big accomplishments that we’re proud of. This is one of the deep questions to ask a guy if you want to know more about his goals and passions in life. It also gives you a sense of what he considers success and the story behind that success.

81. Is your career right now your dream job?

Again, another question about career. While we don’t always end up with our dream job, this helps you see his drive and determination to achieve the career he truly wants.

Also, it enables you to know the story behind how he ended up in his current job. Since these questions are all about getting to know your man, this one is pretty good. [Read: Follow your dreams – all the amazing reasons why it’s worth it]

82. What are the three values most important in a relationship?

It will cause friction when you have conflicting values with the guy you’re dating. So by asking him this, you’re seeing if your values align and whether you share some of those values to make a relationship work. 

Say, for instance, one of his values may be shared belief or faith, and you don’t have that same dedication. It might be a struggle later on. So, pose this serious question to ask a guy to find out. [Read: Ways to know if your relationship is worth keeping]

83. If you weren’t here right now where would you be?

This question lets you know if this person is having a good time or if they think they would be having more fun somewhere else.

84. What is a childhood TV show that you would still watch now?

Not only is nostalgia a trend but reminiscing on your childhood loves can bring you closer. You may have grown up a country apart, but both woke up before everyone to watch your favorite cartoon when you were kids.

Not all deep questions to ask a guy have to be super serious! [Read: 65 couples activities and fun things to do that’ll make you feel closer than ever]

85. What is something I would be surprised to learn about you?

When you just meet a guy, you probably are anticipating finding out his job, maybe his favorite Netflix show, and what music he likes. But learning something out of the ordinary is where you go from just meeting to really getting to know each other.

So, maybe he is going to tell you he plays guitar or surfs. Or maybe that he can’t even boil water. No matter what it is, it is bound to be interesting. So push the limits a little. [Read: 22 flirty secrets to impress a guy and leave him totally obsessed with you

86. Do you believe in monogamy

This is a tricky yet serious question to ask a guy. Depending on what you’re after, you either get the perfect response or hear something you wish you hadn’t.

In most cases, if you’re looking for a relationship, hearing that the dude’s just not down with monogamy can be an instant spark killer.

87. How would you describe yourself in one word?

This is one of those perfectly good questions to ask a guy because it reveals so much about him, and it’s coming from his own mouth. 

When women describe themselves, their habit is to be self-deprecating. When men describe themselves, they tell you EXACTLY who they are. If a man tells you he’s lazy, generous, stingy, selfish, or talented, believe him. [Read: Self-concept – how we create and develop it to control our happiness]

88. What job would you have if money was not an issue?

A lot of people put their passions to the side in order to get a “normal” job, so seeing where his passion lies when money has no bearing on his life gives you an interesting insight into him.

It’s one of the serious questions to ask a guy because you’ll learn a lot about him with one simple question. [Read: How to tell if a guy is playing you – 40 signs he’s just using you]

89. How many hearts have you broken?

Every man breaks at least one heart. So, if he says none then he’s either lying because the number is much higher than he wants you to know, or he’s incredibly naive. Or emotionally disconnected. Or both.

He might not want to talk about it, so don’t push it, but it’s one of the serious questions to ask a guy to at least try to find out.

90. If you could master any craft or subject, what would it be?

This question brings out a side of him that indicates any hidden talents he has. It also shows you his deeper interests and what kind of ambitions he has. A man who doesn’t want to get better at any subject or craft is a man with no passion in life. [Read: Signs of low self-esteem and 5 ways to increase it]

91. How many times have you been in love?

Always be incredibly cautious of men who have made it pretty far into their lives and have never been in love. Men who don’t know how to love someone else can’t be changed by you; they need to be able to change themselves.

As far as deep questions to ask a guy go, this is probably one of the most searching.

92. Do you watch porn?

Most men who claim that they don’t or have never watched porn are complete liars. Not all men enjoy watching porn, but almost all of them have watched some at some point or been curious about it in some form.

Also, asking him this question probably throws him off and gets him out of his comfort zone. [Read: 108 casual-yet-deep questions to ask a guy to get to know him in minutes!]

93. What’s your life mantra?

What words of wisdom does he live by? What philosophical quote speaks to him the most? And what thoughts get him out of bed in the morning? Having a strong life mantra can be very powerful when it comes to shaping your values and motivations.

94. What would your autobiography be called?

A lot of people secretly dream of penning a series of memoirs one day. Find out what his would focus on. Is he the hero in his own story or the misunderstood villain? Would his book be a comedy or a tragedy?

This deep question to ask a guy is pretty revealing and sometimes sets the whole tone for who he may be deep under all the bravado and cologne. [Read: 85 very flirty questions to ask a guy you like and leave him thinking of you]

When is the right time to ask your boyfriend serious questions?

Is there a right time for these serious questions to ask a guy?

Yes and no. It’s never a good idea to sit your boyfriend down and fire questions at him one after the other because it might feel like an interrogation.

It’s also not advisable to ask some of the more serious questions after you’ve just met, as it could make him think you’re rushing.

You’ll know when you’re connected enough to explore some of these questions. You can also go for one of the less serious options first and see how he responds. If he opens up willingly, you can throw a couple more in. Then, wait a while and try again.

Of course, if he’s stressed out or not particularly happy about something, it’s not ideal to try and have a deep conversation. Feel it out, and go with your gut on this one, but remember these deep questions to ask a guy whenever the opportunity arises.

[Read: 42 secrets to communicate better and ways to fix a lack of it]

The key to a healthy relationship is being honest. If you can’t be honest in the beginning, what makes you think things will get better? These serious questions to ask a guy will help you learn all the important details in no time!

Liked what you just read? Follow us on Instagram Facebook Twitter Pinterest and we promise, we’ll be your lucky charm to a beautiful love life. And while you’re at it, check out MIRL, a cool new social networking app that connects experts and seekers!

Vinod Srinivas Serai
Vin Serai
Vin Serai is the founder of LovePanky.com, and has delved deep into the working of love and relationships for almost two decades. Having dipped his feet in almo...