Think that knowing some serious questions to ask your boyfriend will scare him off? It all comes down to how you ask to find the answers you seek.
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 is nothing but, well, crazy. These serious questions to ask your boyfriend can help you avoid that.
Being yourself is the key to any successful union, including being honest and asking uncomfortable questions. For sure, 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 become a major kink in the relationship chain if not addressed early on. [Read: How to communicate in a relationship – 16 steps to a better love]
The importance of serious questions to ask your boyfriend
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 children or if you see yourself getting married at some point, are important topics to agree on.
The problem is, many people avoid serious questions such as this because they worry it’s going to make the guy run a mile. It will if you ask him on the first date, but after a short while, if he’s not open to answering the odd question like this, do you really want to be in a 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. [Read: 10 communication techniques to finally get them to open up to you]
Deep questions to ask your boyfriend and get to know him better
These are the best deep questions to ask your boyfriend. Uncomfortable, yes, but necessary to take things to the next level with trust and honesty.
1. Are there things you have done in your 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.”
Giving them the floor to make any confessions about their past ensures you never get blindsided. [Read: How to get to know a guy you want to date]
2. What type of guy were you before you met me?
Is he the serial monogamist, or the 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 your boyfriend you should always attempt to ask. [Read: Avoid them like the plague – 16 types of guys not to date]
3. What were your old girlfriends like?
This is one of the serious questions to ask your boyfriend 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 learn what it was about the other relationships that didn’t work. This could help you avoid making the same mistakes. [Read: 17 relationship deal breakers you need to fix if you want to be a good partner]
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 relationship, it provides you with an insight into what he has been through before. [Read: 13 secrets signs your boyfriend’s not over his ex]
5. Have you been in love before?
Knowing whether he thinks he has been in love before tells you whether he has the emotional maturity to get in touch with his feelings.
You have to have something to compare your feelings to, and if he hasn’t ever been in love, then how does he know what love is or when to recognize it? [Read: Manchild alert! 23 signs you’re dating an immature prick]
6. Who was the first girl to break your heart and how did she do it?
We all have baggage in our past. Knowing what is in his issue suitcase helps you navigate difficult times with him.
By using this deep question to ask your boyfriend, you can even reassure him that you aren’t his ex, nor would you ever do what she did.
7. What is your five-year plan?
Does his five-year plan involve a family and wife, or is it all about his career?
Guys who have plans rarely veer from them, 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 he’s grown a real pair]
8. Do you like children and do you want to have them?
This is one of those deep questions to ask your boyfriend to reveal his future wants. Women typically put off this question because we fear scaring the guy off and make them think our biological clock is ticking.
The truth is that no relationship is going to be healthy if you want different things out of life and children are about the biggest change a relationship goes through. [Read: Emotionally unavailable man – 25 red flags to look for]
9. What is your biggest pet peeve?
Those little things we do to irritate each other at the start don’t seem that big. But after time, they become deal-breakers. Find out what his biggest pet peeve is so you know if it is something inherent in you or something you are capable of avoiding.
This is one of the most serious questions to ask your boyfriend that may look playful on the surface, but actually gives you great information for the future.
10. What is a deal-breaker to you?
What is it that he simply can’t live with in a relationship? You need to know this to make sure that your needs and values are in alignment. If they’re not, it’s simply not going to work out. [Read: Relationship deal breakers you need to look out for]
11. Do you think divorce is okay?
When you get married, no one ever thinks they will get divorced, but there are some with a greater commitment to seeing it through. While others think if it isn’t going so well, divorce is a way out.
It is important you both are on the same level of marriage commitment. [Read: The 14 telling signs it’s time to give up on a relationship]
12. If you do have chldren, is it important what religion they are raised?
Even if he isn’t actively religious, the faith he raises his children may be very important to him. And, if you aren’t the same, that could pose some serious problems not just for you two, but your families as well.
13. What are your political beliefs?
Politics are something 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: 15 big relationship questions you must answer before the next level]
14. What do you think about prejudice?
We all hide our prejudice when we start dating for fear of judgment, but if he has some serious prejudices against some group or religion, that is something you may want to know 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 in his life? Is it your family first, or the peripheral family, that guide 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.
17. Do you expect your wife to 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 because if you both see things differently now, it’s not going to improve in the future. [Read: 21 things that will turn any girl into a crazy girlfriend]
18. Will you 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: How to talk about money with your partner without fighting about it]
19. If you were in trouble would you hide it from your wife?
This is one of the deep questions to ask your boyfriend that’ll give you an insight into your future together.
Is his wife his confidant or is she just an accessory? If you want to marry someone who you share everything with, but he wants to keep things to himself, that creates issues and you’ll feel like he hides things.
It is a very complex road to go down.
20. What is more important, 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 a 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, and he has credit card debt that is out of control, that can create huge problems. Make sure you are on the same financial page to avoid potential drama in the future. [Read: How to make a relationship last – 19 love commandments]
22. How strict were your parents?
We tend to parent the way we were parented or go completely the opposite. How did his parents raise him and does he think that it was the right way or completely 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, draining your savings account just because he felt like he needed an impulse buy? Or does he think he should discuss it with you? [Read: 10 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 even if it wasn’t comfortable or something anyone wanted to talk about?
25. Would you ever look at my phone or through my personal things?
If he starts spying, you will too, and then the trust slowly gets chipped away. [Read: Boundaries in dating – How far is too far?]
26. What do you remember your parents fighting about?
Were his parents disconnected, fighters, or good communicators? You tend to do what you grew up with *or the exact opposite of it!*, so knowing how his parents related is a good indicator of how he might communicate with you.
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 just what he does; then those are the things you need to know. You will be doing them forever if things last. [Read: 17 personal things to ask a guy to get the inside scoop]
30. Would you be okay if your wife was more successful than you monetarily?
This is one of those deep questions to ask your boyfriend that highlights his character. How comfortable is he with letting you shine even if it makes his star not so bright all the time?
31. Have you ever been in trouble with the police?
For sure, he might have had some problems when he was younger and changed. You can’t judge him by his past, but you should ask if you want to be sure he’s really changed. [Read: Dirty secrets from your past]
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.
After all, it’s better to be warned about the crazy that may come your way.
33. Do you believe in having children outside of marriage?
Some people are dead against it, others don’t mind. It’s important to know where he stands on it, so 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’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 brother being the favorite.
This can change his outlook on life, so it’s one of the serious questions to ask your boyfriend and find out. [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. [Read: Why you should run if you see these early relationship red flags]
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 more important to you or money?
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 best to know.
39. Do you see a future with me?
Ah, the most awkward of them all but one that we all want to ask, secretly! It’s one of the deep questions to ask your boyfriend that will probably be a make-or-break one. So, proceed with caution. [Read: 150+ deep relationship questions every couple must ask each other]
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 from then on?
41. What do you think about our sex life? Do we have enough sex?
It can be awkward to come right out and ask his opinion on this. You might also 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 between the sheets right now, maybe this chat will change all of that! [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 perhaps in other people. It could be that he’s too hard on himself completely and you can reassure him about it all.
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 must-ask serious questions to ask your boyfriend. [Read: How to deal with regret and learn to face your reality for what it is]
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, we all need things in a relationship and unless we 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.
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 response, so be prepared to tell him what you love about him too!
48. Who is your role model in life?
It is his father? Mother? Who does he look up to?
49. If you could live anywhere, where would it be?
Let’s see where he dreams of. Perhaps in the future you can start making plans to move there, if it’s a place that you both love equally. [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 question 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 to do the same. [Read: 12 arousing sexual fantasies to try in real life]
51. Have you ever been in love before?
Are you the first? Or his second?
It’s true that not everyone who has been in multiple relationships has actually been in love. Maybe it was pure lust, or maybe he thought it was love but in the end, he realized it wasn’t.
52. Do you feel 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: What does it mean to be vulnerable? 15 ways you can open up more]
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 and instead, they choose to internalize their hurt.
By asking 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 a thought – they’re usually not rooted in anything realistic.
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?
Hopefully, he’s comfortable enough to tell you now. [Read: 60 get-to-know-you questions for a new romance]
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 and he’s thinking about a soccer team, you might want to think about a compromise conversation!
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 at least. [Read: How to talk about past relationships and not piss your partner off]
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’s not, 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 on the same page here, otherwise you may end up with murky waters to deal with 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 will then understand whether he’s remorseful or not. [Read: What is cheating in a relationship? The truth most people ignore]
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 you share 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! [Read: Healthy relationship – 27 signs, qualities, and what it looks like in real life]
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 outright doesn’t, but he might hint at one particular person who makes him uncomfortable, etc.
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 his strengths and weaknesses to be. [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 all 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 question will tell you!
68. Where 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, and in some ways, that’s often a better situation. It means that he fell for your personality rather than just settling for looks. [Read: Science of attraction – 17 things that are far more sexy 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.
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, you simply do more of it! [Read: Words of affirmation – How to use them and 20 examples to say it right]
When is the right time to ask your boyfriend serious questions?
Is there a wrong and right time for these deep questions to ask your boyfriend?
In some ways yes and in other ways, no. It’s never a good idea to sit your boyfriend down and fire questions at him one after the other at any time. It’s also not advisable to ask some of the more serious questions after you’ve just met.
You’ll feel 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 such as this. Feel it out and go with your gut on this one.
[Read: Lack of communication in a relationship and why it signals the end]
The key to a healthy relationship is being honest. And, if you can’t be honest at the beginning, what makes you think things will get better? These deep questions to ask your boyfriend will help you learn all the important details in no time!
