40 Deep Questions to Ask Your Boyfriend & Answers You MUST Know (2024)

Learn some deep questions to ask your boyfriend ahead of time and then, when you want to have conversations, you can pepper them in and find answers!

There are many things we keep hidden during the beginning of a relationship. The problem is, these things we keep from our significant others are typically the things haunting the relationship later on. If you hide the crazy for too long, and then let it all out at once, it is nothing but, well, crazy. These deep questions to ask your boyfriend can help you avoid that.

Being yourself is key to any successful union, including being honest and asking uncomfortable questions. If you get to a point in your relationship where things are getting serious, proceed with caution.

Those things that you think are not such a big deal become a major kink in the relationship chain if not addressed early on.

All those little voices in your head making you question things your boyfriend does and whether it will be an issue later are there on your mind for a reason. Yes, they will be a problem. Especially, if you don’t clear the air by asking those deep questions no one really wants to ask.

[Read: 30 serious questions to ask your boyfriend and create a real bond]

The 40 most important, deep questions to ask your boyfriend

The problem in most relationships is that we are afraid to ask intimate questions upfront. It’s for fear we’ll make someone uncomfortable or send them a message that we are moving too quickly.

But when you don’t ask the important questions, you run the risk of falling in love with someone who isn’t right for you.

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. [Read: How to get to know a guy you want to date]

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.

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?

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 deal-breakers a guy won’t come right out and tell you about. By learning what broke up his old relationship, it provides you with insight into whether he has been hurt or cheated on.

It will also tell you if there was something that simply wouldn’t do for a relationship to move forward. [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, avoid triggers like trust problems. 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.

There are some who absolutely can’t live with them and those who can’t live without. Just make sure you are on the same page before falling in love. [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.

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.

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 doesn’t attend mass, the religion 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 bra-burning 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.

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?

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. [Read: 21 things that will turn any girl into a crazy girlfriend]

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?

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 tell everything to, but he wants to keep things to himself, that creates issues of closeness and feeling 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.

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 for you two. Make sure you are on the same financial page to avoid potential problems 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 the completely 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 isn’t comfortable or something anyone wants 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 indication of how he will 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 because 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 highlight his character. How comfortable is he with letting you shine even if it makes his star not so bright all the time?

31. Do you have any debt?

It might make you cringe to ask, but you need to know whether he’s knee-deep in credit card debt now, or run the risk of issues later. [Read: 17 brilliant yet simple ways to save money as a couple]

32. 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.

33. 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.

34. 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]

35. 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.

36. 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 good to know.

37. 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]

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

This is a deep question to ask your boyfriend 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!

39. 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.

40. 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]

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? By the time you feel comfortable asking the most important questions, you will be in love, and it will be too late. But these deep questions to ask your boyfriend will help you learn all the important details in no time!