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20 Fun Things to Ask Your Boyfriend to Get to Know Him Inside & Out

If you want to get to know your boyfriend better, you need to have great conversations. These things to ask your boyfriend will help you get started.

fun things to ask your boyfriend

As much as you may assume you know someone very well, there are times when you realize there’s so much more to learn about them. And the best way to know more about someone is by, well, just asking them! That’s where these things to ask your boyfriend can really help you.

The truth is, you think you know everything about a person, but the reality is often different.

It doesn’t matter if you’ve been with your boyfriend for a while or not, there are probably still things you don’t really know, or didn’t realize. It could be a thing from his childhood or an opinion he has. Asking questions helps you to find these things out and then you can really say that you know him!

Of course, if you’re going to ask questions, it means you have to be prepared to give answers too. It’s only fair! Don’t fire question after question at him like he’s in a job interview, but a few peppered into the conversation here and there will give you plenty of knowledge.

[Read: 25 topics to text or talk about with your boyfriend to feel closer]

Things to ask your boyfriend to really get to know him

The problem with getting into a daily routine with someone is that you no longer have in-depth conversations that reveal who they are. You make them supper or buy them a sweater that you know they’ll love, but do you have any more important conversations?

Some of the questions are deep, some are less so, but they’ll certainly reveal a lot. [Read: 56 romantic questions to ask your boyfriend and feel instantly closer]

1. If you had your dream job but made very little money, would you still be happy?

If you’re wondering about things to ask your boyfriend, this question really shows you his true intentions in life. Does he want a lot of money or would he rather be poor but do something he loves? It’ll show you a lot about his drive and dedication. He might surprise you!

2. Be honest, do you believe in love at first sight?

Some guys are hopeless romantics who believe this is to be true 100%, but others would say this is a complete myth.

It’s great to know which side your boyfriend falls on. If you’re a true romantic and he tells you that he doesn’t believe in love at first sight, don’t despair. It’s actually a good thing. It means he takes the time to get to know someone before committing his heart, and that’s a cautious yet sensible approach for long-lasting love. [Read: The truth behind love at first sight]

3. What’s your opinion about life after death?

Do you believe ghosts exist – or their spirits – or whatever you want to call the afterlife? Maybe you do and your boyfriend doesn’t believe in this at all.

It can tell you a lot about his beliefs and it’s also just a fun question to ask. It’s not something you necessarily have to agree on, so don’t panic if you have differing views.

4. Has anyone ever cheated on you?

The answer to this question can tell you more about how your boyfriend operates in this relationship than any other question. If he’s possessive, controlling, or even just insecure without those other qualities, this could explain why.

Plus, it’s always good to know if this has happened in your boyfriend’s past. This is one of the most important things to ask your boyfriend.

Remember that he can also turn any question around and ask you too. If you ask this question, be prepared for him to say “what about you?” Always be honest, because the whole point of these things to ask your boyfriend is to deepen your connection through honesty and openness. [Read: What is cheating in a relationship? The truth most people ignore]

5. Could you ever forgive someone for cheating on you?

This is a great follow up question because his answer could mean a lot about who he is as a person. If he just can’t forgive something like this, it also shows you how important this offense is to them in a relationship.

However, do reassure him before you ask him this, and don’t just come straight out of the blue with it – he might wonder why you’re asking and if you’re hiding something! [Read: Are you cheating? 8 accidental ways you could be cheating without realizing it]

6. Describe your faith, or lack of one

Knowing someone’s faith is extremely important. Even if you don’t agree with it or see eye to eye on certain things about their beliefs, it’s great to know how their mind operates when it comes to this subject.

He might not have a faith, or it might be that it’s something he’s still figuring out. Either way, it’s one of the important things to ask your boyfriend.

7. If you could do one things with your life, money not a factor, what would it be and why?

If you really want to know your boyfriend’s true passions, ask him this question. You’ll get to see how he would truly be happy if money was never a factor.

You may not have even thought about this as being one of the things to ask your boyfriend but it gives you a lot of important information about who he is as a person. [Read: 30 fun and super cute questions to ask your boyfriend to have a laugh]

8. What has been the best day of your life so far?

Good things happen to people every day. But when someone has a “best” day, you should know about it. It can show you just what is most important to them and what makes them the happiest.

It might not even sound like anything that earth-shattering to you, but there will be a small detail in there that made it ultra-special for him. [Read: 60 get-to-know you questions for a new romance]

9. What is the one thing you wish your parents knew about you?

Whether they answer with a dirty little secret of something they once did or a profound message that they truly wish their parents knew, you will learn a lot about their relationship with their parents with this question.

If they try and shy away from it, it could be that they don’t really have a great relationship with their folks. That’s another conversation you can have, when you both feel comfortable talking about it.

10. If you could have a do-over for one thing in your life, what woud it be?

This question can show you what your boyfriend’s greatest regrets were and maybe it will shine a new light on why he does things a certain way.

Of all the things to ask your boyfriend, this is a very crucial one because it tells you about the things he wishes and the things he regrets. [Read: The different kinds of regret and how to deal with it]

11. What’s the worst thing you would do for a million dollars?

This is assuming he doesn’t already have a million dollars. If that’s the case, lucky you!

But some people will say they’ll commit murder for that kind of money, while other people say the worst they would do is steal something. His answer could speak volumes about his character. What lengths will he go to for that kind of cash?[Read: How well do you know me? 35 fun questions for couples]

12. What are you the most ashamed of in your life?

Of all the things to ask your boyfriend, this one is really telling. Everyone has something that they’re ashamed of and knowing what your boyfriend is ashamed of is a powerful thing to know.

They have to be really vulnerable and open up when talking about this topic. It’s probably not the best question to ask if you don’t know your boyfriend that well, i.e. you’ve only just started dating. Perhaps put this on the list of things to ask your boyfriend once you’ve been together a little while longer in that case.

13. If you could change one thing about yourself, what would it be?

Not only will this highlight an insecurity they have, but it could be something that you love about them. Then, that will give you the opportunity to tell him so he feels better about it.

We all have insecurities and hearing someone say that they love that thing about us, can help us to overcome that hang-up. [Read: 12 common insecurities of men that most women have no ideas about]

14. Do you think your parents are proud of you?

Knowing how your boyfriend sees himself in his parents’ eyes will help you to understand how he sees himself in relation to other authority figures – and even how he sees himself in relation to you.

When you are still wondering about things to ask your boyfriend, don’t forget to ask about his family using a question like this one. Again, if he doesn’t have a great relationship with his parents, this question may hit a nerve. In that case, tread carefully and don’t push it.

15. Would you move across the country for your dream job?

Is his passion to have his dream job strong enough to drive him across the country – or to another country? If the answer is yes, then you also know what your future could look like. He might tell you exactly what his dream job is and where it may take him.

If you end up together in the long term, that could be something you need to know about. Then, you can work out how you feel about the possibility yourself. [Read: Follow your dreams – All the amazing reasons why it’s worth it]

It could also mean that he values his career choice more than anything else in his life. How do you feel about that? [Read: Love or career? How to make the right choice in life]

16. What is a character trait you value most in a person?

What makes your boyfriend respect someone? What character trait does he respect, admire most, or desire most in a person he comes across? This is one of those things to ask your boyfriend you need to pay special attention to, because it clearly shows the values he would be hoping to see in you as well.

All of us have core ideas and principles in life that are built because of our upbringings or the way we see life. What are his? And most importantly, do you see yourself having these traits in you?

17. When/if you have kids someday, what’s the one thing you hope they grow up knowing about you?

This will give you insight into something that he probably doesn’t tell anyone else and that he probably wants most people to know about him.

You’ll be able to understand what he sees as his most important attribute. It could also tell you almost instantly whether he wants children or not – assuming you’ve not been together long, you might not know yet.

18. What do you think is the most important thing in a relationship?

If he says showing affection and you think it’s communication, then the two of you could be on completely different pages – which could cause issues down the road.

Talking about what’s most important now could be a savior. Questions like this are vital things to ask your boyfriend. [Read: 50 questions to ask and find out if someone’s right for you]

19. If you could describe yourself in only one word, what would it be?

Not only is this a fun question because it makes them think really hard about one SINGLE word that describes them, but you’ll get to see how they see themselves.

You could help them out and respond with a single word that you feel sums them up. It might be something similar, or totally different!

20. Do you believe in having a soul mate or that love is a choice?

Does he think there’s someone – or even multiple people – out there for everyone and you’ll find them someday? Or, does he believe in love being a choice? Knowing this information won’t necessarily change anything in your relationship, but it’s interesting to know, nonetheless.

[Read: Real soulmates – 20 signs you’ve found the love of your life already]

You should know the real version of the boyfriend you’re dating and not just what he shows on the surface. With these things to ask your boyfriend, you’ll get to know more about him than he could ever explain to you.

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