20 Things to Ask Your Boyfriend to Get to Know the Real Him

graceDo you really know your boyfriend? Put yourself to the test with these things to ask your boyfriend, and you’ll know just how well you know him.

As much as you may assume you know someone very well, there are times when you’d 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! And that’s where these things to ask your boyfriend can really help you.

I hate when I’m having a conversation with my boyfriend and he says something that just blows me away. Not because I’m surprised, but because I thought I knew him better and knew his opinion on the matter. So this basically means I hate being wrong about how well I know him.

That being said, I think most of us don’t really know our boyfriends that well. We might know their favorite meal, what show they binge watch on a Monday night, and even what their dream car is, but do we really know who they are as a person?

Things to ask your boyfriend

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?

I, for one, would prefer to always converse about the important things in life. I would like to have the relationship with my boyfriend where I know with full certainty that if he was in a coma or otherwise impaired, that I would be able to make the choices that he would make for himself if he could.

That’s a very high standard to hold my relationship to, I know, but that’s how I want it to be. And I’ve found that with these things to ask your boyfriend, I have been able to open him up and get to know the real him.

#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.

#2 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.

#3 What’s your opinion about life after death? I personally believe ghosts exist – or their spirits do – or whatever you want to call the afterlife. However, my 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.

#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.

#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.

#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.

#7 If you could do one thing 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.

#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.

#9 What is 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.

#10 If you could have a *do-over* for one thing in your life, what would 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.

#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.

#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.

#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, and this will give you the opportunity to tell him so he feels better about it.

#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.

#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.

#16 What about across the world for your dream job? Across the country is nothing but a short flight, but to move across the world for just a job… it could mean that he values his career choice more than anything else in his life.

#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.

#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 that are like this in nature is one of the most vital things to ask your boyfriend.

#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.

#20 Do you believe in having a soul mate or that love is a choice? To me, I think that there’s someone – or even multiple people – out there for everyone and you’ll find them someday. But my boyfriend believes in love being a choice. This was something I was really glad to know early on because it definitely changed how I felt in the relationship – not necessarily in a bad way, though. But it is something that’s good to know.


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.

Source: lovepanky