20 Serious questions to ask your boyfriend

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By: Naveen B

Is your boyfriend the love of your life? Do you want to spend the rest of your life with him?

If so, it’s important to know that the early days of dating are just that — early days — and while you can’t anticipate everything that will happen between now and your wedding day.

If you’re seriously starting to think about what life with him would be like. But before you make any big decisions, you want to make sure he’s really right for you—and not just what you want him to be!

You should consider some serious questions to ask your boyfriend as an opportunity to discuss the future of your relationship with honesty and openness.

Asking serious questions to your boyfriend can seem like an intimidating idea, but it’s actually one of the best ways to get to know each other better.

Also read: 31 Deep questions to ask your boyfriend (Be evolved after this conversation with him)

Whether you’re worried that you might get too serious or simply need to know how he feels about certain things, asking him these serious questions will help you to understand the man in your life better and help you move forward in your relationship together.

Here is the list of 20 deep serious questions to ask yourself to get to know your boyfriend better and ensure that he’s someone you can build a lifelong relationship with.

Recommended reading for you: 25 tricky love questions to ask your boyfriend

Serious questions to ask your boyfriend

Questions to ask your boyfriend 20 Serious questions to ask your boyfriend

1. If you have only 3 hours to live, what would you do?

This is a sort of rapid-fire question. It will challenge your boyfriend to think of life and how precious it is, when in fact you are also thinking how precious he is in your life.

A guy doesn’t always need to be told they are important in someone’s life, but instead how important they are with these questions.

They may not give you an actual answer for it because they don’t know what to say, but their thoughts behind their answers can be just as telling about their character!

Either way, you just want to get him talking about himself more than anything else!

2. Have you ever cheated on me?

This serious question will create a serious discussion between you and your boyfriend. It’s better to start talking about this serious topic right away than find out later that he did cheat on you.

If he said no, then you can trust him again. However, if he said yes, it means that there is some problem in your relationship that needs resolution as soon as possible.

In any case, both partners should be honest during such conversations for the future development of relations.

Most men would definitely say no to save their relationship. But, accidentally if he slips his tongue or confesses his infidelity that would show his honesty.

However, if he is guilty about it, you both should have a constructive discussion to prevent this in the future if you both are truly committed to each other.

Recommended reading for you: 350+ Questions about love that make you think

3. How often do you think of other women s#xually?

This serious question reveals his sexual confidence and fidelity. If he says he doesn’t think about other women, you may not feel that confident in him—or that sexual connection.

After all, men are often thought of as more promiscuous than women (which isn’t always true). If you’re concerned about his answer here, tell him what you want: 

For example, I like it when you think of me while we make love. That way I know we both get maximum pleasure from our time together.

Are you ready for a serious relationship?: You both probably want to know if you’re on a path towards something deeper—the question is whether you want that as well.

But be warned: He might answer yes, even if he doesn’t have those feelings for you—maybe because he wants a long-term partner and maybe because he wants to keep things casual.

Also read: 100 Trap questions to ask your boyfriend (Persuasive and Funny)

4. f I can’t stop thinking about you, are you thinking of me?

This question tells about the connection between you and your boyfriend. The answer would give you a complete idea of how much he loves you or not.

If he thinks of you too often, it’s a good sign that he might have strong feelings for you.

However, if he says no then it means that he doesn’t have much feeling towards you at all.

Of course, that’s not always true but, on average, it’s a good indication. If you are wondering what are some things to talk about with your boyfriend then you can ask him if he thinks of you too often.

You don’t have to wait for special occasions to ask these questions. You can use them on a regular basis because they are actually very important in understanding how he feels about you.

Knowing these things will surely help you win his heart more easily and make him love you more deeply every day. 

Also read: 33 Trick questions to ask your boyfriend to see if he loves you

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

This question will make him reflect on himself, but it’s likely that he’ll think fondly of you. You can actually learn a lot about how much he loves you by asking about things he’d change about himself.

He may say something like I would be better at communicating my feelings for you, or I would be happier if I had more time with you, which tells you that he’s thinking about spending quality time with you and appreciates all of your positive qualities.

He might even say something negative like I wish I were better at making decisions in certain situations, which shows that not only does he respect his own strengths and weaknesses but also values yours

Also read: 50 Relationship questions to ask your boyfriend (Deep & serious topics)

6. What makes you a man?

This question is a bit offensive, as it will question his existence itself. However, it will also reveal how he will tackle that kind of situation and how strong-willed he is.

If he can handle such an inquiry with respect and composure. After all, men face trials and tribulations every day; they deal with problems too big for them; they handle rejection; pressure; money matters (or its lack); heartbreaks, and disappointments—heck!

Even if we speak about finances or making up an embarrassing moment that could make him uncomfortable by bringing those feelings up again.

If you want what’s best for him and you can put those small things behind you – then any relationship stands a great chance at succeeding in the long term.

If you want a guy who can handle stressful situations with ease, then you might want to give him a try after going through his answer.

The best thing about getting serious answers from a guy is that you can learn a lot about them in a short amount of time.

So take some time from your schedule and have an open chat with your boyfriend about what makes him tick.

Also read: 50 Trick Questions Ask your Boyfriend

7. When was the last time you lied to me and why?

This serious question will make sure that you and your boyfriend aren’t spending time together and not communicating.

If he cannot be honest with you about something as little as a lie, then there may be bigger things going on. Lying by omission is still lying. If you find out that he has been less than truthful, then confront him about it immediately.

Do not wait until you are ready to forgive him because there is no such thing as forgiveness when it comes to infidelity or something worse. 

The only thing that ruins a relationship is lying, and if you’re willing to forgive lies, then he will do it again.

You can’t change another person; all you can do is remove yourself from their situation and put it back in their hands. If they want things to work out between you two, then they will be honest with you. Which tells you what kind of man he truly is inside his heart and mind.

8. Why do I have a feeling that you are just using me as a s#xual partner and nothing more?

This question will bring out some honest feelings from him, without you actually having to be vulnerable and open up yourself.

If he says no or gets angry, it is most likely true. If he gets upset, or explains how he feels about you, then there might still be hope! Either way, it will definitely create an interesting conversation with him.

However, just remember whatever he answers, you don’t take it personally. He doesn’t know what he feels until he is in that situation, so there’s no need to feel hurt or angry.

Just keep an open mind, and maybe even laugh about it! After all, these are only two little words.

But if you truly think there might be something more than friendship between you and him… These next couple of questions will help reveal his true feelings toward you!

Remember, though – do not over-analyze every single answer to every question – men are simple creatures.

9. How would you prove your loyalty to me?

This genuine question will help gauge just how much your partner cares about you.

If they can’t even think of a single way they could prove their love and devotion, then it’s probably time to think twice about the status of your relationship.

And remember: Loyalty is a two-way street—so you should be able to answer it too! Just be careful, because if you’re not actually ready for a serious relationship, but he is, things might get awkward when he doesn’t want what you don’t have to offer him.

10. Describe a “Woman” in 3 words.

This is such a serious question that will help you determine if he sees women as people or objects. 

Is he clear about who they are? 

Or does he see them only in terms of what they can do for him?

What does his response tell you about how he thinks about girls/women in general? 

It might be an indicator of an unhealthy relationship, particularly if his answer is demeaning or disrespectful. Even worse is when a guy answers with sex because it shows that women are nothing more than an object for him to use.

Even though, don’t just judge him and jump to conclusions right away. Sometimes some men are not that articulate in expressing their thoughts and emotions. 

So, try to be patient with him. Perhaps his answer was influenced by culture or past experiences. Not all women will like women described only in terms of motherhood (not all girls want kids) or love (not all girls are looking for love).

Also, they might appreciate more complex adjectives like compassionate or strong-willed or witty or spirited, etc. Try not to let your bias towards them cloud your judgment of how he views them as human beings.

11. How are you different from other men?

This question will allow you to understand how he defines himself. It’s a good idea to learn what separates him from other men.

If he thinks that there is nothing really special about him, that may be a sign that you’re not his type of woman.

On another hand, if he can tell you all of his strengths and what makes him different from other guys, that’s good news for you!

There’s a high chance that he’ll treat you differently and also pay more attention to you.

12. What are your 5 core principles in life?

This question will allow you to really dive into their mindset, and it’s a good way for you two to know more about each other.

What are their morals? Their values? Their hopes for the future?

Once you start considering these kinds of serious questions to ask your boyfriend, there are no right or wrong answers. You just want to get an understanding of what they believe in.

They should be able to do the same for you as well so that you can decide if they’re right for you.

If not, no hard feelings because now at least you have a better idea of who they are as a person before becoming committed or serious with them! 

The main thing is that honesty is important in any relationship, but especially one that’s new.

13. How would you rate yourself from 0 to 10 in terms of honesty, truthful, trustworthy respectively?

This serious question will help you evaluate whether or not you can trust him with everything that is going on in your life. If he says 8, then I’d say are you being honest?

He might even want to follow up by asking how did I reach my rating. The next question you should ask is Do you respect me enough to do what I tell you even if you don’t agree?

If he says yes, let him know how important it is for a relationship to have open communication and respect each other.

Be an open book – if he knows he can trust you with whatever may come, then that’s one less thing that could ever tear you apart.

You’ll also feel more comfortable talking to him about issues that might arise if you know for sure you’re telling him everything. Most of all, it’ll make you both more willing and eager to be honest with each other.

It can be pretty hard at times to tell someone exactly what’s on your mind, especially when it comes to emotional or serious topics.

However, being able if possible makes all of your relationships stronger. If anything negative happens, there are no surprises because both parties are aware of them before they start acting too involved in their relationship.

14. How many past relationships have you had and how many of them are still in contact with you?

This question will help you know how much experience your boyfriend has in relationships. If he’s had one other serious relationship, it could be a sign that he doesn’t have what it takes to remain faithful.

If he has two or more past relationships, it could be a sign that he is emotionally unavailable or even addicted to being in love with someone else. Both are serious warning signs that should tell you something about his character.

If he says he doesn’t have any past relationships, it could be a sign that he’s lying or hasn’t had enough experience to know what he wants or he just doesn’t want to hurt you by talking about his past.

Sometimes, it’s true and good that it’s better not to discuss the past. We all had our own pasts but one thing we could remember as we grow old. We become mature and our priorities will change and as well as our personalities too. If this is the case, then it’s good for your relationship.

15. What are relationships and marriage mean to you?

This question will show his maturity and understanding of relationships. He’ll have a difficult time answering it, so he may even put some thought into it before replying.

This may be a hard question for you to answer as well, but doing so could make all of the difference in your relationship.

After all, what’s more, important than sharing similar core values? By opening up with each other on these topics, you can gain great insight into each other’s thoughts and potentially save yourself from unnecessary arguments down the road.

16. How would you approach conflicts and misunderstandings between us?

This question will give you an idea of how well he handles conflict, his communication skills, and if he is open-minded.

If you don’t think you’ll be able to stomach it, tell him what kind of approach you like instead. Conflicts happen in any relationship.

However, how couples deal with them can make or break their compatibility. Learn about his approach by asking him how he would handle certain conflicts that can arise in relationships (jealousy, cheating or misunderstandings).

17. What would be your first response if I cheated on you?

This question will test his self-confidence and sense of security in a relationship. If he says that he would be emotionally hurt, then you have a very secure guy on your hands.

He’s been down that road before and doesn’t want to travel it again. However, if he tells you that he would slap or punch you in retaliation, then run for cover.

This is one of the serious questions to ask your boyfriend. It will give you a big picture of how important trust is in his relationship. How he answers might help you determine whether or not he’ll cheat on you.

If he says that it would be devastating, then you should probably listen because most likely, if something did happen, his reaction would be similar. 

If he answers with something like, Oh well…at least I know she likes me, then don’t get mad because it could mean that he doesn’t place too much value on having a girlfriend who won’t cheat. 

Either way, it’s helpful to know what kind of relationship foundation you’re building together by answering these questions honestly and knowing just how much you can trust each other in case things ever take a turn for the worst.

18. If my very low self-esteem, insecurities, fears, depression and anxiety affect my mental health, what will you do?

This question will let him know how you are feeling, but it also gives him a chance to tell you how he is going to help you through whatever struggles you are facing.

He may have had no idea of how serious these issues were if you haven’t told him before. This question requires an understanding that mental health issues are just as serious as physical health issues, and shouldn’t be kept inside or hidden from others.

After all, being in a relationship doesn’t mean giving up on yourself. Your wellbeing should always come first! If he tells you that he wants to help with these problems, make sure that he follows through on his promise.

Depression is nothing to be ignored or scoffed at; it can cause severe damage over time if left untreated.

19. Will you marry me right now?

This question will give you an insight into how serious he is about you. If he says no, take a step back and look at where you stand in his life. Does he take time out of his day to make sure you are happy?

Most men dream of having a family with a woman they love and if he does say no, you should give him some space to get his life in order before taking any next steps.

On another note, if he says yes then it’s time for a celebration! You have managed to find someone who loves and cares for you as much as you do them! It’s also important that you know what each other’s expectations are for your future together.

20. Do you have any serious questions that you would like to ask me?

This question will tell more about yourself and shows that you are an understanding person. And also indicates that you didn’t get offended by any of his responses. 

When you encourage him to ask similar serious questions to you, it will represent how open you are to have a deep conversation and ready to get to know each other better and build a strong healthy relationship if you and your boyfriend are compatible. 

It can be very serious or just for fun, but it will give an insight into what he is like as a person. And trust me, you don’t want someone who is too serious or too childish.

The key is finding that perfect balance.

If he does have any weird questions for you, it could be a way of showing his true colors so pay attention to how he acts during these types of discussions because ultimately these are things you should know before deciding whether or not someone is right for you.

Final thoughts

Openness and communication are the keys to any successful relationship. If you’re in a new relationship, it’s important to start sharing more about yourself and gain an understanding of what he likes and doesn’t like in life.

If you’ve been together for a while, it’s also important that you continue communicating with one another so you can continue building trust and open lines of communication between each other.

Also, you can be thinking seriously about commitment when considering such serious questions to ask your boyfriend.

Does he see himself married in five years? What is he looking for in a wife? For many people getting married is not enough.

Instead, they want something deeper than just love. The best thing about these serious questions is that it will give deep insight into his personality which will lead to discussing how serious we both are concerning your future plans together.

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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