55 Serious Questions To Ask Your Boyfriend

Dating experience | | , Expert Blogger
Updated On: July 28, 2023
bonding experiences for couples

As a relationship progresses from the rosy honeymoon period to the deeper trenches of commitment, there are some serious questions to ask your boyfriend that can help you understand your relationship better. And why should you not ask them? Getting to know your boyfriend and also understanding what things you may or may not be on the same page about, is essential to any relationship.

The first few months of dating are full of romance, butterflies and endless coffee dates. This is the period where love seems like the most beautiful feeling in the world and you cannot seem to get enough of the other person. It is even a time when you fall for everything about them, including their flaws and quirks. This feeling of puppy love is the reason we seek love at all. 

But soon, a time arrives when coffee dates, kisses and butterflies in your stomach stop being enough. When you start falling in love for real, you might suddenly want to hit the brakes and say, “Oh no!” because you’ve suddenly found yourself in a whirlwind of serious emotions that you didn’t see coming from a mile away. 

55 Serious Questions To Ask Your Boyfriend 

Table of Contents

Suddenly realizing that you’re totally and completely in love can take you by surprise, but this is also an alarm ringing to introduce a new period in your life where you could indeed be in a serious relationship that could also be long term. 

So, as you set foot into what could possibly be a proper boyfriend-girlfriend situation, you should do a little bit of homework beforehand. Don’t get us wrong. We don’t mean to kill the love or the rush of excitement that you’ve gotten used to in the past few months. That’s indeed the best thing about being with someone. But so is the process of understanding your boyfriend better.

Think about how you need new and better skills when you level up on a video game. Similarly, covering all bases and being clear about your expectations and understandings in a new relationship will leave you better prepared as you level up in your relationship, too. 

Thus, consider these serious love questions to ask your boyfriend. It might seem premature or too particular at first. But you know that good communication is the key to any relationship. So, start your new relationship on the right note by using these questions to familiarize yourself and prepare yourself for what’s to come into your life. 

Related Reading: 21 Do’s And Don’ts When Starting A New Relationship

1. How do you like to spend time alone? 

This is a lovely way of getting to know somebody and how they operate. One of the serious questions to ask your boyfriend to get to know him better, this way you’ll know what to expect from him. Does he want to pick up a book and hit the neighborhood park on a sunny day or would he rather slog and finish up work at the nearest Starbucks? 

2. What is your biggest pet peeve? 

Maybe when you’ve been flirting over text for some time and want to dive into grave talks with your boyfriend, you can start on a lighter note with a question like this. Before getting into very serious questions to ask your boyfriend, consider something simpler like this one. Who knows, the answer could surprise you.

3. Are you a religious person? Serious yes or no questions to ask your boyfriend

Religious or spiritual, phrase this question the way you deem fit. When you are getting serious with somebody, it is nice to understand what kind of life they lead and spirituality can be a big part of that. With such serious yes or no questions to ask your boyfriend, you can understand exactly what you are walking into.

4. Have you ever made a person cry? 

One of the deep questions to ask your boyfriend, this could open a treasure chest of stories he might tell you. It could be an old flame, an argument with a friend or simply offending a stranger accidentally in public. Try this question out with your boyfriend today. 

deep questions to ask your boyfriend
Ask him straight up if he’s ever made someone cry and you might be surprised

5. What causes are you passionate about? 

Animal welfare, mental health, human rights or feminism – whatever it may be, it is good for you to know it. A person’s passions are a fundamental aspect of their personality and with this question, you’ll know exactly what they consider important in the world. 

6. What do you love most about me?

The list of serious love questions to ask your boyfriend is absolutely incomplete without this one. Get a little romantic and ask him what it is about you that really drew him toward you. There are many reasons you love someone. What are his?

7. How do you lift yourself up when you are feeling low? 

Music, the gym or throwing on some noise on the TV – what is it that your boyfriend does to cope? We all have our unique ways of dealing with things but now you know what to expect when he’s run off after a fight with you. 

8. Have you ever been cheated on? 

Thinking of serious questions to ask your boyfriend about cheating? Well, this one has to top the list. How careful is your boyfriend with his heart now, and has someone left him completely shattered in the past?

Related Reading: Confession Story: Emotional Cheating Vs Friendship – The Blurry Line

9. What is non-negotiable in a relationship for you? 

Now that you two are really together and doing this, try to get some major deep relationship questions out of the way. Knowing his likes and dislikes is one thing. But what kind of partner is he expecting you to be?  

10. Do you have any phobias? 

Hopefully, he’s not commitment-phobic or all these questions will go in vain. This may not seem like a very personal question but it doesn’t hurt to know what your partner may be scared of. 

11. Are you a forgiving person? 

Being forgiving in itself is an admirable quality to have but this is also an important question because one cannot overstate the necessity of forgiveness in relationships. You definitely want to know if he’s going to hold grudges for weeks when you cancel on a date. 

12. What song is the background track to your life? 

This is one of the cute serious romantic questions to ask your boyfriend. Our music choices represent us very deeply. So instead of asking him to curate a whole playlist (which you still can and should do), just ask him what song resonates with him the most. Pay close attention to the lyrics when you put it on. 

very serious questions to ask your boyfriend
His music choice can tell a lot about himself

13. Do you have a good relationship with your family? 

Family is important territory to cover when thinking about serious questions to ask your boyfriend to get to know him better. Relationships with family can be complex, so pay attention to this one.

14. What do you find offensive? 

Consider this as one of the most important serious questions to ask your boyfriend to get to know him better. One’s family values and personal, moral ideas are reflected greatly in how we answer this question. Make it a point to add this one to your list; you might even be surprised at some of the responses. 

15. Do you believe in the institution of marriage? 

Not a great question to ask over text because it’s always nice to discuss such important topics in person. But definitely pop this one when you have a chance. No, we aren’t planning a wedding already but it doesn’t hurt to know if someday there might be a reason to do so. 

16. What do you admire most about yourself? 

I don’t know about you but I personally love a man who is the right amount of self-aware and self-loving without being a narcissist. So, the answer to this can really go either way.

17. Tell me about when you fell in love for the first time

Stories of young love are sure to bring you two closer and make you feel more vulnerable than ever and asking about them can make for one of the best serious romantic questions to ask your boyfriend. No matter how long ago it was or how immature it was, your first love often teaches you the biggest lessons you recall for a lifetime. 

18. What were you like in high school? 

Open up an interesting can of worms about his high school stories with such serious questions to ask your boyfriend. Was he coy, a Mathlete, a jock or some kind of rare all-rounder? No need to judge but your past personality can tell a lot about how it has shaped one’s present self. 

19. Are you a feminist?

One of the more serious yes or no questions to ask your boyfriend. I can’t speak for everybody else but this would probably be the foremost of the serious questions to ask your boyfriend for me. You could replace the same with any other ideology that fits your own story and belief system and make this one of the serious questions to ask your boyfriend to get to know him better.

Related Reading: How Does Feminism Benefit Men

20. Are you an optimist or a pessimist? 

Or even a realist for that matter? Another way to rephrase this would be: “Do you view the glass as half empty or half full?”

21. If it was your last day on earth, how would you spend it? 

He better say “With you in my arms”, but even if he doesn’t, don’t get into any relationship arguments over this one. With this question, you’ll really know what are the few simple things that make him happy and satisfied. 

22. Where do you see yourself in 10 years? 

One of the most serious questions to ask your boyfriend, you should use this one to understand how he likes to live his life. Is he a planner and has his entire life mapped out in front of him? Or is he relatively laid back and prefers to let each day surprise him? 

23. What was your first impression of me? Serious questions to ask your boyfriend about your relationship

We’re surprised if you have not had this discussion with him already. It’s always interesting to discuss first impressions with anyone because they are often so different from how you’re perceived once a person gets to know you better.

serious love questions to ask your boyfriend
This could be one of the serious love questions to ask your boyfriend

24. Have you ever made any bad choices? 

This is one of the necessary serious questions to ask your boyfriend about his past. Who he is can be determined greatly by the choices he made to arrive there. Not everyone is happy with the choices they have made but this way, you can understand what he thinks he could have done differently and whether he is self-aware or not. 

25. What makes you wake up in the morning? 

If he says, “My old French press”, do not be disheartened. But press him a little further to give you a more serious response. Is it his family, friends or his job that motivates him to get through the day and keep moving through life? And if he says, “You”, awww! 

26. Do you have any regrets from your past? 

When a guy is able to introspect and reflect on past decisions and past relationships in front of you, it means he’s definitely feeling close to you and trying to develop a connection here. If he is able to discuss his regrets with you, it’s a good sign because that means he’s ready to open up to you. 

27. Which movie makes you cry? 

If he says,, “Hachiko- A Dog’s Story“, I’m sold and definitely in love. If he says. “Star Wars“, I’ll just go ahead and yawn. What a clever way to get a glimpse into things that make your boyfriend emotional. 

28. Do you like kids? Serious yes or no questions to ask your boyfriend

If you are indeed seeing and planning a future with this person, let’s definitely get these pertinent questions out of the way. You do not want to scream “I’m pregnant!: with a smile on your face, expecting him to match your enthusiasm, only to be disappointed. 

Related Reading: Should I Have A Baby? Decide To Go Ahead With These 12 Reasons

29. Tell me about one of your quirky habits 

Sounds silly, we know, and does not exactly fit the bill for serious questions to ask your boyfriend, but pop this one anyway. It’s still a little something for you to understand him better and why he is the way that he is. 

30. What is your take on live-in relationships? 

One of the very serious questions to ask your boyfriend, present this one nicely before he thinks you want to live together and runs in the other direction. It is a good way to understand if a live-in situation is on the horizon for you two. 

31. Do you think money can buy happiness?

 This is kind of a cliché, but this question definitely lets you tap into a person’s ideologies in a very simple way. Whether he says yes or no, don’t judge him for either. It’s just a conversation worth having with the person you love. 

serious questions to ask your boyfriend about his past
What is his take on money and happiness?

32. Name 3 things that make you angry

No, we are not diagnosing any anger issues with this one. It’s just an interesting way to understand what kind of things upset your boyfriend. Is it ketchup on pizza or a working Saturday? 

33. Are you happy with how your parents raised you? 

Thinking of serious questions to ask your boyfriend about his past? Well, it doesn’t get more serious than this. Our relationships with our families go a long way in defining us. A subtle and less intrusive way of finding out his views on his family is by using this neatly phrased question. 

34. Are you close with your friends? 

This is like a rephrased way of trying to find out how sociable your boyfriend is or isn’t. Does he have a close-knit circle of three or a clubbing group he meets with every Friday? 

Related Reading: How Spending Time With Friends Helps Improve Your Relationship

35. What was your biggest learning in the past year? 

Find out with this question what are the little things that have changed your boyfriend as a person. It will help you know how he processes his wins, losses and learnings in life. 

36. What is your take on polyamory? 

Our nature with relationships and love is ever-evolving so it doesn’t hurt to ask if your boyfriend is interested in being polyamorous or wants to make some open relationship rules. It’s important to ensure you two are on the same level of commitment when you start out, to avoid any major surprises. 

37. Are you an overthinker? 

So next time you know whether to bother him or not when he randomly starts gazing into the distance. With this question, you’ll understand how exactly he deals with stressful situations and how much he likes to ponder over a problem.

serious questions to ask your boyfriend about cheating
Does he spend a lot of time overthinking things?

38. What is your greatest fear?

Our fears are major indicators of how we might behave in relationships. From the fear of snakes to fear of commitment, it could be anything. You are going to definitely want to include this in your list of serious questions to ask your boyfriend to get to know him better. 

39. What’s your favorite memory of me? 

With this one, you’ll be able to pinpoint exactly what your boyfriend loves about you so much. Does he love how you go crazy upon seeing the ocean or how you peacefully unwind in front of the television after a long day? Making new memories is essential to a relationship but so is figuring out your favorite ones with each other. Add this to your list of serious questions to ask your boyfriend about your relationship now!

40. Are you happy with your job? 

It’s vital to understand how fulfilled or unfulfilled one is in their present circumstances. Is he happy-go-lucky and chooses to go with the flow or is he seeking something more worthwhile in their career? 

41. Do you have a possessive nature? 

Is he going to be freaking out every time you grab drinks with your guy friends? To each their own but it would be nice to get a heads up about the same. So, pop this question when you can and you’ll know what kind of a person you might be dealing with. 

42. Do you believe in finding ‘the one’? Serious romantic questions to ask your boyfriend

Love can be a tricky thing to understand and we all deal with it and learn from it in very different ways. With this question, you’ll understand whether he’s on the search for the one or if he just likes to enjoy the present relationship the best he can. 

43. How would you describe your sense of humor? 

Definitely, a great question to understand how far his humor ventures into the deep or dark territory. What we laugh at is a great indicator of how we think. This way, you’ll also know how comfortable he is with dark or inappropriate humor or if he has a dry sense of humor

44. What is a piece of relationship advice you’d like to give your younger self? 

This question is extremely meta and will definitely keep his mind occupied for a fair bit. Such serious questions to ask your boyfriend bring out vital pieces of information that help you understand what to expect from your own relationship with him. 

Boyfriend Stories

45. Have you hidden anything from your family?

Tapping into his past and his secret side, it can be interesting to see how he would possibly react to this once. Will he take offense and brush it off or is there something darker that is worth finding out? 

46. What are your goals in this relationship? 

Perhaps the most confrontative in the list of serious love questions to ask your boyfriend, show some courage and have this discussion with him about relationship goals. Before you put both feet into the relationship, understand how much of himself he’s will to put into this too. 

47. Who is your role model?

While understanding your partner and his personality is one aspect of deep questions to ask your boyfriend, you should also try to understand what he sees and likes in other people. His role model is a reflection of what he considers worthy of love and respect in the world. 

48. Have you ever cheated on somebody? Serious questions to ask your boyfriend about cheating

Sounds like a pretty controversial thing to ask but it couldn’t hurt to try. Despite your own stance on cheating, it is a good idea to get a fair idea of what your boyfriend’s stance on the same might be. 

Related Reading: Relationship Advice For Men – 21 Pro Tips By A Woman

49. Which book changed your life? 

What we feed our minds has a lot to do with who we become as people. Knowing his favorite book is like a read into his own personality. Hopefully, he doesn’t say Twilight or something along those lines.

50. Name 3 things you are most thankful for 

One of the more serious questions to ask your boyfriend is to honestly ask him what he cherishes most. This will tell you what are the few things he considers most important in his life. But please cut him some slack if you’re not on the top of that list. 

51. Have you ever lost a pet? 

This is seemingly not one of the more deep questions to ask your boyfriend but if he indeed has, it could be a gateway to many other stories and emotional baggage that he would not have revealed earlier. Losing a pet is a truly traumatic experience and something you’d definitely want to know about, if he has. 

52. What do you think is life’s greatest common goal?

Getting real deep now, this is a great philosophical question to ask your boyfriend or anyone else really for that matter. The way he responds to this will truly give you an idea into what he devotes his life to. The key to the question is the way it has been framed. So do not forget about this one!

53. Is there anything you would change about me or this relationship?

One of the necessary serious questions to ask your boyfriend about your relationship, this could go well or really, really badly. Be open to hearing him out and giving his point of view instead of blame-shifting.

54. Could you possible forgive a cheater?

Such serious questions to ask your boyfriend about cheating should be navigated very carefully. You don’t wanna piss him off! But also, be receptive to his answer as well.

55. What is the one thing according to you that will make the world a better place?

If he says, “More dogs”, then you need to cuff him, and cuff him now! A cute answer like this takes the cake. But anyway, on a more serious note, this is one of the more serious questions to ask your boyfriend to get to know him better you should definitely ask.

These are some very serious questions to ask your boyfriend and remember that these could come with their own follow up questions too. Try not to throw them at him all at once like some rapid-fire round. Give him time to process them and be honest with you while you do the same for him. Don’t sit at the edge of your seat constantly when he’s responding. These aren’t meant to scare you but to bring you two closer! 

33 Questions To Ask Your Significant Other To Know Them Better

21 Beautiful Things To Do With Your Boyfriend At Home

50 Things To Talk About With Your Boyfriend And Know Him Better

Ask Our Expert