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

One of the best things about a relationship is that you get to know more about your partner with each passing day. 

This is especially fun in the beginning when there is so much new and exciting stuff going on all the time.

However, as time passes and things start getting more serious, it can be easy for both of you to start taking each other for granted.

You may think that since he knows everything about you, you can take it easy and not bother considering deep questions to ask your boyfriend.

Also read: 50 Relationship questions to ask your boyfriend (On interesting topics)

After all, isn’t it only when we’re getting to know someone that we ask them about their family, their childhood or their hopes and dreams?

However, this is exactly why asking deep questions can help both of you keep the romance alive even when the honeymoon period is long over.

Asking your boyfriend deep questions about his feelings and opinions can really strengthen your bond by helping him open up more and bringing out more of his inner thoughts and feelings.

And give you a better understanding of him as a person. Asking him the right questions can also make him fall even more in love with you, so he can’t get enough.

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

So, If you want to test your boyfriend’s love and realize whether he is a potential spouse then consider these deep questions to ask your boyfriend.

31 Deep Questions To Ask Your Boyfriend

Very deep questions to ask your boyfriend 31 Deep questions to ask your boyfriend (Be evolved after this conversation with him)

1. Which type of person are you s#xually attracted to most often? Are they a specific body type, hair color, age, or ethnicity? Why is that someone who turns you on? 

Learning more about his s#xual preferences and his expectations for his ideal partner can be a good indicator of what he’s looking for in an overall relationship with someone. 

A lot of people have different standards when it comes to s#x and who they sleep with versus whom they spend their lives with.

So it’s important that he knows that having one preference doesn’t mean he won’t find someone attractive as long as she meets some other desired qualities as well.

2. Would having a family ruin a career for someone like yourself who is very goal-oriented and focused on working hard and achieving in order to set a good example for their children one day?  

If you want to start a family, it’s best that he knows how important starting a family will be to you (even if you haven’t actually made any plans yet) so he can understand how much time, energy, and money will go into raising kids. 

While having children shouldn’t necessarily influence whether or not he wants to marry someone, his values definitely should change as soon as they become parents.

Because they’ll have more responsibilities than they ever imagined that won’t just affect them but everyone around them too. 

3. What do I mean when I say marriage?

Does it mean we’re engaged or does it just mean we’re moving forward in our relationship by being exclusive with each other for an undefined amount of time until something better comes along?

It’s always good to know where your partner stands regarding commitment. People are different and react differently to similar situations.

Therefore, it’s vital that you learn what his thoughts are on exclusivity before you get serious about him.

Because he might break up with you rather than propose after only a few months of dating if marriage isn’t even something he thinks about at all despite calling himself religiously single.

4. What are some things about me that make me attractive to others?

It may seem cheesy, but receiving compliments goes a long way in making us feel loved and appreciated.

Therefore, asking what makes him attracted to you beyond physical appearance might help give you insight into why he loves spending time with you in addition to wanting physical intimacy from you most of all. 

5. If there was no such thing as money, how would life be different and better for humans, specifically yourself and those close to you? 

Money doesn’t buy happiness, but it certainly helps tremendously. Answering these questions honestly can shed light on what kind of person he really is. 

Are his interests, monetary or altruistic?

Is he willing to risk hunger over keeping all of his money in a bank account or will knowing that people will starve without food, motivate him to donate whatever funds he has toward charitable causes or aid organizations? 

Also read: 100 Trap questions to ask your boyfriend (persuasive and funny)

6. Do you think love and respect go hand-in-hand, separately, neither—or are they mutually inclusive entities? 

Why is respect necessary for love between two people when both partners obviously deserve love in themselves regardless of anything else? 

A lot of times love alone isn’t enough to sustain a romantic relationship between two people once disagreements arise and compromises must be made.

Asking questions like these is a great way to find out how likely he is to compromise or walk away from you. 

7. Do you see love as a feeling, or as a decision? 

You are never going to love everything about every person you date, but you will continue loving them anyway. 

Loving someone means deciding that, in spite of your differences and disagreements, they’re still worth giving another chance and growing together instead of letting conflict tear apart something that could be amazing. 

8. Have you ever been in love? How did it happen? How did you know it? How did you show it? Have you been in love since then? 

Being in love is a complicated and confusing experience, especially when that person isn’t sure how they’re supposed to act or behave because they don’t want to scare someone off or upset them unintentionally. 

Therefore, it’s smart to ask these questions about his past relationships if you truly care about your future with him because he might be afraid of hurting your feelings.

However, he can’t hurt your feelings if he isn’t capable of love which will directly impact your quality of life together as a couple. 

9. What are your favorite and least favorite elements of my body? 

No one’s perfect, but we can all use a boost sometimes. One way to reassure him that you like what he sees is to ask him what he likes and dislikes about your body. 

While it might be tempting to take his critiques personally, try to remember that his response will usually be filtered through his own personal preferences. 

If he says something you disagree with, question it! And if there’s something you want to improve about yourself, now’s a good time to talk about how you can work on it together. 

10. How important is an intimacy to you? 

Of course, it’s important to him otherwise he wouldn’t be with you. But when it comes to intimacy, there are levels.

Some people place a high priority on an emotional connection while they have no desire for intimacy; others aren’t looking for anything more than casual hookups.

Make sure that you two are on the same page about how intimate your relationship will be and what you expect from one another in terms of affection and intimacy.

If your boyfriend isn’t interested in kissing or cuddling, is that a deal-breaker. If his idea of intimacy is falling asleep next to you and waking up in your arms, are you OK with that?

Also read: 20 Serious questions to ask your boyfriend

11. Who is your greatest influence? 

What about that person inspires you to be better than you are today?

We all have people in our lives who push us to be better and achieve more, but it’s not often we hear exactly what it is about them that inspires these feelings of improvement. 

Since he’s already been changed for the better because of someone else, hearing how he’s affected will remind him of his potential as well as instill a sense of gratitude. 

12. If you had one wish, what would it be? 

When was the last time someone asked you If you could have any wish, what would it be? This kind of question gets straight to the heart of your partner by challenging their relationship with reality.

When you step outside yourself to imagine an entirely different life without practical limitations or boundaries, your mind can get creative in ways that even surprise you!

13. Have you ever done anything illegal? 

It doesn’t matter if your relationship is long-term or new; revealing something private—even if it’s silly—will build intimacy by creating a moment where neither one of you could censor yourselves.

Plus, revelations like these make everyone feel a little bit naughty in a fun way! 

14. Do you regret marrying me? 

When marriage still carries such social stigma from older generations, asking your husband if he regrets being married to you adds another layer of intimacy between partners while relieving stress on both sides.

Remind each other that though divorce rates are high especially in America right now, committed marriages do exist and value can be found within those relationships.

15. Are you comfortable sharing something no one knows about you? 

This question may get an uncomfortable pause from most guys, which means he needs to answer it even more.

Sometimes we aren’t completely honest with ourselves either, so being open about moments like these reveals true character. 

Also read: 50 Trick questions to ask your boyfriend to test his love and loyalty

16. How do you want me to treat you after 10 years together? 

You might never know until then (not that you should hold off for ten years), but there’s always room to grow.

Asking your guy how he wants to see himself treated reminds him to put some weight behind treating you well when times get tough instead of turning into a resentful version of himself. 

17. Would you rather listen to me talking about my exes, or tell me why I’m wrong? 

Instead of wallowing in self-pity (or having low self-esteem), just let yourself know that even the coolest human beings have quirks and bad habits and sometimes they slip out before they can apologize.

By recognizing that nobody is perfect, your own shortcomings won’t seem so important anymore!  

18. What is your opinion of a woman who makes out with men she isn’t emotionally involved with? 

There are men and women who have high standards and only sleep with people they can envision having a relationship with, whereas there are also plenty of individuals who just like to have fun.

While sleeping around casually can be fun, it’s not ideal if you want to start a more serious relationship eventually. 

It may be helpful for him to explore his opinions on casual fling so that he can determine what his boundaries are when it comes to potential romance down the road. 

19. Do you believe women who act in s#xually provocative ways are asking for s#xual assault? 

On average, about two-thirds of s#xual assaults are perpetrated by someone known to the victim.

Contrary to what many people think, molesters don’t fit a certain profile—they could be anyone from a friend or neighbor to an acquaintance at school or work. 

Not all s#xual assault is unwanted—there are cases where victims flirt or dress provocatively and say no but do not struggle and it is interpreted as consent.

If you really want a man who can respect your boundaries and values, he shouldn’t blame you for being victimized regardless of what you wear or how you act. 

20. What kind of girl did you have a crush on in high school? 

And why was that girl your crush? This can provide insight about what kind of woman he finds attractive and if it lines up with your personality.

Maybe you are similar, maybe not, but more than likely he’ll be more comfortable talking about his past crushes than imagining who they would be today. 

21. What’s something you wish, I would do more of in bed? Is it harder to do with me or someone else he used to date? 

Some of us tend to be naturally aggressive, dominant, or submissive in bed—and we all have different preferences for speed and what’s considered rough versus gentle.

Figuring out how much he prefers going slow or fast and whether he likes more oral or penetrative stimulation can give you a lot of insight as to what his style is like and whether he prefers being active or passive in bed.

For example, if one s#xual position makes him org#sm quickly and easily, you know that knowing his tendencies will help when you want to try something new during intimacy. 

22. What’s your favorite activity for a first date? 

Even if you think you know his answer, consider why he chose it. Maybe he’d prefer bowling because he’s not nervous being physically close to someone while they both flail their arms wildly at balls.

While some first dates have gotten a bad reputation over time, there’s no reason why yours shouldn’t be fun.

Figure out how to get creative, whether that means joining a local sports league together or adding s#xual tension into ballroom dancing lessons as you move through each lesson together. 

23. What’s your idea of a perfect date? 

Is it dinner at an expensive restaurant or a night in watching movies and cuddling on the couch? It’s important to make sure you’re both on the same page about what constitutes a romantic evening, because it may be a reflection of what he expects from you as his girlfriend.

This is also something that can give you insight into his hobbies and interests, so ask about them if he mentions them.

For example, if he says that weekend afternoon bike rides are his favorite pastime, suggest going out for breakfast on Saturday morning and biking around town; maybe buy him a new set of gloves for Christmas.

These simple questions will give you plenty to talk about over dessert or coffee later that day.

24. If you could spend a day anywhere in history, where would it be? 

Where would you have gone and what do you think of your trip? People often look to historical places for inspiration, so if he’s thought about what historic place he’d like to visit, chances are he has a particular outlook on life that he sees reflected in history.

Ask him why his ideal destination is significant to him and how it made him feel. These kinds of questions can tell you a lot about his priorities and ideals.

He may have gone on multiple trips or wished for something different—by understanding why his first choice is perfect for him, there may be some clarity gained as to what choices are possible for him personally and professionally going forward. 

25. What is your greatest insecurity? 

This question is particularly good if you’re in a relationship with someone who tends to be a bit self-deprecating and doesn’t talk about his feelings much.

Hearing him discuss his deepest insecurities, and seeing how he reacts when talking about them, can be a great way of determining if he can maintain an honest, intimate relationship with you. 

26. When often do you usually want to see me, hear me or have any discussions? 

Having a conversation about what each of you expects in terms of communication can clarify a lot of communication concerns—like how often you should call, whether s#xting is appropriate and if so, how often, etc.—before they even become problems in your relationship.

Don’t assume he knows you want him to text as soon as he gets home or assume he doesn’t care whether or not you text back because it takes him 20 minutes! 

27. What are your dating deal breakers? 

Do you find tattoos on women s#xy or trashy? How would you feel if a date was five minutes late, or he called an ex to see if they were free that night? 

Knowing what’s acceptable and unacceptable in your boyfriend’s eyes will give you a good idea of how open to compromise and change he is, and what kind of relationship he’s looking for in someone. 

28. What is your most prized childhood possession? 

What about it gives you that sentimentality? You may think you know what he values most, but he’s probably got more than one sentimental object in his life.

It can tell you a lot about how he views relationships and other people in his life when someone else figures so highly into his heart and mind.

29. Do you ever get jealous? Why or why not?

Jealousy is one of those tricky issues that can either push your relationship in a positive direction or destroy it, depending on how you handle it.

If he answers yes to your question, ask him to tell you exactly what his jealousy triggers are and what he does when they occur.

Then explain how your relationship operates so he understands where your boundaries are (with you and others) and that those boundaries aren’t changing. 

As long as his behavior doesn’t cross those boundaries, let him know that jealousy is okay—just check in with him to see if it’s too much! 

30. What do you think about s#x before marriage? 

This can be a difficult question to answer if he’s shy, so try letting him know you’re not going to judge him for his answer. 

If he says someone older than you, ask why. If he says someone with a more slender body type, ask how that impacts her other qualities. Getting to hear what turns him on will open your eyes and might encourage you to try something new in bed together. 

It also helps keep both of your fantasies and desires in mind as partners in order to better meet each other’s needs. 

31. Does a woman need confidence in order for s#x to be good?

Men generally respond well when they feel like they are able to please their partner and having confidence goes a long way toward making that happen. 

That said, you can get an idea of what he looks for in a partner from both sides of that equation and create your own internal guide.

You can set boundaries around what’s off-limits in bed and make your needs clear without setting them aside altogether—it just depends on how you’re comfortable doing so.

If there are parts of your se#xuality or fetishes that you aren’t open to exploring with him, bring it up before he suggests trying anything new.

This will give you time to think about how you’ll respond if he asks something specific like that in bed and will also let him know where your boundaries lie.

It might sound simple, but having an open dialogue about s#x is definitely important and should be addressed more often than it is! 

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Naveen Bommakanti

Naveen is Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry.

Naveen’s expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few.

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