40 Questions To Ask Your Boyfriend About Yourself

Relationship Advice | | , Tech Journalist & Writer
Updated On: April 11, 2024
questions to ask your boyfriend to see if he is serious about

Does your boyfriend know you as well as you think he does? What are some good questions to ask your boyfriend about yourself? Maybe you want to build a deeper bond with him. Or maybe you just want to have fun in the form of a great interactive session. Either way, the queries ahead will make the process both fun and insightful for the two of you.

Besides, imagine if you get to know that your partner is not compatible with you — A year after you start dating. That will be a problem, and you don’t want that. To avoid that pain, you might want to jot down these questions to ask your boyfriend about yourself, and see where you both stand.

40 Questions To Deepen Your Understanding With Your Boyfriend

Table of Contents

If you’re planning a long-term relationship, you need to know if your boyfriend is as invested as you are. All you need are some personal questions to ask your boyfriend to see if he is serious about you. It is also important to take this exercise as a gauge and not a test. All his answers will not be to your satisfaction, we can bet on it. But you can gauge his intent and investment in the relationship.

If you’re satisfied, fun questions and deep conversations like these will open the doors for more honest communication later. This might even compel you to find more things to tell your boyfriend about yourself. See how it’ll help build a better connection between you two?

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1. What was your very first impression of me?

The popular quote that says “first impression is the last impression,” did it prove right or wrong in your case? It’s not exactly poetic. Just a very fun way of knowing how you have evolved in your boyfriend’s eyes.

2. Am I a good kisser?

Kisses are always very special, not just because of the health benefits of kissing. More importantly, they lead to an intimate connection that makes you two stronger as a couple. This is one of those deep questions to ask your boyfriend about yourself. It can turn out to be pretty funny too as sometimes kisses may not exactly be as dreamy as we imagine them to be. Either way, this is a great thing to talk about. But only ask if you’re okay with some gentle feedback.

Related Reading: Physical Signs He Really Wants To Kiss You

3. Do I make people feel special?

A good way to get to know yourself better. Some people have an inherent ability to not just make their close ones feel special, but pretty much anyone they come across. That is a beautiful quality to have and something that your partner might definitely be into. With this question, you will know how your partner feels about you in this regard. This could be one of the most romantic questions to ask your boyfriend about yourself.

4. What’s my conflict technique?

We all have different ways to handle conflict and if your partner knows yours, it definitely shows that he loves you and is serious about you. Conflict resolution strategies in relationships are important. This is one of those personal questions to ask your boyfriend about yourself, and something he should definitely know about if you both have seen your share of disagreements.

5. What is the most attractive quality in me that pulled you right in?

This may seem like one of the easiest questions to ask him about yourself. However, it is definitely going to be tricky for him. There may be a gazillion things about your partner that attracted you the most. However, there will always be that one thing that pulls you instantly, like gravity. The same goes for your partner and the answer to this is going to be rather wholesome.

Related Reading: Science Of Scent: This Is Why You Have To Smell Good To Attract Attention

6. How well do I balance my emotions?

One of the most underrated questions to ask your boyfriend about yourself. At some point or other, whether we are having a terrible day or just random mood swings, we have overreacted to things. Moreover, these overreactions bug us later and we wonder if we could have handled the situation differently.

The same could happen in a relationship and knowing if you overreact before/during fights will allow you to become more cautious and handle the conflict better. The answer to whether you balance your emotions well or not will create more room to work on yourself. That will automatically pave the way to creating a balanced relationship.

7. What is annoying about me?

Of course this one made it to the list of good questions to ask your boyfriend about yourself! You probably don’t want to know the answer to this, but this is also the one answer you HAVE to know. Knowing what annoys your boyfriend the most will either help you understand your flaws and work on them or will lead to a discussion on why your partner finds perfectly reasonable behavior annoying. A good way to introspect for both of you.

8. What are my best traits?

This is where you take a deep dive into how much your partner notices and knows about you. What you think are your best traits may be the ones that he comes up with too. If that is not the case, he will unveil a separate set of aspects that he loves about you.

From typical female physical features that attract men immensely to specific personality traits that belong to you, this might be the moment he chooses to spill all his love for you. Get a few tissues, you might tear up.

10. Am I a secure person?

Who does not get insecure in relationships? But there’s a thin line that you shouldn’t cross. Excessive insecurities need to be talked about. This question gives him that chance. And your partner’s answer is ‘your’ chance to grow as a human being and soulmate.

Even if he feels that you’re very secure, it’s still a good thing to confirm from time to time. This is definitely one of those tricky questions to ask your boyfriend about yourself, though, and it needs to be addressed.

Related Reading: Dealing With An Insecure Boyfriend? Here Are 16 Coping Tips

11. What is my biggest fear?

You definitely know of your phobias and biggest fears, but does your partner know about those too? Ideally, he should, as it helps connect two individuals on a whole other level. Do you fear losing your dream job? Or never achieving it? Are you scared of losing your friends? Or about your mental health? Knowing such things is of paramount importance as you can help each other face certain fears.

how well do you know your partner quiz

12. What qualities matter the most to me?

Everyone has this set of qualities that they look for in their partner. You chose him as your partner for a reason and this is a fun way to see if he knows why you love him. From making sure that your arguments do not cross an unhealthy limit, being patient with each other and being good listeners, to finding ways to achieve a work-life balance – There could be the small things that matter the most to you.

13. Whom am I close to in my life?

This is one of those deep questions to ask your boyfriend about yourself. There’s no denying the fact that there is always this one person or a group of friends that we fall back on. It could be your parents, your best friend, your chosen family. These people are there for you and they feel the same way about you.

Maybe you both will end up laughing about the kind of silly antics you and your group of friends carry out now and then. Or some tears will be shed as you appreciate your loved ones together. If he knows and respects the people you are close to, he is an absolute keeper. Such wholesome, funny questions about your personal life will help you understand where you stand with him.

Related Reading: Healthy Family Dynamics — Understanding The Types And Roles

14. What are my favorite cuisines/dishes?

So, it is one of those days when you are terribly low and are craving your soul foods, big time. We have all been there. Your boyfriend will surely know about your favorite dishes and this is an adorable way to find out. Take this opportunity to mess with him a little.

15. Do you think I am your soulmate?

This is an excellent question to cleverly know if he has long-term goals with you or not. This is a really good question to ask your boyfriend about yourself to see how invested he is in you. Besides, you have probably already noticed some early signs you have found your soulmate. Did he spot them too?

16. What do you think turns me on the most about you?

This is one of the most intimate questions to ask your boyfriend about yourself. There are probably a dozen different things about you that turn him on. However, if he can pinpoint what exactly turns you on the most about him, things will definitely get spicier.

17. What hits the spot for me when we make love?

If you’ve been going through a dry spell, this might just end it. It’s important to know if your boyfriend knows and appreciates what you like in bed. Besides, this is where you can have long conversations about taking your sex lives to the next level. One of the most romantic questions to ask your boyfriend about yourself, it can lead to a discussion on the importance of sex in your relationship.

18. What are my coping tools and mechanisms?

This can be tough to answer. Understanding when a partner needs space or time for themselves is a very mature quality to have. Maybe you like to meditate, jog, paint, or play with your dog. If your partner knows the answer to this question, he is a keeper. One of those hard yet super important questions to ask him about yourself in a serious relationship.

Related Reading: How To Nurture Space In A Relationship

19. What do I like and dislike about myself?

Self-awareness is very important – Knowing about your weaknesses allows you to work on them and knowing about your strengths boosts your self-confidence. And when your partner knows what you like and dislike about yourself, it’s a bonus! There are things that men notice about women on the first date and things that they start liking or disliking about them in the later stages. Talking about it all could be pretty empowering actually.

Besides, to know if he notices you, this is the perfect question to ask. He might even have the funniest thing to say to this. The two of you might laugh your heads off, or he might make you roll your eyes. Can definitely be turned into one of the funny questions to ask your boyfriend about yourself.

20. What does your family like the most about me?

If you want questions to ask your boyfriend to see if he is serious about you or not, this is it. If you have been in a relationship for quite some time now, it is essential to know if he sees you as a temporary affair or a serious partner. It will be evident from what he has told his family about you.

Moreover, knowing whether his family likes you or not is important. You can then come up with a plan to get their approval or interact more with them.

hard questions to ask your boyfriend about yourself
Strong relationships are all about communication and asking the right questions

21. What stresses me out the most?

Be it piled-up work or just a bad day in general, getting stressed out is not a pleasant feeling. You feel suffocated, but if your partner knows what’s causing all that stress, he will know what to do to relieve it. So, talking about what stresses each other out is important to help each other out.

22. What are my dream destinations?

This is something the two of you should really talk about. It helps in making plans, saving up, and traveling together. So, if your partner gets this right, that’s awesome. Make plans already! If not, let him in on your travel desires and ask him about his dream destinations too. The couple that travels together, stays together.

Related Reading: 55 Best Ice Breaker Questions For Dating

23. Do you ever feel that I’m over-possessive?

Everyone gets a little possessive at a certain point in a relationship. Things only flare up when you or your partner start getting over-possessive. It could suffocate you and, gradually, the relationship gets toxic and falls apart. If you show these traits, let your partner talk about it. Listen, analyze, and understand where he’s coming from.

If he has noticed clingy girlfriend signs, then work through it together. This question might make your partner ask if he’s been over-possessive about you; in that case, feel free to air your grievance as well.

24. Am I supportive of your and other people’s goals and aspirations?

If you are supportive of people’s goals and aspirations, that is a wonderful quality to have. However, maybe you have restricted him from doing something he always wanted to do. Or maybe you dismiss people’s ideas without realizing you’re doing so. Getting to the bottom of this question is going to help you become a better human being.

25. Who are my top five celebrity crushes?

Why is this important, you ask? This one’s just for fun. However, this helps you understand what your partner knows about you. Everyone has celebrity crushes and talking about them helps create a more open space to breathe in. Sometimes, in relationships, where over-possessiveness is a major issue, talking about it helps ease things a bit.

This can be turned into one of those naughty questions to ask your boyfriend about yourself where the two of you burst into laughter. Besides, it is also one of the most playful ways to make your guy jealous for a minute. Remember to end it with a kiss, though.

26. When do I like getting intimate with you?

You cannot be sexually charged throughout the day. There are those particular hours when your sexual emotions hit their peak. If your partner has been attentive, he will know exactly when you like it and when you don’t. This will make you appreciate your boyfriend more and know that he is definitely into you.

Related Reading: Top 75 Sexiest, Dirtiest ‘Never Have I Ever’ Questions

27. What is my biggest sexual fantasy?

Who does not have a list of sexual fantasies? However, what is your biggest and wildest sexual fantasy? Let him guess it. This is an excellent opportunity to spice things up a bit in bed! One of the most flirtatious questions to ask your boyfriend about yourself.

28. What are my biggest insecurities?

Boyfriend Stories

As human beings, we are not perfect and never will be. Flaws are beautiful and understanding them is what makes you embrace them and work toward self-improvement. When you ask this, keep your ego aside. This question needs to be handled with utmost care and respect.

Each and every one of us is flawed. If your boyfriend is trying to be honest about it, respect that and listen. There’s a huge chance to work upon yourself here. This becomes an important lesson when you are insecure in a relationship. It shouldn’t be left untouched and needs to be talked about.

29. What is the one thing that makes me stand out from the crowd?

If you are looking for tricky questions to ask your boyfriend about yourself, this is going to be one hell of a bumpy ride for him! It is worth seeing him get all worked up for a bit and give you an honest answer. Will definitely pull you two closer.

30. What do I love the most about my job?

Sharing your ambitions and career goals with each other is an important aspect of a relationship. If your boyfriend knows why you do what you do on a regular basis, it shows that he respects you for the work that you put in. Or maybe there is something else you love to do and want to pursue in the future. You can and should talk all about it.

Related Reading: 51 Deep Relationship Questions To Ask For A Better Love Life

31. What is my go-to color?

At first, this may seem like an ordinary question. However, the importance of colors in our lives is underrated. The kind of connection we feel with our preferred colors is beautiful. We often associate them with ‘good luck’ or something that gives us a ton of confidence, like that favorite outfit of yours. If your boyfriend knows of your go-to colors, this is yet another sign that he pays attention to detail. That is indeed a commendable quality to have.

32. What gets me emotional?

There could be a variety of things that hit the spot for you and get you emotional. It may be taking a bite of your favorite dessert, reading a certain book, listening to a track, watching a movie, spending time with family, etc. This is one of those deep questions to ask your boyfriend about yourself that will strengthen the emotional intimacy in your relationship.

33. What are my favorite songs or movies?

There are probably multiple movies that capture you completely. Maybe you like the screenplay, maybe the director is your favorite, or you’ve been following the career of an actor religiously. This is another one of those trick questions to ask your boyfriend about yourself. Let’s see how he fares.

If he knows the answer, this lets you know that he pays attention to detail and remembers the things that mean the most to you. Of course, given the fact that you have talked about it at some point.

34. What’s my favorite book or author?

You know how it feels when you’re deeply immersed in a good book, right? Ask your boyfriend about your favorite book or author to see if he’s tuned in to your emotional and intellectual vibes. Sharing this literary connection can bring you closer and prove he’s paying attention to what gives you comfort and joy.

35. Do I prefer quiet nights at home or going out?

This question helps determine whether your boyfriend is truly attuned to your daily life and preferences. If he knows whether you prefer a cozy movie night or a night out, it shows that he values your comfort and happiness. He may already be crafting experiences that cater to your personality so that you feel you’re with someone who understands and respects your choices.

Related Reading: 36 Beautiful Things To Do With Your Boyfriend At Home

36. What are some of my long-term goals and aspirations?

A dream house? Winning five million dollars in the lottery? Adopting a fur baby? Long-term goals are about what you envision for your future. Sharing them with your boyfriend is like opening a window into your dreams. It’s a way to evaluate if he’s interested in being a part of your journey and supporting you in reaching those milestones. When he knows your aspirations, it’s a sign that he’s ready to align his life with yours and work together toward shared goals.

37. How do I like to celebrate special occasions like birthdays or anniversaries?

Special occasions are a chance to make beautiful memories, and discussing how you like to celebrate them lets your boyfriend know that these moments are important to you. By sharing your preferences, you’re allowing him to create memories that resonate with your heart. And you can do the same for him. This is one of those great bonding questions for couples to strengthen their relationship.

38. What’s my favorite childhood memory or story?

Childhood memories often hold a special place in our hearts. Sharing them with your boyfriend is like unveiling the foundations of your personality and experiences that shaped you. It’s a way to invite him into your past, your family, and the pivotal moments that defined your early years. In doing so, you’re encouraging him to appreciate the essence of who you are today, thus deepening your emotional connection.

39. What are some of the small gestures that make me feel loved and appreciated?

Love is not just about grand romantic gestures. It’s often the small, everyday acts that carry significant weight. By talking about the little things that make you feel cherished, you’re providing him with valuable insights into your love language. It’s a way of saying, “This is how I feel loved, and I’d like you to know.” These discussions cultivate a relationship built on affection, kindness, and an understanding of each other’s emotional needs.

40. What’s my most cherished possession or sentimental item?

The items we hold dear are often linked to profound emotions and memories. Sharing these possessions and their stories is like going through personal chapters of your life. It’s a step toward building trust and emotional intimacy, inviting him to explore the layers of your past. These conversations can be heartwarming and strengthen your bond, as you both appreciate the sentimental value of these treasures.

Key Pointers

  • If you are thinking about long-term stability and compatibility, you can use these questions to ask your boyfriend to see if he is serious about you
  • Asking these questions will allow the two of you to be vulnerable and honest
  • There are many deep questions to ask your boyfriend about yourself as well, to strengthen mutual understanding
  • Toward the end of it, he will know more about what you like and dislike, and vice versa. This is important for the longevity and quality of your relationship

By the end of the day, communication is definitely the key to ending all hardships in a relationship. It is even important to have a smaller but separate list of hard questions to ask your boyfriend about yourself, if you want. Especially in times of conflict. Turning your face away from each other is not going to solve anything, while getting out of your comfort zone and having difficult conversations will. Whether you think that your relationship is losing the spark or you just want to take it to the next level, these 40 questions are all that you need with you.


1. What can you tell your boyfriend about yourself?

Pretty much everything. Transparency is an important element in a healthy and serious relationship. Of course, if you think he’s not the one and this is a temporary fling, you do not have to be completely honest. That’s completely your call.

2. What secrets should my boyfriend know about me?

From your fetishes and wildest fantasies to embarrassing personal stories, these are some of the things to tell your boyfriend about yourself. You can talk about anything and everything with him if he makes you feel safe and comfortable enough. But if you are too selective about personal topics, you are probably going to run out of beautiful conversations pretty soon.

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