55 Romantic Questions to Ask your Boyfriend (2022)

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Cute romantic questions to ask your boyfriend 1. Have you traveled in the past? If so, where did you travel? 2. Where is your dream location for a vacation? 3. If your paycheck could be any number, what would your career be? 4. Do you prefer dogs or cats? Would you want one as a pet in the future? 5. Where do you want to live if you had to choose to stay in one place for the rest of your life? 6. If you could learn any instrument with ease, which instrument would you learn how to play? 7. What is your favorite activity to do in your free time? Would you like to do that activity with me? 8. Where do you want your first apartment or house to be located? Do you picture yourself staying there long? 9. If I needed to describe you in three words to a friend, which three words should I use? 10. When you are having a bad day, what usually cheers you up? 11. What is your favorite place to go out to lunch? How come you like this place in particular? 12. What is your favorite music to listen to? What music puts you in a romantic mood? 13. What is the next romantic movie you and I should watch together? 14. What is the most romantic or impactful book you have ever read? Would you recommend that book to me? 15. What career paths other than your current path have you seriously considered in the past? 16. If you won a million dollars from the lottery, what would you do with the money? 17. If you could return to a year in your past and relive your life starting from that age, what age would you return to? Deep romantic questions to ask your boyfriend 18. What is your biggest aspiration in life? 19. What is your biggest regret from your past? 20. If you could redo anything in your past life, what would it be? 21. What is the biggest loss you have experienced? 22. When was the last time you were truly happy? 23. What is something that your parents did during your upbringing that you want to make sure you also do if you end up having children? 24. What is something that you struggle to tell people about yourself that you want to share with me? 25. What is your biggest flaw? 26. What is your biggest fear about the future? 27. What is one of your fondest memories of us together? What about when we have been apart? 28. Which of your parents do you see the most in your own personality? 29. What makes you feel most protected and secure? 30. When was the last time you felt truly angry at someone or something? 31. If you could change one of your personality traits, which would you change? 32. Do you consider yourself an introvert or an extrovert? 33. Do you consider yourself as an optimist, a pessimist, or a realist? 34. Do you ever compare yourself to others? If so, who? Romantic questions to ask your boyfriend about your relationship 35. What should we prioritize in our relationship? 36. Do you want to have kids sometime in the future? If so, how many? 37. Is there anything that you think we should change about our relationship? 38. Would you rather have a relationship with constant communication or room for some space? 39. Do you see marriage in our future? 40. What sort of love language lifts you up the most? 41. Do you think that we are soul mates? 42. What do you think our biggest strength is in our relationship? 43. When you imagine our future, what do you picture? 44. When was the moment you realized you were in love with me? 45. What are the positive things about being in a relationship? 46. What was the first thing you noticed about me that caught your attention? 47. Where is your favorite place to go on a date with me? 48. What can I do to make you feel the most loved? 49. If you were to describe me in three words, what would they be? 50. What is something that you see or do that reminds you of me? 51. What is your biggest turn-on that I do in bed? 52. Have you ever gotten jealous of me with other guys? If so, when? 53. If we had never met, where do you think you would be now? 54. Is there anything that I may do that would make you rethink our relationship? 55. What is a big reason why you love me? Other College Posts You May Like

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Asking questions is the key to keeping healthy communication between you and your boyfriend! Lighthearted questions can open up the conversation to more in-depth subjects and also keep you in a great mood for the rest of the evening.

Asking deep questions can form a close bond between you two and bring you both closer than ever before. Relationship questions can be beneficial for you to continue to improve your relationship and stay honest with each other if there is something that needs to change.

I have put together a comprehensive list of romantic questions to ask your boyfriend to form more of a bond between you and him! These questions will not only help you get to know your boyfriend in a more romantic way, but they may also spice up your relationship.

By asking these types of questions, you may have a tighter bond and a better understanding of your boyfriend’s thoughts and feelings.

Check out this list of 55 romantic questions to ask your boyfriend!

In this post:

  • Cute romantic questions to ask your boyfriend
  • Romantic deep questions to ask your boyfriend
  • Romantic questions to ask your boyfriend about your relationship

Cute romantic questions to ask your boyfriend

1. Have you traveled in the past? If so, where did you travel?

This is a great question to begin a lighthearted conversation about traveling! You get to learn more about your boyfriend’s interests and also share your own.

It lets him think back to a fun trip that he has taken in the past and maybe even think about what the trip would have been like if you had also been there.

2. Where is your dream location for a vacation?

Your boyfriend may have not even thought about his dream vacation before, or if he had, it was only in his dreams! Asking this question can create a space for him to build up hope that one day you and he could make that dream vacation come true!

3. If your paycheck could be any number, what would your career be?

Everyone is always so focused on the size of a paycheck when looking for a job to pursue. Asking about his choice of career while omitting the paycheck roadblock might actually help him consider options that he had only set on the back burner!

4. Do you prefer dogs or cats? Would you want one as a pet in the future?

If you have your heart set on getting a dog or a cat in the future, then this is the perfect question to ask! You could even learn about your boyfriend’s past pets and where his head is at when thinking about getting a pet in the future.

It is a great way to see if he sees your relationship as something that could last for a long time. It seems to me that getting a dog or a cat tends to be something couples do when they are planning to be in that relationship for a long time!

5. Where do you want to live if you had to choose to stay in one place for the rest of your life?

This is a long-term sort of question. But also can be quite a romantic question to ask your boyfriend as it shows that you are trying to plan a living location with him.

This can open up the conversation to a planning session where you too can really take the time to consider all your options when it comes to finding a long-term place to live.

6. If you could learn any instrument with ease, which instrument would you learn how to play?

Another great question to ask to keep the conversation lighthearted. You could ask this question while on a stroll around the town or even at a music venue where it would be very fit!

This is also a chance for you to share any instruments that you are able to or interested in learning how to play. This could also be your chance to come up with ideas for a birthday or Christmas gift for him in the future!

7. What is your favorite activity to do in your free time? Would you like to do that activity with me?

This is a cute and flirty question as you are showing your boyfriend that you want to partake in activities with him and that you also prioritize his enjoyment in the activities.

You can come off as genuine and caring when asking such a question and get some great ideas for days when you both have some free time to fill!

8. Where do you want your first apartment or house to be located? Do you picture yourself staying there long?

This is another great romantic question to ask your boyfriend because it could show him that you are planning to be with him for the long run.

I love asking my boyfriend this question because he loves planning for the future and I think asking him this question begins a conversation that he is really excited about!

9. If I needed to describe you in three words to a friend, which three words should I use?

Although this is a pretty thought-provoking question, it can also be asked in a nonchalant way that keeps the conversation light and casual.

It could also get your boyfriend to remind you of the qualities that he values in himself and remind you of what you love about him!

10. When you are having a bad day, what usually cheers you up?

This romantic question can be asked in a compassionate way that shows your boyfriend how much you care about how he is feeling.

It can show him that you want to make sure he is doing okay. I love this question because it can help you find out exactly what you can do when your boyfriend needs cheering up.

11. What is your favorite place to go out to lunch? How come you like this place in particular?

You could pretty much ask this question at any time of day and at any event during which you are with your boyfriend! Even at a time when you both are hungry and looking for a good place to have lunch!

You can also learn more about your boyfriend’s food preferences and even learn about places you and he could go on a future date night!

12. What is your favorite music to listen to? What music puts you in a romantic mood?

This question is so versatile, and can be very sexy in the moment! You might even catch your boyfriend off guard and surprise him with talk of romance.

It could get him thinking about what music he would want to listen to while in bed with you and that could be a real turn-on! This question is definitely one of those you could ask while on a dinner date with the plan of saving dessert for when you get home!

13. What is the next romantic movie you and I should watch together?

Everyone loves a good Netflix and chill night! But is it sometimes a challenge to find the right combination of a chick flick and adventure for both you and your boyfriend.

By asking your boyfriend this romantic question, you could get his honest opinion on the type of movie he would find romantic to watch with you.

14. What is the most romantic or impactful book you have ever read? Would you recommend that book to me?

Books can sometimes be the eye of the soul. I love asking my boyfriend what books he likes because it gives him a chance to share his favorite topics and any insightful lessons he has learned from those certain books.

This question is also a way for him to feel like his opinion and advice on books is valued. He gets to give you recommendations on books that he cherishes and has enjoyed reading!

15. What career paths other than your current path have you seriously considered in the past?

This is a romantic question that can help your boyfriend dig into his past dreams and aspirations. He will have the chance to reminisce about the possible paths he could have taken in his early years.

He may even get emotional about why he ended up pivoting into his current career path. The conversation following this romantic question could also lead to a chance for you to share your own career goals with him!

16. If you won a million dollars from the lottery, what would you do with the money?

Though the chances of your boyfriend winning the lottery are pretty slim, him becoming a successful man in the workplace may not be as impossible. So asking him what he would do with the prize money could be valuable information later on in your life together.

17. If you could return to a year in your past and relive your life starting from that age, what age would you return to?

This is a very thought-provoking romantic question that you can ask your boyfriend while also asking yourself. What age would you return to?

With you both thinking about the answer, it gives you both a chance to share an age that you really enjoyed from your past during which the other person did not know you. You may be surprised by how much you can learn about each other just by asking this simple question!

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Deep romantic questions to ask your boyfriend

18. What is your biggest aspiration in life?

Thinking about aspirations can create a motivational conversion where you both get to learn about each other and share your support for each other’s goals in life.

I love asking my boyfriend this question because it gives us both a chance to share with one another what we prioritize in life other than each other.

We get to make sure that while we are going off and aspiring to be the people we want to become, we are also able to unwaveringly support each other along the way.

19. What is your biggest regret from your past?

This deep romantic question may draw tears as it will bring up a negative memory that your boyfriend might not have shared with you before.

This is a great question to ask when you bother are in the mood for a deep and insightful conversation. One in which you practice the valued virtue of active and respectful listening.

20. If you could redo anything in your past life, what would it be?

If you already know a few of the things your boyfriend may regret doing in his younger life, asking him about redoing any of those actions could show him that he does have a chance to move past those mistakes and improve his decisions in the future with you.

This is a perfect question to show your boyfriend that you want to make anything possible for him to move forward with.

21. What is the biggest loss you have experienced?

Many people have trouble talking about the major losses they have experienced in their lives. This is a question to ask your boyfriend when it seems that he needs to let it out.

When he is having a bad day but hasn’t been ready to tell you why, or when it just seems as though something is bothering him. By asking him about a loss he has experienced, you can give him a shoulder to cry on and also make him feel less alone by even sharing a loss that you have experienced as well.

22. When was the last time you were truly happy?

To brighten the conversation, you could ask your boyfriend about the last time he was truly happy! He could then share a fun experience he had or a fond memory with you that he cherishes.

This could create a real bonding time for you broth to reminisce about a special time when you both were happy with one another.

23. What is something that your parents did during your upbringing that you want to make sure you also do if you end up having children?

If you want to learn more about your boyfriend’s relationship with his parents then this question is the way to do that!

You could also learn about what your boyfriend values in ways of parenting and you could make sure you both agree on certain things before taking the next step toward parenthood.

24. What is something that you struggle to tell people about yourself that you want to share with me?

This emotion-provoking question may bring up a negative memory that your boyfriend has been hesitant to share with you.

You could not only learn about that particular memory of his, but also learn why he didn’t feel comfortable sharing it with you before. He may take this time to get something off his shoulders that had been weighing him down.

25. What is your biggest flaw?

Though you do want to learn about the positive aspect of your boyfriend and the reasons you love him as much as you do, there are also important things to know about him such as the flaws he sees in himself.

As people tend to see more flaws than good when looking at themselves, this could be a way for you to point out the fallacy in his idea of his own flaw.

Or you could even learn about something he is actively working on to improve himself.

26. What is your biggest fear about the future?

Everyone has fears about the future, no matter how big or small. By asking your boyfriend what those fears are for him, you could learn if you both share any of the same fears.

You could also learn how you can further support him and even make sure that those fears don’t come true in your future.

27. What is one of your fondest memories of us together? What about when we have been apart?

An important part of any relationship is the memories you both get to create together. But another important part is the memories you make when you are apart.

By asking your boyfriend about his fondest memories when you were both together and apart, you could reaffirm the benefits of you spending time in your own space and remind yourself that you don’t need to spend any waking minute of every day with him.

28. Which of your parents do you see the most in your own personality?

If you have met boyfriend’s parents before then you may already have an idea about which one he sees more in himself.

But, if you have not gotten to know them before, you may learn more about them by just asking this deep romantic question. I know that I have even learned a lot about my boyfriend through getting to know his parents!

29. What makes you feel most protected and secure?

A valuable part of any relationship is the mutual feeling of security and protection. Asking your boyfriend about what makes him feel both these ways could create a mutual understanding of how you can make sure you bother are always feeling the best you can in your relationship.

This could also strengthen the longevity of your relationship!

30. When was the last time you felt truly angry at someone or something?

Though it may not happen as commonly as other emotions may, anger might come up in various situations and it is important for you to be aware of how your boyfriend acts when he is feeling angry.

Asking a question about the last time he felt angry could help you learn about how he dealt with the situation so you can be more prepared for the next time he feels angry at someone or something again.

31. If you could change one of your personality traits, which would you change?

This is another way for you to learn a bit more about your boyfriend’s personality. He may even have traits that he is proud of and might want to highlight for you!

I enjoy this question because I think it gives your boyfriend a chance to share positive aspects of himself with you.

32. Do you consider yourself an introvert or an extrovert?

There are many different personality types and it is important for you to be aware of your own and your boyfriend’s personality type. I definitely consider myself an introvert with a bit of an extrovert personality when I am in a social setting, and my boyfriend is about the same.

Your personality may clash with or be very similar to your boyfriend’s personality and being aware of which could be a real help when in a social setting with him.

33. Do you consider yourself as an optimist, a pessimist, or a realist?

This is another great romantic question to ask your boyfriend to get to know him on a deeper level. Though this is a pretty serious question, it could be a great beginning to a nice insightful conversation!

34. Do you ever compare yourself to others? If so, who?

With many people sharing everything impressive about their lives on social media, it can be very easy for us to compare ourselves to others. It can even become self-deprecating.

Getting to know what your boyfriend compares himself to can help you understand his insecurities without him even realizing he is sharing them all with you!

Romantic questions to ask your boyfriend about your relationship

35. What should we prioritize in our relationship?

Your boyfriend may have a different idea of what he wants to prioritize in your relationship. Asking him this straightforward question can give you the insight you need to make sure you are both on the same page when it comes to priorities in your relationship.

36. Do you want to have kids sometime in the future? If so, how many?

Asking about your boyfriend’s plans for kids is a great way to tap into what your future may look like! Get to know what he wants to do in case you may have different opinions.

I love talking about kids with my boyfriend because I think that though we both have some contrasting options, the more open we keep the conversation the more we will be able to keep our plans flexible.

37. Is there anything that you think we should change about our relationship?

Though your relationship might be going smoothly and you are both satisfied with it, there still could be underlying possible changes that could make your relationship prosper even more! Just poor a soothing glass of wine and talk it over.

38. Would you rather have a relationship with constant communication or room for some space?

Though many couples believe that they need to have constant communication with their significant other at every waking minute of the day, it does seem to benefit some couples to designate some time to spend with themselves or with friends.

This romantic question about your relationship could help you both talk about the importance of your social lives and make it okay for you to go off and have some space from each other in a healthy way.

39. Do you see marriage in our future?

This may seem to be the constant elephant in the room. Does he want to marry me? You may ask yourself this question way too often for comfort, so why not just check in and see where he is at on the subject?

Maybe he will surprise you or affirm your suspicion of the need to take things in your relationship more slowly.

40. What sort of love language lifts you up the most?

The five love languages are words of affirmation, physical touch, gifts, quality time, and acts of service. Knowing each other’s love languages could be key in keeping communication about your sex life and also keep you closer than ever before!

41. Do you think that we are soul mates?

It may sound a bit testy to your boyfriend, but this question could give him the chance to affirm to you his love for you and your relationship. It can open up the conversation to give you bother a space to share how close you are with each other and how much you value each other.

42. What do you think our biggest strength is in our relationship?

If your boyfriend hasn’t thought about how he is contributing to your relationship, then asking him a question about his biggest strength in your relationship can help identify where he is either giving a great effort or lacking in some way.

Make sure you are honest with him after he answers this question because this is your chance to share where he might be able to improve in your relationship.

43. When you imagine our future, what do you picture?

When you imagine your future with your boyfriend, do you think it aligns with his own imagination? If you are unsure of this, then asking him about what he imagines your future to look like can clear the air and give you a solid understanding of where you are both at in that moment.

44. When was the moment you realized you were in love with me?

This sweet and short question will make your heart race! Ask your boyfriend this question and he may even blush as he thinks back to the time when he first knew he was in love with you.

45. What are the positive things about being in a relationship?

Being in a relationship comes with many challenges. Asking your boyfriend to think about the positive aspects of being in a relationship can remind you of why you continue to deal with those challenges.

This can become a really important conversation if there is ever a time when you both feel distant or like you may be struggling in your relationship.

46. What was the first thing you noticed about me that caught your attention?

This can be a cute conversation to have with your boyfriend on a date night! You can both share with each other what you are attracted to about each other!

I love asking my boyfriend this question because I feel that reminding each other of what we find physically and mentally attractive about each other spices up our relationship not only in social settings but also in more intimate times.

47. Where is your favorite place to go on a date with me?

Date nights can be a great way to keep the bond with your boyfriend strong! Picking a fun or relaxing way to spend those dates is an important part of the process!

Having it be enjoyable is definitely important when staying in a positive mood during the date.

48. What can I do to make you feel the most loved?

It is so important to make sure that your boyfriend feels loved when he is around you! Asking him this question can give you the inside scoop as to what you can do to make sure he is feeling loved in your relationship.

Even though I ask my boyfriend this question sometimes, I make sure to ask him it multiple times throughout our relationship because his answer tends to change with time as well.

49. If you were to describe me in three words, what would they be?

Though you may already have words in mind to describe yourself, hearing these words from your boyfriend can be heartwarming and boost your confidence! Ask this question when you get a chance because believe me, it will make you blush no matter what he says!

50. What is something that you see or do that reminds you of me?

I love this question because it is something not many people have thought about before! I have found that you do tend to pick up little habits or say the same phrases as your partner after spending time with them for a while.

This is a cute and romantic way to remind yourselves of those cute personality traits that you both have in common!

51. What is your biggest turn-on that I do in bed?

This is a funny question to ask because I am sure your boyfriend would love that you know what turns him on in bed, he just might be hesitant to tell you. Therefore, asking him this question will give him the chance to let you know!

It can also help you know that you are doing the right things to turn him on! You can also share with him what he does that turns you on!

52. Have you ever gotten jealous of me with other guys? If so, when?

Chances are, your boyfriend has felt jealous of you in the past when you have been in social settings. If you have any guy friends, you may have already experienced his jealousy.

I find it important for him to be able to voice those feelings as he may be trying to hide them. But if they build up too much, they could cause more harm than good.

53. If we had never met, where do you think you would be now?

This could be an opportunity for you both to talk about how much your lives have changed in a positive way since meeting each other.

54. Is there anything that I may do that would make you rethink our relationship?

This romantic question you can ask your boyfriend is a serious, yet vital question to make sure you keep your relationship a positive one.

55. What is a big reason why you love me?

This adorable question, I just had to end this list with! Though there are challenges to a relationship, there is a big reason why you love your boyfriend and why he loves you. Make sure to remind each other of this reason as often as you can!

The best part of this list of questions is they can be asked at any time! You can ask your boyfriend these romantic questions while on a date, over text conversations, over a phone call, or even just while driving or walking on an errand run!

That’s a wrap. This article was all about romantic questions to ask your boyfriend. Was it helpful? Share the love on social media.

55 Romantic Questions to Ask your Boyfriend (1)

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