155 Questions to Ask Your Boyfriend and How To Get Him Open Up

Good and Cute Questions to Ask Your Boyfriend

You probably know a lot about your boyfriend since you might have asked him subtle questions while he was still your crush. Now that he’s your official beau, you’re probably enthused to get to know him even more. Because why not? A healthy relationship should be rooted in sheer honesty and trust, right?

Or, perhaps, you wonder what else is there to ask since you’ve been together for quite a long time now. In spite of that, the vault of relationship questions would never run out to a zealous lover like you.

You might just have a tinge of uncertainty, worrying if it is alright to ask him certain questions… or if your question would sound silly or worse, dead serious.

But hear this out!

No matter what those questions are, as long as they come from the heart, then speak. It may warrant proper timing but that love you have for him entitles you to ask him those questions, especially when all you ever want is that you and your boyfriend stay together for the longest time possible.

We can help you! You might have the same questions and just want to know if it’s alright to ask them. Go ahead and run through our list. Get some pointers with our quick tips if you are not wholly sure about it.

Best questions to ask your boyfriend

These questions are not only things that you can talk about with your boyfriend but they can also be your juju if you wish to keep that “romantic sparkle”.

Deep Questions

Deep Questions to Ask Your Boyfriend

Do you ever have that inkling of wanting to ask your man questions that you think are so deep that you end up not asking at all for fear you won’t get answers? Or that he might think you are invading his privacy?

And so to avoid that potential stab straight to your heart, you simply bottled them in? Don’t worry. You may still ask him deep questions, especially if you sincerely want to get to know him a lot deeper. But before you dig into something, consider these tips.

How to ask your boyfriend deep questions:

  • Timing. Deep conversations are best when the timing is right. Find the perfect timing.
  • Warm up. Before you dig down deep, try some tiny and tender “scoops” first. When it feels smooth and comfy, you probably can start digging deeper.
  • Set up the mood. Set up the room like it is the most comfortable place in the world to be vulnerable. Candlelights are quick fixes.
  1. Would you rather be good? Or would you rather be right?
  2. Do you believe in life’s purpose? Have you found your purpose in life?
  3. Are you satisfied with what you have (or have been doing) in your life? Have you been living the life you dreamed about?
  4. Is there something you wish to pursue or fulfill?
  5. What do you believe in? How about the things that you cannot believe in?
  6. What’s the most meaningful thing you have ever done? Why?
  7. For you, what’s the most important trait a man (or a woman) should have?
  8. What makes you admire a person? Is there someone you look up to? Who?
  9. Do you have any secrets that you wish you could tell someone? Can you trust me with it?
  10. What is something that someone could do to lose you?
  11. Do you believe in second chances?
  12. What is an ideal girlfriend for you?
  13. Is there anything that you would likely choose something (or someone) else over me? What is it?
  14. Will you still be friends with an ex?
  15. Is it alright with you with me having a male best friend?
  16. Have you cried for someone? Have you cried because of love?
  17. What happens when you’re upset? How can I help you when you’re feeling upset?
  18. What makes you angry? Have I already made you feel angry?
  19. What is too much love?
  20. Is jealousy love?

Good and Cute Questions to Ask Your Boyfriend

Good and cute questions to ask your bf are supposed to be like that. They are there to make the conversation feel nice, sweet, endearing. These questions are best asked when you want to express your stark affection while demurely probing if he is to you in the same way spellbound.

How to ask your boyfriend good and cute questions:

  • Is he ready for such questions? If not yet, you may want to reconsider and endure a bit for that ideal moment.
  • Take a cue from him. If he starts asking you questions, that could mean it’s the perfect time to fire away yours!
  • Is it a good purpose? What is the question for? Remember that your question is supposed to make both of you feel good talking about it. Some questions are essentially cute but may rather be “unsafe”, such as “What do you dislike about me?”, “Do you still find me pretty?”, or “When was the last time you thought about me?”. You can still ask them but try to be very cautious so as not to push your luck.

Good and Cute Questions to Ask Your Boyfriend

  1. Where do you want us to travel next?
  2. What’s our next adventure?
  3. What do you want for lunch (dinner or breakfast or snack)?
  4. Are you ready to binge-watch and chill?
  5. Which movie have we watched that you’d want us to watch again?
  6. What’s the most memorable line in a movie (or a song) that we watched (or listened to) together?
  7. What’s the most unforgettable moment that we spent together so far?
  8. If you can take me anywhere else, where would that be?
  9. How can I make you smile during a rough day?
  10. If you could take me on a date right now, what would it look like?
  11. How can I kiss your troubles away? How can I make you feel better?
  12. What do you think will cheer me up?
  13. Is there something you’re hoping that we can do together?
  14. Would you like to hear the song (poem) that reminds me of you?
  15. Would you like to know the first time I realized you are very special?
  16. Do you want to hear the story of how and when I fell in love with you?
  17. Why the loving gaze?
  18. Do you want to know how much I miss you?
  19. Which time of the day do you miss me the most?
  20. So, what’s the first thing you’ll do when you see me?

Fun Questions

You probably want to know how to make your boyfriend happy in ways beyond the usual. Well, one of the ways is to ask him funny questions that actually are meant to make him laugh. Here are 21 questions that you can fire away. But first, read these tips!

How to ask your boyfriend funny and hilarious questions:

  • Before you ask these questions, you should probably need to ask yourself a few things, like “Will it offend him?” … “Is it the proper time?”. Consider how he’s feeling at the moment.
  • You could start with a seemingly serious line like “You know, I have something that I’ve been wanting to ask you…”

Fun Questions to Ask Your Boyfriend

  1. What’s the craziest, silliest idea you think that we should try?
  2. What’s the goofiest thing you’ve ever done? Would you do it again?
  3. What’s the grossest thing have you done that you thought you could take, but no, and so still regret it?
  4. What’s the weirdest thing you’ve ever done while drunk?
  5. What’s your guilty pleasure?
  6. Have you ever approached a complete stranger that you thought you knew?
  7. What’s the meanest, best comeback have you ever done to someone? Have you played on someone?
  8. Have you ever done something illegal accidentally?
  9. Is there something that you did and felt proud of but not anymore?
  10. Which part of your body do you think is just weird?
  11. How do your relatives call you? What’s your nickname?
  12. Which food would you rather die starving than eat?
  13. What’s the one thing you would never share with anyone?
  14. What’s the weirdest fad that you tried and thought was cool back then?
  15. Have you worn something that you regret to this day?
  16. Do you have any weird habits?
  17. Have I made you feel awkward? … embarrassed?
  18. What do you do when you’re bored? How do you kill time?
  19. If you could make a toon or an anime character come to life, who would it be?
  20. If you could create a holiday for something, what would it be and when?
  21. Do you have a victory dance or chant?

Personal Questions

Here are some questions to ask your partner to get to know him at the personal level. These juicy questions to ask your boyfriend could help you understand him a little more.

How to ask your boyfriend some personal questions:

  • You might have to answer the question first and share a part of your personal journey with him.
  • Understand that he might not open up yet, especially if he feels he isn’t ready to talk about them for now.
  • When he feels he’s ready to share, be ready. His answers might surprise you. He could be sharing a part of his life that calls for your full attention.

Personal Questions to Ask Your Boyfriend

  1. What was your most cherished moment when you were a child? when you were still a teen?
  2. If you are confronted with having to choose to fix something about yourself, what is it?
  3. Have you liked someone who didn’t like you back?
  4. What’s a perfect day for you?
  5. Who is your favorite famous celebrity?
  6. What is your most prized possession?
  7. What’s something about you that you feel most proud of? … you feel most embarrassed?
  8. Who is your favorite relative?
  9. Do you love pets?
  10. Is there someone you wish you could reconcile with?
  11. When was the last time you cried?
  12. Have you had any near-death experiences?
  13. Have you tried dealing with your fears?
  14. What’s the scariest thing you’ve ever done?
  15. Are you into sports? Have you joined any contests? How did it go?
  16. Do you have a hidden talent (skill) that most people don’t know about?
  17. What is something that you truly care about that others think you don’t?
  18. Is there someone in your life you wish you could have talked to before they were gone?
  19. Is there something that you find simply amazing and beautiful while most people don’t?
  20. How do you cope when life gets tough?

Romantic questions about your relationship

The years you’ve spent with your boyfriend could mean plenty of memories spun together.Perhaps, it is even time to move to the next level by considering a lifetime together, forever.

How to ask your boyfriend some romantic, sexual, and serious questions about the future:

  • Some of these questions could be a step up to your relationship, like moving in together or before getting engaged. Therefore, these important questions are ideally asked to your significant other before you take your relationship with him to the next level.
  • His answers to these questions could gauge how much both of you are willing to compromise. Meet him halfway.

Romantic questions to ask your boyfriend about your relationship

  1. How do you intend to keep me?
  2. For you, how much sex should a healthy, happy couple have?
  3. How important is sex in a relationship?
  4. If I am not in the mood for sex, what are you going to do about it?
  5. What do you think about prenups?
  6. What’s your view about marriage? … divorce?
  7. What could possibly stand in the way of us being together for the rest of our lives?
  8. Do you prefer a small or a big family?
  9. What values would you like our future kids to learn?
  10. How do you picture me as your wife?
  11. How does our relationship inspire you to be a better man?
  12. What would you do if someone said something bad about me? about us?
  13. How and where do you see us in the future?
  14. What’s an ideal home for you?
  15. What’s your ‘me-time’ like?
  16. What’s the best way to handle arguments?
  17. How do I approach you if you’re disappointed in me? What should I do to calm you down?
  18. Do you have any big pet peeves that I might not like or could annoy me?
  19. Am I doing something that I may not be aware of but bothers you?
  20. Which of the things have I done for you so far that you think you won’t forget?
  21. If we will be apart, do you think our relationship can still work?
  22. What’s a perfect getaway? How often should we travel together?
  23. Do you like to cook? Would you wash dishes, clean the house, and do other chores for me?
  24. Why do people fall out of love? What would you do if you feel you’re falling out of love with me?
  25. Would you risk your life for me?

Serious Questions

If you’re thinking about what to talk about with your boyfriend, these serious and possibly hard questions to ask your boyfriend are your options. They are meant primarily to discover about your boyfriend’s past, the people in his life, his general worldviews, and his existential premises.

How to ask your boyfriend some serious questions:

  • Make it clear. Avoid vagueness. Otherwise, he will likely misunderstand it.
  • You could be digging about his past. Pay attention when he brings it to light. He may not be willing to talk about it again. So, listen with your heart.
  • You might not like or agree with what he might say. So, guard yourself well. You may air your side but do not attempt to insist your views on him.

Serious Questions To Ask Your Boyfriend

  1. Is there something you want to tell me but are too afraid to say? Can we talk about it?
  2. Have you ever broken someone’s heart?
  3. When was your first heartbreak?
  4. Why didn’t it work with your ex?
  5. What do you think is more important? Career or family?
  6. Are you comfortable with my friends? … my relatives?
  7. Can you fall back in love with someone you fell out of love with?
  8. How do you define cheating? What is cheating, what is not?
  9. When you say you did it because you love me even if I don’t want you to, what do you mean by that?
  10. If we are no longer together, will you stop loving me?
  11. What’s the best approach in reconciling conflict or differences with me?
  12. Do you believe in white lies?
  13. What are your religious views?
  14. What are your political views?
  15. Do strong independent women scare you?

Flirty questions

These flirty questions to ask your boyfriend are meant to bring you closer together. And they work pretty well, too, for couples who are miles away. Texting your boyfriend these questions to turn him on will make him think of you and long for you even more.

How to ask flirty questions to your boyfriend:

  • These questions are meant to romanticize the moment. And so be prepared with sudden romantic gestures or physical intimacies.
  • Do not worry about initiating a topic about sex. Do not feel embarrassed or awkward. Get creative and intimate with words.

Flirty questions to ask your boyfriend

  1. Do you find me irresistible?
  2. What’s one thing about me that you find the most attractive?
  3. What are you going to do if I touch you and kiss you right now?
  4. Do you like my perfume?
  5. Do you want me to warm your body up with mine?
  6. Where do you want me to kiss you?
  7. Do you work out? Do you like to see me work out?
  8. Top or bottom?
  9. What’s the wildest, craziest sexual fantasy you have?
  10. Have you tried sexting?
  11. How long should I wait?
  12. What’s a nonsensual word that just sounds sexy?
  13. Am I a good kisser?
  14. Do you want us to try something new?
  15. How do you want me to touch you? Where?
  16. Where do you want to touch me?
  17. What do I taste like?

Random Questions

Random Questions to Ask Your Boyfriend

These random questions may sound too weird and silly to ask your boyfriend but they are just too interesting not to ask.

  1. When did you start having feelings for me?
  2. Can love be measured?
  3. What makes a woman’s love different from a man’s love?
  4. What is love?
  5. Who invented love?
  6. I know you love me. But do you like me?
  7. I will never get enough of you. So, what are you gonna do?
  8. Why are we so perfect together?
  9. Are we soulmates?
  10. If we switched genders, would you still like me?
  11. If we are movie characters, who are we going to be?
  12. How would you describe us as a couple? I think we are a perfect match!
  13. What’s your zodiac sign?
  14. If you would have a superpower, what would it be?
  15. What’s the best way to waste time with me?
  16. Do you love stars?
  17. What’s your favorite word?

How to get your boyfriend to open up

Establishing a deep connection with your boyfriend isn’t just about physical intimacies. You can also touch his heart, mind, and soul by exchanging words, thoughts, and vulnerabilities. So, how can you get your boyfriend to open up to you? Here are some tips:

  • Know what to ask your boyfriend and what not to. Start with something classic. When he feels comfy, he will likely tell more.
  • You may want to answer the question first. Chances are, he might return the question. And so, it’s best that you’re prepared. Be ready to open up. Confide. Unbosom.
  • Why would you like to ask him your question? Having a clear purpose will help direct the course of the conversation. Besides, he might be asking you why and so you will be obliged to state your reason, which sometimes may be his basis whether to answer or not.
  • Acknowledge that getting an answer from him may not be today. Timing is everything. Find the most suitable time. Or, you can create the moment. Set up the mood. Cuddles! Or simply sitting next to him works just fine. It doesn’t have to be looking at each other in the eye. In fact, this stance may be intimidating for him to speak up – unless, of course, when all is said and done, then, such a romantic gesture might call for it. x
  • Make sure you aren’t busy too! Listen to him. Hear his story. Follow up with more questions and make the most out of the sweet opportunity.
  • When he answers your question, be as open-minded as possible. If you don’t agree with what he just said, instead of cutting him with your own view, consider replying with lines like, “That’s interesting!” or “That’s new!” (which imply that your views are somewhat different from his). Make him explain by following up with a question and you might be surprised with what he is about to say. It’s not really about being on the same page or agreeing with him even if his views defy your own. Rather, make him feel that your feelings won’t change even after laying bare his most intimate thoughts and that it is safe to take that risk with you.
  • Know your limitations, too. If your questions are meant to help strengthen your relationship, you might as well set boundaries and make them known before letting him answer you. If you are not comfortable with where the topic is going, then, do not encourage him to tell you more.

Final Thoughts!

Refuse relationship standstill. Be inspired by our more than 100 questions among the myriad of things to ask your boyfriend. Hearten your relationship through deepened and intimate connections.

Asking questions – from anything silly to something truly meaningful – helps a romantic relationship bloom in requited love, faith, and solace that shall never be found anywhere else but in each other’s company.

“Remember that everyone you meet is afraid of something, loves something, and has lost something.”
— H. Jackson Brown, Jr.


By Maria Victoria Gonzaga

Last Updated on July 13, 2022