When you’re trying to find out as much as you can about your beau, a few cute questions to ask your boyfriend will help you get the conversation flowing.
Getting to know your boyfriend might sound easy, but how well do you really know him? Let’s be honest, men are complex creatures. You might think you know everything there is to know, but when you delve a little deeper, you’ll be surprised at what you’ll learn with these cute questions to ask your boyfriend.
Weird and wonderful conversations are underrated in our opinion. There is nothing wrong with sitting there and talking about absolute rubbish. Go ahead and ask silly questions, then try to second guess their answer and work out just how much you actually know them. [Read: These serious questions to ask your boyfriend will help you develop a deep bond]
Why questions are great for couples
Asking random questions is a great way to get to know your partner and it takes the pressure off the whole process. The cute questions to ask your boyfriend you’ll find below help you to learn more in a fun and easy-going way.
Then, you don’t have to read between the lines and you’ll find that with just one or two questions, you’ll be having a deeper conversation very quickly. [Read: 42 happy and naughty ways to keep a relationship exciting, fun, and fresh]
Cute and fun questions to ask your boyfriend
If you’re struggling to come up with a few questions to ask, or you’re just not sure which direction to go, check out these cute questions to ask your boyfriend. Then, figure out what his answers might be.
1. What is your favorite way to pass the time?
Everyone has something they like to do when they’re alone, bored, and just trying to waste a little time. Some people like to read, others like to sing, and some people like to just watch Netflix.
Ask him what his favorite way to waste some time is and see if it matches up with yours. Maybe you can start wasting time together! [Read: These red flags in a guy will only end in your broken heart]
2. What toy did you play with most when you were a child?
This is one of the cute questions to ask your boyfriend because it helps him remember his childhood.
He’ll probably sit there with a cute smile on his face, remembering all the fun toys he used to have.
3. If you had to choose a favorite animal, what would it be?
You can learn a lot about a person by the type of animal they like best.
For instance, people who like dolphins might be calm and serene. Or people who like bears might be protective and fierce. [Read: 20 deep questions to turn any guy into an open book]
4. What is the best dream you’ve ever had?
He might not remember it, but he’ll probably make one up anyway. It still tells you a lot about him. This is one of the cute questions to ask your boyfriend because it tells you where his mind wanders during sleep.
5. What five words would you choose to describe me?
This is definitely high up on the list because it tells you a lot about what he thinks and feels about you. It’s always interesting to let someone else describe you.
While you might not totally agree with the words he comes up with, it’s a fun conversation nonetheless. [Read: Get to know who you really are with these questions]
6. What did you think about me when you first laid eyes on me?
You’ve asked him the words he would choose to describe you, and now you want to know what he thought of you the first time he saw you. It might surprise you. [Read: 20 signs of attraction in the first conversation]
7. If I felt sad, how would you cheer me up?
This is interesting to know because if you are sad at some point in the future *hopefully not*, you can give him pointers now on the best way to make you smile.
8. How would you describe your perfect date?
When it’s your turn to organize date night, this information will come in handy indeed.
Of course, you can also tell him about your perfect date and give him some ideas for when it’s his turn to surprise you with a fun night out. [Read: 16 things every girl wishes for on a perfect date]
9. If you could choose any dessert, what would you choose?
Is he going to choose a sophisticated chocolate éclair or a fun-filled ice cream sundae? It might seem like a pointless question to ask, but not all questions have to have a deep, underlying meaning. [Read: Signs of a boring relationship? Here’s how to bring back the fun]
10. What would your dream career be?
If there were no barriers to choice, no need to train for years, or find the money to go back to school, what career would he choose to have?
This tells you a lot about him and the things he finds interesting. It’s one of those cute questions to ask your boyfriend that can help you really get to know him better too.
11. Who was your hero/role model when you were a child?
Was it a family member? A close friend? Perhaps it was a cartoon hero or maybe Superman!
Ask him who his hero was and watch his face break into a smile as he remembers all the fun from his childhood. [Read: Be your own hero – what it means and how to take control of your life]
12. Which is better – hamburgers or hotdogs?
This is silly, cute, and pointless, but it’s one of the fun questions to ask your boyfriend nonetheless. Which do you like best?
If he likes hamburgers, maybe you can make them for dinner, and if he’s a hotdog kind of guy, head out to a funfair for date night and enjoy some hotdogs!
13. If you could talk to anyone for 10 minutes, living or otherwise, who would you choose?
He might choose a family member that has passed or he might choose his favorite celebrity. Again, his answer will tell you a lot about what he finds important in life and the types of people he holds dear. [Read: Old love letters and memories – keep or throw them?]
14. What is your favorite thing about me?
Go on, you’ve been dying to ask! It’s one of the cute questions to ask your boyfriend, and it’s also a huge confidence booster for you! [Read: Steps to emotionally connect with someone and feel closer]
15. Are you a tea or coffee kind of person?
You might already know this, but if you don’t, it’s a good way to find out what his favorite drink is first thing in the morning!
16. If you were running for President, what would your key policy be?
Would it be banishing animal cruelty, climate change, taxes, or something else entirely? It’s fun to find out what’s important to him. [Read: Dating your opposite – how to know if you can make it work for you]
17. Sweet or savory?
Most people like sweet or savory best. Of course, most of us like both, but if we had to choose, we’d opt for one or the other.
This is one of the cute questions to ask your boyfriend that allows you to find out his preferences and his tastes. Maybe you can cook for him based on his answer!
18. Do you prefer the sunset or the sunrise?
There’s a point to this question – you get to find out whether he’s an early riser or not! Maybe you already know, but his answer might surprise you. Once you know, you might want to base a date around his answer. [Read: Romantic dinner date ideas – 17 fun dates you will both never forget]
19. If you could go back and study any subject, what would it be?
Most of us look back on our education and wish we’d studied something differently or a little more. Some look back and wish they’d gone into a totally different career altogether.
20. What would you do on a cold and snowy day?
The point of this question is to find out whether he would prefer a cozy, snuggled-up date with hot chocolate and a roaring fire, or if he’d like to head outside and enjoy the snow!
Maybe he would say skiing, snowboarding, or building a snowman. He might even suggest a snowball fight! [Read: Top 50 amazing first date ideas to wow your date]
21. What is your go-to dish when you’re cooking?
Most of us have a dish that we go to when we’re trying to impress someone. Or, we have a dish that we always cook because we’re so good at it. Once he tells you, suggest he cooks it for you on a date night.
22. What is your guilty pleasure?
We all have one! Ask him what his guilty pleasure is but remember that you need to return the favor and tell him yours too. It’s only fair! [Read: Shhh, don’t tell! Secrets you’re allowed to keep in a relationship]
23. Do you think about me when you’re out with your friends?
Now, he’s probably going to say that yes, of course, he does. But watch his body language for the real answer!
Guys tend to get totally wrapped up when they’re out with their buddies, but if he thinks of you, that means you’re pretty special to him.
24. What song reminds you of me?
Music is a powerful thing and it often transports us back in time or makes us think of specific people. You might be surprised by his answer and let’s hope it’s something romantic! [Read: 20 most romantic songs for the one you love]
25. What’s the worst thing you have ever done while drunk?
Prepare for this answer! We’ve all done stupid or crazy things when we’ve had a few too many to drink. Finding out his drunken confession might make you laugh or gasp in shock.
26. If you could live in a huge mansion, how would you decorate it?
Would he turn it into a bachelor pad or would he go for something a little more classy? Let’s hope that if one day he ends up with a mansion, he asks you to help him decorate it and live there too!
27. What would you choose if you could change your name?
Maybe he likes his name the way it is, but most people wish they had a funkier name. [Read: 45 funny questions to get to know someone better instantly]
28. What food do you want to try that you’ve never had before?
Lobster, frog’s legs, snails, the list goes on. What does he want to try? Let’s hope it’s nothing gross because maybe he’ll suggest you both try it on a future date night!
29. Do you hear the words or the music?
There are two types of people – those who listen to the words and those who listen to the beat. Which category does he fall into?
If he listens to words, he’s pretty deep. If he listens to music, maybe that means he’s a budding musician himself. [Read: The best songs to make out to]
30. What is number one on your bucket list?
Does he want to go skydiving? Maybe he wants to travel the world. How about learning how to do a particular skill?
By understanding the number one choice on his bucket list, you learn more about what he aspires to and dreams about. [Read: Couple’s bucket list – 20 things every couple needs to do]
31. If you had your dream job but made very little money, would you still be happy?
This is one of the fun questions to ask your boyfriend and it really shows his true intentions in life. Does he want a lot of money or would he rather be poor but do something he loves?
It’ll show you a lot about his drive and dedication. He might surprise you!
32. Be honest, do you believe in love at first sight?
Some guys are hopeless romantics who believe this to be true 100%, but others would say this is a complete myth. It’s great to know which side your boyfriend falls on. [Read: The truth behind love at first sight]
33. What’s your opinion about life after death?
Do you believe ghosts exist – or their spirits – or whatever you want to call the afterlife? Maybe you do and your boyfriend doesn’t believe in this at all.
It can tell you a lot about his beliefs and it’s also just a fun question to ask. It’s not something you necessarily have to agree on, so don’t panic if you have differing views.
34. Has anyone ever cheated on you?
The answer to this question can tell you more about how your boyfriend operates in this relationship than any other question. If he’s possessive, controlling, or even just insecure without those other qualities, this could explain why.
Plus, it’s always good to know if this has happened in your boyfriend’s past. This is one of the most important things to ask your boyfriend. [Read: What is cheating in a relationship? The truth most people ignore]
35. Could you ever forgive someone for cheating on you?
This is a great follow-up question because his answer could mean a lot about who he is as a person. If he just can’t forgive something like this, it also shows you how important this offense is to them in a relationship. [Read: Are you cheating? Accidental ways you could be cheating without realizing it]
36. Describe your faith, or lack of one
Knowing someone’s faith is extremely important. Even if you don’t agree with it or see eye to eye on certain things about their beliefs, it’s great to know how their mind operates when it comes to this subject.
He might not have a faith, or it might be that it’s something he’s still figuring out. Either way, it’s one of the important things to ask your boyfriend.
37. If you could do one thing with your life, money not a factor, what would it be and why?
If you really want to know your boyfriend’s true passions, ask him this question. You’ll get to see how he would truly be happy if money was never a factor.
You may not have even thought about this being one of the fun questions to ask your boyfriend but it gives you a lot of important information about who he is as a person. [Read: 30 fun and super cute questions to ask your boyfriend to have a laugh]
38. What has been the best day of your life so far?
Good things happen to people every day. But when someone has a “best” day, you should know about it. It can show you just what is most important to them and what makes them the happiest.
It might not even sound like anything earth-shattering to you, but there will be a small detail in there that made it ultra-special for him. [Read: 60 get-to-know-you questions for a new romance]
39. What is the one thing you wish your parents knew about you?
Whether they answer with a dirty little secret of something they once did or a profound message that they truly wish their parents knew, you will learn a lot about their relationship with their parents with this question.
40. If you could have a do-over for one thing in your life, what would it be?
This is one of the fun questions to ask your boyfriend because it can show you what his greatest regrets are and maybe it will shine a new light on why he does things a certain way. [Read: The different kinds of regret and how to deal with it]
41. What’s the worst thing you would do for a million dollars?
This is assuming he doesn’t already have a million dollars. If that’s the case, lucky you!
His answer could speak volumes about his character. What lengths will he go to for that kind of cash?[Read: How well do you know me? 35 fun questions for couples]
42. What are you the most ashamed of in your life?
Everyone has something that they’re ashamed of. They have to be really vulnerable and open up when talking about this topic.
It’s probably not the best question to ask if you don’t know your boyfriend that well, i.e. you’ve only just started dating.
43. If you could change one thing about yourself, what would it be?
Not only will this highlight an insecurity he has, but it could be something that you love about him. Then, that will give you the opportunity to tell him so he feels better about it. [Read: Common insecurities of men that most women have no ideas about]
44. Do you think your parents are proud of you?
Knowing how your boyfriend sees himself in his parents’ eyes will help you to understand how he sees himself in relation to other authority figures – and even how he sees himself in relation to you.
When you are still wondering about things to ask your boyfriend, don’t forget to ask about his family using a question like this one.
45. Would you move across the country for your dream job?
Is his passion to have his dream job strong enough to drive him across the country – or to another country? If the answer is yes, then you also know what your future could look like.
He might tell you exactly what his dream job is and where it may take him. [Read: Follow your dreams – all the amazing reasons why it’s worth it]
46. What is a character trait you value most in a person?
This is one of the cute questions to ask your boyfriend you need to pay special attention to. It clearly shows the values he will hope to see in you as well.
All of us have core ideas and principles in life that are built because of our upbringings or the way we see life. What are his?
47. When/if you have kids someday, what’s the one thing you hope they grow up knowing about you?
This will give you insight into something that he probably doesn’t tell anyone else and that he probably wants most people to know about him.
You’ll be able to understand what he sees as his most important attribute. It could also tell you almost instantly whether he wants children or not. [Read: 19 things you must do as a couple before having a baby]
48. What do you think is the most important thing in a relationship?
If he says showing affection and you think it’s communication, then the two of you could be on completely different pages – which could cause issues down the road. [Read: 50 questions to ask and find out if someone’s right for you]
49. If you could describe yourself in only one word, what would it be?
Not only is this one of the fun questions to ask your boyfriend, but it makes him think really hard about one SINGLE word that describes himself. You’ll get to see how he truly sees himself.
50. Do you believe in having a soul mate or that love is a choice?
Does he think there’s someone – or even multiple people – out there for everyone and you’ll find them someday? Or, does he believe in love being a choice?
Knowing this information won’t necessarily change anything in your relationship, but it’s interesting to know, nonetheless. [Read: Real soulmates – 20 signs you’ve found the love of your life already]
51. Did you have an imaginary friend as a child?
If not, what type of friendships did he have? Was he a social butterfly, or more of the shy, silent type?
52. What was/is your favorite superhero?
Every superhero has their own cool thing. What is it that he wishes he could do for the world? This is one of the fun questions to ask your boyfriend because it tells you the skills he wishes he had.
53. What was your dream car growing up?
Was he all about the muscle car, the speed and sexiness of the Lamborghini, or did he simply want the new Mazda that his dad brought home in second grade? [Read: 15 awkward questions guys wish they could ask girls]
54. What is your greatest accomplishment?
This is one of the cute questions to ask your boyfriend because it allows him to gush about something he’s proud of. It will also help you find out what he values in life.
55. What is your first memory?
What are the things that stick with him? If he remembers only the terrible things, he is likely more of a pessimist. But if he remembers that he won a drawing contest, he may celebrate his accomplishments more. [Read: How to think positively and reprogram your mind to become a more positive person]
56. Who was your first crush?
The first crush a guy has can shape not only the women that he chooses in the future but also the way he enters a relationship later in life.
57. Did you like school?
Some people thrive in a classroom environment, whereas others favor more active, hands-on learning. Find out which way your guy leans with this question.
58. What was your favorite movie as a kid?
Was he more of a fantasy guy, a slasher lover, or a regular comedian? What entertains him the most? Does he want to laugh, cry, be inspired, or be scared out of his wits? [Read: What are you passionate about? How to find and own your true desires]
59. For how long did you believe in Santa?
This is certainly one of the cute questions to ask your boyfriend, but let’s hope he doesn’t still believe! You really don’t want to be the one to burst his bubble.
60. Did girls ever make you nervous?
Was he a ladies’ man from the get-go or more of the silent observer type? Usually, a boy who is comfortable around girls remains that way. A more reserved man may have a harder time communicating his feelings. [Read: The 20 cutest, most adorably awkward moments we all go through in a new relationship]
61. Were you an early or late bloomer?
Puberty is very unkind to most of us. If you grew really tall too fast, you felt awkward. Yet, if you were the runt of the group, you had something to prove.
This is one of the fun questions to ask your boyfriend because it will take him back to those awkward, teenage years.
62. Have you ever been a momma’s boy?
Momma’s boys normally don’t change. Even if he is one, if he can at least admit it to himself, chances are more likely that he’ll have a better handle on controlling relationship issues that may stem from this trait. [Read: Avoid them like the plague – 16 types of guys not to date]
63. Who taught you about the birds and the bees?
Where did he get his information about what a relationship is?
If he learned it from his parents, he likely got the whole “respect” talk. If he learned it in the locker room, he probably learned that it’s all about the “scoring.” [Read: Losing your virginity and having sex for the first time]
64. When did you have your first drink?
More adventurous people might have their first risk-taking behavior early on. If he’s still waiting for his first beer, then you know he doesn’t like to play with fire and does things by the book.
65. Have you ever had a summer love?
Summer loves are different from other types. They’re the ones that you fall head over heels for, throw abandonment to the wind, and blow your friends off for.
Has he ever just let go and given all that he has to a short-term love affair? This is one of the cute questions to ask your boyfriend that may reveal some serious memories. [Read: Things a boyfriend MUST do if he wants to prove his worth to you]
66. What is it about a house that makes it feel like home to you?
Does he feel attached to things and physical locations, or the people in them? This is another cute question to ask your boyfriend because it potentially reveals some useful information for the future. [Read: Undeniable signs he wants to spend his life with you]
67. When you’re gone, what do you want people to say about you?
This is one of those fun questions to ask your boyfriend that’ll tell you a lot about the way he wants his life to turn out. What does he value in life and think is important to do while you’re here? [Read: 22 early warning signs of a bad boyfriend all girls must look out for]
68. Where do you see yourself when you’re 70?
What are his goals? Not just monetarily, but personally and emotionally?
69. What food reminds you of me?
Maybe it’s his favorite dessert, or something a little more meaty? Either way, it’s one of the fun questions to ask your boyfriend because it’ll probably make you both laugh!
70. How often do you think about me throughout the day?
Of course, he’s going to tell you that he thinks of you all the time, but it’s a cute and fun way to initiate a conversation about how you miss one another when you’re not around.
71. Does it make you smile when I send a text message?
Again, he will no doubt say it does, but check his body language on this one – it never lies! [Read: The 80 best cute texts for him]
72. What is your favorite thing about our relationship?
He might say how you can talk about anything, or he might jump straight to sex. Either way, it’s a fun and useful starting point to talk about your relationship, how you both feel about it, and where it might go.
73. What’s the one thing you want to do together that we haven’t done yet?
Keeping things fresh in a relationship is important and this is one of the fun questions to ask your boyfriend because it allows you to come up with new ideas.
If you’ve become stuck in a rut, this question might help you get out of it. [Read: 33 awesome date ideas every couple should try]
74. What is your favorite kind of date, and what do you think mine is?
This is a useful question to find out if you’re both on the same page. Maybe he thinks you like super-romantic dates but in reality, you like to get out and do something. You can use this to set the record straight!
75. What is the best compliment I’ve given you?
He’ll probably remember it and will love reminding you, so you can tell him again!
76. What is your idea of a perfect Sunday afternoon?
Find out so you can incorporate his ideas into the next weekend you spend together. [Read: 25 couples activities that make you feel loved and closer than ever]
77. Countryside or city?
Again, this is one of the fun questions to ask your boyfriend that gives you food for thought. If you want to plan a weekend away, you could use his answer to decide where to go.
78. What’s your favorite pet name for me?
If you don’t like what he calls you, now is the time to put him straight!
79. How often is your brain on autopilot?
If he goes through the motions on autopilot a lot, it could mean that he’s not satisfied with his job or where he is in life. The answer he gives you could be very telling indeed. [Read: I’m so bored with life – 20 ways to bring the spark back]
80. If you could eat one food for the rest of your life, what would it be?
Let’s hope it’s something nice because you’ll probably be eating it too! This might not be deep and meaningful, but it’s one of the fun questions to ask your boyfriend to find out more about his likes.
81. What is your weirdest pet peeve?
We all have them, and it’s useful to know what his are, so you can avoid showing them to him!
82. Name a time when you’ve laughed in an inappropriate setting?
We’ve all done it, and it’s one of the fun questions to ask your boyfriend so he can share his embarrassment at his social faux pas! [Read: 15 types of humor and how it affects relationships]
83. Have you met any celebrities?
If he’s met someone you love, you’ll probably be super jealous. But, he might have met people you don’t like, and then you can find out what they’re really like.
84. Where is your go-to destination when you want to relax?
This is another cute question to ask your boyfriend because he will share his secrets with you. He might like to take you some time, too. [Read: 15 reasons why you should travel at least once a year]
85. Have you ever pranked someone before, or have you been pranked?
This could be a fun answer to hear! If he’s a prankster, you might want to keep your eye peeled for pranks coming your way. But, if he’s been pranked before, he might not have liked the experience and will tell you about it.
86. What is your most embarrassing moment?
We’ve all got one, and when you ask this question, be ready to share your embarrassing moment in return. It’s only fair!
87. What’s your weirdest habit or quirk?
Unless it’s something seriously weird or freaky, don’t be put off when he tells you this. It’s one of the cute questions to ask your boyfriend because it gives you an insight into his real character. [Read: Avoidable habits that will change your life for the worse]
88. Did you go to summer camp?
If you did, you can share stories of summer camp. If he never went and you did, you can tell him about your experiences instead.
89. When was the last time you laughed the hardest?
Of course, the follow-up question to this would be why and what happened. Maybe he’ll recount the tale and you’ll both end up laughing hard once more!
90. If you had to listen to one song for the rest of your life, what would it be?
Of course, if you had to listen to it for the rest of your life, you’d probably end up hating the song after a while! But, it’s interesting to know about his favorite types of music and particular songs. [Read: 20 most romantic songs for the one you love]
91. How do you think we are similar?
This is one of the cute questions to ask your boyfriend because it helps to bond you together. There are bound to be things that make you totally different from one another, but surely there are one or two things you share in common?
92. If you had a pet unicorn, what would you name it?
Oh come on, this is one of the fun questions to ask your boyfriend for sure! He might not have an interest in owning a pet unicorn, but finding out the potential name could be very interesting!
93. Let’s say you were going to design an ice cream flavor – what would be in it?
Is he all about the full-on chocolate flavors, or does he prefer something fruity? [Read: How to be funny around guys and make them crave your company daily]
94. What is your least favorite food?
Let’s hope he doesn’t say something that you really love!
Go on, get asking these cute questions to ask your boyfriend!
These cute questions to ask your boyfriend are a mixture of fun-filled, pointless, deep, and searching.
This mix will allow you to get to know your guy a little better, but will also make the conversations you have fun and avoid heavy discussions that kill the mood and make you feel less than lighthearted. [Read: Getting to know someone – how long does it take?]
Remember to only ever ask questions that you’re comfortable answering too! If you ask him what his favorite thing about you is, the most natural thing in the world is for him to ask you what your favorite thing is about him!
So, choose your questions carefully, and be sure to have your own answers ready to go.
[Read: What does it mean to be vulnerable? Ways you can open up to each other]
Thinking of some cute questions to ask your boyfriend means you get to know him on a slightly deeper level. Go on, try them!
The post 94 Super Cute Questions to Ask Your Boyfriend for a Fun, Happy Conversation is the original content of LovePanky - Your Guide to Better Love and Relationships.
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