100 Cute Questions to Ask Your Boyfriend That Will Make Your Love Even Stronger

In my past experience, boyfriends are not always the most open. I think it’s because they weren’t given many chances to express themselves. Now, you can change them. It is always lovely when a person opens up to you, and my 100 cute questions to ask your boyfriend are perfect for you boo.

I have found that taking out time to ask your partner really shows in your relationship later. They take notice of the fact that you have specifically prepared a whole list of 100 cute questions to ask your boyfriend for them. They feel seen and loved. I highly advise asking your boyfriend the questions I’ve written to make them feel valued and appreciated.

The 100 cute questions to ask your boyfriend I have prepared are perfect for every occasion, no matter where you are in your relationship with your boyfriend.

Tips to Ask the Questions

Before you take out your phone and read off my list of 100 cute questions to ask your boyfriend, I would suggest that you read my tips first. These will prepare you to ask the questions and make sure that the entire conversation flows smoothly.

It is important for you to remember that you are not interrogating them, these questions should be asked to get to know them better
Make sure that your tone is soft and polite. It should convey that you are asking the questions because you would love to get to know them better
Some of these questions are personal so be mindful of them. Caution your boyfriend ahead of time and give them the choice of opting out of answering the question
You should tell him in the beginning that there is no right or wrong answer. Remind him that he is not being tested and you will not mind any answer of his
Be receptive to their body language and keep your body language open and loving
It would be best if you could set the mood a little like lighting some candles safely, having their favorite snacks out, making the seating comfortable, and other things that he would like

Romantic Questions

Our 100 cute questions to ask your boyfriend start with romantic questions. I have the most cute and full of love questions listed down. These questions will not only tell you a lot about your relationship but also increase the love between you two.

What is a nickname you want to call me?
Who do you love most in the world? And why do you love this person so much?
Do you think that you would have gone out with me if we had met in high school?
Whenever we fight, how do you feel after it? Does it bug you like it bugs me?
Do you think our astrological signs are the perfect match? Which are your two favorite astrological signs?
What would you say is your best ability when it comes to me? What do you do for me that you are really proud of?
Would you say that I am your biggest weakness? Like, if you lose me, you’ll lose your happiness?
How do you see this relationship going? What do you expect from this relationship and me?
Can I ask why your previous relationship ended? Who ended it? Do you think that you made any mistakes in that relationship?
If we were to get married, how do you see us handling everything? Like who would do which chores?
If we ever got around to getting married, would you buy me gifts and take me on dates as you do now? Would you love me the same or more after we get married?
Do you think that we are competitive with each other? Do you think that it’s the playful kind? Would you say that we should take it down a notch?
According to you, what is it that makes us perfect for each other? What do you love the most about us? Did you think we were perfect for each other as soon as we met?
What is the thing that you love most about me? What is the thing that you don’t like about me?
What did you think of me when we first met? Like, what was your first impression of me? And, what was the one thing that you remember the most about our first date?
Okay, this next question is a bit personal and sensitive. I just want you to know that I don’t care about whatever you’ve done in your past. I care that you are loyal and amazing to me now. Having said that, did you ever cheat in any of your past relationships?
If we ever got stranded on an island, what are the ten things that you will pack? Keep in mind, I am there with you and you have to think of me as well.
If we get a lot of money today from somewhere, where do you think we should go on vacation? The vacation can be as long as you would want.
Babe, do you think that there is a life after this one? If yes, do you think that we will end up there together? What do you think it’ll look like for us?
If you get a million dollars tomorrow, how much would you spend on me? What would you get me with the money?
What is the best gift I have ever given you? What did you love about it? Guess why I thought of that gift for you.
Do you think that we should have our own song? Like, appoint one to us, something that we both love. Which song do you think it should be? We should really think over this one.
Out of all the vacations we have taken together, which is your favorite vacation? Why do you love it so much? Would you like to take it again soon?
What is your favorite thing to do on our date nights? What do you want to do on our next date? You can choose whatever you want and I promise to go along with it happily.
If I told you that I am taking you somewhere special for our next date, what would your guess be? What do you think we will do on the date? I’m not picking your brain for my next idea, I just want to see if you will guess correctly.
If I ever have to move to another city for work, will you move with me immediately, no questions asked?

Personal Questions

Under our 100 cute questions to ask your boyfriend topic, I have jotted down questions that will give you an insight into their preferences. It is important to get to know the real nitty gritty stuff of a person’s life if you want to be close to them. If you decide to ask them personal questions, my advice is to be respectful of them and their boundaries.

What is a childhood memory that you still remember clearly to this day?
What is one secret that you have never told anyone? Why have you never told anyone about it?
Is there a hidden talent in your arsenal that you haven’t told anyone? If yes, what is it?
What is one dream of yours that you are too embarrassed to say out loud? Why do you think that you don’t tell people about this dream of yours?
What is the one thing that you are so passionate about that you could go on for hours on the subject?
If you ever get stuck or life puts you down, what do you do to get back up again?
Do you remember the moment you first realized that you love me? Why was it that that particular
Do you believe that humans deserve kindness, regardless of what they have done?
What is the one thing or person that inspires you in your life? Why do they inspire you?
What is one thing that you have always wanted to do but never did? Also, what stopped you from doing it?
What have you done in your life that makes you super proud of yourself?
When was the last time you felt vulnerable? What happened? How did you get back from it?
Do you see me in your future? If so, am I there 5 years later? Am I with you 30 years later?
If I was to ask you your biggest fears, what would you say?
What are you insecure about? How do those insecurities show up in your life?
Do you think that your past relationships affected your views on love? What are the effects?
Do you think that you’re a guy who values commitment? What does commitment mean to you?
What was the moment when you felt the strongest connection to me? What were we both doing?
Say that I want to show my love for you, how should I do that? How would you define your love language?
How do you feel about marriage and starting a family? Have you ever thought about these things with me in mind?
Do you think that something like karma exists? Do you think that you have ever done something bad and its karma will back to wreck your life?
If you didn’t have to worry about money, what would you be doing right now? Do you think you would even hold down a job? Maybe you would live like a nomad.
Do you like being in the kitchen? Which is your favorite dish to make? How often do you cook in a week?
If you had the power to talk to someone from your family in the beyond, who would it be? Why did you choose that person? If you don’t mind me asking, what would you guys talk about?
What would you say is your guilty pleasure? Why do you think it is that thing particularly? How often do you indulge in this guilty pleasure of yours exactly? How long has been it a guilty pleasure for you?
What are some of your habits that I should know about? I would really love it if you will be completely honest with me.

Questions to Get to Know Them

Now that the personal questions are out of the way, it’s time to get to know them. To compile my list of 100 cute questions to ask your boyfriend, I have noted down a few that’ll help you know their personality better.

What is your favorite trip that you have taken?
If you were given the choice of a talent or skill, what would you choose?
If you were to name a book or movie that has impacted you greatly, which one would it be?
What do you do on the weekends?
If you had the chance to meet any historical character, which would it be, and why would it be that person?
At the end of a long day, what do you do to relax?
Is there any dream or goal of yours that you are working toward these days? If yes, what is it?
What is the most thrilling thing that you have ever done?
Can you tell me the best advice that you have ever gotten?
You have been given the gift of switching lives with someone in the world for 24 hours. Who would you choose and why? Also, what would you do in those hours?
How do you handle the monotonous periods of your life?
How are you kind to others? What are the ways you are generous to someone else?
What is your favorite quote of all time?
Is there an activity like a hobby that you have always wanted to try out but never did? If yes, what is it?
What do success and happiness mean to you? How do you see them manifesting in your life?
What do you think supporting a person means? How do you think a couple should support each other for the growth and stability of their relationship?
If I ask you to choose five words to describe your personality, what would they be? Take as much time as you need.
What is your ideal day? Describe it in detail, I would love to know every little detail.
What are the values of your life that you will never let go, no matter what? Tell me why are they so important to you.
What is the earliest memory from your childhood? What were you doing? How old were you then?
Have you ever met someone famous? Did you get a picture of them or an autograph from them? Were they nice overall? What did you guys talk about?
Who is your favorite celebrity? Do you have a crush on this celebrity? Also, who was your first celebrity crush?
What is your favorite sport and which is your favorite team and player? Do you watch their tournaments pretty regularly? Why do you like that player so much?
If I told you that I would order you anything for our next meal, what would you choose? Remember, there are no limits.
Are you a shower singer like do you sing when you are bathing? If so, which songs are your favorite to sing? Do you choose different genres for different moods? Do you dance in the shower?
Do you think there is such a thing as soulmates? Do you think everyone has only one soulmate or more than one? Lastly, do you think that I am your soulmate?

Would You Rather Questions

The last stop on our list of 100 cute questions to ask your boyfriend is the category of would you rather questions. These are fun questions that you can bust out to pass the afternoon and have a nice time. It will tell you a lot about your partner’s likes and dislikes.

Would you rather live in the past, present, or the future? What is the reason behind your answer?
Would you rather have lots of riches but no peace or live a simple life with an abundance of peace?
Would you rather have the superpower of flying or being invisible? Also, explain your answer so I can know how your beautiful brain works.
When you see yourself retiring, would you rather retire in a busy city like New York or a peaceful countryside cottage somewhere?
Would you rather choose to read people’s minds or to teleport anywhere in the world you want? If you pick the first one, would you really want to read my mind 24/7?
Would you rather never eat again or never sleep? Of course, that is assuming that both choices would be healthy and safe for your health.
Would you rather possess a rewind button or a fast-forward button? If you choose the rewind button, do you think it says that you are a nostalgia lover?
Would you rather have an unlimited supply of wisdom or a pool of gold coins like Scrooge McDuck? If you say the gold coins pool, what would you do with all that money? Would you buy me anything?
Would you rather be known for your good deeds or be notorious for your bad deeds? Do you think that you have it in you to do enough bad things that they’ll make you famous?
Would you rather be mute forever or always speak whatever is on your mind? I know that I would love to hear whatever you have to say.
Would you rather have the knowledge to be able to speak all the languages of this planet or have the power to talk to all animals? If you choose the animals option, imagine how cool it’ll be, you would be like a Disney princess.
Would you rather have control over everyone’s emotions or have power over the weather? I hope you know that you won’t need to control my emotions because I will always love you.
Would you rather have the ability to breathe underwater and be able to bear all the pressure or traverse space without any suit? I think that the underwater power would make you like Poseidon.
Would you rather be powerful like Superman or have the power of telekinesis like Jean Grey?
Would you rather have no internet forever or no heating or air conditioning unit? I know it’s a tough question so you take your time, babe.
Would rather have picture picture-perfect memory or be able to forget anything you want?
Would you rather have a life where nothing is set and written or a predictable life with no surprises?
Would you rather be a jack of all trades or a master of one trade?
Would you rather have powers over fire or be able to control water like Percy Jackson?
Would you rather have the ability to heal anyone’s pain or stop any harm that may come their way?
Would you rather live with me forever or have a billion dollars? Remember, in the first scenario, you will be immortal.
For a date, would you rather stay in and chill out or go out for a wild night?
Would you rather be celibate or never walk again?
Would you rather live alone your entire life or have a partner that you constantly fight with?
Would you rather have me as your official “chooser” of outfits or someone professional?
Would you rather do a job that is illegal but gets you a lot of money or a job that doesn’t pay a lot of money but helps loads of people?

I always encourage my readers to personalize the questions to suit their situation and boyfriend. Remember, they are one of a kind which means that they deserve that you take your time and care with the questions.

Now that you have gone through cute questions to ask your boyfriend, what do you think? Have you ever found any other questions that have helped get to know your boyfriend? Do let me know in the comment section below.