186 Fun and Silly Questions to Ask Your Boyfriend

Isn’t it exciting to have fun with some silly questions with your boyfriend? Silly questions might sound a little stupid but this will be very interesting. Take out some leisure time from your busy schedules and sit together. Add some humor to your silly questions and break the ice between you both.

Boys love random and fun questions in their conversations so you must have a bundle of these questions. These questions will also work even if you are in a long-distance relationship. On text or call, you can randomly throw up these questions to your boyfriend.

Your boyfriend may be a little conservative but it is your responsibility to make him feel comfortable and open. All you need to do is, slip the right question at the right time. This will help you discover a different yet unique side of the person. Guys hide many secrets and emotions. They can be shy too, sometimes more than girls. It is on you how you make him open up to you so he speaks whatever is in your mind.

Your questions can act as an opportunity for them to speak their heart out and bring out the best in them. Sometimes guys guard their emotions and do not open up easily. Having a fun and cute Q and A with them might help them in opening up. Relationships are very sensitive you know, they come with a handle with care tag. Put up these questions very randomly and see how he reacts. His reaction will bring smile of the faces with you both and smiling together will add spark in your bond.

The questions might be silly but make sure they are proper. To know someone closely, it is important to know about their personal choices and experiences. When you are asking questions make sure you use right words and encourage him to give as much details as possible. Topic can be anything, just ask questions properly. Don’t make him feel if you are not interested in what he is speaking so talk to him decently. Try to interact with him.

Fun and Silly Questions to Ask Your Boyfriend

Here’s a list of silly questions that you can use while talking to your boyfriend:

What would you name your unicorn pet if you had one?

Which animal would you have as your pet and what will you name them?

If you were supposed to invent ice-cream flavour, what exactly will it look like and what will you call it?

In your teenager, who was your celebrity crush?

Who is your current crush and your first crush?

Have you ever watched children’s show because you were bored and had nothing to do?

You prefer starters, main course or deserts?

Would you rather go on a holiday with group of people or alone? Which is the destination you would never visit for your holidays?

Which drink do you hate the most?

Which song lyrics irritate you the most? Apart from lyrics what annoys you the most?

Do you pee in shower? How often do you do that?

If you had a chance to give super power to your soft toys, what would you give them?

Would you prefer changing into a 2 dimension or a three-dimension?

If you had a chance to change into a cartoon character for few days, which one would you prefer?

Do you like cold drinks on cold days? Which drink do you prefer the most?

Do you feel like dressing up for Halloween? Which characters do you like the most?

Which is the worst thing you have ever has in your breakfast or lunch and would never want to eat again?

What is your take on horoscope? Have you ever changed your plans because of it?

Do you like to sing in car when you are alone or are you a bathroom singer?

What will you do if one day you are declared as the richest person in the world? What is the first thing you will buy?

Do you like talking to animals, birds, plants or anything from nature?

What’s the weirdest thing you have ever done or noticed on a date?

What would you do if you knew how to fly? Which bird you like the most in sky?

Will you come home when I am home alone to have few drinks with me?

Do you like what I am wearing?

Do you like playing truth or dare? What is the most interesting dare you have every got?

Who was your favourite web series character? Do you want to become like it?

Which movie did you watch recently which was funny? Would you recommend it to others as well?

Do you prefer being friends with your ex? How often do you think about her?

How are momos and dimsums different? Have you ever thought about it seriously?

Which celebrity couple can be compared to us? Do you think we really vibe like that celebrity couple?

Have you ever tried to put makeup on your face secretly o tried to wear heels?

Which is the best organ according to you? Which of your sense work the most?

How would you describe the way I smell?

Which is the weirdest name of humans you have ever heard?

Have you ever caught yourself on fire while you are cooking in the kitchen? Have you ever burnt cake?

If I was a dessert, what would you want me to be? Why would you choose that particular dessert?

If you had an option to steal one thing from someone, who would it be and what would it be? Why is it so important that you want to steal it?

Would you mind if you were invisible for one week?

Which movie sequel do you want to make? Do you have ideas for it?

What would you name your DJ band if you own one?

Which is childish thing you love doing? How much scolding have you suffered from your parents?

Do you break phones? How many have you broken?

How are your friends? Who is your best friend and how many mischievous have you done?

Do you like hanging out on a Friday night with your friends? Which bar do you like visiting the most for parties? Have you ever got drunk and created a scene?

Which is the most embarrassing invitation you have ever witnesses?

If you got stuck on a deserted Iceland, what five things would you carry with yourself?

If you had an option to meet someone who is dead, who would it be and what would you talk to them?

What would you name yourself if you had an option to change your name?

Do you have any annoying friend? How do you deal with them?

What is the worst food combination you have ever had? Have you ever tried food pranks on anyone?

Is there anything that annoys you for literally no reason? How do you deal with it?

Which is the stupidest myth you have ever believed in? How did the reaction come out?

When was the last time you laughed your heart out, what was the reason? Is there any person who makes you happy with small gestures?

Which is one of the most embarrassing moments of your life? How do you feel when you recall it?

If you wake up one day and find yourself 5 years ahead in time, what will you do? How would you react to the situation and what is the first thing you will do?

If you had to play a prank on someone, who would you choose to and why? What will the prank be about?

If you go on a date with someone for the first time, what is the one silly and fun thing you would never mention?

What is the one thing you can eat for dinner every day? How often do you eat that food nowadays?

What is the most embarrassing gift you have ever received? Did your friends ever gift something that you can’t tell publically?

What things you do in public secretly that you are embarrassed of?

Have you ever hooked up in a public place? How daring was it for you?

If you became famous one day, how do you want people to recognise you?

Which purchase do you regret the most? Why was it a non useful item? What did you do after realising it a worthless product?

Which is the weirdest wrong number you have ever received? What did the person demand you from the other side of the phone call?

Which is the one thing you can’t imagine your life without? How will you manage everything if you lose it once in life?

If you could back in college, what is the one mischief that you want to do but could not?


No doubt, romance in a relationship is very important but sometimes fun will add some excitement in life. These are very light questions and you both would have a good conversation. To build your relationship healthy, you can take out some time or even randomly throw any of these questions to him. Even if he is upset or sad, set a momentum for the questions and ask these questions to him.

Make him feel special and needed even when you are asking these questions. These mood freshening questions need not to be planned; you can normally ask him and bring smile on his face. Make him giggle by continuing the conversation and add fun elements to it. Tell him your experiences also and don’t make it a one way conversation. These questions are not the only once to rely on, you can make a list of your own questions which can be silly and fun as well.

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