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80+ Fun Questions to Ask a Boy to Know Him Inside Out

Starting a conversation can be one of the hardest things ever. But we’ve got you these 83 questions to ask a boy so you don’t have to worry anymore!

These fun questions can help you know just about everything about the boy you like or maybe even your boyfriend.

If you want to break the ice between you and the guy you like, use these funny, romantic, and other different types of questions to ask a boy and get to know him even better.

All of these questions to ask a boy will open the gates to a deeper connection and bond, something so many people struggle with in this age. So enjoy the list, write down your favorites, and have fun going through them with the guy you like.

Funny Questions to ask a Boy you like

funny questions to ask a boy

Ask these funny questions to a guy to get to know him inside out and learn how humorous he can be.

What’s the one thing you wish you could unsee?

There are things which we don’t like at all and wish we could unsee it or never see it again. Find out the thing the guy you like would like to unsee.

What’s your grossest personal habit?

All of us do gross things when we are alone in the room. The guy you like must also have something gross as their habit. Ask them to find it out.

What’s the most embarrassing thing that’s ever happened to you in public?

Everyone experiences embarrassing moments in their life. This is the chance to know theirs by asking them this question.

If you could choose one movie character to marry, who would it be?

This is a great question to know what he wants his dream girl to look like, and see how closely you stack up! It will be interesting to learn what his “ideal woman” would be like.

How would you describe yourself in three words?

Would he reveal his positives, or are his answers self-deprecating? How we see ourselves can also be a reflection of how we would like to be seen, so pay attention to his answer.

If you had five lives, what would you do that you wouldn’t do with only one?

This might be a good chance to know about his bucket list or the things he wants to do at least once in his life.

When’s the last time you lied to your parents and why?

We all at some point in our lives have lied to our parents, whether about our grades at school or about the fake signature we did of our parents (yes, I had done it too). The guy you like must have had some lies to tell their parents too.

What was your absolute worst bathroom experience?

questions about worst experiences

Maybe some of the people can relate to this as having bad bathroom experiences is not really rare. Know about their experiences. Were they out of toilet paper? Or were they out of handwash?

What would you say if you had to pretend to like a present?

Receiving a bad present or not liking a present someone gifted you is very common. But everyone handles it differently. You can find out how would he react if given a bad present. Would he be appreciative or just tell the person he doesn’t like it? It would tell a lot about his personality.

What’s one thing you have never been good at?

This can be a fun and lighthearted question. Some of us just suck at doing some of the things, and it can be fun to bond over them, and laugh a lot about it!

What’s the funniest thing you’ve done to get a crush’s attention?

When we have a crush or we get attracted to someone, trying to get their attention is a common behavior. There are times when we do extreme and funny things to get their attention. These can be fun questions to ask a boy you want to know more about.

Who was the last person you cyberstalked?

Stalking people on social media has become common. There are different reasons for people stalking others on social media handles. Ask the guy you like this question to know who was the last person they stalked on Instagram or Facebook and why did they do so.

What is one behavior that makes even the hottest girl instantly unattractive?

This is just a very useful thing to know about a guy you like as you can avoid doing that very thing in the future.

Would you date two people simultaneously if you could get away with it?

If you wanna know he is a loyal person or not, this is the perfect question to get to know about his loyalty.

What’s your biggest pet peeve?

Different people find different things annoying. Some people can find late replies annoying and some can find one-word replies annoying. You can get to know their pet peeve and avoid doing it so they don’t get annoyed.

What’s your go-to flirting move?

We all have different ways in which we flirt with others. Your crush might have a unique way of flirting or a go-to flirting move. Ask him this question to find it out.

What is the best way to end a long day?

questions to as a boy about parties

We all have a happy place we like to go to after a long and hard day, and that place says a lot about who we are and what makes us happy. It can be going home to their pet after a tiring day or going to a club to party in order to release their stress.

What would you immediately do differently if you knew no one would judge you?

We all hold back our opinions because of the fear of judgment (which is rampant in this day and age of social media!), and to abide by social values and standards, but what if we could let it out for once without being judgedNow, this can be an intriguing question to ask him.

What is something everyone always gets wrong about you?

People usually tell us about the first impressions we give them. Your crush might too have an impression that everyone gets wrong. It can be their temperament or maybe their age.

If you had 1 million dollars to donate to a charity of your choice, which would it be and why?

I guess we all can agree that if we had enough money, we would donate some of it to a charity. Some would like to donate their money to an orphanage and some to an animal shelter.

What’s the biggest secret you’ve kept from your best friend?

Sharing secrets with your best friend is a compulsory thing to do. When we tell people that we would never tell anyone about a thing, our best friends don’t count in “anyone”. But there may be some secrets that you just cannot tell your best friends. Ask them this question to find out what he has been hiding from his best friend.

What’s one thing you always procrastinate on?

Procrastination comes naturally to all of us. There are some particular things we procrastinate on. It can be cleaning your room, doing laundry, or cleaning the dishes. This can be an interesting question to get to know about their laziness.

Would you rather eat fish food or cat food?

I know it is weird but an interesting and fun question to ask.

If you could trade places with a famous person for a day, what’s the first thing you’d do?

Switching lives with someone would have been so fun if it was possible. Alas, it is not. But it won’t hurt to imagine it and ask others too about what would they do if it was a real thing that could be done.

If you could be a member of the opposite sex for a day, what’s the first thing you’d do?

Almost all of us must have had thoughts like “I’d have done this if I was a guy” or “I would have done that if I was a girl”. What would have your crush done if he was a girl for one day? Ask this question from them to know about it.

Questions to ask a Boy about Relationships

questions to ask a boy about relationships

Use these questions to ask a boy you like to know how romantic they can be and how would he treat the girl he dates.

What’s the most romantic thing you’ve ever done?

Find out if he even does romantic moves for someone.

What do you think is my best feature?

This one would keep the compliment train going.

Are you aware of how amazing you are?

Get to know if he is a confident person or not. Does he think of him as an amazing person or finds himself annoying and unlikable?

At what point in a relationship do you let your guard down?

Letting your guard down means being vulnerable. You only let your guard down with someone when you completely trust them. Trusting someone completely can be pretty scary as no one would like to get hurt. Ask them about the time when they know it is finally the time to let their guard down and trust the person they are in relationship with.

What are you looking for in a girl?

It can be a good opportunity to grab by asking them this question and try to apply it to yourself. You can totally become an ideal girl for him after knowing what he likes about a girl.

When’s the last time you felt butterflies?

Try to find out when was the last time he felt excited in terms of attraction and who or what caused those butterflies.

What’s the worst pickup line you have ever used?

This can only end in tears of laughter and you can later tease him with the silly things he once did.

Do you think that guys should always make the first move?

It is not really a rule (which society thinks it is) that guys should make the first move. Ask him about his opinion on this one.

What would you do if I kissed you?

This is going to take a lot of courage to ask. It can either break your heart or make your heart. All the best!

What is your biggest turn off?

Asking him this question about his biggest turn off early can be a game-changer and can help you a lot later.

Do you ever get shy around me?

Find out if he ever gets nervous around you or if he feels comfortable being with you. He will often feel nervous around you if he likes you or is attracted to you.

How do you feel about being single for a long period of time?

Does he feel refreshed or is it lonely for him. He might also be focused after his last break up.

What was your very first impression of me?

This can be an interesting yet scary question to ask for which you need to be ready. It can be a good impression or even be a bad impression.

Who was your first love?

This memory often leaves an impression. Be careful while asking this question to a boy you like as it can open old wounds too.

What do you value in a relationship?

What does he value the most in a relationship, is it love, respect, or is it time and communication?

Would you rather be called sexy or smart?

Ask these kinds of questions to a boy you like to know what he wants you to notice about him. His intelligence or his looks?

What’s the most romantic date you’ve ever been on?

question to ask a boy about dating

Was it a picnic or watching the sunset or laying under the stars or maybe a long walk around a lake?

Would you change your religion just to be with someone?

How much does spirituality mean to him? Does he value his religion more or the person he is in love with?

Deep questions to ask a boy

deep questions to ask a boy

These questions to ask a boy can help you look at life and other things through his perspective.

How would you rank the following in importance: family, career, love life?

Personally, I could never answer questions like these, but you can give it a try. Use these kinds of questions to ask a boy to get to know about his priorities.

Which would you prefer: having a baby without a partner or a partner without a baby?

This can be a very hard and thought-provoking question. This can be the most difficult situation to face and the most difficult decision ever to take for someone.

Do you believe in giving people second chances, and why?

Does he believe in forgiving people or does he hold grudges towards other people?

What is your definition of a “perfect life”?

We all think about living our lives in a perfect way. Your crush also might have his own definition of a “perfect life”. Ask him about it to find it out.

How do you define evil, and do you believe that a person can be evil?

For me, only the intentions can be evil, their way for life can be evil, and we should fight evil not the person. Although, everyone has different opinions and you should find out theirs.

Would you lay down your life for someone?

Some of us would be ready to lay down our lives for our parents and some of us would do so for the person we love. Find out who would your crush or boyfriend would lay down their life for.

Do you believe that each of us has a soul mate?

Soul mates are the people who you bond with immediately and it feels like you have finally found a long lost missing piece of your heart.

Imagine that you are tasked to re-design society – what changes would you make?

This can be an interesting question to know how he wants the world to be. Whether he would want to change some laws or maybe even remove some laws completely.

Have you made someone cry?

deep question to ask a boy

Is says a lot about a person who has made a person cry by hurting them, may it be emotionally.

Can you remember the last time you cried, and what was the reason?

This might be a little personal question to ask, but if he feels comfortable with you, you are good to go.

How would you spend your remaining time if you found out you only had 10 days left to live?

You can get a chance to know about his bucket list and about the things he wants to do at least once in his life.

What was your most memorable birthday?

Some people like to celebrate their birthday with their family or with their friends, or maybe with both of them. Some people also like to celebrate their birthday alone without partying. Find out in which category does he fall in.

How do you wish people will remember you after you’re gone?

How people want others to remember them when they are gone says a lot about them. Some want to be remembered as hard-working and successful and some want to be remembered as famous and rich.

Use these random questions to ask a boy to get to know them inside out

random questions to ask a boy

Here are some additional questions to ask a boy which are amazing and could be useful for you to know them.

  • Do you believe in the afterlife?
  • How old were you when you had your first kiss?
  • What is your proudest achievement?
  • If you could go on a date with any female celebrity, who would it be?
  • Have you ever cheated on someone?
  • Have you ever told a big lie and gotten away with it?
  • What is something your parents gave to you that you hope to pass on to your kids?
  • If you could live anywhere in the world, where would it be?
  • What keeps you up at night?
  • Do you believe in karma?
  • What is something you’ve been wanting to do for a long time but never seem to get around to doing?
  • What is your favorite family memory?
  • Is it better to be liked or respected?
  • How do you cope when things are not going your way?
  • Is there a film or cartoon character who is very much like you? In what way?
  • Is there any part of your personality that you feel you need to improve? If so, which part and why?
  • As a force, are we humans creative or destructive?
  • Is happiness a state of mind or we need to act in order to achieve it?
  • When was the last time you laughed so hard?
  • What are the top five things you are grateful for?
  • How would you describe your perfect vacation?
  • Which one is a better situation: broke or lonely?
  • Would you visit the moon for one day if you could?
  • When was the last time you had the best day ever?
  • Do you listen to other people’s advice, or do you prefer figuring things out yourself?

After looking at all the questions to ask a boy, now the question that pops up is how would you know you’re asking the write questions.

Follow these steps to pick the best questions to ask a boy you like

1. Know your comfort

You should know what stage of the relationship are you and the guy you like are on. You cannot use personal questions to ask a boy you like if you have just started talking to them.

Similarly, you cannot ask too many questions when you are still friends because it might be a little weird to them as they might not be comfortable with you yet.

2. Set the right mood

You can maybe start asking questions by starting the truth or dare game, or maybe just ask them to play this game of asking questions alternatively.

This way, they’d get a chance to get to know you too.

3. Choose only a few questions

This list of questions above might be big, but that does not mean you have to ask all of these questions. You don’t want them to feel like they are being interviewed.

Choose only a few questions to ask them and get to know them.

4. Enjoy the conversation

girl punching a boy

Always remember to enjoy the conversation and not just ask questions for the sake of knowing them.

Use some funny questions to ask a boy after asking deep or personal questions to lighten up their mood.

Well, that’s a wrap!

The answers to these questions will hopefully surprise, inspire, and move you.

While using these questions to ask a boy, always remember to keep their answers confidential and a secret. They have shared everything with you because they trust you. I’m sure you don’t want to break their trust after the efforts of getting to know them.

Remember to use appropriate questions and enjoy having the conversation with him.

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