221 Interesting Questions To Ask Your Best Friends

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Imagine you’re all set to make new friends this year; how would you go about it? What are some of the questions to ask friends that will get you closer to them? As much as it’s great to make friends naturally, building a connection with them requires time and effort. One of the best ways to do that is by creating a questionnaire with fun, quirky, personal, and deep questions. So, design a set of questions with a mix of everything, and enjoy the sharing session that is bound to unfold between your best friend and you. To get the ball rolling, we’ve curated a list of questions to ask your friends that is sure to deepen your bond.

Questions To Ask New Friends

New friends are like can entice you to explore them further. From giving you the topic to text your friend to opening a long rally of reactions and counter questions, these conversation starters will help you break the ice.

Do remember
Sharing something personal or sensitive right away may not be comfortable for many. So, take it slow as you begin this fun game with your new buddies.
  1. What is your favorite possession and why?
  1. What do you like to do in your ‘me time?’
  1. Which foreign language do you like and why?
  1. Which is your favorite festival?

    Favorite festival question to ask friend

    Image: iStock

  1. What is your favorite dish?
  1. What kind of exercise do you prefer?
  1. Which horror movie character scares you the most?
  1. How would you react if I told you aliens abducted me?
  1. What do you fear the most?
  1. Do you have any phobias?
  1. Name three of your favorite movies.
  1. How would you describe yourself in three words?
  1. Do you take pride in your vocabulary? What’s the most interesting word you know?
  1. If you were asked to become the curator of a museum for a week, which museum would you pick?
  1. Do you have a weird morning routine?
  1. Has there been any instance when you have forgiven someone and regretted doing so?
  1. Which medical condition are you most scared of and why?
  1. What, according to you, should be your spirit animal?
  1. What are three of your favorite natural smells?
  1. Do you consider yourself brave?
  1. How experimental are you with your cooking? How often do you succeed?
  1. What is your guilty pleasure?
  1. Which band is your favorite and why?
  1. Which adventure sport have you never tried but would like to?
  1. Which is the weirdest ice cream flavor you have had?
  1. What type of music do you enjoy the most?
  1. What unique quality do you look for when you make new friends?
  1. Has there been an incident when you laughed out loud at the most inappropriate moment?

Questions To Ask Friends To Know Them Better

Some friendships click, while there are others wherein you have to put in extra effort to get the conversation flowing and strengthen that bond.

Quick tip
To keep the conversation even more exciting, reply to their answers and keep it a two-way conversation.
  1. Did you ever wish to be a tiny ant so that nobody could notice you? Why?
  1. How often do you lie? What was your last lie?
  1. Given a choice to change your citizenship, which country would you choose?
  1. What would you like to eat all by yourself without sharing?
  1. How often do you feel the need to admire yourself?
  1. Who is your inspiration?
  1. What is your idea of a perfect day?
  1. Has there been a moment in your life when you wanted to treat yourself for doing something well?
  1. Are you happy with your career choice?
  1. Would you like to associate with any activism?
  1. What is it about nature that affects and inspires you the most?
  1. Given a chance to choose an alternative career, what would you choose?
  1. If you could choose a celebrity as your BFF, who would it be?
  1. What are you most likely to do in the event of a natural calamity?
  1. Do you like keeping up with the changing trend?
  1. How do you relax after a tiring day?
  1. Who is that one person from your school with whom you want to connect again?
  1. Do you nurture any prejudices?
  1. What are your top five pet peeves?
  1. Is there a book you have read several times but would like to read again?
  1. What is the first thing you look for when you meet a person?
  1. What is the most disgusting thing that you have tasted?
  1. Which board game do you like to play with your friends?
  1. Have you ever had any weird or annoying friends?
  1. Would you like to swim in a pool or explore the ocean’s depths?
  1. What do you prefer, a shower or bath?
  1. Have you ever faced any mortal danger?
  1. How disappointed do you get when things don’t go your way?
  1. Have you ever been tempted to run away from home?
  1. Which sport are you terrible at?

    Which sport are you terrible at?

    Image: iStock

  1. Of all the books you have read, which is your favorite?
  1. Do you believe in life after death?
  1. Do you often change your opinion about things?
  1. When was the last time you were so involved doing something that you lost track of time?
  1. What is your way of relieving stress?
  1. Is there a particular skill you are good at but embarrassed about?
  1. Would you rather be an average-looking genius or a good-looking dumb person?
  1. Which teacher has had the most positive influence on your life?
  1. Who would you turn to when you need a partner in crime?
  1. What is the oldest piece of clothing you have?
  1. Are you a ‘work to live’ or a ‘live to work’ kind of person?
  1. What values do you hold most dearly?
  1. Which question makes you feel trapped?

Questions To Ask Your Best Friend

Are you confident that you know everything about your best friend? Think twice, for there may be several subjects you may not have touched. These questions will help you figure out how in-tune you are with your best friend.

Do remember
Keep your phone on silent mode while playing the game. Constantly checking the phone could take away the fun of the game.
  1. Have you ever lost your way?
  1. What do you think would spell doom for our friendship?
  1. Which friends’ duo from the movies do you associate our friendship with?
  1. Describe your most embarrassing moment.
  1. If you had to change your name, what would your new name be?
  1. Which is your favorite memory of our friendship?
  1. Do you think it is better to have a huge gang of good friends with different personalities or one true and trustworthy friend?
  1. How differently do you think life would treat you if you hadn’t been my friend?
  1. Is there anything you want to tell me to understand you better?
  1. How comfortable are you with your weaknesses?
  1. How much control do you have over your life?
  1. How would you want your epitaph to be read?
  1. Have you ever broken the law to save someone you care about? If not, would you?
  1. Is there something I wouldn’t believe about you?
  1. What do you dislike the most about my personality and attitude?
  1. Do you remember the moment when we first became friends?
  1. If you were to work undercover, which identity would you prefer to take up?
  1. If you were invited to dine with the defense head or your favorite celebrity, who would you choose?
  1. If you were given $2 million on the condition that you cannot spend it on yourself, what would you do with it?
  1. Is there something you did that you wish you could go back and undo?
  1. Which emotion do you associate yourself with the most?
  1. What is it that you fear the most about getting old?
  1. If your best friend asked you to lie for them, would you do it, despite knowing you could get into deep trouble?
  1. What’s the best practical joke someone played on you?
  1. Have you ever snooped around and found out something you wish you hadn’t?
  1. Which of your friends are you proudest of and why?
  1. Which unhealthy food do you crave when you feel low or depressed?
  1. Who is that person you detested at first sight but are good friends with today?
  1. Was there something you were 100% sure of until you found out you went off on a tangent?
  1. Who comes to your mind when you think of the words ‘sophisticated’ and ‘classy?’
  1. What are the two bad habits you would find the hardest to give up?
  1. Is there a place where you are banned?

Fun Questions To Ask A Friend

Silly, surprising, and unusual—answers to some of these questions will get you laughing and rolling on the floor. Go ahead, shoot them!

  1. Do you spend time looking for shapes in the clouds?
  1. Is there a particular dream you wish you had every night?
  1. If you were a genie and asked to grant a boon to your parents, what would it be?
  1. What would you choose if God asked you to pick three random things that would be abundant in your life?
  1. If you were to write a book, where would you base your plot?
  1. Which is the evil side of your body? Left or right?
  1. Do you give names for random animals, birds, and insects you see?
  1. How often do you feel an intense desire to hit someone on their head and run?
  1. Given a choice to choose a wild animal as a pet, what would you choose?
  1. Have you ever laughed so hard that you peed your pants?
  1. If money wasn’t an issue, would you still work?
  1. Are you a dessert or an ice cream person?
  1. If you could trade places with a singer, who would it be and why?
  1. Do you wish to live in a magical world where you could get anything at the snap of a finger?
  1. What type of humor do you categorize yourself into—witty, dark, or slapstick?
  1. Have you ever tried to figure out the logic behind cartoons?
  1. What are the things you daydream about?
  1. Which scientific invention do you think is the best gift to humankind?
  1. What do you miss the most about your childhood?
  1. Which is the ridiculous style trend you ever saw?
  1. If you were blessed with a superpower, what would it be?
  1. Which part of your body would you want to get a tattoo inked?
  1. If you could trade places with a toy, which toy would you like to be and why?
  1. What is the craziest thing you have done and enjoyed it?
  1. Which luxury item will you splurge on if you won a lottery?
  1. If there was an auction of stuff owned by celebrities, what would you buy?
  1. Do you agree that you get the best of ideas when you are sitting on the throne?
  1. Does your dream car exist? If not, what is so unusual about it?

    Which is your dream car?

    Image: iStock

  1. What is the stupidest reason you have ever given to bunk school?
  1. Would you like to learn swear words in different languages so that you can use them on unsuspecting targets?
  1. What are three of your favorite words? How often do you use them?
  1. At what age do you wish to remain permanently?
  1. Have you ever convinced someone to do something silly? What was it?
  1. What is that one opinion or belief that others consider useless, but it is your priority?
  1. Stranded on an island, what would you like to grow if you were given seeds?
  1. Are you happy with your name? Given a choice to change it, what would you like to call yourself?
  1. If you could create a virtual reality world of your own, what would it look like?
  1. If cartoon logic replaced the rules of physics, what are the three things you would want to try?
  1. What is your favorite slang word?
  1. Which celebrity do you think enjoys undue importance?
  1. Is there an awkward thing that happens to you almost regularly?
  1. What do you see in a person before you come up with a nickname for them?
  1. Have you ever farted and blamed someone else for it?
  1. What would you choose, unlimited food or drinks?
  1. Where do you prefer to go, a space station or an ocean floor exploring ship?
  1. Which country do you feel is the most aloof and why?
  1. What is the weirdest conversation you have heard between children?
  1. Do you think children are innocent or smart?

Deep Questions To Ask Friends

Solidifying that bond of friendship requires the right blend of deep questions to ask at the right time. However, make sure you are all ears while listening to your friend’s answers.

  1. Have you ever faced a traumatic or challenging situation in your life that helped you understand people better?
  1. What are your notions about creativity?
  1. Have you figured out what you want to do with your life?
  1. Where do you think thoughts go when you forget them?
  1. Do you agree that procrastination can do good to you?
  1. Do you talk loudly to your ‘inner self?’
  1. What do you think is wrong with our society?
  1. Is there any instance in your life you would want to change?
  1. Given a choice to change something in history, what would you like to change?
  1. Do you think people will become better if they just let go of the pretensions they carry?
  1. If you knew you just had a month to live, what are the three things you would do on priority?
  1. Will you try something life-threatening just for the experience or choose to play safe?
  1. How would you like people to remember you?
  1. Do you believe in the ‘law of attraction?’
  1. Have you ever been involved in an act that saved someone’s life?
  1. What is that one mistake many parents make that damages their children’s attitude?
  1. Which social stigma do you think society should let go of?

Weird Questions To Ask Your Friends

You are compelled to think outside the box when you know someone too well. Hit your friends with these weird questions when they least expect them.

  1. Of all the conspiracy theories that exist, which one do you believe?
  1. Which parallel world would you like to visit?
  1. Given a choice to rule a planet, which one would it be?
  1. What do you like to have around your desk when you are working?
  1. How would you spend the extra time if you could do without sleep?
  1. If you had the power to become invisible for a week, what would you do?
  1. If you ever built a theme restaurant, what will the theme be, and how far will you go to achieve the effect?
  1. If you entered a cryogenic stage, what would your reaction be when you wake up?
  1. Given a choice between a packet of uncooked spaghetti and a stack of fresh paper, what would you prefer to eat?
  1. Is there a mystery that you wish you could solve?
  1. Would you like to waste time, effort, or money?
  1. How long do you store expired stuff before deciding to throw it out?
  1. If there were anything like a healthy addiction, what would you like to be addicted to?
  1. Have you ever felt bad or sided with a villainous character in a movie?
  1. Is there a subject you feel should be included at the school level?
  1. If a biopic were made on you, which actor would you like to play your role?
  1. If the entire humankind were to do one thing at the same time, what would it be?
  1. If you found a gadget that would allow you to relive one day of your entire lifespan, which day would you choose?
  1. If you were given a choice to be reborn, would you choose a human or animal birth?
  1. If you were asked to make two rules that everyone has to follow, what would they be?
  1. If you were asked to choose a home to live in from a book or a movie, what would you choose and why?

    A home to live in.

    Image: iStock

  1. Is there any food that you think never existed? Why?
  1. If you could exist without eating food, what would you like to survive on?
  1. What are the situations under which you wish you could trigger a smoke bomb and disapparate?
  1. If you had to pretend to be an artist for a week, what piece of art would you create?
  1. Provided with every possible comfort, would you agree to be imprisoned in a room without human contact?
  1. If an interaction with your future self were possible at this moment, what message would you like to give?
  1. If you think of life as a game, what would you like to play?

Questions To Ask Friends When Bored

Would you like to have a long conversation with your friend and make them forget what to say next? Be prepared with random question arrows to shoot at your friends.

  1. What would you name your boat if you had one?
  1. What do you do when boring relatives turn up at your place?
  1. Do you have the habit of collecting weird stuff that nobody wants? What do you do with it?
  1. What’s the most unusual or funniest way someone hurt you?
  1. Which fictional character do you think would be the most boring or interesting to meet and why?
  1. If you were offered a role in any movie, which director would you like to work with?
  1. Has there ever been an instance when you screwed up everything, and fortunately, nobody found out?
  1. What food do you love the most but consider it a pain to eat?
  1. If you were asked to design the most exciting obstacle course, what obstacles would you include in it?
  1. Which mythical creature do you wish to see come alive?
  1. Which three spells would you like to learn first if someone agreed to teach you real magic?
  1. What would you make people do if you were to possess them as a ghost?
  1. If world-famous monuments were being sold, which one would you buy?
  1. If you could ask God one question, what would you ask?
  1. Would you still eat food that’s past its expiration date, provided it smells and looks fine?
  1. Do you believe in the possibility of computers and clones taking over the world?

True Or False Questions To Ask Friends

Friends coax you to reveal secrets. Whether you wish to go into the details or agree to disagree, true or false questions are bound to open up a huge closet of secrets.

  1. Do you always think a lot before saying anything?
  1. Is it true that you believe yourself to be a go-getter who would rather die than quit?
  1. Are you conscious about what you buy so that you can support the sustainability cause?
  1. Do you always forgive others’ mistakes?
  1. Do you sing in the shower every day?

    Sing in the shower.

    Image: iStock

  1. Do you agree that making prank calls is your favorite activity?
  1. Did you ever pretend to have a phone call to get away from talking to someone?
  1. Do you tend to talk non-stop when you are stressed?
  1. Are you so absent-minded that you often walk into the wall or forget why you called someone?

You can ask these interesting and fun questions to your friends while having a sleepover, getting together, or when you are trying to make new friends. Asking each other questions can help you know more about one another and develop a bonding as you share experiences and memories. We have divided these questions into several categories to make it easier for you to pick out the ones based on your preferences. So go ahead and choose the ones that intrigue you the most and spice up the conversation.

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