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250 Questions To Ask Your Best Friends

Imagine this, you’re at the party and you’re new here. So many new faces, chattering voices, laughing loudly and then you look over at the table nearby and you think, “Oh My God. I know her from my biology class. Oh no she’s looking at me. What do I do? WHAT DO I DO?!” Social anxiety has officially taken you over.

It’s a very common situation that most of us often fall into. It can be you in your new office, new class or a new friend group. It’s natural for some of us to be at a loss of words and not know what to talk about even when we try so hard. Human life is more or less, constantly being defined by the social network a person maintains. Studies also show that people often look for friends with good social skills which makes friendship development much easier for both parties.

You must have heard of the phrase, “The way to a man’s heart is through his stomach.” Well, let’s tweak it and say “The way to a successful friendship is through curiosity!”

So, what if, we can provide you with some very exciting questions to maintain the sizzling conversation that you wish to have with your friends or best friends. Want to know what they are? We suggest you keep reading!

Table of Contents

Funny questions to ask your friends

Feel like your conversation is becoming bore and mundane? Here are some rib-tickling questions for you to get you and your friends a good laugh!

Would you be embarrassed to show your naked childhood pictures to me or any other friend?
You are on a date. You drank a lot of water and now you have to pee. The washroom is all full. Would you choose to go to the opposite sex washroom or hold it till the date ends?
As a child, have you ever picked your nose and stuck the booger on someone you didn’t like?
Have you ever sung a song loudly on public transport, only to realize you had your earplugs on?
What is a weird kind of smell that you like? (Eg; Smell of Petrol, Fevicol, etc. )
You’re swimming in the sea and you get gulped and stuck inside a huge whale. What do you do?
Have you ever worn underwear for more than a day?
Have you ever been in a situation where you’re on a video call with your friend and your family embarrasses you?
If you ever lose your underwear in the swimming pool while swimming with your friends, what would you do?
Have you ever done something that was attributed to the opposite gender?
Do you have an unusual trait? What is it?
What is the one fantasy you wanna complete before you die?
Will you be okay if a meme is made about you and it goes viral?
What is the one embarrassing game you would still play?
What are the one weird talent that you admire a lot and you want to learn it?
Have you ever screenshotted a conversation with a person and by mistake sent it back to the same person?
As a child, what is the most disgusting thing you remember eating?
Look around you and come up with the best pun you can.
Imagine you are mistaken for someone who is a dictator of a Middle Eastern country under war. The dictator looks like your twin. You are asked to come back to your country as the authorities think you’re the actual dictator. Would you go?
In kindergarten, do you remember being in a situation where you were punished and told to get out of the class and stand outside, but you ran away?

Good questions to ask your friends

These questions will give a good kickstart to your new and budding friendships.

Do you believe in sun signs? If yes, would the sun sign of a person affect your liking/ preference for a person?
Would you rather be stuck in your favorite video game or your favorite movie?
If you had a choice, would you wanna belong to the 80’s generation or the current generation?
If you get an island gifted to you, what would you name it?
As you know about the current issue of the Corona Virus. Would you break your friendship with someone who has this disease?
What is the funkiest look/ makeover you’d give to yourself?
You are an astronaut. You get sucked into the black hole and end up on a new planet, with the perfect climate and unlimited resources. Would you start living there or would you try to find your way back to your home planet, Earth?
What is the most beautiful eye color according to you?
What is the funniest pickup line someone has ever tried on you?
What is more romantic for you, the beach or the hill station?
What should be done to a child prodigy or a gifted child according to you?
The city has blacked out and there is no electricity. Everything is dark and you are stuck in an alley. What do you do?
In your opinion, what is more your style; to dress simple or to dress extra?
What is the most creative thing you’ve done that you’re proud of?
At night, you’re in your house and you’re sleeping. A serial killer enters your house. How do you save yourself?
Do you think a college-level education and a degree is still required if you get a successful job immediately after you complete high school education?
If you could make a revolutionary change, what would it be?
Do you believe that one’s outcome is all dependent on their hard work or is some sort of luck also involved?
What is the most ridiculous and most stupid thing you’ve done in a desperate situation?
If you had to run away from your house to go on a vacation with your friends, how will you leave? Will you write a small letter, leave a note, or something else?

Deep questions to ask your friends

Want to get to know your friend better? Here, these questions will help you along the way!

What is the most unusual, weird fear you have?
It’s 2050. The world has ended due to a catastrophe and there are barely any resources left. Would you want to be a survivor or prefer to die instead?
As a child, what is the first memory you have of your parents?
If I become a ghost and try to contact you, would you talk to me?
Would you want to sneak out of the house in the middle of the night or early in the morning?
If today was the last day of your life, what is the biggest regret you’d have? How would you make up for it?
You wake up one day and you’re the only one left in the world. You have the whole planet all to yourself. What is the first thing you do?
Have you ever gotten so engaged in a book that once it got over, you found it hard to adjust to your reality again?
Would you want to know your future, provided you can’t change it?
What is the silliest fear you have?
What according to you is the best murder getaway?
What is something that gives you major nostalgia?
It’s 3 A.M. and you feel sad. What will you do to make yourself happy?
What kind of a parent will you be?
You know that someone has a terminal illness and you are also aware that you are slowly falling in love with them. Will you stop yourself?
You’ve been in hypersleep and you have woken up after 100 years when everyone you know is dead. The world has changed; nothing is how it was before. What is the first thing you do?
Would you want the same life after you die?
What is the one trait for you that will make you break ties with someone no matter how close you are to them?
Imagine you were in a long term relationship and you and your partner had decided to move to one place for college/job. The relationship doesn’t work out and before you move to the new place, the relationship ends. Would you still move to that place for the job/college where you have already worked everything out?
What is the one thing about nature that can get you emotional?
When you were little and you had to hide, which was the best place for you?
Have you ever seen a dream which turned out to happen in real life too?

Questions to ask your best friends about yourself

Ever wondered what your best friend thinks of you? How your relationship is? Be sure to ask these questions!

If you get to know that I am an international wanted criminal, would you still be my best friend?
What is the weirdest judgment you had about me?
Have you ever wished for something good/bad to happen to/for me? What was it?
If you get the chance to become me, what is the one thing you’d change about me?
It’s World War 1. Both of us are each other’s enemies on the battleground. Would you attack me?
If you and I lived together, how would our house be like? Describe it.
If you could give me a makeover, what would you do?
We’re clubbing on a Saturday night. I get drunk and my ex calls me. Would you let me talk to him/her?
What is the one deal that someone has to make with you to get you to betray me?
What according to you is my best feature or the best thing about me?
Name the top 3 songs in your playlist that will describe me?
Which is the strongest body part of mine according to you?
What if you’re in a friendship tie with me where you’re the one who mostly apologizes because you keep your care for the person before your ego; would you continue being friends with me?
What matching tattoos would you get with me?
Name 5 of my best features in about 10 seconds.
If you promised someone to keep a secret from everyone, does that include me, or will you share the secret with me?
Imagine you and I are going to be living in different places for years. However, we make a pact that after years, when we grow up; we’ll meet each other again. What is the one thing you’ll give me so that I don’t forget the pact?
What is the worst prank I could do to you?

Weird questions to ask your friends

Every once in a while you daydream and wander off to the weirdest corners of your mind which pours out questions, pushing your curious doors. Why not open these doors and bombard your friends with this crazy weirdness? Want some help? Here are some questions you can ask them!

Would you rather have long nose hair or long hair in your ears?
You have one wish, you can have anything you want, on the condition that you have to do something disgusting like, lick sweaty feet. Would you do it?
Would you wear my used underwear if it’s an emergency and you have no other option?
Would you rather have thick hair on your body which cannot be removed, ever or have no hair on the body at all, which also includes no hair on your head, eyebrows, etc.?
You have two options. Either you have to bath every 5 min. to stay clean or, not having a bath at all. What option would you choose?
Imagine you are a scientist, experimenting in the laboratory alone in the night. The experiment goes a little haywire, and somehow you get shrunk and stuck in the computer. What will you do now?
You can only have nails or eyebrows. What is more important?
Suppose all communication is lost in the world. You need to be with people so that you can be there in times of emergencies. The limit is only five people. Who are those 5 people going to be for you?
Would you have rather have rotten teeth, smelly armpits or bad breath for your whole life?
Imagine that one place you always wanted to go to or something you always wanted to have, but it’s at the end of 20,000 stairs. Would you climb it?
Imagine that a cult asks you to join them and tells you that they will take care of all your expenses for a lifetime, but if someday they need you to sacrifice you, soul for them, you will have to do it. Will you join them?
While tasting new food, do you smell it first or eat it first?
Have you ever slept in one place and woken up in another place?
You’re in a restaurant and the button of our jeans pops open and gets lost. What do you do in that situation?
As a child, what is the worst that you ate and it got stuck inside you? How was it taken out?
What will you do if you meet your twin?
Do you have an OCD habit that you can’t compromise with?
You are writing a book where the characters become alive. How will the characters be?
You get lost in the Bermuda triangle. What is the smartest thing you do?
You’re in a jail where the convicts make clubs and elect leaders for it. They also have an election in jail for the same. Would you stand for the elections?
You have lice in your hair that cannot be treated. Will you leave it like that or go bald?
You are the world’s best psychologist. How do you use that talent to take over the world?
You get to know that you are being filmed for a youtube video without your knowledge. Would you let it keep going or would you make them stop it?

Questions to ask a new friend

Sometimes, when you make new friends, it gets difficult to connect with them. You know you like them but, are you finding yourselves to be too nervous to break the ice? Here are a couple of questions to help you with that.

Would you rather be light as a feather or as heavy as a rock?
I am offering you food. However, you see a bottle of poison in my hand and get skeptical. When you ask me what it’s for, I tell you I was going to throw it away. Would you trust me?
Imagine that you are kidnapped. You are being held at gunpoint. The kidnappers ask for money. Would you give me your credit card information to get the money for you?
Have you ever approached someone you found familiar but he/she didn’t remember you?
You’ve made a new friend and you see that they have food stuck in their teeth. Would you tell them about it?
Your friend uses your phone to activate Instagram on it, but she/he forgets to log out. Would you snoop into his/her inbox and private messages or would you tell her/him about it so they can logout.
What is the best thing about being a boy/girl/man/woman?
When you go shopping, do you need your goodies to be from a high-class brand or as long as the goodie works for you, you will buy it, even if it doesn’t belong to a known brand?
Does it frustrate you when you’re humming a song but you can’t seem to point out which song it is?
Have you ever had a crush on an animated character?
Have you gotten your wisdom tooth out yet? If not, knowing how painful it is, will you get it out?
Are you the kind of person who prefers to work in a team or work alone?
Are you the kind of person who gets drunk and would get accidentally married?
As a child, what is the one thing that your parents would do to get you to do what they wanted?
What is the most romantic weather for you?
What is the one hobby/activity that calms you down?
What is the most important thing for discipline that will change you but you’re too lazy to do it?
What is the one thing that if taken away from you will make your life meaningless?
If you and I wouldn’t have been friends, what is the one wrong judgment you would’ve made about me?
Would you believe it if someone says that the world is going to end by getting flooded and we need to start building a huge boat?

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Interesting questions to ask your friends

Imagine you’re at a party and everything is starting to boil down, everything is starting to get boring. However, we got you! We are listing some questions below for you to be the one to spice things up!

You’re allergic to dogs. Would you still keep a pet dog with you?
Would you rather hear everything way too loud or not hear anything at all?
Would rather get everything and be unhappy or have nothing and be happy?
You have to get rid of one body part of yours to be stronger, to get rid of any bodily liability. Which body part would it be?
If a good spirit wants to contact you, would you talk to it?
The temperature regulator of your shower is broken. Would you have a bath with water too cold or water too hot?
What is scarier, a snake crawling in your stomach or worms in your ears?
Imagine the one thing that makes you very angry. You are so angry that you might kill someone. Now, tell me about the one thing or person who can calm you down.
A YouTuber tells you that you need to jump from the cliff to a 10,000 ft. drop and they will save you. This will make you world-famous. Would you do it?
The earth has stopped revolving around the sun. One half of the Earth is stuck in the day time, the other half in the night time. Which half of the Earth would you want to live in, provided you can’t change it after you make the choice?
Which is the scariest or the worst horror/ scary movie to be stuck in?
When you were little, what was the first dream profession of your life?
Which is the one subject that you struggled with in school? Would you be willing to go back and study it if, in return, you are offered your dream job?
Would you be willing to completely give up junk food for abs?
What is the first thing in a person when you see them approaching you?
What kind of a person are you; the one that would prefer a court marriage or the one that would prefer a full-fledged marriage ceremony?
What is the one sport that you would want to be famous for?
What is the one change in your personality that you would want to make?
You write for your school paper. A murder has taken place in your school. Would you want to investigate and prepare a story for your school paper?
If you had an assistant or a butler to remind you of your daily tasks, organize your daily appointments, would be more punctual and procrastinate less or would you still be lazy?
What is the one era in the timeline of humans that caught your eye? Describe the one thing about that era that attracted you to it.
There is a strange box outside your house and it says ‘do not open’. It could be a bomb. Are you curious enough to still want to open it?
What would you want to become in your next life?
Imagine you’re at the Oscars and you’re nominated for some category. You receive an award but then you get to know it was a misunderstanding. Nobody has realized it yet. Would you keep the award?

Difficult questions to ask a best friend

The most fun and interesting things don’t always have to be the most simple. Let’s level up and give your friends some head-scratching questions!

It is the last day of your life. Would you save yourself, which has no certainty or would you make the most out of that day?
Imagine that you’re the president of the country. You are in a situation where you can either save a member of your family or the country. Who would you save?
The world is ending and it’s a zombie apocalypse. Would you save a child, a doctor or a family member?
Would you rather be the biggest giant in the world or would you be a rat-sized human?
If you could have a choice in molding your personality and your options are to be too rude or too sensitive, what would you choose?
You’re on a stranded island and you’ve been here for days. You are very hungry and the only edible item available is a watermelon that has worms in it. Would you eat it?
Imagine the one thing you want the most. Now imagine the most difficult thing you have to do for it. Would you do it? Tell me about those things.
You are in a trust fall. You have 5 seconds to choose someone for the trust fall, someone who will catch you when you fall backward. Who do you choose?
You’re in a situation where you have to sing a song perfectly or you will get shot in the head, which song do you choose?
Would you rather hurt someone with the truth or care for them with a lie?
Imagine that you’re almost dying, and there is no assurance that you’re going to be saved. However, you get to know that someone in the same hospital needs a heart transplant or they will die. A heart transplant will surely save them. Would you save that patient?
You buy groceries and the cashier ends up giving you some extra money along with the change he gives back. Would you keep it?
Would you take a job which takes up a lot of your time but give you a lot of money?
You’re a judge in a criminal court. You know that the person being tried in front of you is guilty of the crime but your hands are tied by the rules of law that says you only have to judge the case in accordance with the evidence you receive. Will you break the rules and arrest the guilty?
You’re a teacher and your favorite student is being abandoned by her/his parents. Would you adopt her instead?
You have been talking to someone you met online and you’re starting to like them. They ask you to meet them in person, would you want to meet them?
You’re in a forest and you’re there for camping. Its night time and it’s a dangerous time of the day. A group of trekkers comes up to you saying a friend of theirs is lost and they need your help. Will you help them?
You’re trapped in a cave and your legs are trapped between stones that have fallen on you. How do you plan on surviving and getting out of there without any means of contact?
Correct to torture and violate the human rights of a terrorist to punish him/her for his/her crimes?
Have you ever been catfished or catfished someone else?
Would you rather be a designer and by anonymously famous or a model and be famous all the media?
If you become the most known robber in the history of robberies, would you want your face to be known and famous?

Fun questions to ask your friends

You’re sitting in your room with your friends on a lazy Sunday afternoon. You don’t have any idea as to what to do. Boredom is hitting you. Worry not, here are somethings you can ask to have a little fun while not having to move at all! Who said you can’t be lazy and have fun?

You have to construct a house with one food item. What food item is it?
Would you rather have the ability to breathe underwater or breathe in space?
(For a Boy) Would you rather wear a bikini and run on the beach or stand in the hot sun for 1 minute?
(For a Girl) Would you rather wear a fake mustache to a party or eat a plate of hot chilies?
Without any experience, would you fly a helicopter or a rocket to space?
You’re building a pool and these are your options. A pool of lotion or a pool of oil. What choice do you make?
Would you spend your whole life in a submarine, underwater, which has all the facilities?
You’re standing at the door or an airplane and you’re ready to do skydiving on the condition that someone else will push you and you don’t know when. Would you do it?
Have you ever set someone up with their crush?
You’re designing your whole house all over again. Describe the plan.
What is the perfect vacation for you?
You have one hour to shop for free in your favorite mall. Which mall do you choose and what are the top shops you visit?
Which is the reality show that you would want to be a part of, and would also want to win? What is the show and what do you win?
You are roaming on the beach and it’s the last day of your vacation. You have to start packing and leave for the airport in half an hour. You suddenly find a map to an island where a gold mine is situated. It can be all yours and it can make you rich. Do you go for the adventure?
Tell me about an embarrassing drunk story.
You know that the haircuts you give turn out to be a disaster. However, only you are aware of the fact. Who do you want to give a haircut now?
What is the most interesting DIY (Do It Yourself) task you have completed?
A hundred billion dollars are dropped from the sky like its raining money. How do you collect that money in such chaos?
If you get to know that you have the power to be successful at everything you’ll do from now on, what all do you do?
What is the one rumor you wouldn’t mind being spread about you?

Hard questions to ask a friend

Sometimes, the hardest of the questions bring out the most interesting answers. Here, we give you a list of questions that’ll give you a chance to know your friends on a level that no one would’ve known till now. Go ahead, what are you waiting for?

If you’re infected by a deadly disease and to save yourself, you have to trade a secret that would ruin your life, would you?
Would you be friends with someone who is a part of a terrorist organization?
You’re all alone in the house, your cell phone battery is almost over. Who would you call?
You are a hostage in a bank robbery. Would you help them for 3 million dollars or would you choose to get out of there without anything?
If a terrorist attacks your city and holds a loved one of yours at gunpoint, would you stand up for them?
The earth has collapsed. You have a ticket to a rocket ship which will help you escape. However, you only have one ticket and there are two people, one is you and one is someone very close to you. Would you save yourself or would you save them?
Euthanasia is the practice of voluntarily ending one’s life who is suffering from a fatal, non-treatable disease. Would you choose it for yourself?
Due to the COVID-19 or the Coronavirus disease, the tickets to planes are getting cheaper. You can go for a world tour for half the price now. Would you go, even if that puts you at risk of catching the disease?
You have lost a bet and now you have to get your ex’s name tattooed on your body. Where will you get the tattoo?
You’re the President’s bodyguard. You fall in love with their son/daughter which is against the rules and will cost you your job which is helping you support your family. Would you break the rules?
Describe yourself in under 10 seconds.
As the most famous archeologist, your next excavation is at a graveyard and you have got the night time slot. You will receive a Nobel Prize for this project. Will you do it?
Do you think someone who has unintentionally and unknowingly spread a global pandemic should be punished and detained?
You are escaping a murder. The entrance is taped with explosives and the whole building is surrounded. How do you escape?
The condition of the COVID-19 detention centres is very bad. However, one of your own family members gets infected with the disease. Do you turn them in to save the rest of your family or do you keep them safe with you and take a risk?
You are a criminal with loads of money. However, over the years, you have become world-famous and the most wanted criminal in most countries. Do you turn yourself in or take the risk?
You are in a war zone. You have 10 seconds before the whole place is bombed. You can either save that one person and put the rest of the soldier’s lives at risk or you can save the soldiers and risk the life of that one who cannot be saved?
You have to dance to a song and impress the serial killer so that he doesn’t kill you. What song do you choose? Can you show us the dance?
Have you ever stood apart from the rest of the crowd, alone, for something you believe in?
If you were living during the time of the Nazis and you were one of the Jews, who were being killed on a large scale, how would you save yourself? Would you want to go to the refugee camp?

Personal questions to ask your friends

Want to know a side of you friends that’ll deepen the bond between you and them? We can help you with that. Just ask these questions and you’ll be surprised to know what your friends are.

Would you hurt a close one for your benefit?
Name one weird fetish that you have. (Eg., some people have a foot fetish).
Did you ever have inappropriate dreams or fantasies about someone from your family?
If you had to block someone from your chatbox, someone you talk to, who would it be?
On your birthday, you have the option to either be alone or call the people you hate. What would you choose?
What has been the most uncomfortable situation you’ve been in with your parents?
You have one chance to kiss your crush, but they have a case of bad breath. Would you still kiss them?
Would rather have the ability to detect lies or the ability to find the truth?
As a girl, would you rather have no periods for your life or would you rather want to stay young forever?
If your personal diary gets lost, how much damage will be done? Will you lose someone close if secrets from that diary get out?
Do you find it comfortable to talk about your sex life with your parents?
You have the chance to call back someone from the dead. Who would it be?
What is the best feature of the opposite gender that might attract you?
What can someone use to bribe you?
Which are the one body scar and the memory attached to it that you remember?
Have you ever been bullied? How did you handle it?
Do you have any message for those going through the same bullying phase like you?
If your children are Gay/Lesbian/Bisexual, will you accept them?
What would you say to your younger self?
Which childhood memory would you want to relive?

Cool questions to ask your friends

Allow your friends to come up with cool and fun ideas that can be hilarious but highly intriguing. However, you can help them with that. Ask the following to give them a nudge in that direction and hear them out!

You have to create a new game for the Olympics. Describe the game and its rules.
You are stuck in a time of the year; you have two options, to be stuck in winter or summers. What would you choose?
Tell me about 5 pieces of clothing that are in your wardrobe, you don’t want to get rid of them but you also, never wear them.
Do you think if we would have lived in the Mesozoic age, the period when dinosaurs were alive, we would have died or made them extinct?
Do you sometimes feel like you’re secretly a part of a T.V. show that you don’t know about but feel like you’re always being watched because of it?
Would you accept the ability to never have to sleep again along with the ability to never be tired again?
What is the most dangerous thing you’ve done in life?
Would rather be an uneducated rich man or a literate poor man?
Would you be a criminal and rob a bank, if you could do it without being caught?
You wake up in the year 2050. What is your first Google search?
If you could be stuck at one age of your life, what age would it be?
You’ve stuck in a maze with traps all around. You only have three lives. How do you get out of there and who’s help would you take?
What is the most daring thing you have done in your life?
You are a rapper. What would your rapper name be?
Where would you hide a dead body?
For a girl; would rather be a Victoria Secret Model or a judge at the show?
Describe the scariest ghost for you.
There is a serial killer in town. He keeps calling you and keeps making demands and if you don’t comply, he will kill you. Do you inform the authorities or do you keep complying in the hope that this will be over soon?
You are a mosquito. What is your strategy to survive?
Robots have taken over the world. How would you conspire against them?
You find a secret safe in your house. Do you share about it with your family members or do you keep it to yourself?