Sex, Dating & Relationship

400 Wacky, Wild & Totally Fun Questions to Ask Anyone—Including Friends, Family & Even Strangers!

Use this list of entertaining questions to start a discussion with anyone, whether they are close friends, family members, or total strangers. These entertaining questions may help spice up any discussion, whether you’re hanging out with friends, at a family gathering, or even on a first date.

400 Wacky, Wild & Totally Fun Questions to Ask Anyone—Including Friends, Family & Even Strangers!

Don’t let this list of amusing questions to ask overwhelm you. There are quite a few, so choose a handful for each situation and move forward from there! The directions that your conversations can take with the help of these amusing questions are virtually limitless.


These entertaining questions can improve relationships with friends and new acquaintances on any occasion. By asking one of these questions, you might learn something interesting about someone. Check out the complete list of entertaining questions below!

400 Wacky, Wild & Totally Fun Questions to Ask Anyone—Including Friends, Family & Even Strangers!

Fun Questions to Ask Anyone

What is your favorite sleeping position of all time?

What is the dumbest way you’ve been hurt?

What are the three scents you like?

What sport will be invented next?

What’s your favorite board game?

Which word would you use if you could only use one for the rest of your life?

Would you rather have intelligence over looks?

What’s your most embarrassing moment in grade school?

Would you rather stay in or go out on a Friday night?

Have you ever thrown someone an extravagant party?

Fun questions weirdest thing eaten

What is the weirdest thing you have ever eaten?

Out of the four seasons, what’s your favorite one?

What is the most absurd thing you’ve been tricked into doing or believing?

What is something that’s true that nobody agrees with you on?

Which instrument has the funniest sound?

Where would you relocate if you were forced to leave the country?

Do you care about what other people tell you?

If you could meet anyone in this world today, who would you meet?

What’s the best type of cheese for you?

What is the greatest risk you have ever taken?

Have you ever thought of what your future baby will be named?

What are those things you’re too old to do but you still enjoy?

What are your pet peeves?

Who’s the messiest person you’ve ever known?

Which of the two smells better, fresh-cut grass or bread baking in the oven?

Who is your all-time favorite Disney character?

Fun questions afraid of ghosts

Are you afraid of ghosts?

Can you carry an elephant?

What’s the worst color that was ever invented?

What is the weirdest text you have ever received recently?

What would you be if you had to wear one Halloween costume every day for the rest of your life?

What is one ability that you believe everybody should possess?

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How many times has your heart been broken?

What is the first thing you do after getting home from a trip?

What are the things you’d spend with a billion dollars?

What are the songs that make you sing along whenever you hear it?

How did your parents meet?

What has been your greatest kitchen mistake?

What’s the craziest bet you have ever made?

Do you believe that love is blind?

Who would you want to trade lives with?

If you were given the chance to steal something, what would it be?

What type of cuisine would you serve your customers if you own a five-star restaurant?

What’s the fanciest event you’ve ever attended?

Who is your greatest enemy?

What food should taste better than its appearance?

What’s the first thing you pack during an out of the country flight?

Do you actively post on social media?

If you could only teach three things to your future child, what would it be?

What is the worst TV advertisement you’ve seen recently?

What’s the most addictive game for you?

What do you usually do during weekends?

If you were given the chance to make your one wish come true, what would it be?

What period would you travel to if you were given a time machine?

What’s the food you usually refuse to share?

What are the hobbies you want to develop?

Fun questions believe in horoscopes

Do you believe in horoscopes?

What was your favorite childhood book?

Would you take it if you had the opportunity to be immortal?

What is something your brain wants to convince you to do but you have to fight it?

Which would be the smartest animal if they could all talk?

What movie makes you laugh even after watching it several times?

What’s your favorite toy when you were a child?

What is the best name you could think for a cat?

Have you ever counted your steps while walking?

Do you believe in heaven?

If you have a million, what are the things you wouldn’t spend?

If you could have lunch with one person from history, who would it be?

What’s the certain product you couldn’t live without?

Fun questions yacht name

What would you name your yacht if you had one?

Where is your all-time dream vacation?

How do you want to die?

What is the most stupid thing you’ve done in your entire life?

If you could sit next to a famous celebrity in a restaurant, who would it be?

If you had 24 hours to do whatever you wanted in this country, what would you like to do?

If you could be a Hollywood celebrity, who would you like to become?

What is your main reason for getting out of bed every day?

How could you politely end a conversation with a person who is so annoying?

What makes your day better?

What is the strangest thing your teacher has ever done?

What is the best color in the rainbow?

Who is the best movie villain?

Would you rather have 20 hobbies or a single passion?

What’s your favorite exotic animal?

How would you describe me based on my outside appearance?

What is your favorite viral video?

Who is your favorite YouTube vlogger?

Fun questions coffee or tea

If you could only drink coffee or tea for the rest of your life, which one would you choose?

What’s your favorite action movie?

What gets you motivated?

What’s the most beautiful country you’ve ever visited?

Would you rather cook or eat at a restaurant?

What is the most useless talent you possess?

What is the craziest thing you’ve done in school?

How often do you replace your bedsheets?

Do you like listening to podcasts?

Do you like to save more or spend more?

What is the weirdest superstition you’ve ever heard?

If dark chocolate is the only available food in this planet, would you eat it?

What are the two things you’d like to ask your pet?

Fun Questions to Ask Friends

What’s the easiest dish to cook?

If you could be any type of object, what would you like to be?

How do you deal with a stressful environment?

Which part of the roller coaster do you usually ride: the front, middle or back?

What quotes do people admire but you think is a total lie?

Do you believe in second chances?

What has been the most flattering compliment you’ve ever received?

Have you tried flirting with a stranger online?

What would you like to change in this country if you were chosen as the president?

Do you have a close relationship with your parents?

What has been your hardest goodbye in life been so far?

Fun questions change name

If you could change your name for a day, what would it be?

Would you rather have a massage or get a facial?

Can you describe to me your relationship with your dad?

Which do you listen to the most: your heart or your brain?

What would you do if you were offered a one-minute ad slot during the Super Bowl that you couldn’t sell?

When was the last time you’ve felt your biggest adrenaline rush?

Who is the tallest member of your family?

What traits did you get from your parents?

Who do you look up to the most?

Can you show me your oldest item inside your closet?

If you could only have one superpower, what would it be?

What’s the best thing to do when you’re alone?

Will you ever imagine having a child named after you?

Do you want to have a cat as a companion or do you want to be a cat instead?

What’s one body part that you wouldn’t even mind losing?

For you, what does a perfect vacation look like?

Which one do you prefer: being controlled or be in control?

What are your phobias?

Do you feel happy to be my friend?

What makes you jealous?

Is there someone you really hate?

Who gave you the best compliment?

Fun questions film to musical

Which film do you want to see turned into a musical?

Do you still believe in Santa Claus?

How would you describe your greatest enemy?

When was the last time you screwed anything up and no one ever noticed?

Have you already experienced writing a journal?

What do you usually daydream about?

If you were given the chance to listen to a singer or a band for the rest of your life, who/what would it be?

What are the things you wish you could easily forget?

What’s the most beautiful part of your face?

Has anyone given you a strange gift?

What’s the weirdest thing on your bucket list?

Have you ever pulled out a tooth just to get money from the tooth fairy?

What are the childish acts you still enjoy doing up until now?

What does your brain try to make you do and you have to resist yourself not to do it?

What three things did your past relationship teach you?

What do you think is the best hangover cure?

What are the foreign languages you’d like to master?

In your own opinion, how smart are you?

When was the last time you’ve ever felt jealous?

What’s the biggest pimple you’ve ever had?

Do you still remember the place where we first met?

Fun questions move for love

Would you move to another country for love?

When was the time you felt really proud of me?

What has been your worst nightmare?

What usually keeps you up at night when you couldn’t sleep?

Were you born for challenges?

Are you confident to face the future?

Who gave you the weirdest gift?

What makes you cry?

When was the last time you cried?

How many concerts have you gone to?

What would our friendship be called if it was a comedy movie?

What would you name your car?

Do you think life after death is really possible?

What is so special about you?

What will you tell your past self?

What movie did you last watch inside the cinema?

Which one do you prefer: summer or winter?

Fun questions believe in aliens

Do you believe in aliens?

What was the best year of your life?

Do you actually believe in soulmates?

What is your biggest accomplishment in life?

What TV series could you watch several times?

Where do you like to go right now?

Where’s the worst-smelling place you have ever been?

Will you be willing to move to another country without your friends and family?

What qualities do you want in a partner who will be with you for the rest of your life?

If you were given the chance to travel back to the past, where would you go?

What do you usually eat for breakfast?

Which store would you like if you could just shop at one for the rest of your life?

What household chore do you hate doing the most?

Who is your role model in life?

Do you really care about the Academy Awards, or do you think they’re just dumb?

Who you share the last slice of cake with if there was just one piece left at your birthday party?

Fun questions celebrity

Which celebrity would you rate as a perfect 10?

What music do you usually play on a road trip?

What are the things that drive you crazy?

What syrup do you like with your pancake: honey or chocolate?

Do you plan to have kids?

What is your most favorite holiday?

What are the things I do that you wish I would stop doing?

What’s the first book you’ve read?

What are the facts about you that you think I would find difficult to believe?

Which body part is your favorite?

What has been the worst phase in your life?

What do you prioritize more: relationship or career?

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What flower is your favorite?

Fun Questions to Ask Your Family

What are your hidden talents?

What’s your most favorite family tradition?

Have you ever been caught while sneaking outside the house?

What’s the meaning of your name?

Do you ever dream of living somewhere else?

What is/was your favorite subject in school?

What are your hopes for the future?

What usually scares you the most?

What’s the weirdest animal for you?

What will be your reaction if you see a ghost?

Fun questions kind of bird

If you were a bird, what kind of bird would you be?

Does my face look funny to you?

Who was your first crush?

What are you actually good at?

Do you hate math?

What’s your favorite lullaby?

What was your reaction when you found out you were going to be parents for the first time?

What is your dream for me?

What would you serve if you were to make a special dinner for the family?

What are the things you love the most about yourself?

Can you guess what I’m thinking right now?

What’s your greatest philosophy in life?

What is the worst decision you’ve ever made?

Where did all of our family traditions originate?

What is your favorite day of the week?

Where did you tie the knot?

What’s the weirdest Halloween costume you have ever worn in your entire life?

What do you miss the most about being a kid?

How do you inspire other people?

Fun questions life song

What is the best song to describe your life right now?

Where do you see yourself in the next 5 years?

Have you ever stolen food from the refrigerator and blamed it on someone?

What do you hate about me?

What’s your favorite car brand?

What would you do if you knew you’d be good in a different profession?

Do you like to exercise regularly?

What’s the worst food you’ve ever eaten?

What is your most cherished possession?

What’s the most valuable thing you’ve learned in life?

What makes you really angry?

If you were a pair of shoes, what brand would you like to be?

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What’s your dream job?

What habits of other people you definitely find disgusting?

Do you still keep secrets from mom/dad?

What’s the extreme challenge in your life that you’ve already overcome?

Have you ever thought of having plastic surgery?

What sound do you hate?

What is your current favorite TV show?

Fun questions seven dwarfs

Which of the Seven Dwarfs resembles you the most?

Without calling 911 when you are in danger, what would you do instead?

What is your favorite dance move when you were a kid?

If you were given the chance to kiss and hug someone, who would that be?

What is the worst punishment your parents gave you?

How many countries have you visited so far?

Have you experienced falling down the stairs?

What are the challenges you never gave up on?

What is one piece of advice you wished you’ve seriously taken?

What do you like most about going to the beach?

Have you experienced being confined in a hospital?

If you are drowning, who do you think would save your life?

What is the most embarrassing moment you had in your workplace?

Who has taught you the best lesson in life?

How would it feel like to cry underwater?

How many times have you traveled by sea?

Who would you want to portray your life story in a movie?

Have you ever composed a song?

What’s the last thing on your bucket list?

How was your wedding?

Which fictional book character would like to meet in the future?

Has anyone tried to kill you?

Who eats the most in the family?

Who is your childhood best friend?

Do you get thirsty in the middle of the night?

What are the qualities you search for in other people?

Fun questions fish get thirsty

Do you think fish ever get thirsty?

Which of the politicians would you like to marry?

How competitive are you?

What family traditions have we forgotten about that you’d like to revive?

If you could be part of another family, whose family would it be?

Who is your favorite athlete?

What is your favorite sports team?

What are the musical instruments you can play?

What would you do if you become lost in a city you aren’t familiar with?

How old were you when you were allowed to have a cellphone?

Can you name 5 things that are hidden inside your bedroom?

Do you feel any pressure right now?

If you could make one word famous, what would it be?

What movie are you going to make if you become a filmmaker?

What is your dream laptop?

How long was your last relationship with your boyfriend/girlfriend?

Which member of your family were you closest to as a child?

Fun questions good at sports

If you could be great in only one sport, which sport would you choose?

Do you see yourself as creative?

Do you know how to change a flat tire?

If you were ever bullied as a child, what did you do about it?

What would you do if ever we were given a special time together?

What type of genre would you choose if you were an author?

What time were you born?

Who do you not trust among your friends?

Are you an impulsive type of person?

Fun Questions to Ask Strangers

Do you keep a really big secret from someone/anyone?

Who is your favorite superhero?

What are the things you’d bring in a zombie apocalypse?

If you could teach a dog one trick, what would it be?

Do you watch the full ad on YouTube or you just skip them?

If someone would let you borrow their car, where would you go?

Who do you think is your celebrity look-a-like?

Why does it still rain in the movies when there is a funeral and then stop right after the burial?

What flower would you prefer if you awoke as a flower one day?

What location would you choose if you had the power to make it disappear?

Where would you rather be: a place with no food but has water or with food but has no water?

What’s the last food you ate?

What was something you really wanted to do as a kid but never had the opportunity to do?

Fun questions pick up lines

Do you know any funny pick-up lines?

Is there something you recently regret doing?

What’s your least favorite board game?

When you reach the age of 80, what will matter the most to you?

Have you ever been caught staring at the opposite gender?

Would you like to be famous someday?

What are your top 5 favorite fast-food restaurants?

Which brand of smartphone do you dislike the most?

Have you ever had to run from the police?

What law would you like to make that every person should strictly follow?

Would you rather be a hero or a villain in a movie?

What’s that certain thing that people always misunderstand about you?

If you survived a plane crash, what would you do next?

Do you like dipping your Oreo in milk?

Are you a collector of something?

What do you think God looks like?

Would you rather wear shoes or slippers?

What’s your lucky number?

Have you recently checked out one of your bucket lists?

Do you like to stalk someone on social media?

Are you smart enough to solve 100 addition problems in 100 minutes?

Fun questions emoji

What is your most-used emoji?

If you could sit on a bench in the middle of a beautiful forest, who would you like to sit next to you and why?

What fruit would you be if you were a fruit?

When the doctor says, “You have 24 hours to live,” what will you do with the time you have left?

Have you ever taken anything out of your possession and failed to return it?

Do you ever believe in heroic deeds?

What is the highest degree of pain you’ve ever experienced on a scale of 1-10?

When you see a homeless person, what is your first thought?

Have you ever dropped something on the floor, then picked it up and ate it?

What is your favorite indoor activity?

What is your favorite outdoor activity?

Do you get bored easily?

If you could choose one imaginary friend, who is it going to be?

What age would you prefer if you could choose any age for the rest of your life, and why?

Where would you go if you could teleport yourself from one place to another?

Are you afraid of going near robots?

Which one do you like: foot massage or hand massage?

How many pizzas can you eat in a minute?

What is a popular food ingredient, spice, or herb that you dislike?

What are the things that take up too much of your time?

Did you ever think that clowns were creepy?

What would you do for an extra hour if you had 25 hours in a day?

Fun questions live for 100 years

Would you choose to live for another 100 years or start over from the beginning?

What do you want me to tell you?

What’s your favorite sandwich spread?

Are you more of a “fix it yourself” or “call an expert” kind of person?

What time do you usually sleep?

What time do you usually wake up?

How many pairs of shoes do you have?

Would you rather visit your ancestors in the past or meet your descendants in the future?

Do you think you would enjoy a love-hate relationship with someone?

Do you spend too much time playing games on your smartphone?

What three things would you want with you if you were stranded on a desert island?

Did you ever think you had superpowers as a child?

Would you spend a thousand dollars on food?

Which toy do you wish didn’t exist?

Which year would you visit if you could travel back in time 1,000 years?

What did you learn today?

What has been the longest time you had to wait for someone?

Fun questions season personality

What season best fits your personality?

What’s your opinion on garden gnomes or pink flamingos?

What would you teach every girl on the planet about men if you had the chance?

What has been the longest plane trip you’ve ever taken?

What vegetable would you be if you were a vegetable?

Would you like to tell me a story?

Do you want to change the world?

What’s a current habit that you want to quit?

Does Christmas mean something special to you?

What is your favorite Winter Olympics sport?

What has been the most severe weather you’ve ever experienced?

What habits are preventing you from achieving your goals?

How do your friends usually describe you?

When no one is around, what do you like to wear?

What did you buy recently?

Could you describe your favorite material object that you already have?

What kind of company would you start if I offered you $50,000 to start one?

What words of advice would you offer to your younger self?

For a day, would you rather be a hobbit or an elf?

Fun questions childhood snack

What was your favorite childhood snack?

What’s your favorite day of the week?

What’s your favorite month?

Who was your favorite classmate?

Do I look attractive to you?

Which of the continents have you already been to?

What style of design do you think is the perfect match for you when it comes to houses?

Have you ever walked out of the cinema without finishing the movie?

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