350+ Best Fun Questions to Ask Anyone [2020]

By January Nelson Updated November 30, 2020

Sometimes it can be really hard to get a conversation going with a person, especially if you’ve never met them before and don’t know them at all. You don’t want to step on any toes or cross any lines, but you still want to get past the surface level of who they are.

So whether it be a first date or the first day of school and you ask an ice breaker kind of question or you’re just having fun with your friends to get to know them better, here’s how you can get things a bit more fun:

Fun Questions To Ask Anyone

If a person you’ve met only once before asked you to pack a bag and go on a fun and spontaneous adventure, would you go?
What is your favorite way to watch a movie: in bed, on the couch, or in a movie theater?
Do you have any fast food horror stories?
If you owned a boat, would you name it or just refer to it as the boat?
Do you have any hidden talents?
Are you more productive in the morning or at night?
Is there a person you look up to?
Are you more of a leader or a follower?
Are you a Harry Potter fan or a Lord of the Rings fan?
What is your favorite board game?
Have you ever stayed awake for 24 hours?
What, would you say, is the worst thing about the state or country you live in?
Who is the kindest person you know?
What is the most fun you’ve ever had?
Do you believe in ghosts?
What is your favorite breakfast food?
Are you a morning person or a night owl?
What’s the last thing you were really excited about?
Are you superstitious?
What TV show could you watch over and over again without getting tired of it?
If you could make a rule that everyone on earth had to follow for one day, what would the rule be?
Who is your worst enemy and why?
What movie would be even better as a musical?
Have you ever set the kitchen on fire while cooking?
What is the weirdest fact you know off the top of your head?
What emojis do you use the most when you’re texting?
If you were cloned, would you be friends with your clone or hate it?
What conspiracies do you believe might actually be true?
Which movie villain do you think had a valid point?
What annoying habit do you think should be illegal?
What is the funniest Wi-Fi name you’ve seen?
What is your favorite mythical creature?
What is your favorite drinking game to play with friends?
In a zombie apocalypse, what would be your weapon of choice?
If there was a TV show made about you, what would the theme song be?
Would you rather live with a professional chef, makeup artist, or masseuse?
What celebrity shouldn’t be famous in your opinion?
Which historical figure would you like to have dinner with?
If you were invisible for an entire day, what would you do?
What television home would you love to live in yourself?
If you could add any sport (real or fake) to the Olympics, what would it be?
Who is the funniest person you’ve ever met in real life?
Which TV family is the most like your own family?
How would you describe your job in one word?
What food do you refuse to eat?
What movie do you quote the most often?
Have you ever been banned from a public place?
Have you ever been arrested?
Who is your favorite athlete? What is your favorite sports team?
What is the worst piece of advice you’ve ever been given?
What is the dumbest way you’ve ever injured yourself?
If you had to flee the country, where would you make your new home?
What is your funniest pet story?
Which one of the Seven Dwarfs describes you the best?
What was the most meaningful compliment you’ve been given?
What three words would your friends use to describe you?
When you were little, what did you think you’d be doing at this age?
If you were in charge of writing the fortunes in fortune cookies, what would you write?
If you were an animal, what type would you be?
If you could turn back time, what day would you relive?
How strict were your parents while growing up?
What is your biggest accomplishment in life so far?
Which one of your friends are you the proudest to know?
If you could ask your pet any question, what would it be?
What is the greatest invention of all time?
What is the scariest movie you’ve ever seen?
What is the kindest deed you’ve ever done?
What is your favorite holiday tradition?
If you could be anywhere in the world right now, where would you be?
What music are people surprised to learn you like?
What are your favorite podcasts?
What was the last show you binge-watched?
Are you a realist or a dreamer?
What song will instantly get you out on the dance floor?
What social media app do you use the most often?
What do you order when you visit Starbucks?
Are you usually freezing cold or burning hot?
If you won the lottery, what would you do with the winnings?
Do you think your younger self would be proud of you now?
What’s the riskiest chance you’ve ever taken?
Which family member do you feel the most comfortable talking to?
Which family member are you the most eager to impress?
What’s the stupidest lie you’ve ever told?
What’s the first story you usually tell when meeting someone new?
Would you rather have a job you love or a job that makes you millions?
What is your motto in life?
Do you believe in astrology? What’s your sign?
What is your most irrational fear?
What was the last thing you crossed off your bucket list?
What is still written on your bucket list?
What movie makes you laugh out loud whenever you watch it?
Where is the weirdest place you’ve ever fallen asleep?
When was the last time you laughed until your stomach hurt?
What is your most controversial pop culture opinion?
Do you stan any celebrities?
How would you prefer to die?
What’s the silliest argument you’ve ever gotten into?
If you could change anything about yourself, what would it be?
What are your hobbies?
What hobbies have you always wanted to take up?
Would it be harder for you to stop drinking coffee or alcohol?
What is your Hogwarts house?
What’s your favorite viral video?
Which characters do you identify with the most?
What is your comfort show that you watch when you’re feeling sad?
What song always makes you burst into tears?
What’s your favorite thing about where you work?
What is your go-to fast food order?
Would you want to know when you’re going to die?
What was your favorite age? Why?
If you had to wear the same outfit for the rest of your life, what would you choose?
What clothing fad do you wish would make a comeback?
What teacher influenced you the most?
What’s the last book you read from front to back?
What’s your most prized possession?

Fun Questions To Ask A Kid

Are you a teacher looking to have a fun conversation with your students? Or, rather, do you remember on the first day of school when the teacher would ask an ice breaker question and every kid would have to go around the room and give an answer? Like, tell me one interesting thing about you.

Well, if you’re looking for some entertainment, here are some fun questions to ask:

What is your favorite color and why is it your favorite?
What is your favorite smell?
What kind of candy do you choose when you go to the movies?
What is your favorite season and why?
What is your favorite food?
What song puts you in a good mood?
Is that your favorite song? If not, what is?
If you could have one superpower, which one would you choose, and why?
If you were at a bakery, what is something you would get: a cupcake, a slice of cake, a brownie, a cookie, or a slice of pie?
What is the name of your favorite movie?
What is your favorite thing to do on weekends?
When was the last time you drank a chocolate milkshake?
What is your favorite dance move?
Who is your favorite superhero?
Who is your favorite Disney princess?
Do you have a favorite toy? What is it?
Would you rather own a pet snake or a guinea pig? Why?
What do you want to be when you grow up?
What scares you the most?
If a genie granted you three wishes, what would they be?
What is your favorite chore?
Have you ever seen a ghost?
What is your favorite stuffed animal named?
If your pet could talk, what do you think they would say?
What’s your favorite thing to draw?
What do you usually dream about at night?
What is your favorite subject in school?
What is your favorite memory with your mother?
What is your favorite memory with your father?
Do you prefer breakfast, lunch, or dinner?
What is your favorite story to read before bed?
Do you have a nickname?
What is the funniest joke you can tell right now?
What was the last thing that made you laugh out loud?
What is your favorite thing to do with your friends?
What is your favorite card game?
What is your favorite video game?
Would you rather become a famous singer or actor?
What song can you sing all the words to?
What is your favorite day of the week?
What do you love the most about yourself?
What is your favorite wild animal?
What is your favorite bedtime snack?
What is your secret talent?
Who is your best friend in the world?
What is your favorite piece of clothing to wear?
What was the best birthday you’ve ever had?
What was the best vacation you’ve ever taken?
What type of books do you like to read? Adventure books or mysteries or romances?
Do you usually like the prince, the princess, or the villain?
What would you do if you had a million dollars?
What is the worst smell?
Do you eat the crusts on your sandwiches?
What is the greatest gift you’ve ever been given?
What’s your favorite activity on the playground?
What age do you wish you were?
What do you think the best thing about being an adult will be?
Do you prefer playing in the sand or the snow?
What is your favorite holiday?
Do you prefer puppies or kittens?
What is your favorite flavor of ice cream?
What does your ideal birthday cake look like?
If you could meet any celebrity, who would it be?
If you could enter your favorite cartoon, which would it be?
Who is your role model?
Would you rather eat a sweet, sour, or salty snack?
What is your favorite vegetable?
What is the grossest thing you’ve ever done?
What word do you find hilarious?
Have you ever eaten a worm or a bug?
Where is your secret hideout?
If you could change your name, what name would you choose?
If you could create a new color, what would you call it?
What country do you wish you could visit?
What is your favorite dinosaur?
What is your favorite planet?
What is your favorite accent?
What is your favorite thing about visiting your grandparents?
What is the silliest thing your parents do on a daily basis?
What was your most embarrassing moment?
Have you ever broken a bone?
What games do you play on the phone?
If you were a teacher, what would you teach?
Who is your favorite sibling or cousin?
Who is your favorite teacher?
What is your favorite room in the house?
Would you rather be a princess or a wizard?
What is your favorite thing about yourself?
If you were a superhero, what would be your weakness?
If you could only eat one thing for the rest of your life, what would it be?
Who would you team up with during a zombie apocalypse?
If you entered a singing contest, what song would you sing?
If you had the opportunity, would you want to visit the moon?
Who is your favorite person to play with at recess?
If you could talk to any animal, which would you choose?
What’s the grossest food you’ve ever eaten?
If you owned a restaurant, what would you serve customers?
If you wrote a book, what would you title it?
What inventions do you wish existed?
If you could time travel, when would you go?
If you could make a rule your parents had to follow, what would it be?
What is your favorite type of sandwich?
Would you rather be stuck in a desert or the ocean?
Do you believe in aliens?
What was the weirdest dream you’ve ever had?
What’s the funniest noise you can make?
Who is the most annoying Disney character?
If you could have any Pokemon, which would you choose?
If you could invent a new holiday, what would it be?
Do you have a crush on anyone?
What is your favorite color crayon to use?
Do you like morning or nighttime better?
What is your favorite thing to do on the computer?
What toppings do you put on your ice cream?
What do you love the most about your life?

Fun Questions To Ask The Person You Like

Let’s say you’re on a first date and want to get to know the person you’re sharing drinks or appetizers with. You’re probably thinking, how can I create a great conversation with this person? Well, what better conversation starter than to ask questions! Get to know their opinions and thoughts by asking random or interesting questions.

If you’re feeling stuck, here are some general and fun questions to ask the person you like and see how they answer:

What is your biggest pet peeve?
What is your favorite song and why is it your favorite?
Do you have an ideal date night idea?
What is the craziest thing you’ve ever done?
When it comes to movies or TV shows or musical artists, would you say you have a guilty pleasure?
What is your favorite pick up line?
Where is your favorite place in the world? Have you been there before or is it on your bucket list?
What is the funniest thing that has ever happened to you?
What is your favorite thing to do after a long day?
What was your worst job?
What was the last thing you said out loud?
Would you say you’re more of an introvert, extrovert, or ambivert?
What is the weirdest thing that has ever happened to you on a date?
Would you say that, for you, going skydiving would be fun or scary?
What is the hardest thing you’ve ever done?
What is your favorite type of music?
What would you say is a good question to ask someone if you want to really know their personality?
What is the most useful thing your parents or caregivers have taught you?
Would you say you’re a bookworm? If yes, what is the best book you’ve read? If no, why not?
What is a relationship dealbreaker?
How many kids do you think you’ll have when you get older?
What is the sexiest name in the world?
What is the least sexy name in the world?
Have you ever sexted the wrong person on accident?
Where is the strangest place you’ve gotten naked?
What’s the dumbest thing you’ve done to impress a crush?
Have you ever written a romantic poem or a song for someone?
What’s the best song to play while making love?
What is the weirdest thing that turns you on?
Did you ever have a crush on a cartoon character?
What was the worst date you’ve ever been on?
What dating app is your favorite? Why?
Have you ever read an erotic novel? Which one?
What is the first thing you notice about other people?
Which one of your physical features are you self-conscious about?
What do you get complimented on the most often?
Which celebrity do people tell you that you resemble?
What’s the longest you’ve gone without dating someone?
How long was your longest relationship?
Do you prefer making love in the mornings or at night?
At what age can you imagine getting married?
Do you want a small wedding or a big, elaborate wedding?
What is your love language?
What’s your favorite sleeping position?
What do you consider the perfect date?
Are you a forgiving person? Do you believe in second chances?
Are you friends with any of your exes?
Would you rather stay at home or go out on the town over the weekend?
What makes you feel the most loved?
What’s your favorite romantic gesture from a TV show or film?
Do you have a close relationship with your parents?
What was the silliest reason you’ve ever lost interest in a person?
Do you believe in love at first sight?
What is your worst relationship habit?
At what age did you have your first kiss?
Who is your favorite celebrity couple?
What TV couple is your idea of relationship goals?
What’s your favorite breakup song?
Which celebrity do you consider a sex symbol?
What’s your favorite meal to cook for two?
What is more important to you: honesty or attractiveness?
Do you sleep naked? If not, what do you wear?
Do you think tattoos are attractive? What about piercings?
Do you like to be the big spoon or the little spoon when cuddling?
When do you think it’s okay to lie to your significant other?
Are you a private person or do you enjoy PDA?
Have you ever had a naughty dream?
How long do you believe foreplay should last?
What is your favorite part about being single?
What qualities do you value the most in a partner?
Have you ever gone skinny dipping?
What’s your favorite type of exercise?
What’s your favorite body part to stare at?
Would you rather go on a date to the movies or an arcade?
Where is the craziest place you’ve made love?
Do you prefer to make the first move or get chased?
Where is your favorite makeout spot?
What love song do you consider overrated?
What traditions do you want to pass down to your children?
Do you prefer good morning texts or goodnight texts?
What piece of clothing do you find the most attractive?
What’s the most risque photo you have on your phone?
Which emoji is the flirtiest, in your opinion?
Do you prefer indoor dates or outdoor dates?
What advice would you give your heartbroken, teenage self?
Have you ever been the third wheel?
Have you ever dumped someone over text?
What accent do you think sounds the sexiest?
Do you believe in soulmates?
If you were going to make a romantic dinner, what would you cook?
What is the most romantic movie you’ve ever watched?
What do you think about before you fall asleep at night?
Have you ever been in a long-distance relationship?
What has your parents’ relationship taught you about love?
Do you have any embarrassing stories about getting rejected?
Would you rather find the love of your life or become a millionaire?
What is your tell when you like someone?
What is the craziest thing you’ve ever done for love?
What is the dirtiest joke you know?
What food do you consider the most sensual?
Where is your ideal honeymoon destination?
What couple song is perfect for karaoke?
How would your exes describe you?
How many pillows do you need to fall asleep?
Which romantic comedy do you consider completely unrealistic?
Have you ever been in a love triangle?
What is your favorite account on social media?
What’s your favorite thing about being in a committed relationship?
Do you fall in love easily?
What side of the bed do you sleep on?
Who was your first crush when you were a little kid?
Do you wear your heart on your sleeve or bottle up your emotions?
What cologne/perfume do you wear on first dates?
Do you consider yourself attractive?
Do you have a type?

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A psychologist conducted a study on intimacy and if there are certain questions that can create a deeper connection and interesting conversation with someone you’re in a relationship with. So if you want to dive in more and ask the deep questions, here are some ideas, inspired by the 36 Questions That Lead To Love:

What is your favorite memory?
If you could meet and have dinner with one celebrity, dead or alive, who would it be and why?
If you could ask one random question to that celebrity, what would it be?
If you could time travel, would you go to the past, or to the future?
What is the best piece of advice you’ve ever received from someone?
Would you want to be famous?
What do you value the most in a friendship?
Do you have any regrets?
Do you believe in love?
If you found out you had one week left to live, how would you spend your time?