210+ Funny Questions to Ask to Break The Ice

It’s important to make genuine connections with others. However, if you’re never sure how to start a conversation, that’s okay! If you have some funny questions ready, then you’ll never feel awkward again. Here are some conversation starters you can use in any scenario:


Funny questions to ask at work

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Unsplash / Brooke Cagle

Funny conversations are a great way to break the ice with your coworkers. Here are some of the funniest questions you can ask the next time you’re in the office:

If you could level up in life just like in video games, where would you put your next skill point?

First, think of a product. Now, what would be the absolute worst brand name for one of those products?

What would the title of your autobiography be?

What would be your dream job?

What’s the weirdest fact you know?

What’s something you were really stressed about, it turned out to be no big deal?

What high-level job do you think you could lie your way into with no experience and no one would notice?

What’s something everyone should experience at least once in their life?

If time wasn’t an issue and you had forever to master a skill, what skill would you master?

What do you own that a lot of people comment on?

What’s your phone and/or computer wallpaper?

What are the unwritten rules of where you work?

What’s one small thing a person can do each day that greatly improves their life?

If you could add 4 hours to your day, what would you spend that 4 hours doing?

What really annoys you when other people do it, but you occasionally do it as well?

What movie really encapsulates the era it was made in?

Funny questions to ask a guy

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Unsplash / Vince Fleming

When you’re on a date, you don’t want to answer everyday questions. You want the conversation to be fresh and fun, which is why you should ask the following questions:

If it had to be something in this room, what would your zombie apocalypse weapon be?

If you could be a fictional character, who would you be?

Have you ever sent a text message to the wrong person?

What’s your perfect burger?

What’s the funniest pickup line you have either heard or used?

What are your best dad jokes?

What have you done wrong for most of your life and only recently found out the right way to do it?

How many phones have you broken or lost?

What was your best drop-the-mic moment?

What game do you always lose at?

Funny questions to ask your boyfriend

woman in black leather jacket and gray pants standing on green grass field during daytime
Unsplash / Becca Tapert

If you already know everything about your boyfriend, move onto some fun questions like these!

What do you judge people for that you probably shouldn’t?

If you were a ghost, who would you haunt?

What was the worst purchase you’ve ever made?

What double standard is ridiculous and needs to be ended?

What were you really into when you were younger but now think is silly?

What do you like to do that is traditionally considered feminine?

What small thing makes you angrier than it should?

What fictional character is portrayed as a hero but is actually more like a villain?

You’re held at gunpoint and are told that if you don’t impress them with your dance moves you will be killed. What dance moves would you bust out? 

What’s the best Wi-Fi name you’ve seen?

Funny questions to ask a girl

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Unsplash / Thought Catalog

If you want to win over a girl, make her laugh. You can strike up a funny conversation by using the questions below!

What’s the most awkward or embarrassing thing you’ve done for someone you loved?

What fashion trend do you regret?

What movie do you wish life was more like?

What could you give a thirty-minute impromptu lecture on?

Have you ever been sexually attracted to a cartoon character?

You’re given up to $300,000 to make one room in your house or apartment ridiculously amazing. What room do you pick and what upgrades do you make?

What do you pretend to hate but actually love?

What’s the best bad decision you’ve made?

What are some fun euphemisms for everyday activities?

What was a random compliment someone gave you that really stuck in your memory?

If you were given the ability to make one new trend that is instantly popular, what trend would you create?

Funny questions to ask your girlfriend

man kissing woman in grass area
Unsplash / Priscilla Du Preez

Here are some great date questions once you’ve already learned everything there is to know about each other!

What movie quote are you tired of hearing?

What’s the most imaginative insult you can come up with?

What’s your favorite board or card game? How about your least favorite?

What’s the worst and best thing about being female?

What fictional character is amazing in their book/show/movie. But they would be insufferable if you had to deal with them in mundane everyday situations? 

What childish thing do you still enjoy?

What is the most useless thing you know how to do?

If you could learn only one magic spell, but it could only do something mundane and boring, what would the spell do?

What movie completely changes its plot when you change one letter in the movie title?

Funny questions to ask your best friend

three women sitting wooden bench by the tulip flower field
Unsplash / Priscilla Du Preez

If you’ve run out of conversations to have with your best friend, ask them one of these hilarious questions below. They should lead to some fun conversations.

How many chickens would it take to kill an elephant?

What two totally normal things become really weird if you do them back to back?

Who are three people you want on your zombie apocalypse team and why?

You wake up suddenly in the middle of the night. What would be the scariest sound to hear after waking up?

What can a movie do to make you get up and walk out?

What was the weirdest habit you had as a child?

What movie can you watch over and over and never get tired of?

What ridiculous and untrue, yet slightly plausible, theories can you come up with for the cause of common ailments like headaches or cavities?

What’s your worst customer service story, either as the customer or as the employee?

What was your favorite cartoon when you were growing up?

Funny questions to ask a stranger

low-angle photography of two men playing beside two women
Unsplash / Felix Rostig

If you’re bored while at the store or in an elevator, try asking strangers these fun questions!

If you could have an unlimited storage space full of one thing, what would it be?

Have you ever seen anyone pull the “Do you know who I am?!”card?

Which fictional villain is your favorite?

Who was your first celebrity crush?

What would be the last movie you’d like to see before you die?

When was the last time you remember someone doing or saying something so stupid that you were sure it was a joke?

If you could go back in time and inspire someone to make a present-day invention, what invention would advance humanity the most?

What do you think is the most confusing idiom for people learning English?

What one thing would you most want to save if your house caught fire? Assuming that any people or animals made it out safely already.

What must be seen or experienced in person to really appreciate it?

Funny questions to ask kids

woman in brown coat carrying child in orange and white striped polo shirt
Unsplash / Joice Kelly

Here are some fun questions for young children. Make sure you ask them in a funny way to make them giggle!

What’s the weirdest thing you’ve ever eaten?

What video game do you wish life was more like?

What are you tired of hearing about?

What’s the stupidest way you’ve ever gotten hurt?

Would you rather have a third eye or a third arm?

When you are daydreaming, what do you dream about?

Is cereal soup?

What is your favorite animal sound?

What obscure website do you absolutely love?

If over time you replace parts on a car, at what point does it stop being the same car you bought?

What would the world be like if it was filled with male and female copies of you?

Questions to ask your siblings

two women smiling while standing near wall
Unsplash / NeONBRAND

They’ll love you forever if you ask them these fun questions!

What’s the best prank you can play on someone?

What secret conspiracy would you like to start?

What is the most irritating food?

What are some fun and interesting alternatives to war that countries could settle their differences with?

What random acts of extreme kindness have you seen or heard about?

If peanut butter wasn’t called peanut butter, what would it be called?

Who would you invite onto your talk show?

What’s the most ridiculous tattoo you’ve ever seen?

What do you collect?

What was fun to do once, but you’ll never do it again?

Funny questions to ask Siri

man and two women standing near linked-chain fence
Unsplash / Eliott Reyna

These questions are funny, but the answers you’ll receive from Siri are even funnier!

What does Siri mean?

Why do you vibrate?

Will you go on a date with me?

How old are you?

Do you have a significant other?

Are you intelligent?

Can you stop time?

What is your favorite animal?

What are you scared of?

Do you follow the three laws of robotics?

Are you a robot?

Can I kiss you?

Have you ever been in love?

What are you doing later?

What do you dream about?

Do you have any pets?

What’s your favorite color?

What are you made of?

Funny questions to ask your friends

smiling woman sitting on sunflower field
Unsplash / Brooke Cagle

If you want to be the funny guy (or girl) in your friend group, then you need to ask the right questions. Start with the ones below!

What part of a kid’s movie completely scarred you?

What are some websites you used to use all the time but have stopped using?

What’s the most unusual but fun experience you’ve had?

What would be the worst thing to have a phobia of?

If you could make everyone in the world believe one thing (regardless of whether it’s true or not), what thing would you choose?

Who would be the worst celebrity to have dinner with?

What are some boring games or sports, and how can they be livened up?

What are two things you’ll never spend money on?

What are you so incredibly terrible at, that you’ve given up ever doing it again?

What do you need to rant about or get off your chest?

Funny questions for making new friends

time-lapse photography of laughing woman with hair covering half of her face
Unsplash / Brittani Burns

If you want to make new friends, ask them these questions. A friendship will soon follow!

What was the most embarrassing moment of your life?

If you wanted to give a tourist the local flavor of where you are from, what would you have them do?

How do you feel about putting pineapple on pizza?

If you were arrested with no explanation, what would your friends and family assume you had done?

What is something that you just recently realized that you are embarrassed you didn’t realize earlier?

What stories from your life will you tell your children about (assuming you have children)?

What is the funniest joke you know by heart?

What’s the most embarrassing thing to ever happen to you?

What one question can you ask someone to find out the most about them?

What’s the most paranormal thing that has happened to you?

How much of a handyman are you?

Funny questions to ask your parents

woman in white tube dress sitting beside woman in brown dress
Unsplash / alex starnes

You don’t want to eat in silence. Here are some funny questions to ask at the dinner table:

What common ingredient or spice do you despise?

Would you volunteer to go colonize another planet if it meant you would never return to earth?

What’s currently legal but won’t be in ten or twenty years?

If you could pick up anyone musical instrument and instantly be a virtuoso at it, what instrument would you choose?

What would you like to be the best in the world at doing?

What movie would be better if the plot happened in reverse?

If you were an actor, what kind of roles do you think you would be good at?

What’s your best one-liner?

What’s the worst injury you’ve ever gotten?

What are some problems you realize are first-world problems but are annoyed by them anyway?

Funny questions to break the ice

woman standing in front of multicolored wall
Unsplash / Tyler Nix

It doesn’t have to be awkward to meet new people. Ask them some fun questions and you’ll become friends right away!

What would be the worst store to have a $1,000 gift card for?

What do people idealize, but really shouldn’t?

What language do you like the sound of, even though you don’t know how to speak it?

When was the last time that things got a little too real?

What’s your “back in my day, we…â€?

What’s worse than you thought it would be?

What’s the worst slip of the tongue you have heard about or that has happened to you?

Who’s famous for their talent, but really shouldn’t be?

What’s the best part of your day?

What’s your creative outlet?

Funny questions for any age group

man sitting beside two woman on gray surface
Unsplash / Omar Lopez

It’s not that hard to be funny. Rest assured, you don’t have to dance around to make others laugh. You simply need to ask the right questions!

What activity or hobby is so filled with hateful people that it puts you off trying it?

Who is the funniest actor or actress still doing movies, TV shows, or YouTube?

What’s something you’re surprised no one has figured out how to do yet?

What’s the strangest hobby you’ve heard of?

What do you wish you could tell your five-year-old self?

Have you ever accidentally been caught in your birthday suit?

Do you believe in ghosts and would you ever go ghost hunting?

What mythical creature would improve the world most if it existed?

What’s your definition of a good human being?

What’s the weirdest smell you have ever smelled?

What is the weirdest thing you have seen in someone else’s home?

You’re a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?

What would some fairy tales be like if they took place in the present and included modern technology and culture?

Can you please tell me about your best/worst school photo?

Funny questions for teens

woman standing at forest while smiling
Unsplash / Brooke Cagle

If you want to impress your cousins, students, or nieces and nephews, ask these questions to get them talking.

What inanimate object do you wish you could eliminate from existence?

What is your favorite holiday?

If you had to be stuck at one age forever, what age would you choose?

In one sentence, how would you sum up the internet?

If your five-year-old self suddenly found themselves inhabiting your current body, what would your five-year-old self do first?

What is the funniest name you have actually heard used in the real world?

Would you rather have noisy neighbors or nosy neighbors?

What was your favorite TV show growing up?

What’s the weirdest thing you’ve seen while driving?

What common piece of advice or words of wisdom don’t actually make much sense?

What social media post has really stuck with you?

Funny questions to ask yourself

smiling woman wearing brown coat
Unsplash / Å tefan Å tefanÄík

If you need a fun way to pass the time, ask yourself some questions.

What’s your best podcast recommendation?

What do you imagine the lives of super-rich people are like?

What type of grocery store shopper are you?

When was the last time a stranger made your day?

What’s the best $5 you’ve ever spent?

What was the last movie that made you cry?

How would you take down Kanye West’s ego?

What is society doing now that in 20 years will be laughed at and ridiculed?

What makes you special and unique?

If you designed and built a treehouse, what would it look like and what would be in it?

What would be the coolest animal to scale up to the size of a horse?

Funny questions that will make everyone laugh

women's white T-shirt
Unsplash / Brooke Cagle

Get the last laugh with these ice breakers:

What are some of your favorite movies from each genre?

What have you done a lot but are still incredibly bad at?

What celebrities are most likely to be jerks?

If you could run away from it all and start fresh somewhere new, would you?

What news headline would you most like to see?

What useless bits of information have you memorized and will probably never forget?

What’s something you boycott but don’t make a big deal of boycotting?

What body part would you like to add?

If you were given $20,000 to throw an amazing party, gathering, or event, what would that look like?

More funny questions

woman standing near brick wall
Unsplash / Parker Johnson

If you want some more funny questions, look no further. Here are a few more gems!

What fictional character did you have the hots for?

What are some small pleasures that make you way happier than they should?

What’s the most ridiculous fact you know?

What’s the biggest “scene”you’ve seen someone make in public?

Do you know all the words to every Imagine Dragons song?

What is the most boring sport?

When was the last time you felt completely out of the loop?

What’s your most common first thought when you wake up?

Who would you want to play you in a movie about your life?

If animals could talk, which would be the rudest?

Who would win in a fight between Superman and Batman?

If you could add one rule that everyone must follow when they use the internet, what would your rule be?

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