260+ Humorous Icebreakers to Ask for Some Chuckles

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Plus, how asking questions and staying curious fosters intimacy

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Last Updated: December 18, 2025

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• For Friends & Family
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• For Dates
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• For Students
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• For Coworkers
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• Deep
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• To Spark Funny Stories
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• 21 Questions
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• "What If" Questions
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• Random
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• Why ask questions?

|Show more |Show less

Asking questions is one of the best ways to learn more about someone else—but so is sharing a laugh! That's why we've compiled more than 260 of our favorite silly icebreaker questions to ask friends, coworkers, first dates, and anyone else you'd like to get to know a little bit better. Plus, stick around for a deep dive into how asking questions can foster connections, and why staying curious is such a crucial part of developing intimacy with other people.

Hysterical Get-to-Know-You Questions

• If you were to be banned from your local library, what would be the reason?
• Can you eat ice cream using your bare hands?
• What’s your favorite piece of random trivia?
• What does the word “OK” mean to you?
• What’s the most creative insult you can think of?

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Section 1 of 10:

Funny Get-to-Know-You Questions for Friends & Family

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1. 
   Learn even more about your loved ones with these goofy questions. Laughing together is a good way to feel more connected with people, and it also boosts your mood! Whether you're hanging with your siblings or an acquaintance you've only recently met, these funny questions are sure to get the giggles going while helping you learn something new (and maybe even surprising) about them.

   • What’s the funniest thing you’ve been caught muttering to yourself?
   • Would you rather always walk backward or talk backward?
   • If you were a noodle, what would you be?
   • What’s the weirdest thing you’ve ever Googled?
   • Would you rather burp glitter or fart confetti?
   • What is the best Wi-Fi name you have seen in your entire life?
   • How long do you think you’d survive in a zombie apocalypse?
   • What is your favorite smell?
   • How do you hang toilet paper: over or under?
   • Which celebrity friendship do you want to embody in our friendship?
   • Have you ever gone a day without wearing underwear?
   • What is it that you keep wanting to smell even though it doesn’t smell particularly good?
   • If you had to marry a cartoon character, who would it be?
   • What’s something that brings you joy that others might not understand?
   • What’s the oddest combination of food you secretly love?
   • Is pizza just an open-faced sandwich?
   • What movie’s plot changes entirely only by changing one letter in the title?
   • What’s the weirdest dream you’ve ever had?
   • What is your favorite song by your least favorite artists?
   • If you could go pro playing one classic board game, what game would it be?
   • What if your favorite childhood toy came to life?
   • Would you rather release a fart that's loud and proud but doesn't smell, or silent but deadly?
   • If you could instantly learn the answer to one mystery or question about the universe, what would it be?
   • If you could master any skill instantly, which one would you choose and why?
   • What’s your least favorite planet?
   • If you were a ghost, who would you haunt and why?
   • If you could swap lives with a celebrity for a day, who would it be, and what would you do?
   • Have you slept in until four in the afternoon or later?
   • If you were a kitchen appliance, what would you be and why?
   • What would your stage name be if you were famous?
   • What’s the most useless thing you know how to do?
   • Have you ever stolen anything from a hotel room?
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Section 2 of 10:

Funny Get-to-Know-You Questions for Dates

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1. Spark conversation on a first date with these silly icebreakers. Getting to know someone you've just started going out with can feel awkward, but some casual jokes and funny questions can ease the tension a bit. These icebreakers will help you wow your date with your sense of humor while also alleviating any first-date jitters you both might be experiencing:

   • What are three items you might purchase at the grocery store to get strange looks from the cashier?
   • Have you ever made a prank call to someone you don’t know?
   • What’s one thing your dogs could say that would completely ruin your image if they could talk?
   • Who was your first-ever crush?
   • If you were to be banned from your local library, what would be the reason?
   • What’s the most hilarious fact you know?
   • Can you eat ice cream using your bare hands?
   • What’s the most creative insult you can think of?
   • What do you think is the worst thing that a person can put in their bio for a dating app?
   • Have you ever fallen off your bike in front of a huge crowd?
   • Have you ever fallen asleep during class?
   • If you could remove one color in the whole world, what would it be and why?
   • What’s the most embarrassing moment in your entire childhood?
   • Which species would be the rudest if all animals could talk?
   • Do mermaids give birth to live babies or lay eggs?
   • Do you still sleep with a stuffed toy?
   • What does the word “OK” mean to you?
   • Which person do you know who totally reminds you of a character in a TV show or movie?
   • What’s the craziest thing you’ve ever done after getting really drunk?
   • Who is the first person on your hit list?
   • Do you sleep with the lights on or off?
   • What is the weirdest food combination people eat that you just can’t get behind?
   • What's a weird food combination you eat that other people just don't understand?
   • How do you react when you find something intriguing?
   • What is the silliest thing you’ve ever seen a stranger do in public?
   • Do you prefer plastic Easter eggs or real hard-boiled eggs?
   • If you could ask me a funny question, what would it be?

Section 3 of 10:

Funny Get-to-Know-You Questions for Students

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1. 
   Start the first day of school off right with these icebreakers for students. Whether you're a teacher who wants to help your students bond or you're a student who's eager to get to know your new classmates, these questions will help break the ice:

   • If you could hang out with any cartoon character, who would you choose and why?
   • If you could add a word to the dictionary, what would you add and what would it mean?
   • If you could meet any living person for dinner, who would you pick and why?
   • If you could make a funny rule that every teacher had to follow, what would it be? How about students?
   • What is your favorite candy or treat?
   • What is your favorite breakfast? Lunch? Dinner?
   • What would your pet name you if it could?
   • What is something you can’t cook?
   • If you could host your own game show or TV competition, what would it be? Who would compete?
   • Would you rather be 12 inches or 12 feet tall?
   • What’s the funniest school uniform you can think of?
   • What would your own language sound like?
   • What's your best celebrity impression?
   • What is your theme song?
   • Would you rather have two noses or three eyes?
   • Would you rather have lobster claws for hands or squid tentacles for legs?
   • If you could eliminate one food so no one could eat it ever again, what would you destroy?
   • What is the weirdest sound you’ve ever heard?
   • Would you rather have to dance like a robot or like a jellyfish?
   • Would you rather burp bubbles or sneeze mouthwash?
   • What is your most used emoji?
   • Have you ever had a teacher call you in class when you had no idea what was going on?
   • If you could give one piece of advice to everyone in the world, what would it be?
   • Would you rather only be able to walk backwards or by taking as large steps as possible?
   • Would you rather move like a kangaroo or a crab?
   • If you could rename any animal, what would you call it?
   • What is the silliest new holiday you can think of? How would you celebrate it?
   • What’s an Olympic sport that doesn’t exist, but should?
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Section 4 of 10:

Funny Get-to-Know-You Questions for Work

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1. Try these office-appropriate questions to get to know your colleagues. Break these questions out on the next team-building day to get to know your coworkers and employees. They're fun, funny, and totally SFW (safe for work)!

   • What do you think is the grossest food in the world?
   • What is your most used emoji?
   • What is the funniest name you have ever heard in real life?
   • Who was your childhood actor/actress crush?
   • What are the unwritten laws at our workplace?
   • What is one article of clothing that someone could wear that would make you walk out on a date with them?
   • If you had played hooky today, what would you be doing right now?
   • What was your first-ever screen name?
   • What’s the most embarrassing fashion trend you used to rock?
   • What was the worst style choice you ever made?
   • What if you could switch lives with any animal for a day—which animal would you choose?
   • Would you rather sweat honey or always smell like cabbage?
   • If you were a wrestler, what would be your entrance theme song?
   • Have you ever been told you look like someone famous? Who was it?
   • If you had to eat one meal every day for the rest of your life, what would it be?
   • If you could bring back any fashion trend, what would it be?
   • If aliens landed on Earth tomorrow and offered to take you home with them, would you go?
   • Does your current car have a name? What is it?
   • If a movie were made of your life, what genre would it be? Who would play you?
   • What did you name your first car?
   • Would you rather always have Cheeto dust on your hands or always have jelly on your feet?

Section 5 of 10:

Funny but Deep Get-to-Know-You Questions

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1. 
   There's no reason a silly question can't also be meaningful! The goal behind asking a funny question isn't just to share a laugh (though that's important); it's to learn more about the other person. And these goofy but deep and juicy icebreakers will probably teach you something you didn't know about the other person:

   • Do you think aliens really exist?
   • If you were famous, what would you be famous for?
   • What’s the very first memory you think of when you think about fun childhood memories?
   • What's the strangest dream you've ever had?
   • How would you show that you were from the future if you were transported 200 years into the past with no clothing or anything else?
   • What things are okay to do occasionally but definitely not okay to do every day?
   • What's the most unusual talent you have?
   • What do you think your last words will be?
   • If you can still remember, what are your funniest childhood memories?
   • What was the first job you ever wanted to have as a kid?
   • What’s your most irrational fear?
   • The zombie apocalypse is coming—who are 3 people you want on your team?
   • What’s the worst thing you’ve done to get out of trouble?
   • What do you typically do when you’re bored?
   • How would you sum up the internet in two sentences?
   • Do you have an imaginary friend?
   • What’s a belief you held as a child that has significantly changed over time?
   • As a child, what was your favorite game to play?
   • What’s one thing you wish we knew five years ago?
   • What was your first-ever concert?
   • What would you do if you could become invisible for a day?
   • If you could design your own afterlife, what would it be like?
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Section 6 of 10:

Get-to-Know-You Questions to Spark Funny Stories

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1. These questions are designed to let them entertain you. Some charming and hilarious questions will get you both laughing, but these provocative questions—from "What's the most embarrassing thing that's ever happened to you?" to "If you had a baby with your most shameful 'hear me out,' what would the baby be like?"—are designed to get them to share a silly, creative, or downright weird response of their own:

   • What's the most embarrassing thing that's ever happened to you?
   • If you had a baby with your most embarrassing "hear me out," what would the baby be like?
   • Can you tell me the most hilarious joke you’ve ever heard?
   • What’s the most ridiculous conspiracy theory you kind of believe?
   • What is the most useless skill you possess?
   • How would you pull off a perfect crime?
   • Have you ever driven someone else’s car without first getting permission?
   • What’s the strangest thing you’ve ever seen someone do in public?
   • Have your parents ever found you trying to leave the house without permission?
   • Have you ever been forced to spend a day with a person you didn’t like?
   • What’s the best inside joke you’ve ever heard?
   • Have you ever peed in a pool?
   • What would you do with the money if you won a lottery?
   • What law would you introduce if you had the chance to make one?
   • Have you ever lied about your age in order to gain access to a bar or nightclub?
   • Have you ever met your doppelgänger?
   • What excuse have you recently used to avoid doing something?
   • If you could ask the president one super silly question, what would you like to ask?
   • Has anything weird or unexplained happened to you?
   • What has been the funniest or strangest thing that has happened to you on a first date?
   • What's the funniest thing you believed as a child?
   • You’re writing your will. What are you leaving, to whom?
   • What's the worst job you ever had?
   • What's the best prank you've ever played on someone?
   • If I were to summon you using black magic, what five items would I need at each corner of the pentagram?
   • If you could be a fly on the wall, where would you land?
   • What's the weirdest gift you've ever received?
   • What are the things you would like to change if you became God for a day?
   • What's a beloved, unusual tradition in your family?
   • What's the most ridiculous thing you've ever bought?
   • Have you ever screwed things up really badly, but nobody noticed? What happened?
   • What would be the outcome if the government decided to make everything illegal?
   • Have you ever lied to your parents about the thing you accidentally broke?
   • What will people be nostalgic for in 500 years?
   • What's the worst first date you ever went on?
   • If extra lives were actually a thing in the real world, how would you be able to get them?
   • What has been the strangest thing a visitor has done at your home?

Section 7 of 10:

21 Questions to Get to Know Someone

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1. 
   Dating coach Imad Jbara likes 21 Questions to get to know someone. "21 Questions [is] like a secret," he says. "I'm telling you, it works like magic." He appreciates this get-to-know-you game because asking open-ended questions is a great way to "[develop] a level of intimacy…[and] figure out more about them. And in learning more about them, you feel deeper and closer."

   • What’s your favorite piece of random trivia? You can only choose one.
   • What character do you love to play as in Mario Kart?
   • If you could have any fictional character's wardrobe, whose would it be?
   • What's your favorite conspiracy theory?
   • What's the most bizarre coincidence that's ever happened to you?
   • Which app on your phone do you use the most?
   • What was the worst haircut you ever had?
   • What's your favorite type of movie snack?
   • What's your favorite thing about your hometown?
   • Have you ever laughed so much that something you were drinking came out of your nose?
   • Have you ever attended a dance by yourself because you couldn’t find someone to accompany you?
   • What’s the funniest book you’ve read?
   • What’s your secret talent?
   • What’s the most random thing you’ve ever bought online?
   • If you could be a part of a family on any TV show, which family would you choose?
   • What’s an unpopular opinion you have that you actually feel really strongly about?
   • Do you have a favorite podcast?
   • When you're done shopping, do you leave the cart in the parking lot or take it back to the store?
   • What word would you add to the dictionary, and what would its definition be?
   • If you could become any mythical creature for a day, what would it be and why?
   • What’s the last thing on your phone that you took a screenshot of?
   • If you could live in any house from a TV show or movie, which one would you choose?
   • What's your favorite song to sing in the shower?
   • If you could travel to any time period in a time machine, when would you choose and why?
   • Have you ever come into contact with human remains?
   • What's the worst lie you ever told as a kid?
   • If you could see one event in the future, what would you want to witness?
   • What are the two totally normal things that become really weird if you do them back-to-back?
   • What’s your favorite urban legend?
   • What's the worst advice you ever received? Did you follow it?
   • If you could invent any gadget, what would it do?
   • If you could have dinner with a famous person (living or dead), who would you choose?
   • What's your favorite movie to watch over and over again?
   • If you were an ice cream flavor, what would it be?
   • You’re the lead character in a video game. What game is it? (You can make one up.)
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Section 8 of 10:

Funny "What If" Get-to-Know-You Questions

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1. Ask silly hypotheticals to make them laugh (and think)! A question like, "What if this date went reeeeally well, and then you learned I was secretly a robot? Would you break it off?" is sure to get them thinking and giggling. Keep the fun going with these other "What if?" icebreakers:

   • What if you were a dog? What dog breed would you be?
   • What if animals could talk? Which species would be the sassiest?
   • If you were not you, who would you want to be?
   • What if you could really sell your soul to the devil? What would you sell your soul for?
   • How many ants would it take to lift an elephant?
   • What if you could only communicate using movie quotes?
   • What if you picked up a book and started reading, only to realize it was the story of your life? Would you turn the page, knowing that you won’t be able to change the events that will unfold?
   • What if you had the power to make any food healthy without changing its taste—what would you eat all the time?
   • What if you woke up and discovered you were invisible? What would you do first?
   • What if you had to live in a video game for a week, which would you choose?
   • What if you could taste colors? What would blue taste like?
   • If you could only communicate using one meme, which one would it be?
   • If you could live forever on earth as it is now, would you? Why or why not?
   • What animal would be much better if it were covered in scales?
   • What if every time you sneezed, you changed color?
   • Would you rather forget who everyone else is or who you are?
   • What would you do or say if you had the attention of the whole world for twenty seconds?
   • If you were a child’s toy, what toy would you be and why?
   • What if you could read minds—whose mind would you want to read first and why?
   • What if you could have dinner with any fictional villain—who would you choose and what would you talk about?
   • What if you could swap places with a cartoon character for a week—who would it be and what would you do?
   • If you were given the chance to have a controller that has the power to rewind or fast forward, which one would you press?
   • What if you could live in any city in the world without worrying about money—where would you live?
   • What if you could teleport anywhere instantly—where’s the first place you’d go?
   • What if you were given the power to change one law—what law would you change?
   • What if you could visit any planet in the solar system—where would you go and why?
   • What if you could talk to one species of animal—what animal would you choose and what would you ask them?
   • What if you could erase one person from history—who would it be and why?
   • What if you could start a secret society? What would be the mission, and who would be the members?
   • What if there are no consequences for every bad behavior? What would you do first?
   • What if you could start a new career instantly with no training—what would you choose to do?
   • What if you could never fail at anything—what would you try to accomplish first?
   • What if we got along reeeeally well, and then you learned I was secretly a robot? Would you still want to be friends/go out?
   • If you were abducted by aliens and then let go again, would you tell anybody? Why or why not?
   • Want more funny "What if?" questions? Check out "180 Funny & Interesting Hypothetical Questions to Ask Anyone"!

Section 9 of 10:

Funny Random Get-to-Know-You Questions

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1. These icebreakers are off-the-wall weird. Ask an unexpected question to tickle the other person and force them to reflect on their answer. These questions aren't just random and weird; they're also downright goofy!

   • If you had to live in one TV show forever, which one would it be?
   • Would you rather have a tail or a third eye?
   • Would you rather have a rewind button or a pause button for your life?
   • If you were a flavor, which one would you be?
   • If an alien landed on Earth, what is the weirdest thing they would see?
   • Have you ever been called out at school for wearing something embarrassing?
   • What’s the most random thing in your wallet or handbag right now?
   • What do you think the first person to milk a cow was actually trying to do?
   • In all honesty, what are some of your guilty pleasures that you are willing to admit?
   • What’s the weirdest thing you’ve given someone as a gift?
   • Have you ever offered to help anyone else with their homework in return for something specific?
   • What do you think would be the worst “buy one, get one free” sale of all time?
   • What would you do if you could replace all of the grass on the planet with something else, and why?
   • Would you rather be forced to wear shoes every second of your life or never be able to wear shoes again?
   • Who would you appoint as the president of the Internet, and why?
   • Who do you wish you could torture for the rest of your life?
   • What musical instrument has the most annoying sound to you?
   • What kind of stuffed animal did you have when you were little?
   • How often do you doodle?
   • If animals could talk, which one do you think would be the rudest?
   • If you could swap voices with any celebrity, who would it be?
   • If you could only eat one color of food for the rest of your life, what color would it be?
   • Would you rather always be 10 minutes late or 20 minutes early?
   • What color would you try if you had to eat a crayon straight from the box?
   • Do you put salt on your cantaloupe?
   • If you could be any inanimate object for a day, what would it be?
   • What would your last words be if this were your last day on earth?
   • Would you rather hiccup nonstop or sneeze nonstop for a day?
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Section 10 of 10:

Why ask questions?

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1. 
   1
   It teaches you more about another person. This might seem obvious, but when you ask questions, typically, you get answers. And when you ask good questions, you often get really interesting answers. Basically, stay curious! Remember, not everyone will come out and tell you things unless you ask. So ask.
2. 2
   It shows people you care about them. Asking thoughtful questions and listening attentively to the answer lets people know you're interested in who they are and invested in your relationship. Show the people you care about that you care about them by asking insightful and probing questions about their life, their day, and their dreams—but also inject some levity into the convo by asking an occasional silly question like, "If you could only eat one food for the rest of your life, what would it be?"
3. 
   3
   It helps you and another person feel closer. Jbara posits that one big reason first dates are so awkward is "people don't feel safe [at] the beginning because they feel like [their date] doesn't know enough about them. But when you actually start getting to know them, and you're listening and being attentive, they feel safer and closer to you."

   • But developing intimacy isn't just for couples—it's a good way to foster closeness with your best buds, family, and coworkers, too!
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