205+ Silly “This or That” Questions for Friends, Coworkers & More

Trying to break the ice and spark a silly conversation? Asking “this or that” questions is one of the best ways to build closer bonds, whether you’re playing with kids, teens, or adults. In this article, we’re providing the ultimate list of funny “this or that” questions to alleviate awkwardness and deepen your connections. Keep reading for funny questions for work, school, and more!

Hilarious “This or That” Questions

Talking pets or talking babies?
Burp butterflies or fart glitter?
Speeding ticket or parking ticket?
Loud neighbors or nosy neighbors?
Hair in the drain or crumbs in the bed?
Talk like Yoda or breathe like Darth Vader?
Be irrationally afraid of cars or digital screens?

Section 1 of 9:

Funny “This or That” Questions for Adults

Ask silly “this or that” questions to make adults laugh out loud. Invite the other players to take a closer look at the world around them with these goofy, random, and embarrassing Qs. They’re sure to get the giggles going and spark a lively discussion!
- Mullet or bowl cut?
- Kiss a frog or lick a slug?
- Fight a kangaroo or a goat?
- Talking pets or talking babies?
- Speeding ticket or parking ticket?
- Always too hot or always too cold?
- Loud neighbors or nosy neighbors?
- Permanent unibrow or no eyebrows at all?
- Live in a house of straw or a house of sticks?
- Be irrationally afraid of cars or digital screens?
- Airport three hours early or running to the gate?
- An abnormally big toe or an abnormally big ear?
- Accidentally send a sext to your dad or your boss?
- Always be followed by a mariachi band or a mime?
- Vomit on your hero or have your hero vomit on you?
- Cheeto dust all over your fingers or all over your toes?
- Tiny feet and huge hands or huge feet and tiny hands?
- Dress like a person from 100 years ago or talk like one?
- Not shower for a week or not brush your teeth for a week?
- Clog the toilet on a first date or your first day at a new job?
- Have your middle school photos or your search history leaked?
- Say your ex’s name during sex or your partner’s best friend's name?
- Get completely drunk after a single drink or never be able to get drunk?
- Ride an elephant to the grocery store or be pulled in a two-horse chariot?
- Wear pajamas to your wedding or formalwear on a first date to a coffee shop?
- Date someone who talks in their sleep or someone who snores like a chainsaw?
- Be stuck in an elevator with your ex and their new partner or with your current partner and their ex?

Section 2 of 9:

Funny “This or That” Questions for Kids

Come up with funny and playful questions to have kids thinking. Whether you’re a kid playing with your friends or an adult trying to connect with your child, asking “this or that” questions is a great way to stimulate imagination, enhance decision-making, and encourage self-expression. Here are some funny questions to help kids voice their opinions and feelings:
- Pet llama or pet penguin?
- Funny faces or silly noises?
- Burp butterflies or fart glitter?
- Hamburger hat or hot dog shoes?
- Toes for fingers or fingers for toes?
- Own a flying horse or a talking pig?
- Invisible cats or glow-in-the-dark dogs?
- Have a rabbit’s ears or a monkey’s tail?
- Jump into a pit of slime or a pit of mud?
- Talk like Yoda or breathe like Darth Vader?
- Line-dancing bears or breakdancing gorillas?
- Spaghetti for hair or marshmallows for teeth?
- Ham for hands or armpits that dispense lotion?
- Lick the bottom of your shoe or eat your boogers?
- Fight 1 horse-sized duck or 100 duck-sized horses?
- Skip everywhere you go or sing everything you say?
- Walk on all fours forever or walk sideways like a crab?
- Have a baseball as a head or a watermelon as a head?
- Ride a magical flying carpet or be the magical flying carpet?
- Always sing instead of speaking or dance everywhere you go?
- Have to high-five everyone you meet or hug everyone you see?
- Have a pet dragon the size of a cat or a cat the size of a dragon?
- Have a nose the size of Pinocchio’s or ears as large as Dumbo’s?
- Wear clothes that are too big for you all the time or too small for you?
- Drink everything with your ears or eat everything with your belly button?
- Transform into a puppy every time you eat something or turn into a cat every time you drink something?

Section 3 of 9:

Funny “This or That” Questions for Teens

Drop funny and juicy questions to deepen your friendship. If you’re playing with new friends or people who don’t know each other well, start with funny “this or that” questions that aren’t too revealing. This allows them to loosen up so everyone has a good time, and you can always move on to “juicier” questions after people feel more comfortable. Some topics you can ask about include their personality, hobbies, interests, and tastes:
- Date a clown or a mime?
- Bad breath or body odor?
- Dad jokes or toilet humor?
- Battle zombies or vampires?
- Bad haircut or bad hair dye?
- Hair for teeth or teeth for hair?
- Be bald or have no eyebrows?
- Room full of spiders or snakes?
- Sneeze glitter or cry hot sauce?
- Be 3 feet shorter or 3 feet taller?
- Mistaken lyrics or misquoted movies?
- Sound like a Minion or dress like one?
- Cuddle a crocodile or kiss a snapping turtle?
- Fart every time you laugh or burp every time you cry?
- Stuck in an elevator with 5 monkeys or with 20 people?
- Only be able to text in emojis or only be able to text in acronyms?
- Spend the day jumping like a kangaroo or waddling like a penguin?
- Sweat sticky lemonade or have your breath always smell like garlic?
- Wear the same socks for a month or the same underwear for a year?
- Accidentally liking your crush’s selfie or wearing a Viking helmet for a week?
- Only listen to music you hate or only listen to music that everyone else hates?
- Always have your shoes untied or always have toilet paper stuck to your shoe?
- Fight prime Mike Tyson for one round or sound like him for the rest of your life?
- Have a permanent duck face in all photos or only be able to type with one finger?
- Forever have a string of snot hanging out of your nostril or always sneeze out a booger?
- Talk like Mickey Mouse when you’re angry or turn into Shrek when you’re embarrassed?

Section 4 of 9:

Funny “This or That” Questions for Students

Bring up funny and relatable scenarios to connect with students. It’s no secret that most students aren’t fans of homework, lectures, or waking up early. So, tap into these topics for a funny round of “this or that.” Here are some hilarious situations that students can relate to:
- Have an elephant or a rhino for a teacher?
- Be able to lift an elephant or outrun a cheetah?
- Be project partners with a dinosaur or a whale?
- Ride a unicycle or a giant inflatable duck to school?
- Gum stuck in your hair or inside both of your shoes?
- Have porcupine needles or shed your skin like a snake?
- Live with one human-size puppy or one mouse-size gorilla?
- Trip in front of your crush or trip in front of your entire class?
- Have detention for a year or get a month of extra homework?
- Have a permanent wedgie or wear a clown nose for a month?
- Sing everything you say in class or only be able to talk in rhymes?
- Have detention for a week or have extra math homework for a week?
- Oversleep every day for a week or not get any sleep at all for 4 days?
- Eat cafeteria food for every meal or never eat your favorite food again?
- Wear a stinky pair of shoes or a stinky pair of socks to school every day?
- Never have to go to school or never have to do chores for the rest of your life?
- Have a teacher who yells at the class or one who whispers everything they say?
- Carry a monkey around all day at school or have a group of raccoons follow you?
- Locked in a classroom that’s overly bright or a classroom that’s totally dark for a week?
- Get a paper cut every time you’re late to class or bite your tongue every time you turn a page?
- Have a locker that opens by making an animal noise or a combination lock that changes every day?
- Have a single pair of eyes on the back of your head or a pair of eyes on each side of your head?

Section 5 of 9:

Funny “This or That” Questions for Couples

Keep the romance alive with these funny and flirty questions. Trying to lighten the mood and connect with your partner on a deeper level? Ask these silly questions to learn more about their preferences, build intimacy, and strengthen your bond as a couple:
- No kids or 10 kids?
- Financial issues or sexual issues?
- Laundry or dishwashing duty forever?
- Hair in the drain or crumbs in the bed?
- Kiss Stewie Griffin or Homer Simpson?
- Live in a board game or live in a puzzle?
- Get matching pajamas or matching tattoos?
- Be in a throuple with a McLovin’ or Michael Scott?
- Have your first child when you’re 18 or 50 years old?
- Fart every time you kiss or sneeze every time you orgasm?
- Matching couple outfits every day or never wear color again?
- Instagram Live all our arguments or never use the Internet again?
- Sing karaoke to me every morning or dance for me every evening?
- Nonstop talking through a movie or pausing to analyze every scene?
- Only kiss with your eyes open or only talk in baby voices for a week?
- Stuck in a theme park for 24 hours or on a plane for 12 hours together?
- Sharing a toothbrush or wearing matching “I’m with them” shirts in public?
- Loudly argue in a restaurant or make out obnoxiously in the checkout line?
- Handcuffed together for 48 hours or swap phones (unlocked) for 48 hours?
- Walk in on your parents having sex or have them walk in on you having sex?
- Only be able to communicate through interpretive dance or only through opera?
- Get caught in an embarrassing situation together or only have it happen to one of us?

Section 6 of 9:

Funny “This or That Questions” for Work

Bond with your colleagues by asking “this or that” questions. If you don’t know your coworkers well, team meetings and projects can be super awkward. However, playing a team-bonding game like “this or that” is the perfect way to ease tension, get acquainted, and spark a lively discussion. Here are some funny and lighthearted questions to help you build good relationships at work:
- Tidy or messy desk?
- Public speaking or skydiving?
- Working hard or hardly working?
- No air conditioning or no heating in the office?
- Always be 30 minutes early or 30 minutes late?
- Have a permanent frown or a permanent smile?
- Always shout or always whisper when you speak?
- Enter the wrong restroom or fart during a meeting?
- Have a constant hiccup or an uncontrollable laugh?
- Get caught picking your nose or scratching your butt?
- Have grandma’s hair or wear grandpa’s clothes all year?
- Always enter a room backward or always cartwheel out of it?
- Dress like a clown or an astronaut to the office for one week?
- Hop like a frog everywhere or slither like a snake everywhere?
- Have 100 cockroaches in your office or have to eat one cockroach?
- Have arms that stretch super far or legs that let you jump super high?
- Have a voice that sounds like a robot or a voice that sounds like a trumpet?
- Ride a friendly dragon to work or arrive in a flying saucer with friendly aliens?
- Always have sticky fingers or always have a runny nose (but never get sick)?
- Always have to sleep in a sleeping bag or always have to sleep in a hammock?
- Forced to say everything on your mind or never speak unless someone speaks to you?
- Have glittery footsteps wherever you walk or scented bubbles come out whenever you talk?
- Eat the same meal for breakfast, lunch, and dinner forever or never eat the same thing twice?
- Have a giant boombox that follows you around playing music or a personal spotlight that’s always on you?

Section 7 of 9:

Funny “This or That” Questions About Food

Include funny questions about food to start a friendly debate. If you’re playing with new friends or people who aren’t that close to each other, food is always a safe subject. Pit 2 gross or weird choices against each other and encourage everyone to elaborate on their answers. This opens the floor where people can talk about their favorite meals and unpopular food opinions:^{[1]
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Research source}
- Eat snails or pig's feet?
- Eat a dead spider or a live worm?
- Only eat burnt fries or soggy fries?
- Eat a raw onion or an entire lemon?
- Butter massage or tomato soup bath?
- Eat a raw egg or a spoonful of wasabi?
- Eat pizza with ranch or cereal with water?
- Chocolatey gravy or beefy chocolate milk?
- Eat a stick of butter or drink a cup of olive oil?
- Only eat unripe bananas or overripe bananas?
- Drink a sand smoothie or eat a mud sandwich?
- Drink a cup of hot sauce or a cup of fish sauce?
- Only eat baby food or only eat super spicy food?
- Drink a milkshake made of pickles or anchovies?
- Eat spaghetti with a spoon or eat soup with a fork?
- Swim in a pool of Jell-O or swim in a pool of syrup?
- Eggs or toast for every meal for the rest of your life?
- Drink a cup of sour milk or a cup of rotten orange juice?
- Iced coffee on a snowy day or hot coffee in a heatwave?
- Eat a cake made of ketchup or a cake made of mustard?
- Chocolate-flavored broccoli or broccoli-flavored chocolate?
- A world without French fries or a world without onion rings?
- Have a tree that grows hamburgers or a tree that grows pizza?
- Play baseball with raw eggs or play soccer with a watermelon?
- Always eat food that’s too cold or always eat food that’s too hot?
- Eat a taco filled with crickets or a burrito stuffed with mealworms?
- Eat a 5-gallon bucket of salsa or a 5-gallon bucket of guacamole?
- Sleep on a pillow stuffed with boiled eggs or a pillow stuffed with fish?
- Eat pizza for breakfast every morning or pancakes for dinner every night?
- Eat Lunchables every day for a year or Buldak noodles every day for a year?
- Only eat canned food for the rest of your life or only eat fast food for the rest of your life?

Section 8 of 9:

Funny “This or That” Questions About Fashion

Throw out silly style and fashion-related questions to keep the fun going. From popcorn shirts to Big Red Boots, there are tons of cringey trends and controversial clothing pieces that people love to hate. Pit two choices against each other and watch a funny conversation unfold. Here are some example Qs for inspiration:
- Uggs or Tabis?
- Tie-dye or acid-wash?
- Ed Hardy or Von Dutch?
- Fedora or newsboy cap?
- Fringe vest or denim vest?
- Skinny jeans or saggy pants?
- Arm warmers or leg warmers?
- Shutter shades or nerd glasses?
- Orange crocs or Big Red Boots?
- Sweater vest or velour tracksuit?
- Popcorn shirts or shoulder pads?
- Foam Runners or Bubble Slides?
- Low-rise pants or parachute pants?
- Be deathly allergic to leather or lace?
- Platform sneakers or peep-toe boots?
- Always wear sneakers or always wear sandals?
- Wear a chicken as a hat or wear frogs for shoes?
- Always be overdressed or always be underdressed?
- Always wear giant clown shoes or have squeaky shoes?
- Wear a wedding dress or a bikini for the rest of your life?
- Wear cargo pants forever or wear your collar popped forever?
- Matching shirts with your pet or matching shirts with your partner?
- Dress like you’re in the ‘80s forever or dress like you’re 80 forever?
- Wear something covered in cat hair all day or wear a stained shirt all day?
- Wear your clothes backward for a week or wear your shoes on the wrong feet?

Section 9 of 9:

How to Play “This or That”

Pit 2 items against each other, then ask the players to choose one. “This or that” is similar to “Would You Rather,” where players take turns asking each other questions and letting the other person answer them aloud.^{[2]
X
Research source} The goal is to answer as quickly as possible and avoid overthinking. You only need 2 people to play, but it’s more fun if you have a large group of 4 or more players. It’s a great way to learn more about others’ interests and preferences, plus spark a lively conversation.
- “Before starting the game, discuss what topics are off-limits,” says dating coach and matchmaker Laura Bilotta.^{[3]
  X
  Expert Source
  
  Laura Bilotta
  Dating Coach & Matchmaker
  
  Expert Interview} This can include things like sex and intimacy, past relationships, or finances.
- Be mindful of your questions and set rules that allow each person to skip a turn. If you think your question might make someone feel uncomfortable, it’s best to save it for another occasion, such as a one-on-one conversation with the other person.^{[4]
  X
  Expert Source
  
  Jonathon Aslay
  Dating and Relationship Coach
  
  Expert Interview}

Expert Q&A

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Question

How can I create my own This or That questions?

Reem Edan
Comedian, Writer and Content Creator
Reem Edan is a comedian, writer and content creator based in Los Angeles, CA. Reem has captivated audiences globally, making appearances on: The Stand Up Sketch Show, SiriusXM, The Netflix is A Joke Festival, Laugh After Dark, Elizabeth Banks’ WhoHaha, and in her upcoming Dry Bar comedy special. She’s brought audiences to tears at renowned comedy clubs and venues across the globe, while simultaneously building an online presence of over 300k followers, and amassing tens of millions of views. Previously, Reem worked at Paramount Pictures, Walt Disney Studios, and STX Entertainment in marketing, and has participated in renowned industry programs like: the NBC Late Night Writing Program, Warner Bros/Rooster Teeth Content Creator Program, and the MGM Writing Program. She was also a writer on the Disney TV Discovers Showcase, penned synopses for Netflix, and even wrote jokes for popular social media pages like Scooby Doo and Tom & Jerry. Reem has a degree in Marketing from the University of Denver.

Reem Edan

Comedian, Writer and Content Creator

Expert Answer

I would go outlandish! The more out of the box, the wilder and funnier it is, the better it works. A great trick is to combine two ideas that don’t naturally go together. That’s where the humor comes from. For example, a crocodile is dangerous and rough, so the opposite would be something super soft and kissable. Then you mash them together and ask something like, “Would you rather kiss a crocodile or cuddle a porcupine?” You want to push it to the most exaggerated, hyperbolic version possible.

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