99 This or That Questions That Make You Think Twice

You might think you know someone pretty well — their favorite snack, their go-to drink, or how they spend a weekend. But sometimes, it’s the little things we never think to ask that reveal the most. Would they rather live in a treehouse or a castle? Watch cartoons or read a comic book? These small choices can spark big laughs and even better conversations. “This or That” questions are a playful way to discover fun facts, share stories, and connect with others—whether it’s a new friend or someone you’ve known for years. They’re perfect for car rides, classroom chats, or cozy evenings at home. It’s one of my favorite games to play with kids because it’s simple, silly, and always makes everyone smile.

How To Play The Game of This or That Questions

Rules of Playing the This or That Game

The rules for playing the “This or That” game are super easy and exciting! One person asks a question with two choices, like “Ice cream or cake?” Then, the other person (or everyone in the group) picks which one they like better. You can also talk a little about why you picked that choice if you want to!

The most important rule is to have fun and respect everyone’s answers. There’s no right or wrong—everyone just gets to share what they like! You can ask as many questions as you want, and it’s a great way to learn more about each other and have some laughs along the way.

This or That Question Funny

  • Always have bad breath or always have sweaty hands?
  • Dance everywhere you are or sing everything you speak?
  • Only eat cold pizza or only drink warm soda?
  • Fight one horse-sized duck or 100 duck-sized horses?
  • Wear clown shoes every day or a tutu to work?
  • Be stuck in a room full of mosquitos or one with a yodeling goat?
  • Have spaghetti hair or maple syrup sweat?
  • Burp every time you speak or fart every time you laugh?
  • Always walk backwards or only be able to whisper?
  • Only be able to use spoons or only be able to use forks for everything?

This or That Question For Friends

  • Eat a whole lemon or drink pickle juice?
  • Wear socks with sandals or crocs with formal clothes?
  • Accidentally like your crush’s old photo or accidentally send a weird selfie to your boss?
  • Laugh in serious moments or cry when someone tells a joke?
  • Have a pet dinosaur or a pet dragon?
  • Always forget your best friend’s birthday or always get them the worst gift ever?
  • Be stuck in a group chat that never ends or have no one ever reply to your texts?
  • Trip in public once a day or get caught singing in the bathroom every morning?
  • Only speak in movie quotes or only speak in song lyrics?
  • Share a toothbrush with your best friend or wear their socks for a week?
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This or That Questions For Teens

  • Text with only emojis or talk in internet slang all day?
  • Go viral for a cringey dance or be totally unknown forever?
  • Only be able to use your phone at 1% battery or only have Wi-Fi in public places?
  • Wear pajamas to school or dress like it’s prom every day?
  • Lose all your followers or accidentally post an embarrassing selfie?
  • Only be able to watch old cartoons or only be able to listen to elevator music?
  • Forget your headphones on a long bus ride or forget your charger during a sleepover?
  • Laugh-snort every time you laugh or hiccup every time you’re nervous?
  • Eat cereal with water or pizza with chocolate sauce?
  • Have a talking backpack or a phone that randomly meows?

This or That Question For Kids

  • Playing with a Ludo or Carrom board?
  • Eat a sandwich made of jelly beans or spaghetti-flavored ice cream?
  • Have a pet dinosaur or a pet unicorn?
  • Become a pro of Free Fire or PUBG?
  • Walk like a robot or talk like a parrot?
  • Live in a house made of LEGOs or a castle made of cookies?
  • Favorite Movie MATILDA or Harry Potter?
  • Have hair that changes color with your mood or shoes that light up when you dance?
  • Only be able to hop everywhere or roll like a ball?
  • Be friends with a superhero or be a superhero yourself?
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This or That Question For Adults

  • Morning coffee or evening wine?
  • Cancel plans or show up but check your phone the whole time?
  • Work from a beach cabin or a mountain lodge?
  • Always forget people’s names or always forget important dates?
  • Unlimited free flights or unlimited free dinners?
  • Have a personal chef or a personal masseuse?
  • Text your ex or accidentally call your boss?
  • Never get stuck in traffic again or never wait in line again?
  • Be the most creative person in the room or the most confident?
  • Forget your wallet or forget your phone when leaving anywhere?

This or That Questions For Couples

  • Movie night in or dinner out?
  • Beach vacation or mountain getaway?
  • Text all day or talk on the phone all night?
  • Surprise date or planned date?
  • Cooking together or ordering takeout?
  • Morning cuddles or evening hugs?
  • Watch a comedy or watch a thriller?
  • Share a dessert or have your own?
  • Stay up late or wake up early?
  • Dance in the kitchen or sing in the shower?

This or That Question of Food

  • Sweet snacks or salty snacks?
  • Pizza with pineapple or pizza without pineapple?
  • Chocolate ice cream or vanilla ice cream?
  • Spicy food or mild food?
  • Burgers or tacos?
  • Pancakes or waffles?
  • Coffee or tea?
  • French fries or onion rings?
  • Sushi or pasta?
  • Smoothie or milkshake?

This or That Question of Fashion and Style

  • Sneakers or boots?
  • Bright colors or neutral tones?
  • Vintage clothes or futuristic fashion?
  • Big sunglasses or tiny sunglasses?
  • Hats or scarves?
  • Denim jacket or leather jacket?
  • Bold patterns or solid colors?
  • High heels or comfy flats?
  • Statement jewelry or minimal accessories?
  • Casual streetwear or classic elegance?

This or That Question Fantasy and Imagination

  • Live in a floating castle or an underground crystal cave?
  • Have wings like a dragon or gills like a mermaid?
  • Speak with animals or control the weather?
  • Travel through time or travel between dimensions?
  • Own a magical talking book or a glowing enchanted sword?
  • Be a wizard or a shapeshifter?
  • Would you rather parachute out of a plane or race through a jungle on a zipline?
  • Have a pet phoenix or a pet shadow cat?
  • Walk through walls or become invisible?
  • Create a world with your imagination or explore one created by someone else?

Hard This or That Question

  • Choose your dream life with no friends or an average life surrounded by friends?
  • Always say what you’re thinking or never speak again?
  • Sacrifice happiness for success or sacrifice success for happiness?
  • Be remembered for changing the world or for loving deeply?
  • Long and steady life or short and thrilling life?
  • Forget your past or never form new memories?
  • Be the inspiring leader or be the trusted helper?
  • Always get what you want but lose what you love or keep what you love but never get what you want?
  • Have unlimited time or unlimited money?
  • Fix your biggest regret or erase your biggest fear?
  • Always be alone or always be in a crowd but feel lonely?
  • Know how the world ends or never know how it ends?
  • Be loved by many but never find your soulmate or find your soulmate but be disliked by many?
  • Give up all your technology or give up all your privacy?
  • Change one major event in history or prevent one major disaster?
  • Would you prefer to lose your voice forever or lose your sense of hearing?
  • Never feel pain but never feel joy or feel all emotions deeply but suffer more?
  • Be famous for a mistake or forgotten for a masterpiece?
  • Always be the teacher or always be the student?
  • Would you prefer a life with clear rules and structure or a life full of unpredictability and freedom?

This or That Question For Students

  • Drawing with crayons or drawing with markers?
  • Reading outside or reading inside?
  • Studying with a group vs. Studying alone
  • Online classes vs. In-person classes
  • Watching cartoons or watching documentaries?
  • Taking notes on paper or on a tablet?
  • Eating lunch in the cafeteria or outside in the playground?
  • Wearing sneakers or sandals to school?
  • Having a class pet or a class plant?
  • Playing chess or playing checkers?

This or That Question about Technology

  • Quantum Computing vs. Classical Computing
  • Augmented Reality (AR) vs. Virtual Reality (VR)
  • Neural Networks vs. Traditional Algorithms
  • 5G Networks vs. Wi-Fi 6
  • Blockchain vs. Cryptocurrency
  • Edge Computing vs. Cloud Computing
  • Artificial Intelligence (AI) vs. Machine Learning (ML)
  • Self-Driving Cars vs. Electric Cars
  • Digital Twins vs. Smart Cities
  • Smart Home Automation vs. Wearable Tech

 

Sports This or That Question

  • Football vs. Basketball
  • Running vs. Cycling
  • Swimming vs. Surfing
  • Tennis vs. Table Tennis
  • Golf vs. Mini Golf
  • Boxing vs. Wrestling
  • Yoga vs. Pilates
  • Baseball vs. Softball
  • Snowboarding vs. Skiing
  • Soccer vs. Rugby

This or That Question of Coworker, Team on Work

  • Remote Work vs. In-Office Work
  • Team Collaboration Tools (e.g., Slack) vs. In-Person Meetings
  • Flexible Hours vs. Fixed Schedule
  • Morning Team Meetings vs. Afternoon Team Meetings
  • Solo Work vs. Collaborative Work
  • Emails vs. Instant Messaging
  • Brainstorming Sessions vs. Individual Work Time
  • Weekly Check-Ins vs. Monthly Reviews
  • Task Management Software (e.g., Trello) vs. Spreadsheets
  • Quick Chats vs. Formal Updates

Conclusion:

This or That questions are a simple yet powerful way to spark fun, meaningful, or even hilarious conversations. Whether you’re playing with friends, your partner, your kids, or just using them as an icebreaker, these questions help people open up, think quickly, and learn more about each other in a lighthearted way.

From deep life choices to silly imagination games, there’s a This or That question for every mood and moment. So the next time you’re looking for a way to connect, challenge someone’s thinking, or just pass the time, pull out a few of these and get the conversation flowing!

FAQs

What are some good this or that questions?

Here’s a great list of good This or That questions—a balanced mix of fun, thought-provoking, and easy-to-answer options for any setting:

General & Fun Questions

  • Chocolate or vanilla?
  • Cats or dogs?
  • Summer or winter?
  • Morning person or night owl?
  • Netflix or YouTube?
  • Texting or calling?
  • Coffee or tea?
  • Pizza or burgers?
  • Books or movies?
  • Sneakers or sandals?

 Deep & Thoughtful Questions

  • Love or success?
  • Change the past or see the future?
  • Be respected or be liked?
  • Follow your heart or follow your head?
  • Know the truth or stay comfortable?
  • Be rich and lonely or poor and loved?
  • Speak all languages or talk to animals?
  • Live in the city or countryside?
  • Trust easily or question everything?
  • Always be honest or always be kind?

 Funny & Silly Questions

  • Only whisper or only shout?
  • Wear your clothes backward or inside out?
  • Eat a bug or sing in public?
  • Have spaghetti hair or broccoli fingers?
  • Always have to hop or always have to dance?

Here’s a fun and simple question to ask:

“Well settled life with a good career or leisure life with no career?”

It’s easy to understand, sparks imagination, and works for all ages!

 Here are 10 good and simple questions that are fun, friendly, and great for conversation:

  • What’s your favorite food?
  • Do you like the beach or the valleys more?
  • What’s your favorite movie or cartoon?
  • Adventure now and comfort forever?
  • What’s one thing that always makes you smile?
  • Do you like summer or winter better?
  • If you had a superpower, what would you want to change from the world?
  • What’s your favorite game to play?
  • Would you rather fly or be invisible?
  • If you get a free visa anywhere in the world, where would you go?
  • What’s your favorite snack?
  • Power to rewind one day or make a good plan for the future ?
  • Do you like rainy days or sunny days more?
  • What’s the weirdest food you’ve ever tried?
  • If you could live the life of someone else, whose life would you choose?
  • What’s your favorite song to dance to?
  • Would you prefer to have incredible speed or extraordinary strength?
  • Which time of the past would you visit if you could?
  • Do you like chocolate or vanilla more?
  • What’s the last thing that made you laugh?
  • If animals could talk, which one would you choose?
  • What’s your dream job?
  • Would you rather live in a palace alone or in a jungle with friends?
  • What’s something you’ve never done but want to try?
  • What’s your favorite holiday?
  • Power or wisdom?
  • What cartoon character do you like the most?
  • Have you ever met someone famous?
  • Do you prefer night or morning?
  • What’s one super silly thing you’ve done?

A good thing to choose for 20 Questions is something familiar but not too obvious — it should be fun to guess!

Here are some great ideas to use:

Good Things to Use for 20 Questions:

  • Toothbrush
  • Airplane
  • Elephant
  • Laptop
  • Ice cream
  • Sun
  • Backpack
  • Book
  • Bicycle
  • Pizza
  • Guitar
  • Spider
  • Soccer ball
  • Robot
  • Tree
  • Candle
  • Rainbow
  • Clock
  • Cactus
  • Kangaroo

These objects are fun, clear, and allow for good yes-or-no questions like:
 “Is it alive?”, “Can you eat it?”, “Is it bigger than a chair?”

Savannah-Blaze-Good-roast-author

Savvanah Blaze

Savvanah Blaze is a master of wit and humor, bringing sharp comebacks and clever roasts to every conversation. With a background in directing and writing comedic short films, she knows how to craft the perfect punchline. At GOOD ROAST, she shares the best funny roasts and witty replies for any situation, making sure you’re always ready with the perfect comeback.