This Or That Questions: Fun, Interesting, and Thought-Provoking Choices
Looking for fun ways to start a conversation, get to know someone better, or simply pass the time with friends? These 99 this or that questions are perfect for almost any situation. From food and travel to relationships, lifestyle, personality, and wild hypothetical choices, this or that questions make it surprisingly easy to discover what someone really likes.
The best thing about this or that questions is their simplicity. You only have two choices, so there is no need to overthink your answer. Pick one, explain your reasoning, and let the conversation take off from there. Some questions are easy, while others might leave you staring at the screen wondering which option you would actually choose.
Whether you’re planning a party, creating a game night, looking for questions to ask your crush, or searching for fun conversation starters, these 99 this or that questions offer plenty of ideas. Ready to see how well you know yourself and everyone around you?
Fun This Or That Questions
These fun this or that questions are perfect for breaking the ice. Ask them during parties, sleepovers, road trips, family gatherings, or casual conversations. Even the simplest choices can lead to hilarious stories and unexpected debates.
“Would you rather have unlimited pizza or unlimited ice cream?”
“Would you rather be able to fly or become invisible?”
“Would you rather have a private movie theater or a private swimming pool?”
“Would you rather spend an entire day at an amusement park or a water park?”
“Would you rather always be five minutes early or always be twenty minutes late?”
“Would you rather have the ability to talk to animals or speak every human language?”
“Would you rather live in a giant mansion or a cozy cottage?”
“Would you rather have endless snacks or endless drinks?”
“Would you rather be incredibly funny or incredibly intelligent?”
“Would you rather spend a weekend without your phone or without television?”
“Would you rather have a personal chef or a personal driver?”
Food This Or That Questions
Food choices can reveal a lot about someone’s personality. These food-related this or that questions are great for friends, couples, family members, and anyone who enjoys talking about their favorite meals.
“Would you rather eat burgers or pizza for the rest of your life?”
“Would you rather choose chocolate or vanilla?”
“Would you rather have fries or onion rings?”
“Would you rather eat pancakes or waffles?”
“Would you rather choose spicy food or sweet food?”
“Would you rather have coffee or tea every morning?”
“Would you rather eat breakfast for dinner or dinner for breakfast?”
“Would you rather choose cake or cookies?”
“Would you rather have popcorn or nachos at the movies?”
“Would you rather eat homemade food or restaurant food?”
“Would you rather give up chocolate or give up your favorite fast food?”
Travel This Or That Questions
Travel is one of the easiest topics for starting interesting conversations. These travel this or that questions can reveal whether someone dreams about relaxing on a beach, exploring a busy city, or going somewhere completely off the beaten path.
“Would you rather spend a week at the beach or in the mountains?”
“Would you rather travel by airplane or train?”
“Would you rather explore a tropical island or a snowy destination?”
“Would you rather go on a road trip or take a luxury cruise?”
“Would you rather visit a famous city or a quiet hidden town?”
“Would you rather travel alone or travel with your best friend?”
“Would you rather stay in a luxury hotel or a cozy cabin?”
“Would you rather explore a jungle or a desert?”
“Would you rather watch the sunrise or watch the sunset while traveling?”
“Would you rather take one long vacation or several short trips?”
“Would you rather revisit your favorite destination or discover somewhere completely new?”
This Or That Questions for Friends
Good friends often know each other’s habits, personalities, and preferences better than anyone else. These this or that questions for friends can test just how well your friends understand you while creating plenty of laughs along the way.
“Would you rather have one extremely close friend or many casual friends?”
“Would you rather have a game night or a movie night with your friends?”
“Would you rather text your friends or call them?”
“Would you rather spend the day shopping or hanging out at home?”
“Would you rather go to a concert or a sports game with your friends?”
“Would you rather have a spontaneous adventure or a carefully planned day?”
“Would you rather be the funniest person in your friend group or the smartest?”
“Would you rather share your biggest secret with your best friend or keep it private forever?”
“Would you rather go camping with your friends or stay at a hotel?”
“Would you rather have a friend who is brutally honest or extremely supportive?”
This Or That Questions for Couples
Couples can use these questions to have fun while learning more about each other’s preferences. Some choices are romantic, some are playful, and others might reveal surprisingly different personalities.
“Would you rather have a romantic dinner at home or at a fancy restaurant?”
“Would you rather receive flowers or receive your favorite snack?”
“Would you rather go on a romantic beach vacation or a mountain getaway?”
“Would you rather watch a romantic movie or a comedy together?”
“Would you rather have a surprise date or plan the date yourself?”
“Would you rather cuddle on the couch or go on an outdoor adventure?”
“Would you rather receive a handwritten love letter or a thoughtful gift?”
“Would you rather spend Valentine’s Day at home or go out for the evening?”
“Would you rather have breakfast in bed or a late-night dinner date?”
“Would you rather take a spontaneous weekend trip together or plan a dream vacation months ahead?”
This Or That Questions for Your Crush
Want to make a conversation with your crush more interesting without making it feel like an interview? These this or that questions for your crush are easy, playful, and open the door to follow-up conversations.
“Would you rather have a quiet date or an adventurous date?”
“Would you rather get a cute text in the morning or a goodnight message at night?”
“Would you rather watch a movie together or play a game together?”
“Would you rather go for coffee or grab ice cream?”
“Would you rather receive a funny meme or a sweet compliment?”
“Would you rather have someone make you laugh or make you feel comfortable?”
“Would you rather go on a sunset walk or a late-night drive?”
“Would you rather have a planned date or a completely spontaneous date?”
“Would you rather spend an entire day talking or simply enjoy each other’s company?”
“Would you rather have someone remember little details about you or surprise you with big gestures?”
This Or That Questions About Personality
Personality-based questions can turn a simple game into a deeper conversation. They encourage people to think about their habits, values, and the way they approach everyday situations.
“Would you rather be extremely confident or extremely patient?”
“Would you rather always trust your instincts or always follow logic?”
“Would you rather be known for your kindness or your courage?”
“Would you rather speak your mind or carefully choose your words?”
“Would you rather be a natural leader or an excellent team player?”
“Would you rather spend your free time being productive or completely relaxing?”
“Would you rather take risks or play it safe?”
“Would you rather be remembered for your achievements or your personality?”
“Would you rather have a predictable life or an exciting unpredictable life?”
“Would you rather always know what people think of you or never worry about other people’s opinions?”
Lifestyle This Or That Questions
Lifestyle choices can be surprisingly difficult because both options may sound appealing. These questions are especially useful when comparing dream lifestyles, daily routines, and personal priorities.
“Would you rather wake up early or stay up late?”
“Would you rather work from home or work in an office?”
“Would you rather live in the city or live in the countryside?”
“Would you rather have a minimalist home or a home filled with everything you love?”
“Would you rather exercise in the morning or evening?”
“Would you rather spend money on experiences or physical things?”
“Would you rather have a busy exciting schedule or a calm relaxed routine?”
“Would you rather cook every meal or order food whenever you want?”
“Would you rather spend your weekend outdoors or indoors?”
“Would you rather have complete financial freedom or unlimited free time?”
Funny This Or That Questions
Sometimes the best questions are the ones that make absolutely no sense until you imagine actually having to live with the choice. These funny this or that questions are designed to create laughter and ridiculous conversations.
“Would you rather have spaghetti for hair or popcorn for teeth?”
“Would you rather sneeze every time you say hello or hiccup every time you laugh?”
“Would you rather have a chicken follow you everywhere or a duck follow you everywhere?”
“Would you rather wear pajamas everywhere or formal clothes everywhere?”
“Would you rather have a tiny elephant or a giant hamster as a pet?”
“Would you rather accidentally send your thoughts as text messages or accidentally say every text you type out loud?”
“Would you rather have your alarm clock sing loudly or tell embarrassing jokes every morning?”
“Would you rather have to dance whenever you hear music or sing whenever someone talks to you?”
“Would you rather only be able to whisper or only be able to shout?”
“Would you rather have your pet choose your clothes or choose your hairstyle every day?”
Deep This Or That Questions
Not every this or that question needs to be silly. Some choices can encourage honest conversations about life, happiness, relationships, ambition, and personal growth. These deeper questions are best asked when everyone is comfortable sharing more meaningful answers.
“Would you rather know exactly how your future turns out or discover it one day at a time?”
“Would you rather have a successful career or a peaceful life?”
“Would you rather be loved by everyone or deeply understood by a few people?”
“Would you rather have the courage to change your life or the patience to accept it?”
“Would you rather erase one painful memory or relive one beautiful memory?”
“Would you rather achieve your biggest dream or help someone else achieve theirs?”
“Would you rather have more confidence or more wisdom?”
“Would you rather know the truth even when it hurts or remain happy without knowing everything?”
“Would you rather be remembered for what you accomplished or how you treated people?”
“Would you rather have unlimited opportunities or unlimited motivation?”
Random This Or That Questions
When you want something completely unpredictable, random this or that questions are the way to go. They can jump from entertainment to imagination to everyday preferences in seconds, keeping the conversation fresh.
“Would you rather read books or watch movies?”
“Would you rather listen to music or listen to podcasts?”
“Would you rather have a dog or a cat?”
“Would you rather play video games or board games?”
“Would you rather spend a rainy day reading or watching movies?”
“Would you rather have super strength or super speed?”
“Would you rather live without social media or live without streaming services?”
“Would you rather always have perfect weather or always have the perfect temperature indoors?”
“Would you rather win a huge lottery prize or receive your dream job?”
“Would you rather be famous for a talent or famous for helping people?”
Why This Or That Questions Are So Much Fun
The popularity of this or that questions comes from their simplicity. You don’t need special equipment, complicated rules, or hours of preparation. All you need is another person who is willing to choose between two options.
These questions can also reveal surprising differences between people. You might assume your best friend would choose the same answer as you, only to discover that they have completely different preferences. That’s where the fun begins.
Another reason this or that questions work so well is that they naturally create follow-up conversations. If someone chooses mountains over beaches, you can ask why. If someone chooses coffee over tea, you can ask about their favorite drink. One simple question can quickly become a much longer conversation.
How to Play This Or That Questions
Playing a this or that questions game is incredibly easy. One person asks a question with two choices, and everyone has to select one. The important rule is that players should answer honestly rather than choosing what they think sounds better.
For a larger group, you can make the game more competitive. Everyone can stand on one side of a room based on their answer. One side represents the first choice, while the opposite side represents the second choice. Suddenly, a simple conversation becomes a fun group activity.
You can also make the game more personal by asking players to explain their choices. The explanations are often more entertaining than the answers themselves.
