101 This or That Questions for Work or Students | Roundup (2024)

Roundup

Want to get to know your team or break the ice in your classroom the fun way? We’ve put together a list of all the best “would you rather” and “this or that” questions you can ask to get everyone chatting, laughing, and connecting.

We’ve paid special attention to thoughtful and mindful questions that get your team thinking about the present and what they have (like “would you rather keep hot running water, or keep coffee in the morning?”), rather than what they don’t have.

If you want to play a ready-made game that asks your group This/That questions and displays a chart of the responses, we have a game you can just launch and play!

Now let’s get to the list!

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Ice Breaker This or That Questions

These light, fun this or that questions are perfect for before a meeting or if you’re a newer group and just getting to know each other.

1. Coffee or Tea?
2. Netflix or HBO Max?
3. Reading or audiobook?
4. Pancakes or waffles?
5. Staycation or vacation?
6. Morning person or night person?
7. CashApp or Venmo?
8. Music or podcasts while driving?
9. Summer or winter?
10. Glasses or contacts?
11. Comedy or drama?
12. Lake or ocean?
13. Crunchy peanut butter or smooth?
14. Marvel or DC?
15. Android or iPhone?

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Funny This or That Questions

Bring a little levity to your next meeting by asking these funny this or that questions.

1. Would you rather be able to fly or breathe underwater?
2. Would you rather only be able to whisper or only be able to shout?
3. Would you rather not brush your teeth for a week or not shower for a month?
4. Would you rather have a bad haircut or bad hair dye?
5. Would you rather a speeding ticket or a parking ticket?
6. Would you rather see babies dressed as animals or animals dressed as humans?
7. Would you rather spend the day indoors or outdoors?
8. Would you rather communicate on Twitter or Snapchat?
9. Would you rather travel 50 years in the past or 50 years to the future?
10. Would you rather be able to fly or be able to teleport?
11. Would you rather have a permanent frown on your face or a permanent smile?
12. Would you rather become a superhero or a wizard?
13. Would you rather never have sweet food again or never have savory food again?
14. Would you rather have to fend off a bear or a swarm of ferrets?
15. Would you rather find out you’re a robot or find out you live in the matrix?
16. Would you rather be on 90 Day Fiancé or Love is Blind?
17. Would you rather be a rodeo clown or a matador?

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This or That Questions for Work and Teams

Want a few SFW questions for your next work meeting? These this/that/would you rather prompts are sure to get the group talking.

1. Would you rather work from home or work in the office?
2. Would you rather work alone or work with a team?
3. Would you rather have lunches out of the office or eat at your desk?
4. Would you rather make a phone call or send an email?
5. Would you rather hot running water or coffee in the morning?
6. Would you rather no more pizza parties or no more birthday cakes?
7. Would you rather always be 10 minutes late to work or 20 minutes early?
8. Would you rather take an all-expenses-paid dream vacation for a month every year at a mediocre job or have your dream job but pay for your vacations yourself?
9. Would you rather go on a hike or a jog?
10. Would you rather go skiing or snowboarding?
11. Would you rather practice yoga regularly or go to CrossFit regularly?
12. Would you rather spend your day off relaxing at home or doing activities out and about?
13. Would you rather have to switch careers every 2 years or stay at the same job the rest of your life?
14. Would you rather get to travel all over the world or travel once to the moon?
15. Would you rather be book smart or street smart?
16. Would you rather go on a road trip or fly?

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This or That Questions for Students

If you’re looking for conversational prompts to encourage thoughtful conversation and to have a little laugh, try these out. Students will love sharing their answers!

1. Explore space or the ocean?
2. Be the size of a mouse for the rest of your life or be the size of an elephant?
3. Go to Hogwarts or the Jedi Academy?
4. Have unlimited candy at a movie or unlimited popcorn?
5. Walk through a rainforest or a desert?
6. Never have math class again or never have English class again?
7. Be a Transformer or a Pokémon?
8. Drive a motorcycle or a sports car?
9. Be the fastest person in the world or the strongest person in the world?
10. Be best friends with Batman or Superman?
11. School start and end earlier or start and end later?
12. Go on a field trip to the zoo or to a museum?
13. Have a longer lunch or a longer recess?
14. Go to prom or go to homecoming?
15. Write a story or a write a poem?
16. Be good at sports or get good grades?

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Serious This or That Questions

If you already have a close team and want to delve a little deeper into your connections, try these more serious this/that questions.

1. Look into your future or change your past?
2. Have the power to be invisible or the power to read minds?
3. Live in a world without disease or a world without poverty?
4. Travel through time or teleport anywhere in the world instantly?
5. Have inner peace or success and recognition for your work?
6. Always feel safe and secure or always feel fulfilled and satisfied?
7. Be able to speak any language fluently or understand animals’ communication?
8. Be able to control fire with your mind or water with your mind?
9. Make all of your decisions based on logic or make all of your decisions based on emotion?
10. Know how the world ends or when the world ends?
11. Forget everything you know or forget everyone you know?
12. Never be able to cry again or never able to laugh again?
13. Have $100,000 to spend on yourself or have a million you can only spend on others?
14. Go to prison or spend your life on the run from the police?
15. Live alone or live with your family?
16. Have more money or more time?

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Controversial This or That Questions

Want to start a lively conversation with your group? Look no further than these fun – but surprisingly controversial – questions.

1. Does pineapple belong on pizza or should fruit not be allowed on pizza?
2. Is a hot dog a sandwich or is a hot dog a taco?
3. Are fries better with ketchup or another sauce?
4. Do rectangular pizzas taste better or do round pizzas?
5. Are introverts too quiet or are extroverts too loud?
6. Is McDonald’s better than Burger King?
7. Is cereal or oatmeal a soup?
8. Is it better to wear shoes in the house or take them off?
9. Which is the worst word: Moist or Phlegm?
10. Is it better to watch movies with subtitles or without them?
11. Is golf a sport or a hobby?

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Debatable This or That Prompts

Instead of questions, we’ve left these as statements. If you know your group can debate without getting too worked up, it’s fun to throw these into the room to see who reacts.

1. All families should have pets.
2. Soccer is a better sport than American football.
3. The Xbox is better than the PlayStation.
4. Clowns are more scary than funny.
5. Dogs are better pets than cats.
6. Vampires are more deadly than werewolves.
7. People shouldn’t have to go to work or school on their birthdays.
8. Humans are the most dangerous animals on the planet.
9. If students have to wear uniforms, so should teachers.
10. All is fair in love and war.

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