100 This or That Questions to Ask Your Colleagues and Family

Heather Harper

We’ve put together a detailed list of 100 such questions and categorized them into thirteen different categories for a wide range of contexts.

Asking icebreaker questions is a great way to introduce a new hire to the team, engage your team and warm everyone up before an important meeting or brainstorming session, or simply help your employees connect and bond as part of a team-building activity. They also make for an entertaining way to pass the time with friends and family members. And while there’s a plethora of icebreaker questions, today we’re dealing with this or that questions.

We’ve put together a detailed list of 100 such questions and categorized them into thirteen different categories for a wide range of contexts.

But before we dive into the questions, let’s cover some this or that question basics first.


What Are This or That Questions?

This or That Questions to Ask Your Colleagues and Family

Frequently Asked Questions

Final Words

What Are This or That Questions?


“This or that” questions, also referred to as either-or questions, offer two options from which the participants need to choose. The options can be funny, outrageous, or totally mundane, but even if neither option applies to you, you still have to take your pick. As you’ll see, you might be given options such as cats or dogs, Pepsi or Coca-Cola, or some challenging suggestions such as going to an exotic location with a boring friend, or going to a city you hate with your awesome friend.

That’s what makes this or that question games so entertaining, in the same way as would you rather questions, yes/no questions, and other similar icebreaker questions require choosing between two hypothetical things or scenarios.

Finally, these questions demand prompt answers, but the good thing is that they can spark longer and quite engaging discussions that reveal a lot about a person. Moreover, they’re a fun way to discover interesting things about colleagues that might not come up through everyday conversations.

This or That Questions to Ask Your Colleagues and Family

When it comes to “this or that” questions, you can prepare random questions with a wide range of contexts and options, or you could opt for a themed approach instead.

For the purposes of this article, we chose the latter, so below, we provide you with 100 “this or that” questions you can use with your colleagues, family members (as well as their kids!), or friends.

1) This or That Food Questions


What better way to know if you can plan lunches with colleagues or go on a picnic with family members than by learning their true food preferences?

There are many ways to ask them, but nothing can quite inspire them to show their true colors as a concise icebreaker question can.

Here are our suggestions, but feel free to expand on the list.

  1. Mashed potatoes or baked potatoes?
  2. Chicken nuggets or hot dogs?
  3. Dark chocolate or white chocolate?
  4. French fries or onion rings?
  5. Ice cream or iced coffee?
  6. Hot chocolate or tea?
  7. Eating onion rings with honey mustard sauce or mayonnaise and sour cream?
  8. Cooking or delivery?

2) This or That Questions for Colleagues


Conversations with colleagues are meaningful on their own, but every now and then, opting for a laid-back approach and “hitting” them with random icebreakers may be just what’s needed to break the office monotony.

You can get as creative as you want with these questions, and of course, feel free to adjust them to suit your current office needs.

  1. Playing card games or playing trivia games with colleagues?
  2. Going on a team-building event somewhere away or staying in the office?
  3. Organizing a team-building activity or just taking part in it?
  4. Do you get along better with loners or social butterflies?
  5. Being poor but happy, or rich but miserable?
  6. Having a very loud colleague next to you in the office or an extremely quiet one?
  7. Dealing with a challenging client or a challenging colleague?
  8. Pizza party or pool party with colleagues?

3) This or That Questions for Couples


“This or that” questions for couples can be intimating, entertaining, funny, condescending, and confusing, but one thing’s certain - they won’t leave anyone feeling indifferent.

Take a closer look at the questions below to see if we’re right.

  1. Drinking red wine or white wine on a date?
  2. Spending the weekend with other people or on your own?
  3. Forgetting who you are or forgetting your partner?
  4. A partner with long hair or short hair?
  5. A partner who’s a night owl or an early bird?
  6. A partner that puts the toilet paper over or under?
  7. A partner who wants to put hardwood floors or a carpet in your new house?
  8. A partner who earns well but struggles to maintain a healthy life-work balance or a partner who earns poorly but has a great life-work balance?

4) This or That Questions About Ideas


Brainstorming sessions, meetings with people who inspire you, or watching masterclasses may awaken your entrepreneurial spirit and get you to be innovative, but answering questions about ideas is another way to challenge your thoughts about certain concepts.

And that’s precisely what the following set of questions is meant to do, both for colleagues in the office, and friends and family members.

  1. Talking to the richest person on Earth or talking to the smartest one?
  2. Spending money to build your own business or spending money to buy stocks?
  3. Setting up a business on your own or with a partner?
  4. Committing your life to helping elderly people or kids in the orphanage?
  5. Free education for all or free healthcare?
  6. Putting an end to wars or ending world hunger?
  7. Getting further education or more work experience?
  8. Being a leader or a follower?
  9. Being your own boss but not having a lot of free time or working for someone till you retire while having enough time for your family and hobbies?

5) This or that Travel Edition Questions


Our travel edition questions will:

  • Make you contemplate your travel choices;
  • Make you want to pack and leave as soon as possible;
  • Help you learn a lot about your colleagues and family members;
  • Allow you to come up with new travel ideas;
  • Help you reminisce about your recent vacation experiences.

If this sounds exciting, dive into our questions right away!

  1. Taking a road trip with your friends or taking a road trip with family members?
  2. Traveling with a small group of people or joining an organized trip by a travel agency with a large group?
  3. Going on a boring road trip with your rich friends or going on an adventure with people on a tight budget?
  4. Going to a water park or amusement park?
  5. Spending your free time wandering in a new city or drinking hot coffee in some local bar there?
  6. Vacation or staycation?
  7. Going on a holiday in Asia or Europe?
  8. Souvenirs or postcards?

6) This or That Work Questions


“This or that” work questions are meant to make you think about your job, reconsider your current work choices, and challenge some work notions and concepts you may have taken for granted (or may not have considered at all).

You can use this set of questions with your colleagues, but feel free to engage in them with your family members too. In fact, having your family answer such work-related questions will help you learn more about their work experiences and how they feel about their current job situation.

  1. A successful entrepreneur or an awesome team player?
  2. A call from work in the middle of the night or right after you wake up in the morning?
  3. Your manager texting you on social media or sending you text messages?
  4. Receiving lengthy emails or long calls at work?
  5. Working on holidays or during weekends?
  6. USB backup or cloud storage for important work-related materials?
  7. In-person meetings or virtual meetings?
  8. Attending a company retreat or the annual company holiday party?

7) This or That Questions for Friends


If you’ve always wanted to learn how your colleagues feel about concepts such as friendship, and how your family members perceive their friends, now it’s your chance to learn all about it.

Take a look at our carefully written “this or that” questions for friends and take your pick.

That said, you can always try these icebreaker questions with your friends too! Wouldn’t it be fun to learn whether your friends think it’s better to have a lot of acquaintances or just a single best friend? Or whether they prefer having a friend who tells the truth to their face as opposed to having a friend who hides the truth just to make them feel better?

Read on to find out more!

  1. Playing computer games or board games with your best friends?
  2. Having a lot of acquaintances or just one best friend?
  3. Sharing your salary with your friends or family members?
  4. Getting a loan from your friend who struggles financially or borrowing money from a wealthy acquaintance?
  5. Owing some people a big favor or owing them a lot of money?
  6. Having introverted or extroverted friends?
  7. Rekindled romance or rekindled friendship?
  8. Having friends that slap the truth in your face or tell you white lies to make you feel better?

8) This or That Questions about Sports, Activities, and Hobbies


Sports, activities, and hobbies are things people usually engage in during their free time.

But talking about them and discussing them in a meaningful manner can be just as productive.

It’ll help you understand what passions your colleagues have outside their regular working hours, how your family members feel about certain activities you may (not) resonate with, and so on.

Who knows? You might just end up doing some activities together or picking up a new hobby you have never considered before.

  1. Going on a roller coaster ride or entering a haunted house?
  2. Playing video games or reading books?
  3. Bumper cars with best friends or people you don’t know?
  4. Football or baseball?
  5. Running or speed walking?
  6. Karate or kickboxing?
  7. Yoga or pilates?
  8. Learning a foreign language or soapmaking?

9) This or That Book Questions


Our “this or that” book questions help bookworms strengthen their love for literature and help those who aren’t quite avid readers contemplate the idea of reading.

Check out the questions below to see if we’re right.

  1. Reading the same book for the rest of your life or never reading a book again?
  2. Someone ruining the ending of a cool book you’re reading at the moment or never managing to finish reading the book?
  3. Having lunch with your favorite author or character?
  4. Meeting George R. R. Martin or J. R. R. Tolkien?
  5. Living in a bookstore or a library?
  6. Reading stand-alone novels or series?
  7. Reading poetry or drama?
  8. First or third character POV?

10) This or That Music Questions for Kids


Few things can make family gatherings or corporate family days as special as having your family members’ or colleagues’ kids there can.

In such instances, it’s good to have backup questions so that you can include the children in your icebreaker plans. Not only will the kids feel engaged and special, but the parents will be grateful too!

There are many themes you can include in your icebreaker questions, but we decided to go with music-themed questions.

  1. Listening to the last song on your playlist for the rest of your life or never listening to any music again?
  2. Spending time at the beach or by the pool?
  3. Going to a concert or listening to loud music on your new music equipment?
  4. Meeting the Jonas Brothers or BTS?
  5. Going to your grandparents’ house or your grandparents’ visiting you?
  6. Pizza or tacos?

11) This or That Movie Questions for Kids


In this part, we invite you to consider our movie-inspired questions for kids.

Who knows? Kids might come across their next favorite movie during one of your icebreaker sessions!

  1. Watching your favorite movie with your stuffed animals or your parents?
  2. Watching your favorite cartoon while drinking hot chocolate or hot cocoa?
  3. Join Hogwarts or Narnia?
  4. Frozen or The Princess and the Frog?
  5. Kevin or Bob (from Minions)?
  6. Christmas movies or Easter movies?

12) This or That Questions About Online Habits


Online habits are easy to build yet hard to discuss, as we may not be quite aware of them fully.

However, it can be such icebreaker sessions that will allow people to become more aware of their digital habits, as well as reconsider them, make different choices, suggest versatile ideas, and listen to what others have to say.

Here are some examples you can use:

  1. Shopping in-store or buying things online?
  2. Spending time scrolling on social media or texting your people?
  3. Engaging in an interesting conversation in a WhatsApp group or listening to pop music on YouTube?
  4. Watching a scary movie on Netflix or watching a musical (let’s say High School Musical)?
  5. Joining online meetings on your new phone or using your old laptop?
  6. Sending text messages or calling people?
  7. No more social media or no more video games?
  8. Chrome or Safari?

13) This or That Geography Questions


Our “this or that” geography questions go hand in hand with our travel edition questions, so feel free to combine them in a way that works for you.

The questions below invite you to consider some unusual concepts, such as whether people will much rather get lost in the jungle or perhaps a larger city, end up being stuck abroad with an annoying friend or an annoying family member, and so on.

Take a look at our list to get started:

  1. Paris or Rome?
  2. America or Europe?
  3. Living in the city or the village?
  4. Being stuck in a foreign country with an annoying friend or an annoying family member?
  5. Getting lost in the jungle or in a vast city?
  6. Going to the beach or to the mountains?
  7. Machu Picchu or the Northern Lights?
  8. Using Google Maps to navigate a new city or relying on where your travel buddy takes you?

Frequently Asked Questions

What are some funny this or that questions?

Funny questions not only make the overall “this or that” questions game entertaining, but they allow people to discover what their colleagues and family members (dis)like, prefer, and how they feel about certain concepts in an unusual and entertaining way.

And even though these funny questions may come across as naive or insignificant, they can actually help participants learn quite a bit about the people around them.

To achieve this in your office or at home, consider the funny and silly questions below:

  1. Eat french fries every day for lunch till the end of your life or never eat french fries again?
  2. Be Sleepy or Grumpy from the Snow White and the Seven Dwarfs story?
  3. Performing in front of a large audience or joining a reality show?
  4. Hiring a stunt double or doing the stunts on your own?
  5. Always ending up without toilet paper when you’re on the toilet or always running out of hot water when you’re taking a shower?
  6. A noisy neighbor or an untidy roommate?
  7. Chandler Bing or Joey Tribiani?
  8. HBO or Netflix?
  9. Bad haircut or a bad dye?
  10. Sneezing or coughing uncontrollably for a week?

Of course, you can always tailor the questions above to suit your current needs or situation. For instance, you might need to adjust the humor for office purpose, but opt for a more relaxing approach with family members.

What are some hard this or that questions?

Hard “this or that” questions are thought-provoking questions meant to inspire people to provide creative responses. They reveal one’s values, fears, and weird thoughts.

They’re called “hard” because both options are usually challenging, and a person is basically expected to pick the lesser evil, at least according to their views. Or sometimes, both options can be equally appealing, so it’s a challenge to opt for one.

That said, although classified as “hard”, they’re actually very entertaining to ask but even more amusing to answer.

Here are some examples of such questions so that you get a general idea:

  1. Dealing with intense pain for a minute or dull pain the whole day?
  2. Having the ability to read other people’s minds or the ability to fly?
  3. Safety and predictability or danger and excitement?
  4. Having terrible body odor or extremely bad breath?
  5. Having extreme emotions or being emotionless?
  6. Reincarnate as a parrot or fish?
  7. Meet your favorite singer or favorite actor?
  8. Meet Albert Einstein or Nikola Tesla?
  9. Be allergic to alcohol or be allergic to chocolate?
  10. Being a teacher in middle school or high school?

How do you play this or that icebreaker games?

Playing this or that icebreaker games can be different in office contexts with colleagues and a more informal family gathering. Let’s explore both options.

1) Playing this or that icebreaker games with colleagues

Playing such fun games with colleagues can be done in different contexts and situations:

  • Casual discussions during office breaks;
  • Team-building events;
  • Introducing new hires
  • Onboarding new interns;
  • Video call polls;
  • Before or after important meetings;
  • Before another main event as a warm-up activity (for instance, before starting a murder mystery game set in an exotic country, you can have everyone engage in travel-related questions or geography ones);
  • Introducing new concepts in the office (for example, if you’re trying to introduce hybrid work in the office, you can host a brief icebreaker session where you’ll ask employees this or that questions such as “Work from home or work in the office”, or “Hybrid work or the good old 9-5 in the office”, and so on, to initiate a discussion and proceed based on your employees’ answers.)

An extra tip: While playing such icebreaker games face-to-face is awesome, sometimes introducing a remote option can prove to be even better.

And platforms such as ours can help you organize these icebreaker endeavors.

Opting for a tool such as QuizBreaker brings many benefits:

  • Encouraging your employees to engage in icebreaker questions often;
  • Choosing the day, the frequency, and the timing of when these icebreaker questions get sent out;
  • Creating your own customized questions or using a set of ready-made 100 cool ones;
  • Everyone having access to emoji reactions and comment threads that enable teams to bond in a much more meaningful way while learning new information about one another;
  • Unlocking achievement badges and new levels as you make progress;
  • Easy access to icebreaker questions as QuizBreaker is mobile friendly but also works well with all internet browsers.

And most importantly, you shouldn’t worry about your team’s data/information as there’s SSL encryption.

Moreover, it’s important to note that QuizBreaker is great for teams of all sizes. It takes less than three minutes to set it up, and the gameplay is around two minutes per round.

You can always take advantage of the 21-day free trial to check whether you resonate with the tool. If you do decide to continue using it, you’ll need to pay $3 per month per user. That said, if you opt for an annual payment option, you just need to pay $2 per month per user.

2) Playing this or that icebreaker games with family

Playing “this or that” questions with family members is a much more spontaneous event. It might just happen during a random weekend gathering, the long-awaited family reunion with relatives you haven’t seen in a while, or it might as well be an organized game event with rules and game instructions.

All in all, such fun games help people get to know each other better and connect, even with their nearest and dearest.

Finally, the “this or that” questions game can be played in many ways. For instance, you can ask a person a series of questions instead of just a single one before moving on to the next. Or you could put people in a few teams and they must choose one option together. To make things even more entertaining, introduce time limits. For teams, you might give them 10 seconds to settle on an option, and for individual players 5 seconds should be enough.

Moreover, you could try to predict what another person will choose and if the person guessing is right, they get an extra point.

As you can see, there are many ways you can play such icebreaker games. You can make the game as simple or as complicated as you need it to be. Just go with the one that seems to resonate the most with everyone, or just try all of them until you see what works for you as a group.

Final Words

All in all, this or that questions are a fun way to bond with colleagues and family members. They’re a source of entertainment, yet they add value to our meetings with people. They’re unusual and chill, yet they help us get to know the people we socialize with.

And while we provided you with a detailed list of such questions, the list is far from complete.

Let us know if there are any awesome this or that questions you’ve come across or created on your own! We’re always on the lookout for more such questions to update our lists.

Heather Harper

Heather Harper

Heather Harper has a Masters in Occupational Psychological from the University of Manchester. She currently works as an editorial writer specialising in organizational psychology - helping teams work better together.

© 2023 SaasMates Pte. Ltd. 24 Raffles Place, #10-05 Clifford Centre, Singapore 048621. Terms & Privacy.