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22 Best Would You Rather Questions Singapore To Ask [2024]

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Would You Rather Questions Singapore

Best Would You Rather Questions Singapore
Best Would You Rather Questions Singapore

If you want to spark an engaging conversation that will make people laugh and maybe even think, a ‘Would You Rather?’ question is a good option.

‘Would You Rather’ is a great icebreaker game as it makes it easy to express your preferences and opinions in a fun and engaging way.

It gives us a chance to uncover hidden traits and preferences that are out of sight but would be rich areas to explore, getting to know more about others.

These questions will help locals make conversation with their friends and get to know each other better or it will also help a visitor who just arrived in Singapore to make new friends and discover our culture.

So, you can use these best Would You Rather Questions in Singapore for 2024 to spice up your chats!

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Best Would You Rather Questions Singapore

Quick Summary

  • ‘Would You Rather’ is a great icebreaker because people are encouraged to reveal their preferences and opinions in the fun context of a game.
  • It offers no right or wrong answer, so no one is encouraged to answer in any particular way.
  • The questions are meant to reveal one’s thought processes and preferences, which makes it a great way to get to know someone.

How Does Would You Rather Game Works?

How Does Would You Rather Game Works? (Credit: TeenVogue)
How Does Would You Rather Game Works? (Credit: TeenVogue)

To begin the Would You Rather game, you present players with a question that provides two alternatives, from which they must pick one.

These scenarios might be fairly difficult, involving moral tradeoffs, and the player must decide.

There is no limit to the number of players, and the game is played formally and informally.

Participants select between the two options, after which they are asked to justify their choice, which leads to comical or enlightening discussions.

The simple structure encourages outwardness, spontaneity and a shake-up of preconceptions, which makes it an effective ice-breaker as well as a subtle means of group bonding.

“Would You Rather” as an Ice Breaker Game

"Would You Rather" as an Ice Breaker Game
“Would You Rather” as an Ice Breaker Game

The beauty of Would You Rather as an ice breaker is that it doesn’t require much in the way of extra details.

It is a collaborative game without a product, i.e, you don’t need any material to play it. This makes it flexible enough to be played everywhere from bar evenings to corporate team building events.

Getting participants to play through scenarios that are at times funny and at times uncomfortably serious, it pushes them out of their comfort zones to talk to each other in ways they might not have otherwise.

It’s not only a great icebreaker but also a good way to loosen the tension at the beginning of a gathering so that the atmosphere can be relaxed and chill.

Regardless of whether you are prompting someone to decide between two unconventional superpowers or pitting them against two equally appealing or daunting scenarios, Would You Rather captures the playful spirit that brings groups together and encourages them to engage in informal debate.

Best Would You Rather Questions Singapore

1. Would you rather see 10 years into your own future or 10 minutes into the world’s future?

This intriguing question forces players to weigh personal curiosity against global awareness.

At the same time, being able to glimpse into your future might better equip you for the difficult choices you’ll have to make.

On the one hand, the ability to predict world events seconds before they occur allows you to prepare for looming global consequences.

It encourages a rich debate about the merits of individual experience versus collective knowledge, and is a great choice as a starter for a lively and thought-provoking discussion.

2. Would you rather give up social media or movies/TV shows forever?

This option forces participants to prioritise one of the modern necessities of digital communication or entertainment.

Abstaining from social media might mean more real-life interactions and more free time as you are not glued to your phone but, on the flip side, you run the risk of missing out on networking opportunities and being out of the loop.

But on the other hand, giving up viewing films and TV programmes might lead to replacing those passive, indoor pursuits with something more active and potentially outdoorsy – or with reading, at least – but it would also mean losing a significant source of cultural conversation or relaxation.

This question encapsulates modern life’s struggle between two leading sources of leisure and information today – and so makes for a fascinating debate about what truly matters in life.

3. Would you rather lose all the money you’ve earned this year or all the memories you’ve made?

The question is so powerful that it forces participants to choose between the concrete good of salary and the nostalgic quality of good days.

It encourages thinking about the things that enrich your life – is it just money or is it the experiences you have built up of feelings, learning, relating to others?

It can thus garner not just a personal sense of emphasis but a public debate about the very meaning of ‘value’, and the difference between the irreplaceable and the possible to recover.

It’s a question that can lead to some interesting discussion and self-reflection about what it takes to make a life worth living.

4. Would you rather have a lifetime of meals from your favorite restaurant or mastering any cuisine you try?

For many, being given unlimited access to their favourite restaurant stands at odds with becoming so proficient at cooking that they could virtually prepare anything.

At the heart of this is the difference in the pleasures of eating and the pleasures of cooking.

The question reflects personal values about food’s place in life, whether it is a love of fast food and its pleasures, or a love of cooking at home and the feelings of accomplishment and pride it can bring.

It encourages a spirited discussion of the pros and cons of efficiency versus innovation, ease versus effort, and the social gratification of dining out versus the intimate delight of cooking at home.

After all, it forces players to think about the wider impacts of their food choices on their life, social relationships and personal satisfaction – a good subject for dinner conversation any day.

5. Would you rather find your true love or a suitcase with five million dollars inside?

This dilemma is rooted in heart versus head: living for the moment versus the call of instant financial security. It’s a great topic for debate.

It forces us to think about what we would rather choose: true love or money? On one hand, being truly in love – if it occurs – is a dream come true for many of us. There are the promises of joy, company and affection.

On the other hand, discovering five million dollars offers the potential to live a life of freedom and the ability to pursue dreams, which is by no means a guarantee of happiness.

This ‘Would You Rather’ question reflects individual priorities, to be sure, but it also sparks a wider discussion about whether happiness can truly be purchased or must instead be born through a relationship with others.

6. Would you rather speak all foreign languages fluently or communicate with animals?

The choice between learning every human language or communicating with animals presents an intriguing reflection on the human urge to be understood and to interact across the boundaries of beings who are not human.

Fluency in all foreign languages would level the playing field, eliminate language barriers, and profoundly improve worldwide communication, cultural exchange and mutual understanding.

It is the passport of the cosmopolitan, the ultimate means of facilitating international travel, work and socialisation.

On the one hand, animal languages hold out the promise of a world once inaccessible to humans; a window into the natural world; a deepening of our connection with other creatures; a key to animal behaviour and minds.

This question touches on age-old human attitudes towards our communication boundaries and our role in the living world, making it a thought-provoking – if sometimes unnerving – conversation piece.

7. Would you rather always be 10 minutes late or always be 20 minutes early?

Making a decision between constantly running late and almost always being punctual requires us to think through the effects of time-keeping on the social world we inhabit.

This question subtly examines values around respect, productivity, and personal anxiety regarding time.

Arriving late 10 minutes for everything suggests a relaxed (at worst, disrespectful of other people’s time) attitude, and could result in missing appointments and even relationships.

On the other hand, arriving 20 minutes early is a more cautious display, which could lead to a smoother day, with increased productivity and opportunities, but it might also be a reflection of anxieties about being late or misusing time.

This ‘Would You Rather’ experiment compels players to weigh how they value and spend their time, and to explore what this reveals about their deeper personality and priorities.

This is what makes its potential to make you consider your normal actions and the consequences of those actions so affecting – an intelligent and potentially powerful addition to the game.

8. Would you rather spend the night in a luxury hotel room or camping surrounded by beautiful scenery?

The challenge is explaining the merits of staying at a comfortable and luxurious hotel, amidst all its amenities, and the merits of camping outdoors among nature’s simple beauty.

It’s a great ‘Would You Rather’ question, touching on players’ values about nature versus nurture, comfort versus adventure, and materiality versus experiential riches.

The forced choice between a controlled, comfortable environment and the tenuous beauty of the wild invites reflection on life preferences – what kind of vacation do you crave, and how much contact with the natural world do you need?

Moreover, framing it in this way invites us to probe the differences between relaxation as an indulgence or relaxation as a more earthy, grassroots experience, and so forth – and, hopefully, the friction and dialogue that arise thereby.

9. Would you rather give up your smartphone or your computer for a month?

This “Would You Rather” question not only brings to light individual preferences but also sparks broader debates about the evolving role of technology in our lives.

This question forces people to think about how they rely on technology, and which device they would be most dependent on.

It shows what is important to a person and how they live: whether they prefer the mobility and portability of the smartphone, or the power and functionality of the computer.

By stressing the trade-offs between the two, it forces us to consider the ways in which technology affects our productivity, our social life, and our leisure time.

Furthermore, it addresses a modern-day issue of digital dependence which renders it a conversation-worthy topic for the times we live in.

Aside from revealing personal preferences, this ‘Would You Rather’ question also opens up broader conversations about where we should draw the line in technologically enhancing our existence.

10. Would you rather be known for your intelligence or your good looks?

Reflecting on the dilemma of being publicly valued for intellect versus aesthetics hits literally close to home.

It forces players to deal with what’s hard about pressing social realities and preferences, as well as what’s hard about their own ethics and what they value enough to sacrifice.

This reflection can also lead to an opportunity for players to discuss their own experiences with the emphasis that society places on body appearance versus mental abilities.

This is a question that leads to deep discussions about the meaning of these values in personal interactions and professional prospects, and it becomes a sensitive and interesting ‘Would You Rather’ scenario.

11. Would you rather land your dream job but make just enough money, or have a terrible job that pays you a million dollars a year?

A simple question that gives players an opportunity to pit the desire to be financially comfortable against the need to be happy with their jobs, and ultimately touches upon one of the most universal questions: if you have lots of money, will you be happy?

12. Would you rather be the funniest person in the room but live an entire life with just enough money, or not be funny at all but have more money than you could ever spend?

This question is about the value of humour to a life, and how it compares with various intrinsic and instrumental goods (such as financial security).

It is a question about trade-offs between intrinsic and extrinsic goods.

13. Would you rather star in a romantic comedy that becomes a classic, or write a horror movie that becomes a cult favorite?

This question is about creative dreams and inclinations: do you want success and fame within the mainstream, or as a cult figure in a niche?

14. Would you rather have an annoying laugh that makes everyone else laugh or have a normal laugh but never find anything truly funny?

This question probes the balance between how we socialise with others, and how much we truly enjoy something.

15. Would you rather eat pizza every day for the rest of your life with your best friend or never eat pizza again but live in a real haunted house for a year?

The question pairs the pleasures of fellowship and good eating with the terror and discomfort that come from being in a haunted house, posing an unusual argument for debate.

16. Would you rather solve world hunger but live the rest of your life with just enough money to get by, or win a million dollars but you can’t contribute to any major world problems?

The question confronts players with altruism versus comfort, highlighting the global impact versus the individual.

17. Would you rather be remembered in history books as the smartest person who ever lived but have the most embarrassing moments of your life publicized, or live a quiet, exciting life where your embarrassments are your own?

This question asks players to weigh recognition and prestige against privacy and self-respect.

18. Would you rather spend your whole life working a job you hate but being able to retire early, or work at your dream job your entire life but never be able to retire?

This question challenges the very grind of life and work.

It pitches the virtues of work-life balance and long-term planning against the more immediate, visceral question of what we’d have left if we were stationary for long enough to discover it.

Are four or five or six hours of fun every day, or a weekend of pure bliss, more worthwhile than any early retirement?

Or should you try to live out your life’s ambitions, pain and all? Could you do that? Like any good question, this one will outlast the game.

19. Would you rather grow your own food in a beautiful garden but never be able to eat out again, or be able to eat at the world’s finest restaurants for free but never cook for yourself again?

It invites a reflection on how self-sufficiency relates to indulgence, between the pleasure of producing what you eat yourself, and the pleasures and realities of eating at an expensive restaurant.

20. Would you rather be your own boss but have bad breath that can’t be treated, or work for someone else but always smell amazing?

This question pits autonomy against self-cleanliness, and encourages players to weigh the benefits of autonomy against the social impact of a physical quirk that is not likely to be readily changed.

21. Would you rather have a house with a swimming pool but live alone, or live in a small apartment but be surrounded by your best friends?

This question highlights the importance of social relationships versus personal space, forcing players to debate the value of material comfort against the importance of emotional fulfilment.

22. Would you rather spend your vacations at an amusement park with a big family that argues all the time, or go on peaceful road trips alone?

The question here concerns the power dynamics of familial relationships and solitude, prompting players to contemplate how leisure activities balance the playful pleasures of the community and the calm detachment of the individual.

Would You Rather Questions Singapore

Via this entertaining series of ‘Would You Rather’ questions, participants are asked to consider, explain and describe their values, preferences, and the reasons that underlie their choices.

But each of these questions poses a challenge to prioritize between ease and adventure, societal norms and personal values, technology and relationship with nature.

In this way, each is an imperfect mirror of personalities and social thoughts alike.

Pondering through such dilemmas not only raises stimulating questions but also helps players familiarise with each other’s perspectives.

This makes the ‘silly’ game an unexpected path to unlock complexities of human psychology and social dynamics.

Frequently Asked Questions (FAQ)

If you have any questions about would you rather questions in Singapore, you can refer to the frequently asked questions (FAQ) about the Best Would You Rather Questions in Singapore below:

How do you play “Would You Rather”?

Give participants a choice between two difficult options, and have them pick the one they would rather do.

It encourages conversation and is a good way to reveal some surprising preferences or values.

Can “Would You Rather” be played with any number of players?

Yes, ‘Would You Rather’ is highly flexible.

It makes for a good one-on-one game or can be adapted for large groups as well.

It’s a great party game, a team building exercise, and an icebreaker activity.

Are there any rules for the types of questions you can ask in “Would You Rather”?

There are no hard-and-fast rules, but questions should be towards the challenging end of the spectrum – without making participants uncomfortable.

They should be respectful and pitched towards the audience.

How can “Would You Rather” questions aid in team building?

In conclusion, ‘Would You Rather’ questions are a great way to enhance team building, not just through communication, understanding and empathy, but also in creating a relaxed environment that encourages team members to share about themselves.

Where can I find more “Would You Rather” questions?

To find more ‘Would You Rather’ questions, you can search online, buy a book, or even write some yourself based on themes relevant to your group.

Rachel Tan avatar

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I'm currently the editor at FunEmpire Media. I've over 8 years of experience in the media industry discovering the best local businesses, places and things to do. From lifestyle, entertainment, food, travel, education and more, I strive to curate the very best in Singapore.

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