Unlimited "Would You Rather" Questions With Customizable AI Generator

FlexOS "Would You Rather" is the free game you need! Pick from 300+ questions or let AI generate them for you. For work, coworkers, team building, and more.


Looking to break the ice and spark engaging conversations at a team meeting, onboarding session, or off-site?

"Would You Rather" questions, also known as "questions, are perfect for that!

Getting to know new colleagues or simply looking to have some lighthearted fun? These thought-provoking prompts are designed to inspire lively discussions and build or strengthen connections in your team.

From food choices to travel destinations, and everything in between, "Would You Rather" questions are a great variation to the typical icebreaker questions and provide a playful and interactive way to discover common interests, uncover unique perspectives, and create lasting connections. 

Plus, it's always interesting to read the explanation behind someone's choice!

Let the choices begin and dive into a world of entertaining dilemmas of:

Or if you want something truly unique, use our free AI Would You Rather Questions Generator at the top of this page.

Would You Rather Questions for All Purposes

Food and Drink

Cooking or being cooked for

Store-bought or homemade

Coffee or tea

Beer or wine

Sweet or savory

Spicy or sweet

Barbecue or vegetarian

Chocolate or vanilla

Ice cream or cake

French fries or onion rings

Tacos or sushi

Pancakes or waffles

Smoothies or juice

Coca or Pepsi

Cheesecake or tiramisu

Ramen or Pho

Ice cream or frozen yogurt

Tacos or burritos

Chocolate chip cookies or brownies

Work and Personal Would You Rather Questions

Early bird or night owl

Hybrid or remote work

Start work late or leave work early

Virtual meeting or face-to-face meeting

Introvert or extrovert

Team player or independent worker

Coffee breaks or meditation breaks

Structured routine or flexible schedule

Windows or macOS

Formal attire or casual wear

Multitasking or single-task focus

Project management software or handwritten to-do lists

Fast-paced startup or established corporate environment

Working in a quiet environment or in a bustling space

Slack emojis or memes

"Bring Your Pet to Work" days or "Bring Your Child to Work" 

Morning meetings or afternoon meetings

Solving problems independently or seeking helps

Spontaneity or planning ahead

Embracing change and adaptability or sticking to established routines

Dance uncontrollably when music plays or be forced to hug everyone you meet

Wake up with a new hairstyle every day or a new colored skin every day

Hobby and Interest Would You Rather  Questions

Vacation or staycation

Piano or guitar

Breakfast or brunch

Netflix binge or outdoor adventure

Summer or winter

Book or movie

City life or countryside

Sitcom or drama

Scary movies or romantic comedies

Singing in the shower or dancing

Camping or staying in a hotel

Pencil and paper or digital notes

Rainy day indoors or sunny day outdoors

Cooking at home or dining out

Action-packed movie or romantic comedy

Skiing or snowboarding

Facebook or Instagram

Art museum or science museum

Video games or board games

Vintage or modern style

Concert or theater show

E-book or physical book

Sunrise or sunset

Home-cooked meal or takeout

Bar or karaoke night

Black coffee or latte

Indoor workout or outdoor exercise

Rain or snow

Cloud or Rainbow

Coffee date or picnic

Reality TV or Movie

Board game night or movie night

Classic art or modern art

Morning meetings or afternoon meetings

Comedy or thriller movie

Rainy day indoors or sunny day outdoors

Live music concert or theater show

Hot weather or cold weather

Barbie  or Oppenheimer

Conan or Doraemon

Pirate or ninja

Sneaker or flip flop shoe

Classical art or modern art

Audiobook or podcast

Panda or penguin

Painting or playing an instrument

Gardening or crafting

Cooking or dish washing

Photography or writing

Yoga or zumba

Running or swimming

Travel and Adventure Would You Rather Questions

Beach vacation or mountain getaway

Flight or cruise

Hiking or biking

Camping or glamping

Skiing or snowboarding

City exploration or countryside retreat

Historical sites or natural landmarks

Adventure park or water park

Go on a solo adventure or join a group activity

Visit a museum or explore a local market

Take a scenic hot-air balloon ride or a hike to a breathtaking viewpoint

Deep Would You Rather Questions

Skydiving or bungee jumping

Pillow fight or water balloon fight

Optimist or realist

Listening to advice or trusting your instincts

Meaningful gifts or quality time

Work-life balance or work-life integration

Taking risks or playing it safe

Open book about emotions or keeping feelings private

Nature hikes or urban exploration

Cultivating a few close friendships or having a wide social circle

Mini-golf or go-kart racing

Karaoke night or escape room challenge

Trusting first impressions or giving people second chances

Embracing change or seeking stability

Be able to read minds or predict the future

Be able to talk to your past self or your future self

Be able to breathe underwater or breathe in space

Money or fame

Spend a year in the past or the future

Super strength or super speed

Eat healthy or eat whatever you want

Explore space or the ocean

Have unlimited international flights or never have to pay for food/drinks

Have your dream house or dream car

Rich and famous or rich and unknown

Camping trip in nature or a luxurious weekend spa retreat

Tattoos or piercings

Win the lottery or land your dream job

Logic or emotion

Talking or listening

Looks or personality

Coffee date or cocktail date

Night in with a book or night out dancing

Intellectual discussions or casual chitchat

Unplanned adventures or well-thought-out itineraries

Learning a new language or mastering a musical instrument

Travel alone or travel with friends

Own a house or travel the world

Live in a house or in an apartment

Have more time or more money

Be really funny or really smart

Be your own boss or work for someone else

Marvel or DC 

Harry Potter or Lord of the Rings

Be physically attractive, or be intelligent

Free will or destiny

Online Gaming or Board Games

Plan Ahead or Live in the Moment

Dine alone or watch a movie alone

Happy songs or sad songs

Break up via text or meet in-person

Tiny home or mansion

Live in one place or move around

Live alone or with a family

Laundry or dishes

Gym or spa

Meet any celebrity or travel anywhere

Pool party or bonfire

Mind reading or invisibility

Your life narrated by Elon Musk or Donald Trump

Find true love or achieve your biggest dream

Family-oriented or career-driven

Ambitious goals or contentment with the present

Financial stability or life's adventures

Embrace your single status with confidence or seek opportunities for meaningful connections

Solo road trip to an unknown destination or a guided group tour

Spa day or solo movie

Try a new workout routine or indulge in a spa day

Experiment with a new recipe at home or treat yourself to a fancy dinner

Yoga on the beach at sunrise or meditation in a tranquil garden

Set personal goals for the next year or focus on career aspirations

Plan a solo travel adventure or explore options for finding a partner

Invest in personal growth or explore new social activities

Embrace your single status with confidence or seek opportunities for meaningful connections

Focus on self-love and self-care or be open to the surprises that life brings

Celebrate your individuality and unique journey or look forward to sharing experiences with a partner

Camping trip in nature or a luxurious weekend spa retreat

Movie marathon with popcorn or a board game night

Cooking a meal together or ordering takeout

DIY home project or hiring a professional

Play a favorite childhood game or watch a classic movie

Go for a scenic hike or a leisurely bike ride

Attend a live music concert or an art gallery opening

Give up feeling free or give up feeling secure

Never eat chocolate again or never see your best friend again

Give up your biggest passion or give up your fondest memory

Would You Rather Questions for Couples

Funny or romantic

Tall or short

Long hair or short hair

Optimistic or practical

Rich or loyal

Movie buff or music lover

Foodie or fitness enthusiast

Travel lover or homebody

Gamer or moviegoer

Texter or caller

Deep conversations or lighthearted banter

Great listener or storyteller

Expressive with emojis or concise with words

Social media lover or tech-free enthusiast

Flirty compliments or playful teasing

Supportive partner or independent partner

Public displays of affection or private moments

Netflix and chill or adventurous outings

Shared interests or learning from each other

Communicate daily or enjoy some space

Travel the world together or build a home base

Shared dreams or individual pursuits

Collaborative projects or separate hobbies

Classic romantic gestures or unique surprises

Fancy restaurant dinner or casual picnic

Surprise gifts or heartfelt handwritten letters

Explore local attractions or spontaneous road trips

Fancy dinner at a five-star restaurant or a cozy movie night at home

Beach sunset stroll or a hike in the mountains

Attend a music festival or a romantic art gallery opening

Spa day or solo movie marathon

Read a book at a coffee shop or take a scenic bike ride

Relaxing bubble bath or outdoor yoga session

Attend a motivational seminar or take up a new hobby

Solo travel to an unfamiliar destination or explore your own city like a tourist

Sign up for a skill-building workshop or volunteer for a cause you care about

Attend a solo karaoke night or a networking event

Engage in a conversation with a stranger or enjoy a quiet coffee alone

Attend a singles' mixer or a themed costume party

Movie night with your favorite genre or explore something entirely new

Attend a comedy show or an improv performance

Go to a live music concert or watch a theater production

Fancy dinner at a restaurant or a cozy homemade meal

Movie night at home or tickets to a live theater show

Go dancing or enjoy a leisurely walk

Explore a foreign country or rediscover your hometown together

Write love notes or exchange playful text messages

Have a deep conversation or share lighthearted anecdotes

Give surprise gifts or plan a surprise date

Host a big anniversary party or plan a quiet getaway

Celebrate with a fancy dinner or a cozy picnic

Attend a live show or a sports game for a special occasion

Recreate your first date or try something entirely new

Have a standing movie night or try a new activity each week

Celebrate milestone events with a fancy night out or a heartfelt homemade gift

Plan dream vacations or focus on career aspirations together

Set goals for a personal hobby or work on joint projects

Continue exploring new adventures or embrace familiar routines

Attend personal development workshops together or pursue individual interests

Explore new hobbies together or encourage each other's passions

Support each other in personal challenges or embark on a joint fitness journey

Revisit favorite travel destinations or explore new ones

Exchange playful banter or share heartfelt compliments

Dance in the living room or cook a meal together while wearing silly aprons

Take candid photos together or exchange funny selfies

Look through old photos or watch home videos

Recreate a memorable moment from your early relationship or make new memories

Reflect on your journey together or envision your future dreams

Hard Would You Rather Questions

Wear a chicken suit for a day or wear a clown wig for a week

Dance like nobody's watching or sing like nobody's listening

Have the ability to talk to animals or speak every language fluently

Travel in a time machine to the past or future

See the future or change the past

Have the ability to breathe underwater or have the ability to fly

Dress as a superhero in public or wear a banana suit for a week

Meet an alien or mythical creature

Smartest person in the world or richest person in the world

Second chance at love or second chance for your career

Time freeze or teleportation

Explore space or the deepest ocean

Meet your childhood hero or your current celeb crush

Meet a bigfoot or a mermaid

Know how you die or when you die

Die in 10 years with no regrets or live for 30 years with lots of regrets

Lose all of the money you earned this year or lose all of the memories you made this year

Get stranded by yourself on a desert island or stranded on a snowy mountain

Live in a world with dinosaurs or a world with giants

Live on a hot air balloon or on a pirate ship

Live in an alternate universe where everything is the opposite of what you know, or live in an alternate universe where you know nothing

Try a food you’ve never tasted or read a book from a new author

Go into the past and meet your ancestors or go into the future and meet your great-great-grandchildren

Have unlimited free food at any restaurant for the rest of your life or unlimited free flights anywhere for the rest of your life

Spend 10 minutes on the moon or 2 weeks paid vacation in Europe

Buy a beautiful cozy home to live with your soulmate or travel the world with your soulmate

Rich friend or loyal friend

Forget everything you’ve ever learned, or forget everyone you’ve ever known

Face your biggest fear or spend a week with the person you dislike the most

Lose all thought or lose all feeling

Never be able to cry again or never be able to laugh again

Setting Relationship Goals or Going with the Flow

Lose your hair or your sense of smell

Spider-Man or Iron Man

Write a bestselling novel or star in a blockbuster film

Have a clown follow you everywhere or narrate your life out loud in a funny voice

Be able to instantly change your appearance or have the power of super speed

Eat a jar of mayonnaise or mustard

Wear a pirate costume or clown costume everywhere for a month

Go back in time to change a past regret or go into the future to see your destiny

Erase the most painful memory or relive the happiest day

Sacrifice your life to save a stranger or sacrifice a stranger's life to save your loved one

Wake up on a random continent or as a random animal each day

Sacrifice wealth or sacrifice wisdom

Never travel again or never learn anything new again

Give up social media forever or give up hugs forever

Never eat your favorite food again or never hear your favorite song again

Always tell the hurtful truth or never be able to express your true feelings

Eating spicy foods makes your head literally explode or eating sweets makes you float away

Never allow yourself to feel jealous and envious or never allow yourself to feel sad and lonely

Give up experiencing romantic love or give up your closest friendship

Give up inner wisdom or outer beauty

Lose the ability to trust others or lose your optimism about the future

Never be able to ask for help when you need it or never be able to offer help when others need it

Never experience heartbreak again or never experience true love again

Turn into a giant blueberry when sad or turn into an avocado when angry

Give up experiencing passion or give up experiencing peace

Never be able to ask for help when you need it or never be able to offer help when others need it

Would You Rather Questions: Commonly Asked Questions

Where should you play Would You Rather ?

“Would You Rather” icebreaker games are perfect for scenarios where we want to get to know others better in a fun and casual way. Some common places and situations where the game is played include:

  • During team building activities at work - Employers and team leaders may facilitate 'Would You Rather' games to help coworkers find common ground and build relationships. It promotes bonding and friendship between colleagues. 
  • At parties, gatherings, events - Playing 'Would You Rather' can help break the ice and get conversations started between people who may not know each other well. It's a simple and engaging game that can set a fun, lighthearted tone.
  • In classrooms and student orientations - Teachers and professors sometimes use 'Would You Rather' questions to help students learn more about their classmates at the start of a term. It's a way to foster connections within a new group.
  • On first dates - People on first dates often use simple 'Would You Rather' questions as a way to discover common interests and break the ice during an otherwise potentially awkward situation.
  • At camps or retreats - Group leaders at camps, church retreats, or other social outings can utilize 'Would You Rather' games to help participants open up and find things they have in common.
  • On long drives or trips - Playing 'Would You Rather' during road trips or long drives is a great way to pass the time and learn more about travel companions.
  • Online through messaging or video chat - Virtual 'Would You Rather' games are popular online and over messaging/video chat platforms as a way to break the ice and get to know someone new.
Visit our best virtual meeting platforms for your remote team meetings and slice up team engagement

Briefly, Would You Rather is commonly played in casual social situations where forming new connections with others is the goal! The simple questions spark fun conversations and reveal shared interests or experiences.

What are similar question games?

Would You Rather questions are often referred to as Either/Or questions and are similar to Would You Rather questions, Yes/No questions, and Rapid Fire questions. 

While the formats differ slightly, all of these question games work well as icebreakers or party games. The goal of all these formats is to encourage interactive, energetic dialogue that reveals tidbits of information about the other person while keeping the mood fun and conversational. For example:

Either/Or Questions:

  • Mountains or beach vacation
  • Marvel or DC movies
  • Tea or coffee
  • Early bird or night owl

Would You Rather:

  • Would you rather be able to fly or become invisible?
  • Would you rather never use social media again or never watch TV again?
  • Would you rather explore space or the ocean?

Yes/No Questions:

  • Do you like spicy food?
  • Have you ever broken a bone?
  • Can you play a musical instrument?
  • Did you grow up in a big city?

Rapid Fire Questions:

  • What is your favorite color?
  • What is your favorite food?
  • What is your favorite movie?
  • What is your favorite song?
  • Dogs or cats?
  • Introvert or extrovert?
  • Beach or pool?
  • Cook or order takeout?

A final note

As we work more distributed than ever, you may wonder how to engage remote employees.

I suggest employing employee engagement strategies to keep your team working well together regardless of location. Practices employee engagement best practices and use employee engagement tools to excel. For the best results, consider working with employee engagement survey providers or using employee survey tools.

You can also deploy various employee engagement activities, like asking Would You Rather Questions, Icebreaker Questions, 5-Minute Team Building Activities, and Virtual Team Building Activities. (For big teams, split them with this Random Group Generator.)

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