73 “Would You Rather” Questions to Break the Holiday Ice
The holidays are the ultimate occasion to catch up with loved ones you haven’t seen for a while—and to get to know the people they love, too. But it can be hard to know where to start. If you want to engage with your stressed-out niece without asking her about college or put your new in-laws at ease, pull up this list and let the conversation flow. Some of these questions are funny, some philosophical, and a few are flat-out weird. But all are appropriate for blended families and multiple generations, and will stave off boredom, keep the peace, and help you bond with just about anyone.
Would you rather...
Be a contestant on Survivor or Love Island?
Have to eat the same dish for every meal for the rest of your life or wear the same outfit every day for the rest of your life?
Have the voice or the hands you had when you were 3 for the rest of your life?
Give up sugar or salt for life?
Watch a movie version of your life directed by an acclaimed documentarian and praised by critics for its extreme accuracy or watch the blockbuster version, with a star-studded cast and a lot of creative liberties?
Get an all-expense-paid trip to Paris or Patagonia?
Speak every language fluently or know the knowledge contained in every published book?
Teleport or read minds?
Suddenly be elected a senator or suddenly become a CEO of a Fortune 500 company?
Wake up each morning to find that a different random animal appendage has replaced your non-dominant arm or permanently replace your bottom half with an animal bottom of your choice?
Trade places with Oprah for a day or get to spend a day with Oprah?
Be way overdressed or way underdressed?
Meet your ancestors or your descendants?
Travel 100 years into the past or 100 years in the future?
Live without clocks or without mirrors?
Be able to breathe underwater or fly?
Have a remote control for your emotions or for other people’s decisions?
Have to speak only in rhymes or have to sing everything you say?
Have an endless personal library or an endlessly bountiful garden?
Have a hat that could teleport you home or shoes that could walk on any surface, including water and walls?
Be able to play any instrument you pick up or perfectly replicate any singer’s voice you hear?
Be the best player on a team that always loses or the worst player on a team that always wins?
Be able to see through any lie or have everyone believe everything you say?
Run for office or run a marathon?
Bring your favorite fictional character to life or enter your favorite fictional world as a minor character?
Be able to show your dreams to others like movies or have a perfect memory?
Have a name that nobody can pronounce correctly or a name that everyone spells wrong?
Have the power to change your hair color or your eye color at will?
Travel back in time to San Francisco in the Summer of Love or to Paris in the Roaring Twenties?
Give a TED Talk or host SNL?
Have a self-cleaning house or a self-filling fridge?
Have perfect recall of names or a perfect sense of direction?
Have your sneezes sound like an air horn or your laughter sound like a duck’s quack?
Eat exclusively at Michelin-starred restaurants or have only home-cooked meals for the rest of your life?
Live in a home designed by a world-famous architect but with bare walls or an extremely average home with incredible art on the walls?
Spend a night in a luxury hotel room or in a cozy treehouse with stunning views?
Have the ability to fall asleep as soon as your head hits the pillow or wake up immediately and happily at the first ring of your alarm?
Be renowned for a breakthrough scientific discovery or for writing a transformative piece of literature?
Teach a subject you love to uninterested students or a subject you dislike to passionate students?
Relive the same day for 365 days or lose a year of your life?
Be a roadie on a tour with your favorite band or an extra on a season of your favorite show?
Live the life of any historical figure for a week or bring any historical figure to live in the current time for a week?
Be a beloved comedian or a respected actor?
Have a personal chef or a personal masseuse?
Have an amusement park to yourself (and 10 guests) for a day or have a weeklong free holiday on a private beach?
Remember every important date (birthdays, anniversaries, appointments, etc.) or never forget where you put things?
Eat only very spicy or only very bland food?
Swim in a pool of warm spaghetti or of dry beans?
Win a Pulitzer for a book you plagiarized from a starving artist or the lottery winnings from a ticket you stole from a single working mother?
Get a tattoo of your celebrity crush’s name on your neck or your least favorite band across your knuckles?
Have a little gnome who makes you answer a riddle in order to use your television or a squirrel who follows you around and constantly steals all your pens?
Walk around with a parrot on your shoulder that gives you empty compliments or a monkey on your back that gives constructive criticism?
Compete on American Idol or on Top Chef?
Have a sidekick who’s a sarcastic talking cat or a loyal but forgetful dog who wears glasses?
Have all your devices stuck on max volume or always have to type in caps lock?
Have fingernails that change color based on your health or hair that changes length based on the weather?
Whistle like a teapot as soon as you reach a certain level of hunger or have a short lullaby play when you reach a certain level of sleepiness?
Become a travel influencer with millions of followers or the CEO of a successful nonprofit organization?
Have the most gorgeous cursive handwriting in the world or a perfect transatlantic accent?
Be born into the British royal family today or 700 years ago?
Brush your teeth with hot sauce or gargle with pickle brine?
Never have anyone celebrate your birthday or be serenaded by the birthday song every time you eat at a restaurant?
Never have a bad-hair day again or never have to shave again?
Live in a cozy cottage by the sea or a chic penthouse in the city?
Magically have an umbrella whenever it starts to rain or have your shoes magically transform into sneakers when you’re in a hurry?
Have to do the worm in any situation where people are dancing or have to loudly sing along whenever someone near you starts singing?
Be missing the last page from every book you read or the last piece of every puzzle you (almost) finish?
Receive one gift you love or 10 gifts you like?
Be a perfect singer but only in the shower or never miss a basketball shot but only when no one is watching?
Start hiccuping uncontrollably whenever you get angry or sneezing uncontrollably whenever you get scared?
Have dinner with Julia Child or Ratatouille?
Travel across the country in a horse and buggy or by tricycle?
Be a musical prodigy or a pro athlete?
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