Would you rather questions are a fun way to get to know someone. When used as icebreakers, these questions can get the conversation started—and even help to keep it going. While the questions themselves are interesting, the answers you wind up getting along with their explanations are bound to be intriguing. Whether you’re getting to know someone while out to dinner, on a long bus or train trip, or even when chatting on the phone, these questions are a fun way to pass the time and learn more about someone new.


  • Would you rather work alone at home or work with a group of people in a high-rise building?
  • Would you rather be a helicopter pilot or a cruise ship captain?
  • Would you rather work at a job you hated by get to retire in ten years or work at a job you love until you die?
  • Would you rather make a lot of money doing something you dislike or make little money doing something you love?
  • Would you rather work indoors or outdoors?
  • Would you rather be a zookeeper or a preschool teacher?

conversation starters work

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  • Would you rather be stranded on a tropical island for a year or stranded in Antarctica for a week?
  • Would you rather travel the world by boat or by plane?
  • Would you rather spend a month in Venice, Italy or Rio de Janeiro, Brazil?
  • Would you rather take an African safari or a volcano tour of Indonesia?
  • Would you rather scuba dive in the Great Barrier Reef or go skiing in the Alps?
  • Would you rather cross North America in a Corvette or a minivan?
  • Would you rather go to Disney World or the Grand Canyon?
  • Would you rather stay in a 5-star hotel in New York City or a bed and breakfast in Provence, France?

conversation starters travel

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  • Would you rather eat your favorite food for a year or a different meal every day for a year?
  • Would you rather give up ice cream or pizza?
  • Would you rather live on McDonald’s meals for a year or Taco Bell’s?
  • Would you rather eat a fried tarantula on a stick or a handful of crickets baked into a burger?
  • Would you rather give up french fries forever or chocolate?
  • Would you rather eat only French food for a year or Chinese food for a year?

conversation starters eat

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  • Would you rather have the power to know what others are thinking or to fly?
  • Would you rather give up social media for a year or video games for a year?
  • Would you rather stop wearing deodorant for a year or stop brushing your teeth for a year?
  • Would you rather live on a farm caring for livestock or in a condo in the city?
  • Would you rather go back in time 100 years or forward in time 100 years?
  • Would you rather go to see an opera or a roller derby?

conversation starters

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  • Would you rather live on a houseboat or in a trailer?
  • Would you rather live in an old house or new construction?
  • Would you rather live without power for a week or running water?
  • Would you rather have a $50,000 new media room or a $50,000 new kitchen?
  • Would you rather all your walls be painted white or every room a different color?
  • Would you rather live in a one-bedroom apartment but have no rent or a large house but have a $3,000 a month mortgage?

conversation starters home

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  • Would you rather die in a plane crash or a sunken submarine?
  • Would you rather be buried in jungle soil or desert sand?
  • Would you rather be eaten by a great white shark or a school or piranhas?
  • Would you rather die by hanging or lethal injection?
  • Would you rather live pennilessly but make it to 100 or live rich but die at age 50?
  • Would you rather die in your sleep or when you’re awake?
  • Would you rather die from Bubonic plague or leprosy?

conversation starters death

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To Do

  • Would you rather take a yoga class or a ballroom dancing class?
  • Would you rather go skydiving or snorkeling?
  • Would you rather climb Mt. Everest or trek to the North Pole?
  • Would you rather direct a comedy film or an action film?
  • Would you rather be a tortoise or a butterfly?
  • Would you rather be friends with Harry Potter or Luke Skywalker?

conversation starters activities

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  • Would you rather bungee jump over a beach or lounge on the beach?
  • Would you rather learn how to play the violin or learn how to embroider?
  • Would you rather play miniature golf or a pinball machine?
  • Would you rather host a poker game or a wine tasting?
  • Would you rather enter a dance contest or a beach volleyball tournament?

conversation starters fun

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  • Would you rather honeymoon in Paris or the Bahamas?
  • Would you rather ride bikes with your partner in Colorado or take a walk together in a London park?
  • Would you rather have a candlelight dinner at home for Valentine’s Day or go out for a night on the town?
  • Would you rather cook for your sweetheart or order take out?
  • Would you rather have a first kiss at the beach or in front of a fireplace?

love conversation starters

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  • Would you rather get poison ivy or the flu?
  • Would you rather spend a year in space or a year never leaving your bedroom?
  • Would you rather win an Olympic medal or an Academy Award?
  • Would you rather have three eyes or three hands?
  • Would you rather have a pet python or a pet otter?
  • Would you rather win a new laptop or a trip to Hawaii?

misc. conversation starters

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