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.


1. Work

  • 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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