Favorite Whip-Around Questions

Activities, Communication, Engagement / /

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Trying to connect teachers – staff – and even students – can get stale.  Our team loves using whip-around to keep us connected – and constantly getting to know each other better.  Here are some of our favorite whip-around questions – and some of these are great ones for students also. Updated Apr 5, 2024!

Favorite Whip-Around Questions: Travel

  • What is one of your most memorable unplanned travel experiences?
  • Where would you live if you had to live somewhere other than where you live now?
  • Are you a beach or mountains?


  • Pineapples on pizza – yes or no?
  • What is your go to comfort food?
  • What meal makes you think of growing up or visiting “home”?
  • Favorite family recipe?

Favorite Whip-Around Questions: Would You Rather

  • Would you rather meet your family’s ancestors or your family’s descendants?
  • Do you snooze your alarm or not snooze?
  • White holiday lights or multicolored holiday lights?

Music / Entertainment

  • What is a movie you can watch again and again?
  • What new artist or music have you been listening to recently?
  • Do you like to dance? If so, what type of music?
  • When’s the last time you were at a place or event with dancing?
  • Which villain do you actually love (or somewhat like)?
  • If you could attend an NPR Tiny Desk concert by one musician/band, who would you select and why?
  • What album have you listened to in entirety?
  • Best concert you’ve been to / been to this year
  • Dream live concert (alive or passed on)
  • If you could play any part or character in a movie/TV show, who would you be?
  • Name a celebrity sighting.
  • Best all time album?
  • If you could be in a game show/reality show which one would it be?

Favorite Whip-Around Questions: Your Past

  • What are some trends or products that are nostalgic to you?
  • What was your favorite extracurricular activity growing up?
  • What is an award you got as a child?
  • Tell us about one of your childhood friends and what you learned from them.
  • What is an embarrassing moment from your childhood?
  • What is the story behind how/why your parents chose your name?
  • What is a proud achievement or accomplishment from middle or high school?
  • What did you do this weekend?


  • Are you a spoon or a knife and why?
  • What is an appliance that you can’t live without?
  • If you could go to a camp for adults, what kind of camp would it be?
  • What is an unwarranted fear?
  • What was your first paid job?
  • What is your favorite hobby you want to do when you retire?
  • Guess the height of a team member or classmate you haven’t met in person yet.
  • What is a word or phrase you know in another language? Where did you learn it?
  • What is your favorite app on your phone? Or which one do you use most?
  • What nonprofit would you choose to endorse if you could only pick one?
  • If you were speaking at a TEDx conference or something similar, what would you talk about?
  • What sound brings you peace?

We’d love to hear from you.  What are some of your favorite whip-around questions?  Email us at hello@possip.com.