Great sleepover questions & conversation starters

Written by our Gather teen ambassador, Noor Skhiri

Are you tired of having the weird, awkward moments at the beginning of sleepovers? These sleepover conversation starters will fill you with joy and excitement and kickstart the party! So if you’re ready to have some epic sleepovers, use these sleepover questions ASAP.

15 Epic Sleepover Questions for Great Sleepover Conversations

  1. Who was your first crush?

  2. Would you rather be an amazing snowboarder OR an amazing surfer?

  3. If you won the lottery, what would you do with the money?

  4. What was your most embarrassing moment?

  5. Would you rather spend one day around people but without your phone OR spend a day completely alone but with your phone?

  6. What is your go-to song when you want to jam out?

  7. What was the very last thing you texted someone?

  8. Would you rather lose three friends OR gain three enemies?

  9. What are the last five pictures in your camera roll? Show them to your friends.

  10. What is something you’ve tried but would never do again?

  11. Would you rather be caught picking a wedgie OR picking your nose?

  12. If you could go back in time and change one thing, what would that be?

  13. If you were “ruler of the world” for just one day, what would you do?

  14. Who is your celebrity crush?

  15. Would you rather become a TikTok star OR an Instagram influencer?


If you liked these sleepover conversation starters and you’re looking for more sleepover questions, try the Gather conversation app for thousands of great conversation starters, recently named “App of the Day” by Apple - only available on iOS!

Madison McClung