2023 Holiday Conversation Starters

Say goodbye to mindless chit-chat with our favorite questions sure to spice up any holiday gathering this year.

Looking back

  1. What was your favorite part of the holidays as a child?

  2. Who’s the most memorable person you’ve shared a holiday meal with? 

  3. What’s the worst gift you’ve ever gotten?

  4. What’s the strangest thing you learned this year?

  5. What moment from this year you’d love to relive?

  6. What’s the single best thing you ate this year?

  7. What’s a common phrase you found out you say incorrectly?

  8. What song most makes you feel like you’re 18 again?

  9. Which movie from 2023 deserves a sequel?

  10. What’s the best nap you’ve ever taken?

  11. What’s the weirdest dream you had this year?


  1. What’s an irrational fear you have?

  2. How do you get into your car? Foot first, butt first, or head first?

  3. Do you eat corn on the cob across or around?

  4. Cutlery in the dishwasher; pointing down or up?

  5. Do you wet your toothbrush before you add toothpaste or after?

  6. What’s the most annoying trait you’ve inherited and who did you inherit it from?

  7. Do you actively wash your legs in the shower or let the soap run down?

  8. What’s your favorite conspiracy theory (even if you don’t believe it)?

  9. Spoon or fork with mac and cheese?

  10. What’s the most overrated film of all time?

  11. Does your cheese grater have a home in your kitchen or does it always go somewhere different?


  1. Which concert are you going to: Taylor Swift’s Eras or or Beyonce’s Renaissance?

  2. You just got tickets to your dream sports event. What is it?

  3. What’s a job you’d be great at but absolutely hate?

  4. What jeopardy category would you win every time?

  5. You’re starting a podcast. What’s the topic?

  6. What’s the first thing you’re buying after you win a $10M lottery?

  7. Would you rather be able to speak all languages or speak to animals?

  8. What kind of plant would you be and why?

  9. Would you rather fly at 10mph or run at 100mph?

  10. Which journalist would you let share your life story? 

  11. If you could only eat three things for the rest of your life, what would they be?

  12. You can snap your fingers and have one nice skill. What is it?

  13. What kind of house pet would you be? Include breed and where you’d live.

  14. At this table, who would win Squid Game?

  15. What cartoon character would want to be stuck on a desert island with?

  16. What kind of fish would you be and why?

  17. What reality TV show would you thrive on?

  18. Which family member would make the best politician?

  19. Who would win in a street fight: Ratatouille or Stuart Little?

Looking ahead

  1. Who will be Time’s 2023 person of the year?

  2. What's a new skill you want to learn next year?

  3. Who will stage the best comeback in 2023?

  4. Make the case for optimism in 2024.

Prefer the list in your email?

Share your email and we'll send you a printable version of the list.