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20 questions: Conversation starters to keep the party lively

Friends at a holiday party

Foolproof questions to keep the conversation flowing

Being with people can be exhausting, even (or especially) people you love. Being with people means you have to talk. And the holidays are all about being with people. It can get to be a drain of psychic energy, especially for introverts, to constantly have to think of things to say.

Thankfully, there are plenty of creative conversation starters to jazz up holiday socializing, even if you dread small talk more than you fear Aunt Agnes’ Jell-O mold.

These 20 prompts will help keep the conversation interesting without treading into unpleasant territory. (For more on that, check out Keeping the peace at the holiday dinner table.) One little reminder: No matter how desperate you are, don’t bring up politics. 

20 topics to get you going

  1. Where did you grow up? As they say, everyone grew up somewhere, and has an infinite supply of stories about their hometown.
  2. What is your dream job?
  3. Have you ever met anyone famous? Or, if you could meet one famous person, who would it be?
  4. Ask about their favorite books, movies and albums of all time. People are passionate about their favorite media. And the best part is, you’ll get to share yours too.
  5. What is the worst movie you’ve seen recently?
  6. If you could have any superpower, what would it be?
  7. Pay a compliment, the more genuine the better. And think outside the box. Do you like the way they talk? Their personal style? Their sense of humor?
  8. What popular trend most annoys you?
  9. What was your favorite subject in school and why?
  10. Tell them about a recent news story you found fascinating –  that could be the truck full of eels that overturned on the highway, a Florida horse rider charged with a DUI. Then, ask them to share one of their favorites. It’s a weird world out there.
  11. What was your all-time favorite vacation and why? And where are you still dying to travel?
  12. What’s your sign, and do you believe in astrology?
  13. What’s your favorite word? Best-case scenario, the whole table chips in and you learn a bunch of new words.
  14. What was your favorite toy as a child?
  15. Do you believe in ghosts… and have you ever seen one?
  16. Ask about their pets. There is roughly a 100 percent chance they’ll pull out their phone and start showing you pictures. So not only do you have something to talk about for a few minutes, but you also get to see some cute animal photos.
  17. What is your guilty pleasure?
  18. Who is your oldest friend, and how did you meet them?
  19. If you could invite one famous person to this Thanksgiving dinner, living or dead, who would it be? Make sure to have your own answer ready, and be more creative than Jesus or Gandhi (my go-tos are Oscar Wilde and Rasputin).
  20. What do you feel most grateful for this Thanksgiving?

When all else fails, bring out the party games: Party games do the work of socializing for you – a blessing for introverts like me.

You’ve got your timeless classics – charades, Jenga, Apples to Apples, etc. If your family is as weird and irreverent as mine (which is to say, very weird and irreverent), you might get a kick out of Cards Against Humanity, a party game for horrible people. The goal of the game? To fill in the blanks with the worst, most evil and offensive answers possible.

This game made for the best Thanksgiving I’ve ever hosted (although it came at the expense of hearing my dad say some things I’ll never be able to unhear).

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