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Friends toasting to the holidays

20 Great Holiday Conversation Starters to Break the Ice and Connect with Anyone

The holidays are a time for family, parties, champagne, and fun (well, fun if you have champagne).

Whether it’s a party with family at Christmas Eve, the company holiday party, or a get together with friends and acquaintances, one thing is for certain: you probably have a lot more opportunities for small talk over the holidays than you typically would any other time.

That’s why, no matter where you are over the holidays or who you’re with, it can be useful to have some handy conversation starters to make sure no conversation ever starts– or goes– dull.

The right conversation starter can spark hours of lively discussion in the right people, helping you kick it off with someone new, build new bonds with coworkers, or just have a blast with family.

Note: If you’re still looking for the perfect gifts for anyone in your life, be sure to check out our inspiring and silly White Elephant gifts and stocking stuffers for under $20.

It's nice when there's stuff in the middle of the table. That's when the best conversations start to happen.

– Daniel Humm

Here are twenty holiday conversation starters to help you make the holidays a time of less anxiety and more good cheer.

20 Holiday conversation starters

  • How do you shop for gifts for the holidays?
  • How do you stay sane during the holidays?
  • What are you looking forward to for next year?
  • What is the coolest gift you’ve ever given someone and why?
  • What is the coolest gift you’ve ever received and why?
  • What’s the best unused business or product idea you’ve ever had? Or an idea you had that you realized someone had already come up with?
  • Who’s the best, or coolest, person you met all year?
  • What’s the most exciting thing that happened to you this year?
  • What’s the most dangerous thing that happened to you this year?
  • What book is sitting on your figurative nightstand right now?
  • What do you think about the holidays? Do you love the lights and bustling December mall vibe or think there’s too much commercialism?
  • What happened this year that you’re grateful for?
  • If you could talk to anyone in the world right now, who would it be and why?
  • What kind of a holiday decorator are you?
  • What do you want for Christmas this year?
  • If you had an hour of free time right now how would you spend it?
  • What is your favorite thing to do with your family over the holidays?
  • What is your New Years resolution?
  • Are the holidays a fun time for you or a drag? (This question is less fun than some others, but many don’t have great holiday memories, so it’s not a particularly happy time for them. But this is great for going deep quickly if they say it’s a drag. If they say it’s a happy time use the follow-up question below.)
    • What is your favorite holiday memory?

Conversation tips for the holidays

Remember not to just leave it at these questions. These are starters, so follow up your question by asking them to tell you more or offering your own view or answer and then following that up with another question.

And don’t make it all about you asking questions. People don’t like feeling like they’re being interrogated, so balance listening with speaking (yes, it’s actually good to talk– you’re not interviewing them!).

Having said that, be the best listener you can be while they’re talking. Most people converse in a way where they’re just waiting for their next chance to speak. Have you ever had a conversation with someone like that? You hate talking to people like that, right? Everyone does, so don’t be that guy or gal.

Overall, just enjoy yourself. Many of these conversation starters are tons of fun if you’re talking to someone receptive so you’ll soon find yourself having a blast, deep in a more effortless kind of conversation in no time.


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