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How to Have Meaningful–But Effortless–Holiday Conversations

This one simple trick can be a great way to get the conversation flowing–without judgment.

A group of young adult friends sharing a happy meal.

Let’s face it: holiday conversations can be awkward, difficult, or downright painful. And although boundary setting is important, in the end we can’t control other people. One thing we can do, though, is to come into potentially challenging situations prepared to do our part. Here’s one of my favorite simple–yet effective–conversational strategies that you can use to get the conversation flowing deeply and with ease.

Consider this: a game of “Would you rather?” with an emphasis on exploration. When done with young kids, this game is often played with silly ideas: “Would you rather wear your pants backwards all day or tie your shoes together?” Switching up the game a little, by asking adults to chose between two positive or neutral things can be a disarmingly fun way to understand people’s core values better.

Try asking questions like these: 

Would you rather be able to fly or be invisible?

Would you rather go back to elementary school or back to high school?

Would you rather give up books or movies?

Would you rather have free time on a sunny day or a rainy day?

Would you rather hang out with people a decade older than you or a decade younger?

The next question, of course, is often: Why? If you can go into this game with a spirit of understanding (not one of convincing people to change their minds) you might find that we can learn a great deal about who others are at their core. The key is to ask questions to which there are no perceived right or wrong answers. No politics or religion, please; veer towards personal opinions and experiences. Whatever the person answering says is the “right” answer–although you might find others sharing why they would answer differently, and this can be fun!

If you’re having trouble getting a person to engage, sometimes it can be helpful to ask them a silly or obvious (to them) question:

Would you rather have to watch football every day for the rest of your life, or never watch it again?

Would you rather be locked in a room with spiders or snakes?

Would you rather eat a salty snack or a sweet one?

One of the things I especially love about this game is that it can be adapted for all ages–and in fact, can be a fantastic way to get people of all ages engaged in conversation together. No matter how long our shared history with people, they can always surprise us. Giving people the opportunity to share what is in their hearts in a fun and low-pressure way can be a delightful way to spend time at the holiday table together.

May your conversations be filled with connection and ease.

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