The Five Best Conversation Starters for Your Holiday Gatherings

Awkward holiday silences and uneasy conversations have a way of cutting your well-planned party short. Armed with the right conversation starters, you could be the one who saves the party. Here’s how to show up prepared to set the tone and change the vibe of the entire gathering.

Ask an “if you could” question.

“If you could have named yourself, what name would your name have been?” Have others in the room guess the answer. Is Mildred, with her velvet tunic and sparkle jeans, secretly wishing she were known as Kim? Half the fun is the guess.

Give a compliment that leads into a question.

“Your cozy turtleneck sweater looks so comfy, Aunt Garnet, and your cookies taste just like I remember. Is this what it was like at your home when you and Mom were little?” A little trip down memory lane is not only fun for you, but a good history lesson for the kids. Just look out for dueling details. “The room wasn’t painted blue, it was periwinkle.”

Purpose a silly “What if” scenario.

“What if people could hear each other’s thoughts?” Sure, you may be hit with, “Then they'd know to be quiet when I'm trying to watch the game,” but it’s worth a shot. Maybe keep this one for the kids to try. “What if jeans were never invented,” might be an easier starting point.

Break up the dicey conversations with a soft sleeve.

“Have you ever felt anything so soft?” you ask, jutting your cashmere sweater-clad arm between the escalating voices. Nothing like a good cashmere sweater to change the focus. You could even tell them all about how you ordered it online from Lands’ End. Share one of our favorite service stories, like how we found a wedding ring in the pocket of a returned robe and shipped it back to the frantic bride. Whew, crisis averted.

Sure, they’re not the best conversationalists. However, the people you gather with during the holidays are the same people who continue to gather with you every year of their lives. That kind of devotion is rare. Rest assured, there will be times in life when you need someone to sit quietly with you. In those moments, you will learn to truly value their holiday hush.

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