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Sure-Fire Ice Breakers to Help Spread Holiday Cheer

Published on November 22, 2022

By Ken Lovering, Travel Writer

There are few things more awkward than the dreadful silence that sometimes hangs over the holiday office party or neighborhood secret Santa exchange. To avoid those moments of uncomfortable shoe-gazing while that guy from the marketing department launches into yet another riveting description of next week’s weather forecast, we’ve got a few suggestions.

A group of people, both young and old, are gathered around a table enjoying a festive meal together, with various dishes and drinks visible in the foreground, and a cozy, rustic interior setting in the background.

There are few things more awkward than the dreadful silence that sometimes hangs over the holiday office party or neighborhood secret Santa exchange. It’s that horrible moment when two people who know they’re supposed to have something interesting to say suddenly… well… don’t. To avoid those moments of uncomfortable shoe-gazing while that guy from the marketing department launches into yet another riveting description of next week’s weather forecast, we’ve got a few suggestions. These conversational ice breakers will not only keep you from falling asleep around the punch bowl but will also help you learn a few interesting things about your colleagues—and you might even make a few new friends along the way.

What’s the most beautiful place you’ve ever biked?

This question may or may not lead to a conversation about travel. Maybe you’ll discover that Al in accounting frequently cycles along a scenic bike trail in his hometown. Or perhaps you’ll learn that, to Carol in engineering, beauty is more anchored in memory than in nature. No matter – it all makes for great fodder for reminiscing and sharing.

If you could have one cycling experience tomorrow, what would it be?

The Giro d’Italia … a ride across America … night riding through Paris. No matter the answer, you may find the eyes of Ryan in human resources become a touch misty as he launches into a wistful treatise about dreams and possibilities.

What’s the most exciting trip you’ve ever taken?

Like beauty, excitement is in the eye of the beholder. This is where you might discover how much exhilaration Mary in accounts payable is willing to pursue. Does she rank skydiving at the top of her list? Or was it the time she took a leisurely barge cruise past the windmills of Holland?

What’s the most memorable restaurant you’ve visited on your travels?

With this one, you’ll get a real sense of what makes a dining experience important – the food, the setting, or the originality? Michelin-starred restaurants might be the top of the heap for Jeff in sales, but too hoity toity for Sarah in operations. Maybe that burger at the tree house restaurant was a sublime experience for Mark in legal—or the savory pho in a tiny eatery in Hanoi. And Janice, the general manager, simply will not stop talk about that hot dog at Coney Island. That’s a great excuse to visit the drinks table again.

Electric assist or not? Go!

You might find that folks fall into three camps here: the purists who will forever rely on their own power, the hybrid riders who see the value of having a little help now and then, and the trend-setters who would never dream of giving up the motor. This could lead to a lively debate!

If you were a guide in your hometown, where’s the first place you’d show me?

Here’s where you’ll learn all about the favorite haunts of Maria in tech support—including a scenic bike path strewn with flowering azaleas, the white marble columns of the local library, and the region’s best sushi restaurant. Her phone number? That’s another question entirely.

Where are you planning to travel next?

Yes, this is also a question for you! Whenever you’re planning your next bicycling vacation, we hope you’ll join VBT. And if you’ll be seeing friends and colleagues at office parties and events, invite them along! Happy Holidays!

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