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Festive icebreakers to spark conversation this holiday season

FESTIVE ICEBREAKERS TO SPARK CONVERSATION THIS HOLIDAY SEASON

Penelope James   |   Fri, 20 Dec 2024

The holidays: a time for family, friends, and… the crushing pressure to bring someone home to meet your Great Aunt Mildred. Okay, maybe not crushing pressure for everyone, but let’s be real, dating during the holidays can feel a little extra. Between the festive parties, the constant barrage of holiday rom-coms, and the inevitable are-you-seeing-anyone-type questions from well-meaning relatives, it's easy to feel the pressure.
But fear not, fellow singles! Because while the holidays can add a layer of complexity to the dating game, they also offer a wealth of opportunities for fun, festive first dates. And to help you navigate those first-date jitters (especially the ones fueled by extra eggnog), we've got some icebreakers that are guaranteed to spark conversation and maybe even a little holiday magic.

Deck the conversation with these icebreakers

If you’re sure your date celebrates a winter holiday during December, nothing beats classic holiday-themed questions as a way to break the ice. They’re great go-tos for setting a light and festive mood.

  • Try asking, “What’s your favorite holiday tradition?” This opens the door for sharing personal stories and creating a connection.
  • Another great one is, “What’s the worst holiday gift you’ve ever received?” This is guaranteed to get some laughs and a chance to bond over shared experiences (we’ve all been there, right?).
  • For a bit of lighthearted debate, you could always ask, “Die Hard: Christmas movie or action movie?” This classic question can reveal a lot about a person’s personality.
  • A great way to talk about music is to ask "What is your favorite holiday song and why?"
  • If you want to inject some playful banter, try some “would you rather” questions with a holiday twist. For example: “Would you rather spend the holidays at a ski lodge or on a tropical beach?” This can spark some fun conversation about travel preferences. Another good one is, “Would you rather only be able to listen to holiday music or never listen to it again?” This one’s sure to get a strong reaction!
  • Foodies might want to ask, "If you had to choose one holiday dish to eat every day for the rest of your life, what would it be?”
  • To show you’re present and engaged in the moment, try some shared experiences and observational humor. Joke about the over-the-top decorations you’re surrounded by or the festive ugly holiday sweater your waiter is wearing.
  • Finally, you could also ask, “Have you seen any good holiday light displays around the city?” This is a great way to suggest a future date if things are going well.

A few words of caution

While it’s great to embrace the holiday spirit, remember that it’s still a first date. Steer clear of overly serious topics like past relationships or intense family drama. Keep the conversation light, fun, and focused on getting to know each other.
So, there you have it! With these festive icebreakers in your arsenal, you'll be well on your way to a successful and enjoyable holiday first date. Now go forth, spread some holiday cheer, and maybe even find a little romance under the mistletoe.


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