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5 Questions for Endless Holiday Conversations

Bart Kloosterhuis

Reconnect with friends, family, and colleagues: 5 questions to start endless conversations during the holidays

Whether you’re a fan of the holiday season or not, we can’t ignore the fact that during the last few months of the year, TONS of people spend LOTS of time, money, and attention on it.

In fact, the 'holiday season' seems to start sooner every year. When summer is over, department stores are decorating their display windows already! Candy canes, stockings, Christmas trees, you name it…

This increasing focus on the holiday season causes “holiday anxiety”. Where does this stress come from? I personally don't think it comes from worrying about eating, drinking, decorations, and presents. I think that it stems from our desire to experience memorable moments with the people that are dear to us.

These days, moments of genuine attention with our loved ones are often disrupted and becoming less frequent. We seem to increasingly lose ourselves in our phones and laptops instead of in a good conversation.

But wait!

There is a simple way to connect: asking the people you care about thoughtful, inspiring questions. Luckily for us, the holiday season is a wonderful time to spark connected conversations with your friends, family and colleagues...without phones!

In this post, I'll share five questions from the Vertellis Holiday Edition that you can ask whenever you're craving a playful, deep, and/or personal chat. Perfect for giving more meaning to holiday gatherings!

5 Questions to Start Endless Conversations During the Holidays

1) What are the three things that gave you the most energy?
2) With the knowledge you have now, what would you have done differently?
3) By this time next year, what do you want to have achieved?
4) What has kept you up at night?
5) What will you do for the first time in your life?

1) What are the three things that gave you the most energy?

This is a good, positive question to break the ice and get everyone chatting. We frequently have a habit of focusing on everything that didn’t go as planned and thus has cost us energy.

By asking what has given you the MOST energy, you encourage the other person to look at things from a different perspective. Hopefully, he or she will keep these 3 things in mind for next year (and it might give you some ideas, too…).

2) With the knowledge you have now, what would you have done differently?

This is the ultimate question for reflection.

Reflecting is a powerful way of acquiring insights into yourself while generating more happiness and self-esteem. By asking this question, you can look at “mistakes” from your past as valuable learning experiences that made you smarter!

3) By this time next year, what do you want to have achieved?

Even if you're not a fan of New Year's resolutions, I do believe that thinking about your goals is very important. If you have a clear view of your ambitions (big or small) you'll be able to achieve them! I recommend sharing your answer to this question in a group—when other people know about and hold you accountable to your goals, your chances of reaching them skyrockets to 95%. 

4) What has kept you up at night?

This can be a challenging question. A lot of people don’t really talk about how or what they’re feeling. “How are you?” is usually answered with “Good!”, and we often don’t get beyond this point.

Sharing what’s bothering you not only helps relieve you (bottling up feelings can often lead to anger, resentment, and even physical stress on the body) but being vulnerable in a social context is also an opportunity for more mutual trust and connection. All these benefits because of one simple question. Even though it might seem confronting, give it a try! 

5) What will you do for the first time in your life?

“A good life is the greatest danger for a wonderful life.”

Setting up your life pretty well and having everything "on track" sounds fine, but a danger actually lurks here. From the moment that everything is “fine”, you are less inclined to work on improving or taking a leap of faith. When you step outside your comfort zone, you actually reap the most rewards!

By asking the question “What will you do for the first time in your life (in the upcoming year)?” you inspire yourself to do new, exciting things. This answer is also great to share with a group because you feel more responsible to actually DO it!

(Team Vertellis recommends making a bet or getting some skin in the game. You'll be more driven to achieve your goal!)

What simple but powerful questions can bring about…

Anxiety over whether the holidays will be memorable and unique isn't necessary when you ask the right questions!

If you enjoyed the questions I shared today and would like more to share at your next holiday gathering, check out the Vertellis Holiday Edition—the ultimate card game that brings friends and families closer together by asking sincere, playful, and reflective questions.

Many interesting, amusing, and moving stories have been shared with the help of this little game.

Fun fact: Vertellis started as a handwritten card game (read more about how Vertellis started here!). After sweeping the Netherlands, the Holiday Edition is now available in 11 countries around the world!

Thanks for reading! I hope we can inspire you with our mission to stimulate time offline and bring people closer together.

High five,

Bart

Holiday Edition

19.99

Vertellis is the ultimate card game for more togetherness. You can look forward to playing every year during Thanksgiving, Christmas, New Year’s, or a casual get together. The game is played wit...


3 comments


  • I bought this game for each of my three grown children and their families last year for Christmas. Just a few weeks ago I played it myself for the first time with two grandchildren, ages 13 and 10. They loved it, and I learned sooooo much about them and their lives. The ten year old declared, “This is really fun!” and has since begged his parents to play it with him. I can’t wait to play the family version with them and the other grandchildren as well.

    Jean Spike on

  • Bought the game immediately when I saw it advertised. Can’t wait until the family is together to play. Brings up a lot to talk about. Never a boring moment

    Susan Wolk on

  • Bought the game immediately when I saw it advertised. Can’t wait until the family is together to play. Brings up a lot to talk about. Never a boring moment

    Susan Wolk on

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