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25 Conversation Starters and Tips for Engaging Holiday Season Conversations

Conversation starters and listening tips for great holiday conversations

Christmas for many in New Zealand is a wonderful - albeit slightly crazy - contrast of traditional, hearty winter roasts and steam puddings consumed on a scorching summer day. Social conversations during the holiday season can be equally contrasting, from sedate family news to rampant political conspiracy debates! But these gatherings are also opportunities to delve into fascinating, fun, and stimulating topics. Here are some conversation starters and listening tips to get you talking.


Going with the flow generally gives us informational-level conversation. It’s that spontaneous exchange of facts such as family activities, current job situations, reminiscing on events, retelling family stories to the next generation, and daily pleasantries like the weather.

I love this level of conversation, especially when sprinkled with splendid repartee, and a thick plastering of puns and dad jokes - a family tradition that isn’t likely to disappear anytime soon!

But I also love the deeper, richer levels of conversation where we share our ideas, emotions, opinions and personal preferences. [1]

Changing gears into deeper conversation - and staying there - is a deliberate choice. Below are some of ways that I cultivate this level of engagement. Try using some of them these holidays.

Begin with a Conversation Starter

Weekly, I meet with two mates for a social catch-up, and to encourage and challenge each other in our various walks of life. There’s usual a point when our conversation switches from the social, informational level to more intentional, personal and relational levels. This switch always happens by one of us asking a question. “What do you think about [xyz]?” “What have you been reading this past week?” “So what’s been on your heart lately?”

In your holiday conversations try deliberately asking a thought-provoking question. Below are 20 conversation starters to give you ideas. Some are reflective. Others are pure fun. But all will give glimpses of people’s experiences, beliefs, opinions, passions, and dreams.

Holiday Conversation Starters

  1. What’s the best holiday experience you can remember?
  2. What are you most grateful for this past year?
  3. What are you most proud of this past year?
  4. If you had one million dollars to give to charity, how would you spend it?
  5. What did/do you want to be when you grew/grow up—and how does that relate to what you do now?
  6. When you think about the coming year, what are you most excited to accomplish?
  7. What new capability do you want to develop next year?
  8. What are the two biggest lessons you learned this past year?

Thanks to Michael Hyatt. [2]

  1. If you could design your ideal job, what would it look like?
  2. What is the most important lesson you’ve learned from your father?
  3. If you were by yourself, and could listen to any music you want, what would it be?
  4. If you could spend a day with anyone on the planet, who would it be?
  5. If you were suddenly the Prime Minister of New Zealand, what would you do first?

Thanks to Michael Hyatt. [3]

  1. What skill or craft would you like to master?
  2. What fact amazes you every time you think of it?
  3. What makes a piece of art beautiful to you?
  4. Who in your family are you most like?
  5. What is a creative gift you have given or received?
  6. What is the most important thing for astronomers to be researching?
  7. You are in charge of making insects a popular food item. You have 1 billion US dollars to achieve your goal. How do you do it?

Thanks to Conversation Starters World. [4]

The Second Question Is When The Memorable Happens

The key to sustaining the conversation you’ve just started and turn it into something truly memorable is to ask a follow-up question.

Listen attentively to the speaker’s answer. Then ask an open-ended question based on what they’ve said. Your question can take the conversation in a number of directions. It can:

  • clarify their answer
  • prompt them to elaborate further
  • build on their reply
  • challenge them to reflect on their answer
  • uncover their underlying belief systems
  • develop rapport and empathy by reflecting any feelings they’ve expressed.

For example:

You: “What fact amazes you every time you think of it?” (Conversation Starter #15)
Other Person: “The fact that a housefly's wing beat is about 200 times a second, and some midges move their wings 1,000 times a second.”
You: “Wow. That’s astounding. So how did you find out about that fact (Elaboration-type question)? Do you have a broader interest in insects?”
Other Person: <Conversation deepens…>

Here are some follow-up questions to try. Modify them to suit your conversations.

  • “Please clarify [xyz] for me?” (Clarifying)
  • “What does that look like for you?” (Both clarifying and encouraging elaboration)
  • “Tell me more.” (Encouraging elaboration)
  • “How do you think [introduce a concept that's related to their answer] relates to [summarise their answer]?” (Building on their reply)
  • “So what do you think are the implications of [xyz] going forward?” (challenging them to reflect)
  • “What led you to that point of view?” (Uncovering belief systems)
  • “You sound [happy, excited, angry, irritated, etc]. Why is that?” (Reflecting feelings)

Stop Talking

To deepen the conversation the person needs ‘airtime’ to fully answer our second (and subsequent) questions. There’s only one way to do this.

Stop talking, at least initially. There'll be time for talking later.

It's easy to think that we give others plenty of airtime. But challenge yourself honestly.

How often do you interrupt people? What about overtalking them? Do you shift the focus of conversation from them and their train of thought, to you and what you want to discuss (more on this below)? Do you ask a question and then immediately answer it? Do you talk so much that the other person has no opportunity to say anything, and instead, stands in awed silence beholding the great orator before them? 😀

If you can relate to any of these scenarios, the remedy is easy.

Resolve to only speak after the other person has finished their point. And then only speak in order to ask another follow-up question.

Knowing that you’re going to ask a question about what they’ve said will force you to listen carefully rather than talk. It will also give them time to fully answer your question and deepen the conversation.

Balance Listening and Talking

Having just advocated the need to listen, we can take listening to extremes. Conversations can become boring for us when we do all the listening. And we risk coming across as uninteresting to the speaker.

Great social discussions occur when everyone involved gets to both listen and talk. For some people this means listening more. For others (like myself) this means sharing their thoughts more frequently, rather than allowing everyone else to do the talking.

Have a go at this - after the other person has finished answering your question, inject an idea or opinion that builds upon what they’ve said. Then, ask another question.

Use Support Responses Instead of Shift Responses

The key to balancing listening with talking is to build upon their thought rather than divert the conversation.

Dr Charles Derber, author of The Pursuit of Attention [5] proposed two concepts: the support response and the shift response.

A support response maintains focus on the speaker and their comments. It builds the conversation in that direction.

You: “What is the most important thing for astronomers to be researching?” (Conversation Starter #19)
Other Person: “Their answer...”
You:True! Researching how to harvest frozen water on Mars is definitely important for establishing a colony there. I think it’s going to be quite a challenge, but that we can do it (injecting a building idea using a support response). Thoughts on how it might be done?

A shift response, however, changes the focus to you and your ideas. Suddenly, you’re no longer listening to understand the speaker. The conversation has been diverted in your direction.

You: “What is the most important thing for astronomers to be researching?” (Conversation Starter #19)
Other Person: “Their answer...”
You:Interesting. Researching how to harvest frozen water on Mars is definitely important for establishing a colony there. I was reading the other day though, that space weather has the potential to cause havoc here on earth (injecting a different idea using a shift response). I’m amazed at how the solar wind affects so much of our lives. Over the next decade astronomers will be… etc.

Attempt to use mostly support responses. Use shift responses sparingly, for example when that topic has come to a natural end, or to draw other people into the conversation.

Draw Others Into the Conversation

The fun of holiday conversations is involving several people rather than just talking one-on-one. 

Others will be paying attention when you start a discussion. Draw them into your discussions too. Seek out their ideas with a shift response.

“Gee, I hadn’t thought of it like that [Janice]. So [Kaye], what are your thoughts?”

Don’t forget the kids. I love their perspectives. They think so differently to adults and often come up with insightful, left-field ideas. Maybe even use fun conversation starters with them and then draw the adults in. Keep asking them occasional questions so that they stay involved and don’t get sidelined by the adults.


  • Begin with conversation starters
  • Ask a follow-up question to deepen the conversation
  • Stop talking in order to listen and to give people time to share
  • Be interesting - balance your listening with talking by sharing some 'building' ideas
  • Mainly use support responses
  • Create diverse conversations by drawing in others, especially the kids.

Great conversations make holiday gatherings memorable. I love learning from others and getting immersed in stimulating, well-reasoned discussions where everyone is cooperating rather than competing. If this level of interaction appeals to you, intentionally trigger them using some conversation starters. Typically, they don’t occur impromptu. Then cultivate the discussion with a few follow-up questions.

What ways do you cultivate holiday conversations? Tell us below.

Please share this post on social media so that others can have some great holiday conversations too!


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About the Author

Hello, I’m Andrew Ward and the Kiwi guy writing most of the stuff on this website. You can read more about my story here.