5 Questions to Ask Your Family and Friends during the Holidays

How to Start an Engaging Conversation

Holidays can be tough. It sounds counter-intuitive perhaps, but it’s true.

Sometimes holidays remind us of people or events that used to be here and now for whatever reason are not.

Sometimes holidays bring us into close contact with people who are important to but very different from us, and just the closeness can create tension.

Often the travel involved can be very taxing on our bodies. In short, holidays can remind us of the brokenness in our lives, past and present.

When I talk with my friends about the holidays, some of them seem genuinely hopeful and excited. But many anticipate the holidays with a measure of anxiety. They just want to make it through without any major blowups or other kinds of pain.

How about you? As you look toward Thanksgiving and Christmas, what emotions are primary for you?

I’m reminded of my friend Josh Riebock’s book Heroes and MonstersIt’s a brilliant memoir, and in it a twenty-something Josh recounts the deaths of his father and mother. All that’s left of his immediate family is his relationships with his siblings, and he could see them all drifting apart from each other very easily. He makes a deliberate choice to reach out, to be a brother who is present and concerned and giving.

What if we made a similar choice? Here’s my humble contribution to that effort. I want to offer five questions you can ask your family and friends. My hope is they will help you engage the people closest to you in ways that are healthy and life-giving.

1. What’s your favorite movie and why?

Movies are a cultural commonality. They make for a convenient place to start a conversation that could take us to unexpected places if we listen closely to what the other person says.

2. If you could visit anywhere in the world, where would you go and why?

The places we long to visit often reveal things that are important to us.

3. What do you consider one of your greatest accomplishments and why?

This is an opportunity to celebrate something that is dear to your loved one. Give them a high five!

4. What’s one of your happiest memories?

This, again, is a reason to celebrate. Relive the memory with them.

5. What are you thankful for?

This one is tried and true for Thanksgiving tables all over the country. It’s a natural question to ask, and again it can be revelatory.

3 Question-Asking Tips

When you ask these questions, remember these three tips:

  1. Leave your phone in a different room and listen carefully! Really listen to what the other person is saying.
  2. Ask follow-up questions. This often is very natural when we’ve followed tip 1 above.
  3. Don’t judge. The person you’re asking may answer differently than you hoped or expected. That’s okay. They are who they are!

I hope and pray your holidays are filled with joy and meaning.

Want these questions on one sheet of paper, divided into boxes for easy printing? If you want, you can cut the questions into cards and then pass them out to folks so they can ask one of the questions. Just CLICK HERE. Happy Holidays!

Question: Which of these questions could you envision yourself asking your family or friends? You can leave a comment by clicking here.

Please note: I reserve the right to delete comments that are offensive or off-topic.

13 thoughts on “5 Questions to Ask Your Family and Friends during the Holidays

  1. Excellent post and great advice! In place of saying grace, we always ask, “What are you thankful for?” at the holiday table. This year, I’m switching my other questions up to be more outward facing: “If there was one person in the world you could help, who would it be?” “If you had $1M to donate, what charity would benefit?” “If you had a superpower, how would you use it to promote world peace?” etc.

  2. Fun questions. I printed them out for Thursday’s dinner. 🙂 I would be most open to asking the movie question- I am always looking for good movies for future viewing.
    Here are two additional questions I received from a client after I shared this blog post with her, that I have now added to my list.
    What is your dream animal to own? and What would you do if you suddenly found
    $4,000,000?

  3. Great post! There is ONE use for the phone at the Thanksgiving table…I use an app (yep, it’s on my phone) that prompts me with these same questions, and more. It’s called Conversation Starter Help. I’m an android user, but I assume there’s a similar one for IOS. I love it because I can use it around the table to start conversations, and it has special topics for appropriate situations too (like if you’re on a date, or at a party, or at work). I pull it out in the car, at the dinner table, or anywhere I want to spark conversation.

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