Some Great Questions to Ask Others During Your Holiday Gathering

Every year, I provide some of my favorite questions to ask others during the holidays. But this year, I wanted to start by reminding us all of the mindsets we need even before we ask the first question.

We all need to grow in at least one category of The Four Mindsets (from The Six Conversations). And when we get these down, we lay the foundation for warm connections. Be curious. Believe the best about others. Express concern. Share your life. If we desire loving and warm connections around the holiday table, we can start here. Most people arrive to a holiday gathering and struggle to believe the best and to ask great questions rooted in interpersonal curiosity.

Next, I’m learning to shift my understanding of what a conversation is for. If you want that warm and loving connection, remember the 3 Fresh Goals of great conversation: encouraging others, helping them in their personal goals, and leading others to a state of awe or marveling.

Encourage. Help. Marvel.

The goal is not to win. The goal is not persuasion to your political position. The goal is not to trap, mock, or shame. Save that for your debate tournaments.

The goal here is loving, warm connection.

Once I’m prepped with the right mindsets and fresh goals, I’m ready to ask some great questions in all the categories of what it means to be human. Here’s a list of 15 questions to start a conversation (especially with children or college students). I also provide an idea of where to go next in the conversation. Here you go:

  1. What are you looking forward to in 2023? (emotional)
  2. What’s frustrating you the most about school / work? (emotional)
  3. What song do you keep listening to? (physical)
  4. Have you changed anything about your room / dorm room / house? (physical)
  5. What have your pets been up to? (social)
  6. Where do you need the most advice right now in your life? (volitional)
  7. Have you tried any new foods / restaurants? (physical)
  8. Your skin / hair / clothes look so great! What is your ritual or secret? How do you get it that way? (physical)
  9. What was your favorite way to procrastinate this semester? (volitional)
  10.  What is the best picture on your phone? (physical)
  11. What question do you not like answering? (emotional)
  12. What question do you like people to ask you? (emotional)
  13. What have you been thinking about lately? (cognitive)
  14. Have you been doing anything to develop your spiritual life? Teach us! (spiritual)
  15. Have your friends made any big decisions lately? (volitional and social)


  • Who else will be / was there?
  • Why do you love it?
  • How did your body handle it? What was it like?
  • What are you hoping to learn? What did you think about that?
  • How did you decide to do that? Tell me the whole story!
  • Does this relate at all to your spiritual life?

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