The Deep Dish

Bonus: Preparing for a Holiday That Will Disappoint


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Courtney and Melissa talk about the gap between our high expectations for the holidays and the disappointment we often feel in others or in ourselves. They discuss how to be pro-active in preparing our hearts to hope in the Lord rather than in perfection, how to bear the fruit of the Spirit while also meeting the practical needs of those around us, and how inviting nonfamily into family holidays can bring great blessing. Whether you are excited about Thanksgiving and Christmas or tired just thinking about them, listen to this conversation and be encouraged!

Resources Mentioned: 

  • 6 Ways to Prepare for a Holiday That Will Disappoint (printable pdf) https://media.thegospelcoalition.org/wp-content/uploads/2025/11/10111351/6-Ways-to-Prepare-for-a-Holiday-That-Will-Disappoint-Printable.pdf
  • The Gift of All Gifts by Melissa Kruger
  • Unto Us: 25 Advent Devotions about the Messiah
  • The Weary World Rejoices: Daily Devotions for Advent

Related Content:

  • This Thanksgiving, Come to the Table
  • How Not to Gossip During the Holidays
  • Preparing for Advent Season

 

DISCUSSION QUESTIONS:

1. How have your expectations for the holidays changed over time?

2. In what ways can unrealistic expectations set us up for disappointment? What helps you hold your expectations in a healthy way?

3. What’s one thing you’re especially looking forward to and one thing you anticipate may be challenging this holiday season?

4. What rhythms or practices help you cultivate gratitude—both during the holidays and throughout the rest of the year?

5. What conversations or interactions do you want to intentionally prioritize this holiday season, and what might that look like in practice?

6. How can your church, small group, or family support those who are experiencing grief, loneliness, or unmet expectations this season?

7. Which fruit of the Spirit (Gal. 5:22–23) do you most want God to grow in you this holiday season, and why?

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The Deep DishBy The Gospel Coalition

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