The Deep Dish: Bonus Episode

Preparing for a Holiday That Will Disappoint

Host: Melissa Kruger and Courtney Doctor
Date: November 20, 2025
Podcast: The Gospel Coalition’s “The Deep Dish”

Main Theme & Purpose

This bonus episode, released just before Thanksgiving, dives into how to approach the holidays when reality is likely to fall short of our high hopes and expectations. Melissa Kruger and Courtney Doctor discuss the gap between our idyllic visions for Thanksgiving and Christmas and what actually happens—with special attention to the tender places this season can touch in our hearts. They offer practical, gospel-rooted advice on managing expectations, handling disappointment, and cultivating genuine joy, gratitude, and hospitality.

Key Discussion Points & Insights

1. The Reality Gap: Why Holidays Disappoint

Timestamps: 02:13 – 04:12

• The episode is intentionally titled “Preparing for a Holiday that Will Disappoint” to center on realistic expectations, not pessimism.
• Both hosts acknowledge loving the holidays deeply, but also highlight the consistent gap between expectations (idyllic, social, and spiritual) and reality.
• Melissa shares a personal struggle: her oldest child won’t be home for the first time due to missionary training, pointing out that many women especially feel pressure to create the “perfect” holiday.

  “There's just some reality that we always have higher expectations than will most likely come to pass when it comes to the holidays.” (Melissa, 03:01)

2. High Expectations: Sources and Impact

Timestamps: 06:36 – 08:26

• Pop culture (Hallmark movies!), social media, and nostalgia all stoke unrealistic visions of family harmony and spiritual warmth.
• These expectations are “normally good”—desires for togetherness, celebration, and meaning—but are still, in many ways, unachievable in a fallen world.
• Both openly process how new life stages (kids marrying, moving for jobs, etc.) bring necessary adjustments.

  “It's the lie that you can have it all, and this is what all looks like.” (Courtney, 08:16)

3. Changing Expectations Through Seasons

Timestamps: 09:53 – 13:52

• Courtney reflects on moving from expectations of a “conflict-free” holiday to intentionally letting go:

  “Learning to let go of the fact that I'm expecting it to be conflict free or that I'm going to be the best version of myself for 10 straight days with 20 people in my house…” (Courtney, 10:47)

• Melissa notes how adulthood changes the holidays—less time off, more responsibilities, busier kitchens, and less rest.

  “Someone has to cook the turkey... I've really had to, in some ways, learn to guard my heart from not heavy bitterness, but just like, well, yeah, it'd be nice to be sitting down with the family playing games, but someone has to cook the turkey, you know…” (Melissa, 12:52)

4. Dealing with Disappointment in Ourselves

Timestamps: 13:52 – 18:41

• Holidays also expose disappointment in our own hearts—not just in circumstances or others.
• Cultivating a heart of gratitude is a year-round pursuit, not something that can be whipped up for a holiday.
• Practical tradition: one family keeps a “thankfulness jar” all year, reading its contents together at Thanksgiving as a ritual to enhance gratitude.

5. Holiday Expectations & the Role of Others

Timestamps: 18:41 – 23:58

• Much disappointment stems from expectations of others’ behavior—hoping they’ll show up with gratitude, get along, or be their “best selves.”
• Both hosts emphasize empathy—everyone brings their own burdens and stories to the table.
• Practicing humility: Recognizing we sometimes cause others disappointment, too.

  “I am responsible for some of the disappointment that other people feel…everybody in the room...is experiencing that moment differently.” (Courtney, 21:59)

6. Practical Preparation for Disappointment

Timestamps: 23:58 – 29:47

• Proactive questions: What specific situations may disappoint me this holiday? How can I plan my responses and actions?
• Try listing two or three things you want to be or do (e.g., be intentionally present with grandchildren) and mapping out meaningful conversations in advance.
• Courtney suggests shifting from a reactive mindset to a proactive one—fostering connection, not only avoiding discomfort.

  “How can we foster conversations we really want to have? Because I think sometimes my disappointment is we were all together and did we really connect?” (Melissa, 28:12)

7. The Church’s Role & Broader Welcome

Timestamps: 30:39 – 36:31

• Deep loneliness marks the holidays for many; the church is called to “set the lonely in families.”
• Practical encouragement: look around to invite others in, even if it disrupts tradition.
• If you are lonely, speak up—ask leaders/pastors for connection.
• Melissa and Courtney share family stories of always making room at the holiday table for the “extras.”

  “Our entire table is going to be richer and more beautiful and more delightful, I think…when I can get really protective of my table…instead of being more generous with that space.” (Courtney, 32:33)

8. Balancing Hospitality and Spiritual Focus

Timestamps: 36:31 – 39:41

• Melissa compares herself to Martha: busyness can crowd out “Mary moments” of sitting with Jesus and being present.
• The “logistics” matter but must not eclipse genuine inclusion and spiritual focus.

9. Grounding Ourselves in Scripture

Timestamps: 39:41 – 46:04

• Recommendation: Memorize Psalms to “turn our hearts;” for instance, Psalm 66 for cultivating praise.

• Advent devotionals and intentional reflection anchor the soul amidst holiday busyness.

• Courtney’s go-to is Galatians 5:22—the Fruit of the Spirit—posted visibly as a character check:

  “Am I being loving? Joyful?... Kind...Good to people? Self-controlled?” (Courtney, 44:10)

• Additional resource: TGC’s printable PDF for a “Christ-centered holiday” with prompts for gratitude, worship, and serving others.

• Melissa: “The most important thing I can do is be, you know, spending time in the Word and in prayer and really taking the time to sit still before him and let my soul be transformed.” (Melissa, 42:58)

10. Looking Forward and Ultimate Hope

• Even in disappointment, the season points us to the future feast in Christ’s kingdom—“One day…there will be no sighing, no sadness, no sorrow.” (Melissa, 47:35)

Notable Quotes & Memorable Moments

On the “Idyllic” Holiday:

“In your mind, you're harmonizing…As if I even know what those are.” (Courtney, 03:31)

On Real-Life Disappointment:

“I was trying not to count how many Christmases and Thanksgivings I will not have all my kids home. And I was just so sad.” (Melissa, 06:00)

On Empathy Around the Table:

“I am someone else's cause for maybe prayer or disappointment…how am I going to deal with her this holiday?” (Melissa, 23:58)

On Hospitality and “Enough”

“If we pull out some paper plates, it's totally okay.” (Melissa, 36:31)

On Spiritual Preparation:

“Consider, think upon these things, prepare your mind for action…and that is just such a great printable.” (Melissa, 46:04)

Important Segment Timestamps

• 01:31 – Beginning of content episode (Hallmark movie confession)
• 03:01 – Why holidays “will” disappoint, not just “might”
• 05:21 – Emotional stakes and family pressure
• 06:41 – Tenderness when family is absent
• 09:53 – Shifting expectations across life seasons
• 13:52 – Holidays exposing disappointment in ourselves
• 17:08 – Year-round gratitude, “thankful jar” idea
• 19:34 – Holiday expectations depend on “other people”
• 21:59 – Recognizing we disappoint others, too
• 23:58 – Specific, proactive holiday prep questions
• 27:03 – Praying for and planning meaningful conversations
• 30:39 – How the church can welcome the lonely
• 36:31 – Hospitality and balancing “Mary and Martha”
• 39:41 – Scripture as holiday anchor (Psalms, Advent devotionals, Fruit of the Spirit)
• 46:04 – Pointing to the “greater feast” to come

Tone & Style

True to the signature “Deep Dish” style, the episode is warm, conversational, and sprinkled with laughter and genuine emotion. There’s a spirit of realism, humility, and gospel hope as Melissa and Courtney draw from their lives and Scripture to equip listeners for the tension between our longings for “the perfect holiday” and the beautiful—but always messy—reality of real life, real families, and real faith.

Final Thoughts

If you’re facing this holiday season with a tender heart, big expectations, or a creeping sense of disappointment, this episode is for you. The hosts gently remind us:

• Disappointment is normal—holidays never measure up to our most cherished visions.
• But each gap, each unmet expectation, is an invitation to humility, gratitude, relationship, and longing for our true and future Home.
• Scripture, prayer, and simple, intentional acts of presence and inclusion can transform even “imperfect” celebrations into times of deep blessing and Christ-centered joy.

Resource Highlights

• “The Gift of All Gifts” (Melissa’s new kids’ book)
• TGC’s printables for Christ-centered holidays
• Year-long jars of gratitude for Thanksgiving
• Galatians 5:22—Fruit of the Spirit as a daily/festive anchor
• Psalms & Advent devotionals for reflection

Standout Moment

“This feast will disappoint. But one day, one day we're gonna be in the new heavens and the new earth and we are gonna feast. And there will be no sighing, no sadness, no sorrow. And our hearts are rightly longing for that.”
—Melissa Kruger (47:35)

For deeper connection, subscribe to TGC’s Women’s newsletter for questions, memory verses, and resources. Visit tgc.org/women.