The Deep Dish – "Siblings, Young and Old"
Podcast: The Deep Dish (The Gospel Coalition)
Hosts: Courtney Doctor and Melissa Kruger
Guest: Jen Wilkin
Date: December 18, 2025
Episode Overview
In this warm, insightful episode, Courtney Doctor and Melissa Kruger, joined by Jen Wilkin, dive deep into the beauty and challenges of sibling relationships—both with the siblings we raise and the siblings we grew up with. The discussion covers everything from sibling squabbles, fostering closeness, handling differences in adulthood, and caring for aging parents. The episode is packed with relatable stories, practical advice, and theological reflections, aiming to help listeners cultivate richer family dynamics and discipleship in the context of both childhood and adult sibling bonds.
Key Discussion Points & Insights
1. Growing Up with Siblings: Family Dynamics and Memories
- The hosts and Jen share their sibling backgrounds, highlighting diverse family structures and the normalcy of both rivalry and affection.
- Jen: Grew up in a blended family with four brothers: “I was tortured a great deal, and I responded with verbal abuse since I did not have physical strength. … I would describe our relationships as loving but adversarial in childhood.” (03:56)
- Melissa & Courtney: Each had one brother, and both recall fighting as kids but also moments of closeness.
- Memorable anecdotes about sibling “torture,” music quizzes, and made-up “twin” alter egos set a tone of humor and candor.
Notable Quote:
“A little bit of sibling conflict is not gonna just kill the whole sibling game. And it’s pretty normal.” — Courtney (08:13)
2. Parenting Siblings: Navigating Conflict and Fostering Friendship
- Letting Kids Work It Out: All hosts agree letting kids work through some conflict is necessary for development but must be guided.
- Jen: “I felt like there was a certain amount of letting them work it out on their own that needed to happen. … The standard was not, hey, the way you solve your problems is by fighting, but there's a recognition that you learn the standard is better by having some fights.” (08:42)
- Conflict Resolution Strategies:
- Don’t always be the referee—help kids come to solutions together.
- Reframe questions during conflict: “Which one of you is being the kindest?” (11:30)
- Role-play apologies, even if they're not heartfelt yet—practice forms the heart’s habits.
- Use biblical stories (e.g., Joseph) to discuss real sibling conflict and forgiveness.
- Long Game Perspective: Emphasize to children that sibling relationships last beyond friendships and stage of life.
- Courtney: "My mom sat us down and talked about, when you’re 80, you’ll still have your sibling." (12:37)
Notable Quote:
“Children learn by doing, like developmentally. That’s what’s true about them. … We give them words for it before they have the right motive to attach to it.” — Jen (13:50)
3. Creating a Family Culture That Values Sibling Relationships
- Practical Traditions:
- Each family member shares what they love about the birthday person (21:30).
- Regular family prayer, with rotations in who prays for whom, fostering intentional listening and care (22:25).
- Family meals as daily “shared experiences,” weekly shared chores, and overlapping spaces (e.g., shared bedrooms) to promote togetherness.
- Intentional Overlap: Strategic choices (limited individualized trips/activities; more shared experiences) reinforce family identity.
- Jen: “The principle … was we looked for as many ways for their lives to overlap as possible.” (23:37)
- Vision vs. Anti-Vision: Not just managing sin/conflict but cultivating a beautiful goal of closeness.
Notable Quote:
“What if we all saw each other as our closest people who we were going to travel through life with and then what do we need to do to get there?” — Jen (24:19)
4. The Dangers of Individualization and the Power of Shared Experiences
- Hosts discuss the current culture of individualization (devices, separate activities) and its impact on sibling bonds.
- Shared adversity (road trips, chores, favorite movies imposed on everyone) fosters happy and lasting memories.
- Jen: Recounts making her kids listen to Handel’s Messiah on long drives—a hated experience at the time, now a cherished memory (28:54).
Notable Quote:
“That avoidance of conflict is not going to build relationship.” — Melissa (27:59)
5. Creative Conflict Management
- Chores done together become arenas for problem-solving and peacemaking.
- Courtney mentions "get along T-shirts" and assigning joint tasks as constructive ways to encourage resolution rather than avoidance (30:50).
6. Adult Sibling Relationships: Growth, Pressures & Blessings
- All three relate how sibling relationships mature—less contact but deeper trust and mutual support.
- Jen: “We are all committed to being good children to our parents in the aging process, and we kind of have like everybody kind of knows their way to contribute to that.” (33:40)
- Melissa: Conversion/bond over faith in high school with her brother; both recognize the reliability of sibling support in crisis.
- Courtney: As adults, sometimes traditional roles shift (e.g., her role as an older/more experienced parent now compared to her brother).
Notable Quote:
“You are a multi-dimensional person who has done some living and you are the same person I knew, but also … just grown up.” — Jen (40:23)
7. Pressure Points in Adulthood: Parenting Styles, Holidays, and Aging Parents
- Cousins & Parenting Differences: Navigating parenting differences (discipline, gifts) can be a source of tension.
- Courtney: “I think just along those lines … everybody has the responsibility to step into their family of origin, continuing to grow out of your original roles.” (42:17)
- Holiday logistics: Scheduling and traditions (gifts given, time spent, expectations) become more complex as families grow (43:37).
- Caring for Aging Parents: Discusses the profound responsibilities and logistics (location, agency, fairness, and expectations) and the cultural shift toward recognizing the privilege (not just the burden) of caregiving.
Notable Quote:
“Your parents are not children… Their interior life is that of an adult. … As much agency as they can retain around their wishes and their preferences.” — Jen (50:36)
“You’re a person to love, not a problem to solve.” — Jen, quoting advice to her mother (52:20)
8. Recommended Resources
- Book: Being Mortal by Atul Gawande—on respecting agency and humanity in caregiving (50:36).
9. Advice for Navigating Sibling Dynamics in Adulthood
- Have philosophical conversations about care before crises arise.
- Recognize siblings as full adults—they are not the child you grew up with but multi-faceted individuals.
- Balance the agency of aging parents with the needs and capacities of their children.
- Use tools like Being Mortal to create a common foundation for these talks.
- Remember: Conflict can be constructive and lead to growth if handled with grace, prayer, and humility.
10. Ending on Laughter and Love
- Asked what she loves most about spending time with her siblings, Jen says, “It’s to laugh. … People have really, really well-developed senses of humor which at times we have yielded as weapons against each other. But we’re a lot older now … just laughing about those shared experiences and memories is some of our favorite pastime.” (54:24)
Timestamps for Key Segments
- Sibling Upbringings and Stories: 03:09 – 08:38
- Parenting Sibling Relationships: 08:38 – 12:34
- Conflict Resolution and Spiritual Formation: 10:49 – 16:57
- Creating Family Culture / Traditions & Overlap: 20:22 – 25:49
- Avoiding Individualization, Chores Sharing: 27:07 – 31:40
- Transition to Adulthood and Caregiving: 33:11 – 50:36
- Navigating Decisions for Aging Parents / Key Advice: 50:36 – 53:33
- Closing Thoughts & Sibling Favorites: 54:24 – End
Memorable Quotes Highlight Reel
- “Children learn by doing, like developmentally. … We give them words for it before they have the right motive to attach to it.” — Jen Wilkin (13:50)
- “A little bit of sibling conflict is … pretty normal.” — Courtney Doctor (08:13)
- “What if we all saw each other as our closest people … and then what do we need to do to get there?” — Jen Wilkin (24:19)
- “You’re a person to love, not a problem to solve.” — Jen Wilkin (52:20)
- “It’s to laugh. … Just laughing about those shared experiences and memories is some of our favorite pastime.” — Jen Wilkin (54:24)
Final Thoughts
This episode of The Deep Dish radiates with honesty, humor, and gospel hope for real families. Whether you’re deep in the trenches of parenting squabbling kids or figuring out care for aging parents alongside siblings, you’ll find wisdom and encouragement here to keep pursuing healthy, grace-filled relationships—with a reminder that God’s design for families is both realistic about conflict and full of redemptive possibility.