Coffee Convos Podcast with Kail Lowry & Lindsie Chrisley

Episode: Natural Consequences, Co-Parenting Guilt, and the Anxiety of Sharing
Date: November 26, 2025

Episode Overview

In this candid episode, Kail and Lindsie dive into the real-life complexities of parenting, co-parenting, family logistics, and shared anxieties about motherhood in blended families. Through personal stories, laughter, and raw honesty, they unpack topics like managing kids' stuff, natural consequences, schoolwork woes, co-parenting guilt, and the emotional aftermath of divorces and breakups. They also get real about the anxiety of "sharing" their children, flexible parenting as kids grow older, and the bittersweet realities of non-traditional families.

Key Discussion Points & Insights

1. Dealing with Kids’ Stuff: Losing, Labeling, and Replacing (03:31 – 09:49)

• Kail and Lindsie discuss the ongoing dilemma of kids losing items like water bottles and sweatshirts. Lindsie expresses frustration about how expensive it gets and details her solution of only buying tiny water bottles to reduce loss and waste.
• Kail elaborates on her "natural consequence" approach: If something is lost, the child goes without, or gets a Walmart hoodie instead of an expensive Nike one.
• Notable Moment: Both hosts admit their own struggles as kids and moms with losing things.
  • Lindsie: "If you lost it, then you don't have a sweatshirt. Okay." (04:42)
  • Kail: "My kids aren't losing stuff at school; they're losing stuff at home." (06:35)

Memorable Moment (03:26)

• Kail tells how her kids drink from water bottles by putting the whole thing in their mouth, and Lindsie shares a horror story about backwash and floaties in a Gatorade.

2. Natural Consequences & Parenting Decisions (05:17 – 09:49)

• Lindsie stands firm on not continually buying things her son loses, backing up her stance with practical examples and refusing to coddle: "You're gonna go to school cold. Natural consequence." (06:15)
• Kail recalls the chaos in her own home with many kids and the impossibility of always tracking belongings.

3. The Shorts-in-Winter Paradox (09:01 – 10:33)

• Kail and Lindsie bond over how their boys insist on wearing shorts all year, regardless of weather, and how they’ve compromised with tights or layering.
• Lindsie: "If you think I'm arguing with you to put on a pair of pants, I'm not." (09:34)

4. Schoolwork, Homework, and Parental Guilt (10:33 – 16:48)

• Kail shares a vulnerable moment where "helping" her son Lincoln with homework actually hurt his grades—she changed right answers to wrong ones.
  • Kail: "Two times. Not once. Two times. He's like, 'Hey, can you check this before I submit it?' Yeah, no problem. Two times. My kid failed." (11:24)
• Lindsie relates, revealing how helping with homework is far harder now due to curriculum changes and online submissions. Both reminisce about their struggles with math and history in school.

5. Sports Gear, Hand-Me-Downs, and Splitting Stuff (18:47 – 24:32)

• Kail talks about trying—and mostly failing—to reuse and pass down sports equipment, especially with so many kids. She laughs about the awkwardness of asking for cleats back from a family friend.
• Lindsie shares the misery of discovering the stench of preteen/teen boy shoes in her car: "When I put it to my nose, I was like, these immediately need to be thrown away." (21:07)
• They debate whether it's worth it to have gear travel between houses, buy multiples, or request extra uniforms for split custody situations.

6. Co-Parenting Logistics in Split Households (21:37 – 25:17)

• Kail describes her system for sharing sports clothing between co-parents, difficulties in getting things returned, and why she buys multiples or requests extra uniforms.
• Lindsie reflects on how proximity makes her situation with her ex easier, but acknowledges it's not as simple for families living far apart or juggling many kids.

7. Sharing Kids Between Households: Guilt & Anxiety (28:03 – 40:38)

Co-Parenting Guilt & Realizations (28:03 – 33:44)

• Kail opens up about the guilt of "creating four broken homes" and how, in hindsight, she wishes she’d chosen differently in some relationships, but never regrets her children.

  • Notable Quote (31:20):

    Kail: "I don't regret my children. I don't regret any of them ... I had no business having any children with Chris, and truly no business having any children with Elijah either."

• Lindsie and Kail both reflect on jumping into relationships too quickly after divorces, and how healing first could have helped.

  • Lindsie: "I think I would have definitely given myself time post-divorce to really, like, truly heal the parts of me that needed to be healed from being married." (32:38)

The Anxiety of Sharing & Custody Schedules (37:21 – 41:13)

• Both moms get honest about the pain and anxiety of "sharing" their kids with exes, feeling incomplete when their children are gone, and the struggle of letting go for their child's happiness.

  • Lindsie (38:13):

    "My anxiety when he's not at this house ... I can't sleep without him in the house."

• Kail shares feelings about now having some of her kids full-time, but still wrestling with hard weekends when they go to their dads.

• As children get older, both women agree, custody arrangements must become more flexible to fit the kids’ needs and desires—even if it’s emotionally hard for parents.

  • Kail: "50/50, the older they get, that doesn't work for us. Like, for Elliot himself ... 50/50 is not ideal. He does not want to settle down at one of our houses and then get up a week later and have to go to the other." (43:11)
  • Lindsie: "If Jackson ever decided, 'Oh, I'm going to, like, stay at dad's house more days than I'm gonna stay with mom,' ... I would honor it because I feel like he's the most important part of the equation." (47:59)

Sibling Relationships & Long Distance Decisions (51:56 – 54:03)

• Kail brings up Bristol Palin’s public post about her son moving to Alaska, using it as an example of honoring children’s needs even when it’s heartbreaking for the parent.

  • Kail: "Like, to me, that was such good parenting ... It would suck and it would hurt, but, like, at some point I would have to be like, okay, like, I get it." (48:45)

• They note the immense importance of sibling bonds and how these must be considered in custody arrangements.

8. Book Discussion: Regretting You and More (54:23 – 58:35)

• Kail and Lindsie discuss movie adaptations of books like Regretting You and It Ends With Us—agreeing that while adaptations are enjoyable, they're sometimes choppy compared to major film productions.

  • Kail: "It feels like It Ends With Us and Regretting You both had very choppy, like, this happened and then this happened." (56:08)

• They also talk about the emotional depth and drama in these stories, and Kail gets excited for Reminders of Him.

9. Foul Play Story: Thanksgiving Gone High (59:32 – 61:56)

• Listener-submitted "foul play" story about a Thanksgiving gone awry when a friend overindulges in edibles before going to the family dinner, culminating in an accidental branding on the arm from a stove burner and a family cover blown.

  • Lindsie: "There’s certain things that we don’t need to do—when going to our grandparents' house and causing a disaster on Thanksgiving, because we’re high, is just like one of those things." (61:04)

  • Kail: "It would not be a fun time to see Kail high, like, it just wouldn’t." (61:56)

Notable Quotes & Memorable Moments

• Natural Consequences for Kids:
  • "You're gonna go to school cold. Natural consequence." — Lindsie (06:15)
• Homework Gone Wrong:
  • "Two times. Not once. Two times. He's like, 'Hey, can you check this before I submit it?' Yeah, no problem. Two times. My kid failed." — Kail (11:24)
• Motherhood Regret Nuance:
  • "I don't regret my children... I had no business having any children with Chris, and truly no business having any children with Elijah either." — Kail (31:20)
• Co-Parenting Guilt:
  • "Like, I made my life harder, their life harder... But I think in during that time, like, I just wanted a family, and I just wanted to be loved, and I wanted to be a wife..." — Kail (31:30)
• Anxiety About Kids Leaving:
  • "My anxiety when he's not at this house... I can't sleep without him in the house." — Lindsie (38:13)
• Reflection on Flexible Parenting:
  • "It's not about battling with Will for time. It's about making sure that my child is fulfilled and where he wants to be." — Lindsie (47:59)
• Sibling Relationships & Heartbreak:
  • "Siblings have to be considered heavily on both sides. That’s tough." — Kail (51:57)

Timestamps for Major Segments

• Kids’ Stuff, Losing, & Labeling: 03:31 – 09:49
• Natural Consequences in Parenting: 05:17 – 09:49
• Homework Failures & Schoolwork: 10:33 – 16:48
• Sports Gear & Hand-Me-Downs: 18:47 – 24:32
• Co-Parenting Logistics: 21:37 – 25:17
• Guilt and Co-parenting Regret: 28:03 – 33:44
• Anxiety Sharing Kids: 37:21 – 41:13
• Teen Choice, Flexibility in Schedule: 44:25 – 47:59
• Book & Movie Adaptations: 54:23 – 58:35
• Foul Play Story – Thanksgiving High: 59:32 – 61:56

Takeaways

• Honesty and Relatability: Both Kail and Lindsie openly share their failures, insecurities, and hard-earned wisdom as moms navigating non-traditional family structures.
• Natural Consequences Work: Letting kids experience the repercussions of losing things (fewer water bottles, cheaper sweatshirts) leads to learning.
• Parenting is Messy and Requires Flexibility: Especially as kids age and develop their own needs, wants, and schedules.
• Guilt is Real in Co-Parenting: Regrets about relationships and family structures are balanced by unconditional love for their children.
• Anxiety of Sharing is Universal: Many parents struggle with time away from their children, but learn to prioritize the well-being of their kids above their own feelings.
• Bittersweet Humor: Despite the chaos, mistakes, and mom-guilt, both hosts find laughter and even some joy in the madness.

This episode is raw, heartfelt, and will resonate with anyone hustling through the real challenges of motherhood, blended families, and self-forgiveness.