• 1 hour 16 minutes
    Crashing Out with Coffee Convos

    CC503: Lindsie and Kail catch up virtually this week to unpack their weekends—from ex-husband-funded pedicure treats and costume mishaps to neighborhood candy bowl theft. The duo also clear the air on the future of Coffee Convos, address the backlash surrounding Crashing Out with Kail, and pull back the curtain on some behind-the-scenes dynamics. Plus, they talk about how they had to explain the term "fluffers" to a bewildered European consultant, read out loud their past text miscommunications, and explain how their "dysfunctional sister" dynamic continues to strengthen their business partnership.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    5 November 2026, 9:00 am
  • 1 hour 3 minutes
    Liverty for Icing

    CC502: In this episode, Kail and Lindsie debate the unwritten rules we ALL love to fight about—from middle-seat plane etiquette, overhead bin usage, date-night check-splitting, and unannounced drop-ins. They start off hot with confessing some misheard song lyrics, directional confusion, and Kail's HIGHLY CONCERNING overnight pizza habits. Which unwritten rules stand and which are officially dead?

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    29 October 2026, 8:00 am
  • 1 hour 14 minutes
    F*ckaround Shoes

    CC501: We're still in Atlanta! Kail and Lindsie continue their conversations around school drills, real estate woes, and the Cornell 7. The duo discuss whether active shooter drills are just traumatizing the kids and why bullet casings found in a backpack deserve more than a slap on the wrist. Plus, Kail shares the latest in co-parenting, how that relates to high interest rates, and why kids treat brand-new shoes like they’re hiking the Amazon rainforest. Lastly, they share their thoughts on the viral Cornell 7 lawsuit and the ridiculous state of consent laws.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    22 October 2026, 8:00 am
  • 1 hour 14 seconds
    Kail for the Congo

    CC500: On today's episode, Kail can't wait to tell Lindsie about extreme athlete Ash Dykes' Congo Basin expedition (could Kail be the next extreme athlete?) They pivot to family fire safety plans, fears of the dark in their big age, and why college football feels more like reality TV. Later, Kail opens up about her family history, the story behind her name change, and her non-traditional views on legal name changes and marriage. Finally, they address the news and public scrutiny surrounding Gypsy Rose Blanchard and the passing of Ken Urker, reflecting on toxic dynamics, online harassment, and mental health.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    15 October 2026, 8:00 am
  • 1 hour 12 minutes
    Tipping Culture

    CC499: On today's episode, Kail and Lindsie abruptly find out about the death of Dolly Parton, which pivots the conversation to the allegations of Michael Jackson and the bizarre psychology of marrying convicted felons behind bars. Kail opens up about her experience with Prison AND Jail Bae (yes, those are two different people).

    Lindsie reads a wild hometown gossip story about a cat hoarding heist that ended in a police chase around a small town, plus, they both recount surviving the financial and emotional exhaustion of "Yes Days". Lindsie debates whether rescuing your kid from the other parent's "lazy day" is an overstep, and they break down a viral TikTok perm nightmare that escalated into full-blown internet cancellation.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    8 October 2026, 8:00 am
  • 58 minutes 3 seconds
    Old School Mops are OUT

    CC498: In today's episode, we're starting off strong with comparing toddler bedtimes against teenagers pulling all-nighters for Fortnite. Lindsie and Kail reflect on sleepover boundaries, and reveal the nightly routines that keep their lives running. From the intimacy of shared showers to steam mops versus traditional buckets, Kail also breaks down her trip across the pond to London and Paris. Hear about navigating high-speed trains, hunting down personalized gifts, and comparing UK food staples and alcohol regulations to life in the US.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    1 October 2026, 7:30 am
  • 1 hour 3 minutes
    Intrusive Thoughts

    CC497: In this NYC edition of Coffee Convos, Kail and Lindsie dive into the chaotic world of intrusive thoughts. Kail’s quick, passing impulses versus Lindsie's detailed, movie-level intruder escape plans. Kail also has some revelations about her hyper-fixations that include but are not limited to crystals, custom beads, Labubus and $1,000 pottery mugs. Are the collections healing the inner child or do they stem from ADHD, OCD?

    Plus, practical strategies for getting kids to clean up their messes! Kail also shares her future home plans to ensure Elliot always has a place to call his own as he approaches college age.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    24 September 2026, 8:00 am
  • 51 minutes 51 seconds
    Hotel vs. AirBnb

    CC496: Fresh off a high-energy show in Charlotte, Lindsie and Kail share the chaotic story of the previous night that involved sharing a little too much with a stranger at the bar. The duo also break down their major frustrations with Airbnb chore lists and cleaning fees, discuss raising kids who are grounded when it comes to money, and Lindsie gives us a dive into Frontier airline economics. Lastly, they share some thoughts on the Jessica Simpson airplane seating debacle.

    https://www.tiktok.com/t/ZTAUub7wh/

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    17 September 2026, 8:00 am
  • 1 hour 15 minutes
    Small Talk in the Elevator

    CC495: From smuggling a crockpot of chili into an movie theater to a scandalous small-town bakery closure, today's episode dives straight into the chaotic world of unwritten social etiquette. Lindsie and Kail tackle elevator make-out mishaps, the creepy goat eyes, and the unpopular way they split bills with friends. Plus, they break down why oversharing with strangers is an art form (ahem Kail) and why email chains are ACTUALLY a little annoying. Lastly, Kail shares details about Elliot's short film project and the beginning of KILLR Productions.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    10 September 2026, 8:00 am
  • 1 hour 21 minutes
    Reducing Carbon Footprints

    CC494: Kail details her first emotional breakdown after adjusting to a celiac-safe diet while trying to order some BBQ. The duo get into a new segment dissecting everyday habits, debating on white noise and box fans versus televisions for sleep, morning vs night showering, and the stress of unread notifications.

    Driven by managing a household of nine, Kail shares updates on her ongoing lifestyle shift to be more environmentally conscious , highlighting localized composting, careful recycling rules, and highlighting Poshmark clothing bundles. Lastly, Kail has beef with saying "bless you" and small talk, and they read some small town gossip revolving a heartwarming neighborhood victory for a family supporting their autistic son.

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    Better Help: This episode is brought to you by Better Help. Visit betterhealth.com/coffee today to get 10% off

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    Items and links mention in today's show:

    Nineteen Minutes: A Novel by Jodi Picoult 

    Luckiest Girl Alive: A Novel by Jessica Knoll

    https://www.instagram.com/reel/DaNfoIHxgp4/

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    3 September 2026, 8:00 am
  • 1 hour 2 minutes
    Celiac Diagnosis & Bending Towards the Chaos

    CC493: The girls are back together and nothing is off-limits! This week, they dive deep into the emotional and practical realities of potentially rebranding the podcast, and celebrate the improvement in their communication with each other. Kail opens up about her definitive celiac disease diagnosis—sharing the lifestyle changes she'll have to make and the steps being taken to get the kids tested. Meanwhile, Lindsie gets candid about setting new co-parenting boundaries, navigating separate back-to-school shopping trips, and processing the reality of an ex moving on. Plus, they debut a brand-new segment, Small Town Gossip, featuring an anonymous listener.

    The book Kail mentioned: Such a Quiet Place: A Novel by Megan Miranda

    Send in your small-town drama, HOA sagas, diner/local business chaos, and multi-generational family feuds, to [email protected] for our Small Town Gossip segment! For full videos head to Youtube.com/@KailandtheChaos

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    27 August 2026, 8:00 am
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