Crying in Chili's

Welcome to Crying in Chili’s — the podcast for anyone currently experiencing a character-building season against their will. Hosted by Courtney Hill, this show dives into career chaos, layoffs, relationship drama, life pivots, bad decisions, quarter-life crises, and all the messy in-between moments that somehow become funny later. Equal parts vulnerable, witty, and unhinged in the most relatable way, Crying in Chili’s feels like debriefing life with your smartest and funniest friends over chips, salsa, and a Presidente Margarita. Expect honest conversations, plot twists, guest interviews, emotional support disguised as comedy, and reminders that nobody really has it figured out. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

Crying in Chili's is a business podcast hosted by Unknown Host, with 18 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Crying in Chili's, a business show with 18 episodes published.

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  Episode #18

  Strong Enough for the Zombie Apocalypse

  Sep 18, 20261h 8m

  This week, Courtney sits down with full-time artist—and the podcast’s first guest she has never actually met before—Sabrina Severance! Sabrina shares how 20 years in retail and visual merchandising helped shape the wildly organized creative she is today, why she packed up her life and moved from New York to Florida and eventually North Carolina, and how she found her way into hosting paint-and-sip events at RBF Champagne Bar. She also casually reveals that she once starred on the Lifetime reality show Big Women: Big Love, where she navigated dating on camera, internet criticism, and a truly (non)committed clout chaser—all while refusing to be anyone other than herself. Courtney and Sabrina also discuss recovering from injuries, rebuilding their strength, preparing for the zombie apocalypse, fighting kangaroos, aging disgracefully at RBF, and why Chili’s Southwest Eggrolls must be protected at all costs. ️ This one is funny, chaotic, unexpectedly inspiring, and proof that sometimes Instagram’s algorithm really does know what it’s doing. Connect with Sabrina: Instagram: @sabrinastyled

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  Crying in Chili's

  Proactive vs. Reactive

  Sep 11, 20261h 19m

  Episode 17: Proactive vs. Reactive Sarah is back, and this time we’re getting therapized. Courtney and Sarah are getting cozy (with eight-month-old Shih Tzu Roscoe serving as a highly questionable guest producer) for an honest conversation about therapy, mental health, and what it actually looks like to do the work. They talk about finding the right therapist — and why it’s completely okay to break up with one who isn’t working for you — plus OCD, grief, sobriety, relationships, CBT, TMS, EMDR, and the difference between learning coping skills and actually using them. At the center of it all: becoming more proactive and less reactive. Courtney and Sarah reflect on how therapy has changed the way they handle conflict, difficult emotions, relationships, trauma, and the deeply unnecessary things life continues to throw their way. Because healing isn't about reaching some magical point where you're officially “fixed.” It's learning how to pause, process, take accountability, and choose how you want to move forward. Also discussed: sweaty little gremlins, four-leaf clovers, sharking and crying, emotionally unavailable men who should probably go to therapy, and the tiny, whimsical things that help get us through the hard stuff. Connect with us: Follow Sarah on Instagram Follow Crying in Chili's on Instagram Resources mentioned in this episode: Psychologytoday.com HiHello Digital Business Cards

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  Episode #16

  Spiraling is Movement

  Sep 4, 20261h 15m

  Spiraling Is Movement — with Jana Coburn What if getting laid off doesn’t send you scrambling back to the life you had before? Courtney sits down with former coworker Jana Coburn to talk about the very weird experience of surviving one round of corporate layoffs… only to get your own personalized layoff a few months later. A year later, Jana’s former side hustle as a travel planner has become her main hustle — and she’s not exactly rushing back to corporate America. They talk layoffs, career pivots, the financial reality behind choosing a less traditional path, adult ADHD, why some of us need a craft to pay attention in meetings, and finding the people who understand the way your brain works. Plus: Disney adults, aggressively detailed spreadsheets, shark tooth hunting, and why sometimes spiraling still counts as forward momentum. Because maybe you don’t always need to have the next step figured out. Sometimes you just need to keep moving. Connect with Jana: Instagram: @customparkplans Website: https://www.customparkplans.com/

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  Episode #14

  Fall in the Right Direction

  Aug 21, 20261h 7m

  Episode 14: Fall in the Right Direction Courtney reunites with longtime friend Emma Yates nearly 20 years after they first met as two tall altos in the back row of middle school chorus. Their friendship took on a much deeper meaning in high school when Courtney lost her older brother, Landon. Emma had already experienced the loss of her own older brother years earlier, giving them a connection neither of them would have chosen—but one that has followed them through adulthood. Now, Emma is a farmer, a new mom, a wife, and once again figuring out what she wants the next version of her life to look like. Courtney and Emma talk about grief and the unexpected ways it can shape us, building a life around work you love without losing yourself to it, the realities of farming, financial stability, motherhood, career pivots, community, and giving yourself permission to change your mind—or not have the next step figured out yet. Also discussed: middle school uniforms, horse breeding, humbling men with extremely niche agricultural knowledge, a woodchuck roommate, a bread-stealing chipmunk, 3 a.m. piglet emergencies, and the comforting realization that sometimes you don't need to know exactly where you're going—you just need to fall in the right direction.

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  Episode #13

  Baggage or Wisdom?

  Aug 14, 20261h 14m

  When Baggage Becomes Wisdom Sarah is back for round three, and this time we're talking about dating, being intentionally single, learning to actually enjoy your own company, and the relationship lessons we had to learn the hard way. Courtney gives the full story behind the sweaty mini-golf date that unexpectedly went viral, including 93-degree weather, a bathroom with no paper towels, an emergency hand-dryer situation, and hundreds of thousands of strangers suddenly having opinions about it. Then things get a little deeper. Sarah shares why she's choosing not to date right now, we unpack the difference between being alone and feeling lonely, and we talk about losing yourself in relationships, anxious attachment, setting boundaries, and recognizing when past experiences are still baggage — or when they've finally become wisdom. Also discussed: dating people who are still legally married, peeing in kitchen sinks, why your friends should occasionally give you a come-to-Jesus talk, and the revolutionary realization that a relationship doesn't have to be the end goal. Sometimes the relationship you need to work on most is the one you have with yourself.

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