Free Failing

Jessica Kastner
  • 5.0 (9)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

Gritty, faith-filled, hilarious conversations for women rebuilding after divorce and other hard life transitions. Author and host Jessica Kastner gets unapologetically real about the stuff we rarely admit, let alone say out loud. Covering everything from the impending doom of perimenopause, the thrills of coparenting, emotional healing after divorce, (anxiously attached but still sexy A+) and the fresh flaming hell that is online dating, Jess soaks up wisdom and advice from amazing female experts, who live to tell.

  1. From Burnout to Body Wisdom: Regulating Your Nervous System After Divorce with Dr. Julie Merriman

    APR 11

    From Burnout to Body Wisdom: Regulating Your Nervous System After Divorce with Dr. Julie Merriman

    What if your exhaustion isn’t just hormones… but a completely dysregulated nervous system? Jess sits down with Dr. Julie Merriman—licensed counselor, trauma specialist, and host of Compassion Fatigue Cure—to unpack why so many high-achieving women hit a wall in midlife, especially after divorce. Dr. Julie shares her own story of divorce, burnout and “crashing hard” in her 40s, and how that experience led her to help women break free from what she calls the “virtuous trap of self-sacrifice.” Together, they dive into the real reason you feel numb, disconnected, and constantly in survival mode—and why bubble baths and surface-level self-care just aren’t cutting it. Let's explore: What’s actually happening in your nervous system when you feel overwhelmed or shut downThe difference between burnout, “identity burnout,” and hormonal changesWhy resilience can become toxic—and how to recognize when it isSimple, practical tools to regulate your nervous system (even in the middle of a panic spiral)How to reconnect with your body and trust your intuition again—especially in dating and relationshipsWhy boundaries feel so hard to set (and how your body can help you set them naturally)We’re not broken—we’re dysregulated. And your our already knows the way back. #nervoussystem #burnoutrecovery #womenover40 #midlifetransition #boundaries #sexafter50 #divorcehealing #divorcedmomDr. Julie Merriman is an author, speaker, and licensed professional counselor with over 25 years of experience rescuing women from what she calls the "virtuous" trap of self-sacrifice. She’s a Ph.D. -certified Sex Counselor and Trauma Specialist and host of the Top 100 Motivational Podcast Compassion Fatigue Cure and the host of the Sexy After 50 podcast. Visit her at:Dr. Julie Merriman Wellness | Nervous System Regulation Grab her book, "In Pursuit of Soul Joy" here! Please like and subscribe if you're a regular listener...it really helps! xo

    47 min
  2. Will We Ever Feel Ourselves Again, After Divorce?

    MAR 24

    Will We Ever Feel Ourselves Again, After Divorce?

    Divorce isn’t just paperwork and custody schedules—it’s identity-shaking, gut-punching, “am I going to be okay?” energy. Jess sits down with therapist, speaker, and Unhitched author Oona Metz, who’s spent 30+ years helping women survive (and rebuild after) divorce… because she’s lived it too. As always, we talk about stuff people don’t say out loud—why divorce can feel so isolating, what women actually need in the middle of it, and how finding the right support can be the difference between spiraling and slowly coming back to life. And of course, we get into the flavorful nuances of dating, after divorce. If you’ve ever wondered “am I going to be okay?”—this one’s for you. #divorcehealing #divorcedwomen #datingafterdivorce #selfdiscovery Learn more about Oona: Website: Oona Metz, LICSW, CGP | Empowering Women+ Through Divorce Support & Therapy​ IG:https://www.instagram.com/oonametz Grab your copy of Unhitched!Unhitched: The Essential Divorce Guide for Women Please like and subscribe if you're a listening friend. It really helps! xo Takeaways: The five stages of divorce: heartbreak, roller coaster, mending, letting go, and new beginningsThe emotional challenges women face during divorce and healingPractical tips for self-care, healing, and rebuilding a thriving life after divorceLearning how to date well, after divorce

    41 min
  3. How To Become Secure In Relationships After Divorce, With Jessica Baum

    MAR 14

    How To Become Secure In Relationships After Divorce, With Jessica Baum

    Why do so many of us keep dating the same person… just with a different name? Jess sits down with nationally-recognized therapist and author Jessica Baum to unpack why our earliest emotional experiences quietly run the show in our adult relationships—especially after divorce. If dating keeps triggering old wounds or you find yourself stuck in the same relationship dynamics, attachment theory might explain why. Jessica breaks down how childhood needs and implicit emotional memories shape the way we attach, trust, and react in love. The good news? These patterns aren’t permanent. We talk about how to recognize your attachment style, heal the core wounds driving your relationship habits, and start building connections that actually feel safe, stable, and secure. Because the goal isn’t just to date again after divorce—it’s to date differently. #attachmenttheory #emotionalhealing #securerelationships #datingafterdivorce #nervous system, divorcehealing If this convo resonates, you NEED Jessica's books! Check them out: Safe: An Attachment-Informed Guide to Building More Secure Relationships Anxiously Attached: Becoming More Secure In Life and Love Connect with Jessica on her socials: Facebook Instagram LinkedIn⁠https://www.jessicabaumlmhc.com⁠⁠ Key Topics Covered: How to identify your attachment style and relationship patterns Why unresolved childhood wounds show up in adult relationships The role of implicit memory in emotional triggers How to break unhealthy dating and relationship cycles Why “supportive anchors” are key to healing attachment wounds Practical ways to build more secure, trusting connections If you're a return listener, please "like" and "follow!" It goes a long way! xo Chapters:00:00Introduction to Attachment Theory and Healing 03:06Understanding Attachment Styles 06:02The Importance of Healing Core Wounds 08:40The Role of Supportive Anchors in Healing 11:52Navigating Relationships and Dating After Divorce 26:47Embracing the Healing Journey 29:28Rediscovering Self and Empowerment 31:50Navigating Relationships and Attachment Styles 35:45Understanding Intensity vs. Intimacy 38:34Processing Divorce and Moving Forward 42:53Prioritizing Health and Personal Growth

    48 min
  4. How Can We Date Better, After Divorce? With Dr. Christie Kederian

    MAR 5

    How Can We Date Better, After Divorce? With Dr. Christie Kederian

    Jess sits down with celebrity matchmaker, psychologist and author Dr. Christie Kederian, a.k.a. the "date doctor" to explore what it really takes to date again after divorce and deep relational wounds. They get into:• Why some “red flags” are actually trauma responses• How to slow down and build real trust• Why dating multiple people isn’t necessarily wrong• The surprising role faith and surrender play in finding the right relationship If you’re tired of overthinking every text, questioning your instincts, or wondering whether love is even worth the risk again—this conversation will give you clarity, confidence, and a fresh perspective. Because sometimes what feels like rejection… is actually God protecting your future.#datingafterdivorce #healingrelationships, #redflags #attachmentstyles #faith-based dating #self-awareness, #loveadvice #moderndating, #relationshippatterns Show notes: Website: Dr. Christie Kederian | Home IG: @thedatedoctorchristie Grab your copy of Dr .Christie's book, "10 Dates to Your Soulmate: A Celebrity Matchmaker's Guide from First Swipe to Forever" Link for free guide: https://drchristie.myflodesk.com/vynot193te  Dr. Christie Kederian is an internationally renowned relationship therapist and former eHarmony matchmaker turned “date doctor.” She earned her bachelor’s, master’s, and doctoral degrees from the University of Southern California in Psychology and Marriage and Family Therapy. Dr. Christie has helped thousands of people create lives they love and find love they deserve. Dr. Christie has been a featured expert in ABC, NBC, KTLA, the Wall Street Journal, the Los Angeles Times, Cosmopolitan, NBC News, and more. Key Topics Healing past relationship traumaDistinguishing red flags from trauma responsesThe importance of self-awareness and trustBalancing faith and modern datingStrategies for dating multiple people10 Dates to Your Soulmate: A Guide to Lasting LoveHealing Past Wounds for Better Relationships"Slow down and build trust""Track habits and red flags""First dates are just the start"

    29 min
  5. Is Anxiety Stealing Your Joy—and What Can You Do About It? with Courtney Devich

    FEB 23

    Is Anxiety Stealing Your Joy—and What Can You Do About It? with Courtney Devich

    Anxiety doesn’t always look the same—and for many women, it shows up right when life falls apart. Jess sits down with author and speaker Courtney Devich (Mama’s Got Anxiety) for an honest, unfiltered conversation about what anxiety actually feels like, how it manifests in different seasons, and how faith and practical tools can coexist when you’re trying to hold it together. Courtney shares her personal journey with anxiety, depression, postpartum struggles, and motherhood—and how those experiences led her to become a voice for women who feel overwhelmed, ashamed, or stuck in spiraling thoughts. Together, Jess and Courtney talk about the unique anxiety that comes with divorce, heartbreak, and major life transitions—and why naming it is often the first step toward healing. They unpack: What anxiety really is (and when it becomes more than “normal worry”) Physical and emotional signs you may be missing Why anxiety often spikes during divorce, loss, and identity shifts How faith, therapy, and medication can work together—not compete Practical ways to interrupt spiraling thoughts and reclaim peace What it actually looks like to let God be your refuge in the middle of panic If you’re in a season where your mind won’t slow down, your chest feels tight, or you’re quietly wondering if this will ever pass—this conversation is for you. You’re not broken. You’re not alone. And this isn’t the end of your story. #divorcedwoman #healingafterdivorce #anxietyhealing #singlemom #divorcedchristian #Godheals Courtney Devich is a speaker and the author of Mama’s Got Anxiety: But It's Not Going to Steal Her Joy. Her writing has been featured in Her View From Home, YouVersion Bible App, and Christian Parenting, among others. As a writer, she uses her humor, honesty, and relatability to encourage women who struggle with their mental health or with their faith. She lives in Michigan with her husband and three kids, but no dog because why add to the chaos?(And here are some links in case you need those too.)Website: www.courtneydevich.comFacebook: www.facebook.com/courtneydevichauthorInstagram: www.instagram.com/courtneydevichauthorTakeaways Anxiety can manifest in various ways and is often situational.Recognizing anxiety is the first step in managing it.Faith can be a powerful tool in coping with anxiety.Community support is essential for those struggling with mental health.It's important to involve children in conversations about anxiety.Therapy and medication can be gifts from God for mental health.Gratitude can help combat feelings of anxiety.Anxiety can serve as a reminder to turn to God.The journey of managing anxiety is ongoing and can fluctuate.Hope and healing are possible through faith and support.

    35 min
  6. Is My Nightly Wine Self-Care… or Self-Sabotage? with Christy Osborne

    FEB 16

    Is My Nightly Wine Self-Care… or Self-Sabotage? with Christy Osborne

    Jess K. sits down with sought-after sobriety coach, speaker, and author Christy Osborne (Love Life Sober) for an honest, funny, and deeply relatable convo about the “mommy wine” trap, drinking as a coping mechanism, and why so many Christian women struggle in silence. Christy shares her story—college drinking, stress in law school, expat pub culture, postpartum darkness, grief after losing her mom, and the moment she realized her glamorous Instagram life didn’t match how she felt inside. They talk about why “dry January” doesn’t always work (hello, willpower trap), how cravings often signal deeper needs (comfort, connection, rest), and Christy’s practical tools like taking thoughts captive and playing the tape forward when the "wine witch" starts talking. This episode is a permission slip to stop pretending, get curious, and try an alcohol fast—without shame, perfectionism, or the pressure to label yourself forever. #SoberCurious #AlcoholFreeLife #AlcoholFree #LentFast t #SobrietyJourney #RecoveryIsPossible Show Notes: -Find Christy at LoveLifeSober.com -Grab a copy of Love Life Sober here -Love Life Sober on Insta Takeaways: Alcohol often has a “job.” Social ease, stress relief, loneliness, reward… figure out what you’ve hired it to do. The willpower trap is real. If the desire stays, willpower eventually loses. Start with thoughts and beliefs, not just behavior. “Take every thought captive” applies to cravings. Notice the thought → investigate the story → replace with truth. Play the tape forward (twice). What happens if you drink tonight? What happens if you don’t? Loneliness is a major trigger—especially for women living alone. The “wine is my friend” narrative is powerful and common. Your body keeps receipts. Sleep, mood, anxiety, and energy often improve quickly once alcohol is out of the system. This doesn’t have to be all-or-nothing. A fast can be an experiment that gives you data, clarity, and momentum. Shame thrives in secrecy. Saying it out loud (to a trusted person/community) is often the first step toward freedom.

    36 min

  7. FEB 10

    Why Do Post-Divorce Breakups Hit Like a Truck?

    Jess K. unpacks why breakups hit differently after divorce — heavier, sharper, and somehow more personal than we expected. You finally put yourself back out there, risk hope again… and then it falls apart. It’s exhausting, humbling, occasionally humiliating., and very tempting to just delete the apps, buy a weighted blanket, and emotionally retire. But in true quasi-delusional fashion, Jess delivers a pep talk for the women who are tired and confused by post-divorce dating, sprinkling in just enough Biblical wisdom to believe love might still be possible. #datingafterdivorce #breakups #datingafter40 #christiandivorce #divorcedwoman #healingafterdivorce #securelyattached Please like and follow if you're a regular! It really helps! xo Quote: "One of the greatest breakthroughs we can have in life is realizing that how someone treats us is a reflection of their emotional capacity-not our worth. People project unhealed wounds."- author Jill Turecki Insta reel (shared during show): https://www.instagram.com/jasmiines.world/reel/DT7-f1hDWEX/

    22 min

  8. JAN 21

    Can We Make Adulting Less Miserable With Habit Stacking?

    Jess K and Jess T break down habit stacking — the ultimate busy-mom hack for getting things done without burning out. From pairing chores with self-care (hello face masks + folding laundry) to turning boring to-dos into mini reward moments, the girls share real-life strategies that actually work for divorced moms juggling everything. If your to-do list feels overwhelming, this episode is your permission slip to work smarter — not harder. #habitstacking #selfcare #productivity #divorce #singlemom #newyeargoals Please like and subscribe...it really helps! xo Chapters: 00:00Introduction and Seasonal Reflections 01:40Understanding Habit Stacking 04:28Practical Applications of Habit Stacking 07:34Motivation and Accountability in Habit Formation 10:12Reward Systems and Habit Stacking 13:23Reverse Habit Stacking and Breaking Bad Habits 15:58Integrating Habits into Daily Life 18:29Social Connections and Habit Stacking 21:39Wins and Fails: Personal Reflections

    36 min
See All (40)

5
out of 5
9 Ratings

About

Gritty, faith-filled, hilarious conversations for women rebuilding after divorce and other hard life transitions. Author and host Jessica Kastner gets unapologetically real about the stuff we rarely admit, let alone say out loud. Covering everything from the impending doom of perimenopause, the thrills of coparenting, emotional healing after divorce, (anxiously attached but still sexy A+) and the fresh flaming hell that is online dating, Jess soaks up wisdom and advice from amazing female experts, who live to tell.

Information

  • Creator
    Jessica Kastner
  • Years Active
    2025 - 2026
  • Episodes
    40
  • Rating
    Explicit
  • Copyright
    © Jessica Kastner
  • Show Website
    Free Failing

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