PODCAST · society
Free Failing
by Jessica Kastner
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.
Episodes
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Are You Avoiding the One Thing That Could Actually Heal You? with Alicia Michelle
Feeling stuck? It might not be your situation—it might be what you’ve buried. Jess sits down with neuro coach and Christian mindset expert Alicia Michelle to reveal how years of emotional suppression kept her stuck—and the turning point that changed everything. Allicia unpacks how unhealed...
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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....
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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...
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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...
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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…
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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…
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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...
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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...
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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...
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Why Is the Mental Load So Heavy for Single Moms?
Jess T. & Jess K. dive into the real cost of single motherhood—the burnout, the emotional whiplash, and the quiet resilience it takes to keep going. They explore how single moms juggle family dynamics, carry invisible labor, and still find joy in the middle of the madness. This episode is equal...
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What If This Year Was Brutal—but Necessary?
In a solidary effort NOT to make the same mistakes in 2026, Jess & Jess reflect, laugh and cringe at some of the greater "wins" and "fails" they've experienced this past year. Reflection can be powerful, when we allow ourselves grace, and also take time to celebrate the victories we often…
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What If Peace Matters More Than Progress This Year?
Jess T. & Jess K. (a self-professing New Year's "junkie") reframe New Year’s resolutions through the lens of real life after loss and starting over. Traditional resolutions can feel exhausting and defeating when you’re rebuilding instead of reinventing after divorce or major life transitions.…
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Is Your Body Smarter Than His Texts?
In this episode, Jess & Jess crack open one of the most underrated superpowers women have: the ability to let your nervous system lead. We’re talking gut feelings, tight chests, instant contractions, and those unexplainable vibes you get on a date that your brain tries to talk you out of. Why do...
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Why Do the Holidays Feel Like Emotional Hunger Games for Divorced Moms?
Jess and Jess dive into the chaos and emotional landmines of being a Type B divorced mom during the holidays. Jess K. confesses to showing up with multiple presents literally duct-taped together, while Jess T. openly admits she has 100% blamed Santa for a last-minute toy swap. It’s hard enough...
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Is Emotional IQ the New Midlife Dating Red Flag?
Jess & Jess dig into the absolute rodeo of dating in your 40s — where emotional maturity is basically foreplay, intentionality is a green flag, and dating apps have become a full-time unpaid internship. If there’s one common denominator among divorced women, it’s this: men in their 40s and 50s...
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Why Does “Boyfriend” Feel So Cringy After Divorce?
Jess K. and Jess T. unpack the latest viral Vogue article asking: Is it embarrassing for grown women to have a boyfriend? From the awkwardness of saying “my boyfriend” post-divorce to the freedom of doing life solo, they dive into how modern women are redefining identity, confidence, and love...
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Who Are We Really, When All the Labels Fall Away?
What happens when the titles we’ve lived under — wife, stay-at-home mom, stepmom, fiancé— suddenly fall away? Jess K. and Jess T. strip down the illusions of identity and talk honestly about what it takes to rebuild from the inside out. Admittedly. It's not easy. Jess K. sometimes wears her...
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One Year After Divorce...Would Jess K. Do Anything Differently?
Jess K. reflects on her life, now one year after divorce—the heartbreak, the healing, and the surprising moments of hope along the way. She shares what helped her most along the way (and what didn’t!), reminding anyone walking a similar road that healing takes time—and that patience and grace for...
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How Can We Avoid Settling When Dating After Divorce?
Jess and Jess tackle the dreaded “S” word of dating: settling. We’ve all done it, justified it, or tried to rebrand it as “being realistic.” But after surviving divorce, do we really have the time—or emotional credit limit—to settle for less than what we’ve been praying for? This convo gets real...
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Cuffing Season After Divorce: Cozy or Just Complicated?
This week, Jess T. and Jess K. get real about whether cuffing season—aka that magical time of year when even the most independent women start wondering if Netflix feels better with someone’s son hogging the blanket-even works for divorced moms. We break down why cuffing hits different when you’re...
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Why is Reframing So Powerful After Divorce?
Jess T. and Jess K. dive into the power of “reframing” — the simple but life-changing practice of flipping negative thoughts and hard circumstances into fresh, hopeful perspectives. From navigating loss and heartache to the everyday chaos of parenting and life stress, shifting your mindset can…
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Can Losing Everything Lead to Finding Yourself?
Jess and Jess dive into what it really looks like to rediscover yourself at midlife (ish!) after divorce. From juggling motherhood with society’s never-ending expectations to holding onto the passions that make you you, change doesn’t have to mean losing ourselves. Let's unpack the power of names...
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The Enneagram at 40: Who Am I Now?
Divorce can leave us asking, “Who am I now?” In this episode, Jess and Jess sit down with professional Enneagram coaches Jasmin Beeney and Theresa Krupicka to explore how we can rediscover our true selves in the aftermath of loss and transition. Whether you’re navigating grief, rebuilding your...
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Finding Confidence After Heartbreak With Ashley Henriott
Jess and Jess sit down with bestselling author Ashley Henriott to talk about her powerful journey through heartbreak, healing, and unexpected reconciliation. Less than a year ago, Ashley and her husband were on the brink of divorce—living apart, with papers ready to sign. But through raw...
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Are We Older and Wiser or Just Older?
Jess & Jess rewind the clock and spill the tea on what they wish they could tell their 20-year-old selves. From learning to love the body you’re in, to breaking free from toxic beliefs, to ditching the dating apps and putting family first—the wisdom list is long (and sometimes a little spicy).…
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Finding Love Again (God's Way) After Divorce, With Yvette Walker
Jess and Jess sit down with speaker, author, and podcaster Yvette Walker to explore what it truly means to date with purpose, discover lasting contentment in God, and embrace the joy of self-growth after divorce. Yvette shares her powerful story of surrendering her relationships to God’s will—and...
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Can We Ever Avoid Post-Divorce Triggers?
Jess & Jess tackle the emotional sucker punches that consistently come flying after divorce—and how to survive them with your sanity intact. From getting blindsided by Facebook time hops somehow making your ex look like Clooney, to hearing way too much from the kids about Dad’s shiny new...
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Girls' Trips. Indulgence or Soul Care?
Fresh off a fun and "memorable" girls' trip, Jess & Jess a make the case for why every woman needs one on the calendar—stat. We’re talking shameless beauty swaps (estrogen cream for your face?!), uncontrollable belly laughs, and the kind of emotional pep talks you just don’t get in the school...
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Post-Divorce Fears. How Can We Replace Lies with Truth?
Are we the common thread in all our failed relationships? Does being a divorced single mom with a house full of kids scare off quality men? Are we not "Christian enough" for the kind of guy we're praying for? In this raw and honest episode, Jess & Jess open up about their deepest fears around...
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How Can We Spot a "Wolf" In Good Guy's Clothing?
Jess & Jess dive into the heart hazards every divorced woman needs to spot when reentering the dating world—especially online. From love bombers and "future fakers" to phony Christians and closet narcissists, how can we tell who’s real? And more importantly—how can we weed out the wrong guys by...
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The Power of Female Friendship. Can A Man Ever Be What Our Girlfriends Are?
Jess & Jess dive into the powerful, unshakable bond of female friendship—the kind that has carried them through every season of life, especially divorce. While relationships have come and gone (yes, even husbands), their sisterhoodhas remained a constant source of strength, healing, and laughter....
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Can We Really Be Happy Alone, After Divorce?
Does independence have to feel lonely? And if we learn to truly enjoy life on our own, will we ever want to remarry? In this episode, Jess & Jess get honest about their shared struggle with codependency in relationships—and how the pendulum can swing too far in the other direction after divorce....
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Aging In Your 40's. Soldier On Gracefully Or Just Get Botox?
Jess & Jess dive into the superficial side of life—from the pressure of staying young and fit in their forties to the moral gray zones of modern beauty trends. Is taking Ozempic “cheating the system”? What about Botox, boob jobs, and facial surgeries from a Christian perspective? Raised in the...
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Coparenting With The Ex. Will It Ever Get Better?
Jess & Jess spill the tea on the wild, unexpected struggles of coparenting after divorce. From awkward run-ins with the ex’s new girlfriend, to clashing parenting styles, to the never-ending scavenger hunts for forgotten items at the “other house” — the insanity can feel endless. It’ll eventually...
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Being Single At Social Events. Plus Or Minus One?
Should we dread, or embrace having no plus one for social events after divorce? Jess & Jess laugh about the awkwardness and difficulty of going on family vacations and showing up to parties alone, while fiercely debating whether they'll be laughing or crying at the singles table at an upcoming...
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To Date, Or Enjoy The Single Life, After Divorce?
How do we know we're ready to date again after divorce? Has Anyone EVER found their soulmate after speed-dating? From the verified horror show that is online dating, to questioning whether or not to date a "non-Christian," Jess & Jess chat about the nuances, perks, and pitfalls that come with...
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Explore Attachment Theory, Or Just Use Chat GPT?
Jess & Jess talk about attachment style-based therapy, asking Chat GPT for boy advice after too much pinot, and how looking for a good therapist is the new Match.com.
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Can Our Silent Fears Lead To Our Loudest Wins?
Jess & Jess talk about the mix of beauty and pain when experiencing major life moments "alone," after divorce. Kids graduations, weddings, milestone birthdays and even personal victories can feel bittersweet and awkward when going it alone (especially if the ex is there). But the feeling of...
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Should We Just Date The Handyman For Help?
Jess & Jess chat about the hidden plights of Springtime for single homeowning moms. From tackling lawn care because the teens are "too busy," cringing daily at the thought of bikini season, and seriously considering dating a handyman just for the help...this episode is for the summertime mamas…
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Am I In Denial... Or Is This Perimenopause?
Jess & Jess talk about the unforeseen joys of getting older. From begrudgingly going to the gyno after more than a decade, to living in staunch denial of perimenopause and consistently failing to look cute in readers...this is what 40 (ish) feels like.
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Living With Adult Children...Blessing Or A Curse?
Jess & Jess talk about the unexpected challenges and hilarity found in living with adult children. From being the third wheel in your own home, to wondering if you can still ground your 21-year-old for slamming the door...no one's really prepared for this "special" season of life.
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ABOUT THIS SHOW
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.
HOSTED BY
Jessica Kastner
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Frequently Asked Questions
How many episodes does Free Failing have?
Free Failing currently has 41 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Free Failing 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...
How often does Free Failing release new episodes?
Free Failing has 41 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Free Failing?
You can listen to Free Failing on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Free Failing?
Free Failing is created and hosted by Jessica Kastner.
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