Free Failing

PODCAST · society

Free Failing

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.

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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 childhood wounds shape our thoughts, relationships, and faith—and why avoiding your emotions may be the very thing holding you back.They dig into:Why avoiding emotions keeps you stuckHow childhood wounds shape your thinkingA simple 3-step method to process what you feelHow to rebuild trust in God in the middle of healingAlicia also shares her powerful ADD method—Acknowledge, Discern, Decide—giving you practical tools to move forward with clarity, emotional confidence, and deeper trust in God.Because you can’t heal what you won’t feel.#emotionalconfidence, #neuroscience, #Christianmindset, #healing, #corewounds, #divorce Please like and subscribe if you're diggin' this podcast...it really helps! xoAlicia Michelle is an ICF-certified Christian life coach and NeuroCoach, author of Emotional Confidence, popular conference speaker, and host of the multi award-winning⁠The Christian Mindset Coach Podcast⁠. Learn more at ⁠AliciaMichelle.comGrab her book here! Emotional Confidence: 3 Simple Steps to Manage Emotions with Science and ScriptureVisit her on socials:Facebook: @theAliciaMichelleCoachIG: @AliciaMichelleCoachYouTube: @AliciaMichelleCoachTakeaways:The importance of acknowledging and processing emotionsHow childhood wounds shape adult thought patternsThe ADD method: Acknowledge, Discern, DecideThe role of scripture and neuroscience in healingPractical steps for emotional healing and trust in GodFrom Suppression to Confidence: Alicia Michelle’s JourneyHealing Core Wounds with Science and Scripture"Invite Jesus into your pain and disappointment""God uses our hard circumstances to grow us""God makes beauty from ashes, even in divorce"

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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.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 RegulationGrab her book, "In Pursuit of Soul Joy" here!Please like and subscribe if you're a regular listener...it really helps! xo

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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 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/oonametzGrab 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

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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 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, divorcehealingIf this convo resonates, you NEED Jessica's books! Check them out:Safe: An Attachment-Informed Guide to Building More Secure RelationshipsAnxiously Attached: Becoming More Secure In Life and LoveConnect with Jessica on her socials:FacebookInstagramLinkedIn⁠https://www.jessicabaumlmhc.com⁠⁠Key Topics Covered:How to identify your attachment style and relationship patternsWhy unresolved childhood wounds show up in adult relationshipsThe role of implicit memory in emotional triggersHow to break unhealthy dating and relationship cyclesWhy “supportive anchors” are key to healing attachment woundsPractical ways to build more secure, trusting connectionsIf you're a return listener, please "like" and "follow!" It goes a long way! xoChapters:00:00Introduction to Attachment Theory and Healing03:06Understanding Attachment Styles06:02The Importance of Healing Core Wounds08:40The Role of Supportive Anchors in Healing11:52Navigating Relationships and Dating After Divorce26:47Embracing the Healing Journey29:28Rediscovering Self and Empowerment31:50Navigating Relationships and Attachment Styles35:45Understanding Intensity vs. Intimacy38:34Processing Divorce and Moving Forward42:53Prioritizing Health and Personal Growth

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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 build real trust• Why dating multiple people isn’t necessarily wrong• The surprising role faith and surrender play in finding the right relationshipIf 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 | HomeIG: @thedatedoctorchristieGrab 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 TopicsHealing 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"

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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 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 missingWhy anxiety often spikes during divorce, loss, and identity shiftsHow faith, therapy, and medication can work together—not competePractical ways to interrupt spiraling thoughts and reclaim peaceWhat it actually looks like to let God be your refuge in the middle of panicIf 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 #GodhealsCourtney 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/courtneydevichauthorTakeawaysAnxiety 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.

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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 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 InstaTakeaways: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.

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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 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! xoQuote:"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 TureckiInsta reel (shared during show): https://www.instagram.com/jasmiines.world/reel/DT7-f1hDWEX/

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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 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 #newyeargoalsPlease like and subscribe...it really helps! xoChapters: 00:00Introduction and Seasonal Reflections01:40Understanding Habit Stacking04:28Practical Applications of Habit Stacking07:34Motivation and Accountability in Habit Formation10:12Reward Systems and Habit Stacking13:23Reverse Habit Stacking and Breaking Bad Habits15:58Integrating Habits into Daily Life18:29Social Connections and Habit Stacking21:39Wins and Fails: Personal Reflections

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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 parts honesty, validation, and reminder that strength doesn’t always look polished.#Momburnout #invisiblelabor #SingleMomLife #DivorcedMomLifeRegular listeners...please like and subscribe! It really helps! xoChapters00:00The Burden of Single Motherhood08:04Navigating Life's Unexpected Challenges16:11The Emotional Weight of Parenting22:17Planning for the Future: Vacations and Responsibilities28:44Finding Balance Amidst Chaos32:46Wins and Fails: Celebrating Small Victories

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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 overlook or minimize through the business of everyday life. Jess K. is vowing to trust her gut this year to avoid the same dating pitfalls. Jess T. is determined to enact some legit form selfcare that includes exactly zero of her five children. Let's hope by this time next year, we're 'cheersing' more than cringing! #newyearsgoals #divorcedwoman #singlemom #Christiananddivorced #Resolutions #newyearnewgrace #thepowerofreflection #lookingbackAre you a continual listener? Will you consider liking and subscribing? It helps our motivation! xo

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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. Maybe this year we choose stability and peace in a season that asks for something gentler.Sometimes faithfulness looks quieter in midlife, and it's not that we're behind...we're just becoming. Now please pass the champagne...#NewYearNewGrace #FaithInTransition #SingleSeasonStrong#MidlifeResetv#HealingNotHustle #BecomingNotBehindPlease like and/or subscribe...it really helps! xo

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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 some men look perfect on paper but your body says absolutely not?Why does “fast and exciting” sometimes feel more like a panic attack than a love story?And how do you tell the difference between fear… and clarity?We’re breaking down:How your nervous system scans for safety before your mind doesWhy “slow is safe” in dating, friendship, and intimacyWhat it means when your body shuts down, tightens, or contractsHow to stop overriding your intuition just to be politeWhy your nervous system keeps the receipts even when your heart doesn’tNo fluff, no clinical jargon.Just two divorced women giving it to you straight, sharing real-life examples, science, sarcasm, and a little bit of therapy language we picked up along the way.Because here’s the truth:Your body isn’t dramatic. Your body is honest.And when it whispers “no”… that’s the answer.Tune in, laugh with us, learn with us, and maybe start trusting your gut again. Your nervous system is the best dating coach you never knew you had.#thebodykeepsscore #datingafterdivorce #datingafterforty #gutfeeling #nervoussystemwisdomAre you a regular listener? Please like and subscribe...it really helps xo

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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 holding down the fort in regular life, let alone juggling the absurd holiday pileup of shopping, cooking, party-planning, and budget acrobatics. And if you’re freshly divorced, the emotional whiplash hits even harder.Throw in a little heartbreak, a lot of logistical chaos, and the pressure to “make magic,” and honestly… we’re ready to call it a season and hide in a blanket fort.Are you a regular listener? Please consider subscribing and liking...it really helps! xo #TypeBMom #singlemom #divorcedmom #holidayoverwhelm

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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 often seem to be missing the emotional intelligence required for a truly satisfying relationship. Did marriage flatten their empathy circuits? Did divorce create a whole generation of men who can’t think or feel beyond themselves? We’re not saying yes… but we’re also not not saying yes.Eternal optimist Jess K. insists the deep-feeling unicorns are still out there. Meanwhile, Jess T. has her solo-travel passport stamped and ready for a lifetime of peaceful, man-free sunsets.Drop a comment and tell us: what’s your midlife-ish dating experience? Are you finding emotionally awake men… or just guys who say they “don’t believe in labels”?Please consider hitting "like" and "follow" if you're a regular! It really helps! xo⁠Visit us on TikTok⁠ and⁠ Insta!#divorce #datingafter40 #datingafterdivorce #divorcedwomen #singlemom #christianwomen #christiandivorce #emotionalintelligenceTakeawaysDating in your 40s is a unique experience.Emotional depth is often lacking in successful men.Finding a balance between emotional connection and practical considerations is crucial.Women often date men who are emotionally rusty after divorce.Deal breakers are essential in the dating process.The ideal partner should be kind, hardworking, and emotionally intelligent.Modern dating requires social skills that many lack.Dating apps have changed the landscape of relationships.Creative approaches to dating can help break the ice.Intentionality is key in finding the right partner.Chapters00:00Navigating the Dating Landscape02:41Emotional Depth vs. Social Status05:29The Quest for Balance in Relationships08:48Understanding the Dating Pool11:18The Challenges of Dating After Divorce14:38Ideal Partner Characteristics17:29Exploring Age Dynamics in Dating20:21Intentional Dating and Deal Breakers23:14The Role of Dating Apps in Modern Relationships27:20Navigating Modern Dating Challenges30:52The Role of Social Cues in Dating35:02Creative Approaches to Meeting People38:34The Frustration of Dating Apps41:56Exploring New Dating Services43:34Wins and Fails in Personal Life

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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 beyond relationship status. Let's talk about...How to handle the “boyfriend demotion” and whether we’re too old to say “my man” without cringing.Does calling someone your “partner” makes you sound evolved… or like you co-own an Etsy shop.Why “situationship” sounds too Gen Z, but “gentleman caller” makes us sound like we live in a Jane Austen novel.The weird in-between of being too old for “boyfriend,” but not quite ready for “life companion.”Realizing that your "person” might actually be your therapist, your kid, or your dog.Please consider hitting "like" and "follow" if you're a regular! It really helps! xoVisit us on TikTok and Insta!#Singlemom #datingafterdivorce #divorcedwoman #datingafterforty #healedgirlera #selfdiscovery #Vogueboyfriendarticle

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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 engagement ring in secret (it's just so pretty). Jess T. crashes out sometimes, juggling the stresses of single parenting 5 (FIVE!) kids. But every day, we're getting closer and closer to becoming the confident, content and resilient women God created us to be...no matter our relationship status.#divorce, #identity, #singlemotherhood, #selfdiscovery, #christianwomen #christiandivorcere #lifeafterdivorce #divorcehealingPlease like and subscribe! It really helps. xoTakeaways:The transition from married to single life can drastically alter one's identity.Single parenthood brings unique challenges and insights into personal growth.Loss of status and security can be a significant emotional hurdle after divorce.Reframing family dynamics is essential for personal healing and growth.Women often feel a sense of pride and identity tied to their marital status.The journey of self-discovery is crucial in redefining one's identity post-divorce.Finding peace and autonomy in being single can lead to greater self-acceptance.The complexity of names and identity can impact how women perceive themselves and are perceived by others.Empowerment comes from embracing one's individual identity beyond marriage.Sharing experiences can help others navigate similar transitions in their lives.Navigating Identity Through Relationship ChangesChapters00:00Navigating Identity Shifts: From Marriage to Divorce05:46The Emotional Landscape of Divorce09:13The Loss of Status and Security14:27Reframing Identity and Family Dynamics18:09The Challenge of Public Identity and Visibility20:56Embracing Change and Identity23:02Finding Peace in Transition26:10The Journey of Self-Discovery26:46Navigating Relationships and Names29:35The Complexity of Identity32:09Empowerment Through Reinvention35:05Wins and Fails in Everyday Life

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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 yourself is key.Please follow this show on Spotify. It really helps! xo#Divorcehealing #Divorcedwomen #christiandivorce #PodcastForWomen #Lifeafterdivorce #startingoverTakeawaysReflecting on the past year after divorce can reveal significant personal growth.Healing requires intentional self-care and emotional processing.It's important to lean on faith during difficult times.Avoiding triggers and being kind to oneself is crucial post-divorce.Setting healthy boundaries with friends and family can aid in recovery.Grief and healing are unique to each individual and should be respected.Dating too soon after a divorce can complicate the healing process.Therapy can provide essential support during transitions.Finding joy in solitude can lead to unexpected happiness.Divorce does not define one's worth or future opportunities.Chapters00:00Introduction and Reflection on Divorce Journey10:37Healing and Self-Care After Divorce20:46Finding Purpose and Identity Post-Divorce

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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 about what settling actually looks like, why we keep getting hooked on the same unhealthy patterns, and how to finally raise the bar in this healed, post-divorce era. No more tolerating perpetual “icks” from 50-year-olds with anger issues. No more swapping our cozy couch for another “meh” date just because we feel like we should. It’s time to ditch the lukewarm feelings, hold out for what we really want (or go after it ourselves), and start dating from a place of confidence, not compromise.Jesus, take the group chat. 🙏#DatingAfterDivorce, #ChristianDivorce, #MidlifeDating #HealedGirlEra, #NoMoreSettling, #RaiseTheBarDatingTakeawaysSettling in relationships can stem from societal pressures and personal insecurities.Understanding our standards is crucial in avoiding settling.Character traits are more important than superficial qualities in a partner.Past relationships can inform what one should avoid in future partners.Self-esteem plays a significant role in relationship choices.Prayer and intuition can guide decisions in dating.Recognizing red flags early can prevent future heartache.Communication is key, but some issues may warrant walking away.Healing from past relationships is essential before entering new ones.It's important to feel like the luckiest person in a relationship.Navigating the Temptation to SettleUnderstanding Relationship Standards"How do you know you're settling?""Pay attention to your body.""You are enough."Chapters00:00The Impact of Past Experiences11:41Navigating Rejection and Self-Worth14:27:The Science of Attraction17:19Recognizing Forced Connections19:31The Challenge of Personal Growth in Relationships21:55Healing and Self-Esteem: The Roots of Settling23:17The Importance of Prayer in Dating Decisions26:11The Power of Prayer and Intuition in Dating26:49Wins and Fails: Personal Reflections31:42Learning from Experience: Avoiding Past Mistakes

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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 40+, and whether a placeholder relationship is ever worth the emotional hangover. From laughing at our own questionable dating choices to side-eyeing the concept of “seasonal love,” we’re asking the real questions: Is cuffing season just cozy fun—or a fast track to emotional chaos?#CuffingSeason #Situationships #PlaceholderLove #DivorcedAndDating #DatingAfterDivorce #ChristianDivorceTakeaways:Cuffing season is a real phenomenon that many experience.The emotional stakes of cuffing season can be high, especially for women.Cuffing after 40 presents unique challenges and considerations.Placeholder relationships can lead to emotional complications.Loneliness can drive the desire for companionship during cuffing season.Cuddling can create emotional attachments that complicate relationships.Navigating casual dating requires self-awareness and honesty.The risks of cuffing season include potential heartbreak and wasted time.Chapters:00:00Introduction to Cuffing Season02:59Understanding Cuffing Season Dynamics05:28Cuffing Season: Gender Perspectives06:30Cuffing Season After 4009:19The Emotional Complexity of Cuffing11:44Navigating Loneliness and Relationships14:04The Risks of Cuffing Season16:40Cuffing Season and Emotional Attachment18:08Cuffing Season: A Reality Check21:04Conclusion and Reflections on Cuffing Season

  21. 21

    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 make all the difference. With a mix of faith, science, and a good dose of humor, this episode gives you practical ways to start reframing your own thoughts and embracing growth along the way.#MindsetShift, #ReframeYourMind #Divorcedwoman #LifeAfterDivorce #ChristianDivorceChapters00:00Understanding Reframing: A Cognitive Approach02:13The Power of Perspective: Shifting Mindsets04:30Personal Experiences: Navigating Life Changes07:15Faith and Reframing: A Spiritual Perspective09:58Big Picture Thinking: Seeing Beyond the Immediate10:59Taking Thoughts Captive: The Role of Faith16:56Scientific Basis of Reframing: Brain Science andTherapy19:18Applying God's Perspective: Renewing the Mind21:33Navigating Support and Accountability24:00The Power of Reframing26:39Destiny and the Illusion of Choice33:53Practical Steps to Reframe Your Mindset35:06Celebrating Wins and Acknowledging Fails 

  22. 20

    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 and identity, the confidence that comes from personal growth, and why it’s never too late to start fresh. Part of divorce is letting go of the painful past and finding beauty in new beginnings—even when life doesn’t go as planned. #divorce #selfdiscovery #personalgrowth #midlife #Christianwoman TakeawaysDivorce can be a catalyst for self-discovery.Maintaining personal identity is crucial during motherhood.It's important to keep pursuing personal interests.Name changes can impact identity and self-perception.Embracing change can lead to new beginnings.Self-care and personal growth are essential after divorce.It's never too late to pursue your dreams.Women often sacrifice their identities for family roles.Finding freedom in self-discovery is empowering.You can start from scratch and redefine your life.Chapters:00:00Rediscovering Identity in Midlife02:04The Impact of Divorce on Self-Discovery05:00Navigating Changes in Relationships and Roles06:17The Struggles of Name Changes and Identity09:09Embracing New Beginnings and Personal Growth12:28The Concept of Jubilee and Renewal21:36Embracing Change and New Beginnings25:12Rediscovering Self and Personal Growth30:46The Power of Time and Healing34:54Pursuing Dreams and New Opportunities35:56Celebrating Wins and Learning from FailsVisit us at the Free Failing podcast - YouTube!

  23. 19

    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 identity, or longing to step into a new season with clarity, the Enneagram offers a roadmap for healing and growth. Learn about the patterns we can release, and the strengths we can lean into as we rebuild. If you’re ready to transform pain into purpose and move forward with greater self-awareness, this conversation will give you both hope and practical insight. PLUS how the Enneagram can revolutionize your dating life!#Enneagram #DivorceHealing #selfawareness #knowyourself #EnneagramAndDatingLearn more about Jasmin and Theresa's Bridge Nine Consulting services here!

  24. 18

    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 self-reflection and honest conversations with God, Ashley discovered a deeper kind of freedom and faith that carried her through the hardest season of her life.This episode isn’t just about the joy of reconciliation—it’s about learning to build an authentic, unshakable faith when everything else falls apart. Ashley’s vulnerable story offers hope, courage, and encouragement for anyone walking through heartache and searching for healing.#confidence #healing, #personal growth #divorce, #reconciliation #traumaInfluencer, speaker, confidence coach, and podcaster Confidence and Coffee, Ashley Henriott shares daily doses of faith-filled confidence with women across the globe. She encourages women to embrace the message that they are never too far from God’s grace to be rescued, redeemed, and released to live a courageous, confident life.TikTok: @Ashleyhenriott  Insta: @Ashley.henriott Buy her book, Confidence is an Inside Job here!Check out her Confidence and Coffee podcast on YouTube.It's book giveaway time! Please follow and comment on Spotify, Apple podcasts or our YouTube channel and your name will be entered in a raffle to win a copy of Confidence is An Inside Jobe (and a scented candle!). We'll announce the winner on Oct. 1st!

  25. 17

    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). But instead of drowning in regret, this conversation is about growth, grace, and moving forward...because we’re divorced, not dead!#youngerself #lifelessons #growth #divorcedwomen #singlemom #christianwomanCome visit us on YouTube and drop a comment here/there on what you'd share with your younger self! xo

  26. 16

    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 how that surrender opened the door to finding her true love. Her journey will encourage and inspire every woman navigating the pain of heartbreak and the hope of new beginnings. #divorcedwoman #Christiandivorce #datingafter40 #datingafterdivorce #divorcerecovery #relationshipgoalsLearn more about author, podcaster and speaker Yvette Walker at postivitleyjoy.com.-Instagram:@positivelyjoypodcast-Facebook: @Positively JoyPodcast-Twitter@ywalkerYouTube : ⁠@YvetteWalker on YouTube-The Positively Joy podcast-Check out Yvette's book, "Journaling His Joy" on Amazon.

  27. 15

    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 life—welcome to the trigger minefield.Some you can dodge. Others blow up right in your face. Jess & Jess share their ever-evolving survival list for when the hits come, as well as how to prevent or diffuse many of them through the joy of new beginnings, learning to reclaim the past, and redefining family dynamics. #PostDivorceLife #DivorceRecovery #MovingOnStrong #EmotionalTriggers #TriggerProof #ChristiandivorceCome visit us on YouTube! xo

  28. 14

    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 pickup line. If you’ve ever felt guilty or unsure about ditching your to-do list for a few days with your ride-or-dies, consider this your official permission slip. Pack the bag, book the flight, and don’t forget the dry shampoo.Visit us on YouTube! Free Failing podcast - YouTube#girlstrip, #girlsweekend, #wanderlust, #girlspower, #friendshipgoals

  29. 13

    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 dating, heartbreak, and self-worth. With courage and vulnerability, they expose the lies we often believe after loss—and speak biblical truth to counter them.Because healing begins with confession, and freedom starts when we choose truth over fear.#FaithOverFear #ChristianDivorce #SingleMomLife #RenewYourMind🎥 We're now ⁠⁠on YouTube⁠! ⁠Come visit us for some face time—and drop a comment sharing the truth or Scripture that’s helped you fight fear and reclaim hope. xoShow notes: -⁠Switch on Your Brain by Dr. Caroline Leaf ⁠-⁠Battlefield of the Mind by Joyce Meyers⁠- ⁠Mel Robbins⁠-2 Corinthians 10:5: "We demolish arguments and every pretension that sets itself up against the knowledge of God, and we take captive every thought to make it obedient to Christ."-⁠God's Limitless Ability to Redefine Your Life⁠

  30. 12

    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 date two instead of date twenty? If you’re feeling exhausted, disheartened, or wondering if any good guys are even out there... this one’s for you. xoCheck out our ⁠YouTube channel here!⁠#lovebombing #futurefaker #datingafterdivorce #divorcedwoman #christiandivorce #singlemom #Lovelanguages #DivorcedChristianWoman #datingOver40Show notes:⁠-How to Identify A Love Bomber⁠-⁠How to tell if the person you're dating is a real Christian

  31. 11

    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. As they explore the idea of remarriage, they ask: Is it truly possible to experience that same depth of connection and unconditional love with a partner? After the heartbreak of divorce, should we even hope to find a man who feels like a best friend? And when dealing with prior trust issues...is that kind of relationship even realistic? Least one thing's for sure: true friends are the treasure of life.#DivorcedChristian#SingleMom#Women #FemaleFriendship #RelationshipGoals #Therapy

  32. 10

    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. From the challenge of being alone to the temptation of becoming hyper-independent, they explore what it really looks like to find balance, and live whole, without a husband. #Codependency #DivorcedMom #JesusWasAFeminist

  33. 9

    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 heart of “purity culture,” where bikinis were labeled the devil’s garb, Jess & Jess reflect on the lasting impact of a modesty-obsessed church and coming of age in the skinny-obsessed ‘90s. #OzempicDebate #DallasCowboysCheerleaders #BotoxDebacles #PurityCulture

  34. 8

    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 get easier… right?!#Coparenting #MomGuilt #DivorcedMom

  35. 7

    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 wedding.

  36. 6

    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 dating again after divorce.

  37. 5

    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.

  38. 4

    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 accomplishing something on our own merits, with only God by our side is also kinda priceless.

  39. 3

    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 who just want to have fun amidst the allergy attacks and fly swatting.

  40. 2

    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.

  41. 1

    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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