Free Failing

Free Failing

By Jessica KastnerSociety & Culture
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Free Failing episodes

  • 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. xo

    Check out our ⁠YouTube channel here!⁠

    #lovebombing #futurefaker #datingafterdivorce #divorcedwoman #christiandivorce #singlemom #Lovelanguages #DivorcedChristianWoman #datingOver40

    Show notes:

    ⁠-How to Identify A Love Bomber⁠

    -⁠How to tell if the person you're dating is a real Christian


    58 min
  • 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 smooth-talking "future planners" to fake Christians and narcissists in sheep’s clothing, how do you tell who’s real? And more importantly—how can you weed out the wrong guys by date two instead of date twenty? If you’re feeling exhausted, disheartened, or wondering if any real “sheep” are even out there... this one’s for you. There is always hope.

    #lovebombing #futurefaker #datingafterdivorce #divorcedwoman #christiandivorce #singlemom #Lovelanguages #DivorcedChristianWoman #datingOver40-How to Identify A Love Bomber

    -How to tell if the person you're dating is a real Christian

    57 min
  • 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


    52 min
  • The Power of Female Friendship. Can a Man Ever Be What Your 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 the painful ones. While relationships have come and gone (yes, even husbands), their sisterhood has remained a constant source of strength, healing, and laughter. As they explore the idea of re-marriage, 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 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

    52 min
  • Red Flags and Gut Instincts. Will We Ever Stop Ignoring Them?

    In their first-ever "fail-centric" episode, Jess & Jess explore the anatomy of Jess K.'s recent date catastrophe, getting real about why we either consciously or subconsciously ignore red flags when dating. Can we ever learn to trust God, and our gut, when it comes to men, or will we continually learn the hard way? Are our expectations too high when it comes to dating after divorce...or should we hold the line when it comes to our standards and dealbreakers? #SingleMomLife #DatingRedFlags #ChristianSingles

    45 min
  • 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

    34 min
  • 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

    1 hr 5 min
  • 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

    58 min
  • 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.

    42 min
  • 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.

    42 min

About Free Failing

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Gritty, faith-filled, hilarious conversations for women rebuilding after divorce and other hard life transitions.

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