Free Failing

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 #lookingback

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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 #BecomingNotBehind

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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 does

• Why “slow is safe” in dating, friendship, and intimacy

• What it means when your body shuts down, tightens, or contracts

• How to stop overriding your intuition just to be polite

• Why your nervous system keeps the receipts even when your heart doesn’t

No 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 #nervoussystemwisdom

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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.

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#TypeBMom #singlemom #divorcedmom #holidayoverwhelm

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”?

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#divorce #datingafter40 #datingafterdivorce #divorcedwomen #singlemom #christianwomen #christiandivorce #emotionalintelligence

Takeaways

• Dating 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.

Chapters

00:00Navigating the Dating Landscape

02:41Emotional Depth vs. Social Status

05:29The Quest for Balance in Relationships

08:48Understanding the Dating Pool

11:18The Challenges of Dating After Divorce

14:38Ideal Partner Characteristics1

7:29Exploring Age Dynamics in Dating

20:21Intentional Dating and Deal Breakers

23:14The Role of Dating Apps in Modern Relationships

27:20Navigating Modern Dating Challenges

30:52The Role of Social Cues in Dating

35:02Creative Approaches to Meeting People

38:34The Frustration of Dating Apps

41:56Exploring New Dating Services

43:34Wins and Fails in Personal Life

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.

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#Singlemom #datingafterdivorce #divorcedwoman #datingafterforty #healedgirlera #selfdiscovery #Vogueboyfriendarticle

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 #divorcehealing

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Takeaways:

• 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 Changes

Chapters

00:00Navigating Identity Shifts: From Marriage to Divorce

05:46The Emotional Landscape of Divorce

09:13The Loss of Status and Security1

4:27Reframing Identity and Family Dynamics18:09The Challenge of Public Identity and Visibility

20:56Embracing Change and Identity

23:02Finding Peace in Transition26:10The Journey of Self-Discovery

26:46Navigating Relationships and Names

29:35The Complexity of Identity

32:09Empowerment Through Reinvention

35:05Wins and Fails in Everyday Life

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.

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#Divorcehealing #Divorcedwomen #christiandivorce #PodcastForWomen #Lifeafterdivorce #startingover
Takeaways

• Reflecting 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.

Chapters

00:00Introduction and Reflection on Divorce Journey

10:37Healing and Self-Care After Divorce

20:46Finding Purpose and Identity Post-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, #RaiseTheBarDating
Takeaways

• Settling 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 Settle
• Understanding Relationship Standards

• "How do you know you're settling?"
• "Pay attention to your body."
• "You are enough."

Chapters

00:00The Impact of Past Experiences11:41Navigating Rejection and Self-Worth

14:27:The Science of Attraction

17:19Recognizing Forced Connections19:31The Challenge of Personal Growth in Relationships

21:55Healing and Self-Esteem: The Roots of Settling

23:17The Importance of Prayer in Dating Decisions

26:11The Power of Prayer and Intuition in Dating

26:49Wins and Fails: Personal Reflections

31:42Learning from Experience: Avoiding Past Mistakes

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 Season

02:59Understanding Cuffing Season Dynamics

05:28Cuffing Season: Gender Perspectives

06:30Cuffing Season After 40

09:19The Emotional Complexity of Cuffing

11:44Navigating Loneliness and Relationships

14:04The Risks of Cuffing Season

16:40Cuffing Season and Emotional Attachment

18:08Cuffing Season: A Reality Check

21:04Conclusion and Reflections on Cuffing Season