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Heal Your Heartbreak

Break Up Bestie
Heal Your Heartbreak
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331 episodes

  • Heal Your Heartbreak

    #330 Why Grief Has No Timeline with Toni Filipone

    2026/07/14 | 42 mins.
    In today’s expert episode, I’m interviewing Toni Filipone, founder of Master Grief and an expert in navigating grief and loss. We discuss her personal story of losing her partner to suicide after going through a brutal divorce, and how even with 30 years of personal development coaching experience, grief left her at a complete loss. We dive deep into why grief doesn’t follow predictable patterns, the reality of “early grief,” and how societal expectations around healing are often unrealistic. We also explore how breakups can bring a unique kind of compounded grief, why it’s common to grieve the loss of a future that never happened, and how to separate facts from the painful stories we tell ourselves. If you’ve ever felt stuck, guilty, or broken during heartbreak or loss, this episode will validate your feelings and offer a fresh, compassionate perspective on moving through grief.
    To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LN

    To get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!

    To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873

    Don’t let stigma stand in the way of support. Start therapy with BetterHelp. Sign up and get 10% off at BetterHelp.com/heartbreak
    Sleep cooler this summer with Boll & Branch during their Annual Summer Event. For a limited time, get 20% off sitewide at BollandBranch.com/heartbreak with code heartbreak.
    You can find DRIVE by Kate Stewart wherever books are sold in print and in eBook and REVERSE wherever books starting on 7/28.
    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • Heal Your Heartbreak

    #329 How to Heal After Infidelity with Lauren LaRusso

    2026/07/07 | 50 mins.
    In today’s expert episode, I’m sitting down with Lauren LaRusso, a psychotherapist specializing in extramarital affairs and author of "Beyond Infidelity." We go deep into the complex world of infidelity—why it happens, how it affects everyone involved (the betrayed partner, the unfaithful partner, and the affair partner), and the unique challenges of healing from relationship betrayal. Lauren shares her own story of navigating betrayal in her marriage and offers powerful insights for those questioning whether to stay or leave after infidelity, unpacking the layers of shame, grief, and recovery. We discuss rebuilding trust (in yourself and others), how to hold space for all your feelings, and why healing after cheating is such a nuanced process. This episode is packed with wisdom for anyone healing from heartbreak, considering forgiving an affair, or looking to better understand the ripple effects of betrayal.
    To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LN

    To get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!

    To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873

    Don’t let stigma stand in the way of support. Start therapy with BetterHelp. Sign up and get 10% off at BetterHelp.com/heartbreak
    Sleep cooler this summer with Boll & Branch during their Annual Summer Event. For a limited time, get 20% off sitewide at BollandBranch.com/heartbreak with code heartbreak.
    You can find DRIVE by Kate Stewart wherever books are sold in print and in eBook and REVERSE wherever books starting on 7/28.
    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • Heal Your Heartbreak

    #328 Are You Missing Your Ex or Being in a Relationship?

    2026/06/30 | 19 mins.
    In today’s solo episode, I’m diving into one of the most common breakup questions I get: are you actually missing your ex, or are you missing being in a relationship? I walk you through how to recognize the difference between missing specific things about your former partner versus the general comfort of companionship. We talk about how feelings of loneliness can show up even long after your breakup, signs you might just be filling a relationship-shaped void, practical tips for navigating those raw, empty spaces in your routine, and why going back to your ex (or rushing into dating) isn’t the answer. If you’re struggling to move forward and wondering how to handle that persistent feeling of missing someone, this episode is for you.
    To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LN

    To get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!

    To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873

    Patio season is here and these deals won’t last! head to Wayfair.com right now to get your outdoor space ready for way less. That’s WAYFAIR.COM

    Upgrade your sleep with Boll & Branch. Get 15% off your first order plus free shipping at BollAndBranch.com/heartbreak with code heartbreak.

    You don’t have to say yes to everything this summer. Find support in therapy. Sign up and get 10% off at BetterHelp.com/heartbreak
    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • Heal Your Heartbreak

    #327 Perfectly Hidden Depression: Why High Achievers Struggle in Silence with Dr. Margaret Rutherford

    2026/06/23 | 44 mins.
    In today’s expert episode, I’m joined by Dr. Margaret Rutherford, clinical psychologist, author, and host of The SelfWork Podcast, to dive deep into the topic of “perfectly hidden depression”—a term she coined and explores in her bestselling book and TEDx talk. We discuss how those who seem “put together” on the outside can silently struggle beneath the surface, why high-achievers and caretakers can be vulnerable to hiding their pain, and how this pattern can show up after heartbreak. Dr. Rutherford shares her personal story, the warning signs of hidden depression, actionable steps for breaking through emotional walls, and how moments of crisis like a breakup can be a catalyst for healing and self-acceptance. If you’ve ever felt like admitting your pain would shatter your carefully-crafted image, this is the episode for you.
    To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LN

    To get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!

    To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873

    Patio season is here and these deals won’t last! head to Wayfair.com right now to get your outdoor space ready for way less. That’s WAYFAIR.COM

    Upgrade your sleep with Boll & Branch. Get 15% off your first order plus free shipping at BollAndBranch.com/heartbreak with code heartbreak.

    You don’t have to say yes to everything this summer. Find support in therapy. Sign up and get 10% off at BetterHelp.com/heartbreak

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • Heal Your Heartbreak

    #326 How People Pleasing Makes Breakups Harder with Dr. Paula Freedman Diamond

    2026/06/16 | 53 mins.
    In today’s expert episode, I’m interviewing Dr. Paula Freedman Diamond, a licensed clinical psychologist, speaker, and author of the new book “Toxic Striving: Escaping the Stress and Burnout of Hustle and Diet Culture.” We talk about the many faces of people pleasing and perfectionism, how these patterns show up in dating and relationships, and how suppressing your own needs can eventually lead to relationship breakdowns or unhealthy dynamics. Dr. Paula shares both her personal experiences and practical therapeutic insights on building real intimacy, navigating conflict, and coping with heartbreak when you’ve always tried to be the “perfect” partner. We also discuss controlling the narrative after a breakup, learning to sit with uncomfortable feelings instead of rushing to fix them, and how embracing your needs and authenticity is key to healing from heartbreak. If you struggle with people pleasing, overthinking, or feeling like you have to do it all, you’re not alone—and you don’t have to stay stuck in these cycles.
    To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LN

    To get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!

    To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873

    Patio season is here and these deals won’t last! head to Wayfair.com right now to get your outdoor space ready for way less. That’s WAYFAIR.COM

    Upgrade your sleep with Boll & Branch. Get 15% off your first order plus free shipping at BollAndBranch.com/heartbreak with code heartbreak.

    You don’t have to say yes to everything this summer. Find support in therapy. Sign up and get 10% off at BetterHelp.com/heartbreak
    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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About Heal Your Heartbreak
Heal Your Heartbreak with your Break Up Bestie is a weekly podcast where each week I walk you through a topic as it relates to healing your heartbreak and helping you move through your break up. Topics include breaking up, healing, dating, and moving into happier and healthier relationships. The goal of this show is to provide hope, support, tips, and to remind you that you're not alone and don't have to go through this alone.
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