• 50 minutes 8 seconds
    #333 How to Break Free From Toxic Patterns with Dr. Adi Jaffe

    In today’s expert episode, I’m talking with Dr. Adi Jaffe, a nationally recognized expert on transformation and author of the book Unhooked. We dive deep into the connection between addiction and heartbreak, and how compulsive behaviors, whether they involve substances or patterns in love, keep us stuck after a breakup. Dr. Jaffe shares his personal story of overcoming addiction, explains concepts like the sphere of influence and fixed versus growth mindset, and offers practical tips for shifting your mindset and changing the behaviors that keep you feeling stuck. We also discuss common struggles after a breakup, like obsessing over things outside of our control and getting trapped in shame cycles, and how to use frameworks like SPARROW and self-compassion to move forward in healing. If you’re ready for actionable advice on how to heal your heart and break unhealthy cycles, 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


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


    Start therapy with BetterHelp. Sign up and get 10% off at BetterHelp.com/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.

    4 August 2026, 8:00 am
  • 18 minutes 52 seconds
    #332 Why Your Ex Appears Happy and How to Handle It

    In today’s solo episode, I’m diving into one of the most common and painful post-breakup struggles: what to do when it seems like your ex is totally fine while you’re still hurting. I break down why seeing your ex “move on” can hit so hard, the spiral of self-doubt it can trigger, and why it’s so important to set boundaries with your friends and social media to protect your healing. I also explore some of the real reasons why your ex might look like they’re doing well—everything from unreliable social media snapshots to the way different people process pain and grief. If you find yourself comparing your healing journey to your ex’s or struggling with thoughts like “Did our relationship mean anything?”, 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


    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.

    28 July 2026, 8:00 am
  • 41 minutes 1 second
    #331 Lessons Learned From Repeated Breakups: Listener Episode

    In today's listener episode, I'm interviewing a man in his late 30s who recently went through the end of a 3.5 year relationship that he moved cities for. We talk about the unique challenges of relocating for love, trying to build a new life while balancing time between a partner and family, and the cycle of arguments that made it hard to move forward. We also dive into how he navigated self-sabotage at the end of the relationship, the guilt and growth that followed, and the powerful steps he's taken to heal, build a new support system, and rediscover peace in his life. If you've ever found yourself stuck in a relationship cycle or struggling to let go, this episode is full of hope, honest insight, and actionable tips for healing after heartbreak.

    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.

    21 July 2026, 8:00 am
  • 42 minutes 30 seconds
    #330 Why Grief Has No Timeline with Toni Filipone

    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.

    14 July 2026, 8:00 am
  • 50 minutes 8 seconds
    #329 How to Heal After Infidelity with Lauren LaRusso

    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.

    7 July 2026, 8:00 am
  • 19 minutes 56 seconds
    #328 Are You Missing Your Ex or Being in a Relationship?

    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.

    30 June 2026, 8:00 am
  • 44 minutes 25 seconds
    #327 Perfectly Hidden Depression: Why High Achievers Struggle in Silence with Dr. Margaret Rutherford

    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.

    23 June 2026, 8:00 am
  • 53 minutes 38 seconds
    #326 How People Pleasing Makes Breakups Harder with Dr. Paula Freedman Diamond

    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.

    16 June 2026, 8:00 am
  • 31 minutes 10 seconds
    #325 How to Create a New Blueprint for Love with John Kim

    In today’s expert episode, I’m joined by John Kim, a licensed therapist, speaker, and author you might know as The Angry Therapist on Instagram. We dive deep into his brand new book "Love Hard on Purpose" and break down the idea of “love blueprints”—the subconscious definitions of love we’re operating from, often shaped by our upbringing, movies, and social media. We discuss how these definitions can set us up for disappointment in relationships, why it’s normal to start out equating codependency with love, and how to create a healthier definition moving forward after heartbreak. John shares powerful visual metaphors for love, gives advice for those feeling like their relationship was a “failure,” and discusses how to actually rebuild and redefine love after a breakup. If you're navigating heartbreak, coming out of a breakup, or looking to heal and love healthier, you won’t want to miss this episode!

    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.

    9 June 2026, 8:00 am
  • 18 minutes 31 seconds
    #324 How to Handle Seeing Your Ex for the First Time

    In today's solo episode, I'm diving into one of the most nerve-wracking parts of post-breakup life: seeing your ex for the first time. Whether you're anxious about a possible accidental run-in, panicking over a mutual friend's wedding where you know you’ll cross paths, or just stuck in a cycle of "what if I see them?", this episode is for you. I break down the three scenarios—imagined encounters, unexpected meetings, and planned events—and share practical tips for protecting your emotions, setting boundaries, and coping with the emotional spiral that can follow. I also share personal stories from my own breakups to remind you that these feelings are completely normal and don’t say anything about where you are in your healing journey. If you’ve been stressing about how to handle seeing your ex, tune in for actionable advice and lots of reassurance that you’re not alone. 


    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.

    2 June 2026, 8:00 am
  • 49 minutes 58 seconds
    #323 How to Heal Your Self-Worth After Heartbreak with Brooke Taylor

    In today’s episode I’m joined by Brooke Taylor, transformational career coach and author of the new book Healing the Success Wound. We dive deep into the concept of the “success wound”—the hidden pain that comes from tying your self-worth to achievement, productivity, and external validation. Brooke shares her personal story of hitting rock bottom while working at Google, dealing with burnout, sobriety, and losing her sense of self after years of chasing external success. We explore how the success wound shows up as anxiety, perfectionism, and even anxious attachment in relationships, and why so many people lose their identity after a breakup. Brooke and I discuss practical ways to rebuild your self-esteem, break free from old patterns, and start truly healing from heartbreak—both in work and in love. If you’ve ever felt lost or worthless after a breakup, or struggled with people pleasing and perfectionism, this episode is a must-listen.

    Take Brooke's free quiz here!


    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


    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.

    26 May 2026, 8:00 am
  • More Episodes? Get the App