Heal Your Heartbreak Podcast

Every Tuesday I have a new episode of the Heal Your Heartbreak Podcast where I talk about a different topic as it relates to break ups, healing your heartbreak, growing in your single life, and moving into happier and healthier relationships.

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Heal Your Heartbreak Episodes

Kendra Allen Kendra Allen

#306: Navigating the Six Stages of Relationships with Thais Gibson

In today's expert episode, I'm interviewing returning guest Thais Gibson—best-selling author, researcher, and founder of the Personal Development School—about her powerful new concept: the six stages of every relationship. We unpack each stage, from dating and the honeymoon phase, through the power struggle, all the way to commitment and the everlasting stage. We talk through the specific lessons and pitfalls that come with each phase, why so many breakups happen in the power struggle, and how even long-term couples can be stuck without ever moving forward. We also discuss practical tools for vetting in the dating stage, communicating your needs, and building safer, more fulfilling partnerships. Whether you’re reflecting on a past breakup or looking to date differently in the future, this is an episode full of actionable insight and hope.

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Kendra Allen Kendra Allen

#305: Why Self-Awareness Isn’t Enough with Kati Morton

In today’s expert episode, I’m joined by Kati Morton—licensed marriage and family therapist, bestselling author, and one of the most trusted mental health voices online. We dive into her newest book, "Why Do I Keep Doing This?" and explore how our desire for control impacts everything from relationships to mental health. In our conversation, we talk about the many ways control can show up—beyond the classic “type A” stereotype—including people pleasing, passive aggression, and perfectionism. Kati Morton shares her own journey with control, and we discuss why self-knowledge alone isn’t enough to change patterns and break free from cycles we know aren’t serving us. We also get into the unique struggle of wanting closure after a breakup, and how we can start to process experiences, sit with discomfort, and move toward more helpful behavior without shaming ourselves into change. Whether you’re currently going through heartbreak or simply looking to understand yourself better, this episode will help you release the illusion of control and find compassion in your healing process.

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Kendra Allen Kendra Allen

#304 Early Divorce Isn’t Failure: Finding Hope After Unexpected Turns with Eve Simmons

In today’s expert episode, I’m interviewing Eve Simmons, an award-winning health journalist who is back on the podcast after going through a life-changing divorce just six months into her marriage. We dive into her personal story, what led her to investigate the trend of early divorces among millennial women, and why there’s so little guidance for young couples splitting up before kids are involved. Eve Simmons shares the common themes she uncovered in her research, like professional success in women, financial complications, and the emotional fallout of an unexpected breakup. We talk about the unique fears faced after these divorces, how shame and loneliness show up, and what it’s like to rebuild your life when the path you planned is suddenly gone. Eve Simmons also opens up about her own healing journey, including finding love again and starting a family, and shares the hopeful lessons she and other women have learned about independence, resilience, and the surprising gifts that can come out of heartbreak. Be sure to check out her new book What She Did Next where she not only talks about her story but many others!

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Kendra Allen Kendra Allen

#303 How a Daily Gratitude Practice Changed My Life and Friendships

In today's solo episode, I'm reflecting on a practice that's been a huge part of my own healing journey—gratitude texting. As we kick off 2026, I share the five biggest lessons I've learned after nearly six years of sending daily gratitude texts with a small group of friends. I dive into how this habit started during my own heartbreak, why it works even when the group isn't made up of lifelong friends, and how it's helped me focus on life's small joys, build deeper connections, and even learn to celebrate my own wins. I wrap up with practical tips and a challenge for you to try starting your own gratitude list—whether you're moving through heartbreak or just looking to bring more positivity into your life.

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Kendra Allen Kendra Allen

#302 Redefining Divorce with Sarah Armstrong

In today's expert episode, I'm talking with Sarah Armstrong, author of The Mom's Guide to a Good Divorce and Vice President of Global Marketing Operations at Google. Sarah is sharing her personal experience navigating her divorce 15 years ago while prioritizing her daughter Grace. We discuss the concept of a "good divorce" and how Grace herself coined the term, the practical ways Sarah kept her daughter's well-being front and center, and how she built her compartmentalization muscle to manage big emotions. We also talk about how to put together a co-parenting plan, what to do when your ex isn’t cooperative, how small details (like family photos around the house) matter to kids, and how to envision a new future for yourself post-divorce. Sarah’s story is full of hope and concrete advice—her book is an amazing resource for anyone navigating divorce or co-parenting and wanting to do it in a way that feels healthy and positive for their kids.

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Kendra Allen Kendra Allen

#301 Transforming Grief and Breakups Through Daily Affirmations with Michelle Maros

In today's expert episode, I'm joined by Michelle Maros, founder of Peaceful Mind Peaceful Life, who just released her new book, Dear Friend: Daily Notes for Contemplation, Connection and Clarity. We dive into the misconceptions and real challenges around affirmations, why hearing supportive words from a friend lands so differently, and how self-compassion and self-trust don't just arrive overnight but are truly muscles we build over time. Michelle Maros shares honestly about her own healing experiences—from grieving her dad at 21 to navigating a tough breakup in her 20s—and how the tiniest daily habits (even something as simple as a morning cup of coffee) helped her move forward. We talk about embracing life’s ups and downs, the power of celebrating small victories, and letting go of the idea that healing has a big finish line. If you’ve ever struggled to trust yourself after heartbreak or felt stuck in the "shoulds," you’ll find so much to connect with here. Plus, we chat about how Dear Friend is designed to be your daily companion and source of hope on the healing journey.

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Kendra Allen Kendra Allen

#300 Managing Anxiety and Breakup Burnout with Dr. Carolyn Rubenstein

In today’s expert episode I’m joined by Dr. Carolyn Rubenstein, a licensed psychologist and wellness consultant who specializes in anxiety and burnout. I was drawn to her unique perspective on anxiety—not as something to “fix,” but as a deeper internal experience that we can learn to navigate with curiosity and compassion. We dive into how anxiety and burnout show up during breakups, why it’s totally normal to feel chaotic and out of control, and how masking our true feelings can be both a helpful tool and a source of long-term exhaustion. Dr. Carolyn shares practical ways to support yourself, compartmentalize the pain while still working through it, and gently poke your head out of those ruminating cycles. We also talk breakup burnout, the power of rituals, and why being kind to yourself is the most important tool you can use. If anxiety during a breakup makes you feel like something’s wrong with you, this episode is a must—so many validating reminders that you’re human and this too shall pass.

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Kendra Allen Kendra Allen

#299 How Keeping Secrets Sabotages Your Breakup Recovery

In today’s solo episode, I’m diving into the topic of secrets and their role in breakups. I explore why we tend to keep certain things hidden after a breakup—whether it's to save face, avoid embarrassment, or keep the door open for a possible reconciliation—and why this is ultimately harmful to our healing. I share some personal experiences from my recovery journey, talk about how secrecy breeds shame and isolation, and offer practical advice on how to start opening up to trusted people in your life. Whether you’re struggling to admit what you put up with or afraid to say out loud what really happened, this episode is all about encouraging you to let go of those secrets so you can truly heal your heartbreak.

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Kendra Allen Kendra Allen

#298 The Five Habits of Hope with Dr. Julia Garcia

In today’s expert episode, I’m joined by Dr. Julia Garcia, psychologist and author of the new book The Five Habits of Hope. We talk about how hope can be a real tool for growth and healing, rather than just a personality trait or toxic positivity. Dr. Julia shares her own personal struggles—from early heartbreak to grappling with addiction and self-worth—and how she discovered resilience through hope. We dive into the five habits of hope she outlines in her book, practical exercises you can try right away, and how to process difficult emotions without getting stuck. We also discuss why hope isn’t about attaching your worth to someone else or an external outcome, and how to lean on others and even “borrow hope” when you need it most. If you’re feeling hopeless during heartbreak, this episode will give you strategies and validation, and maybe even a path forward.

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Kendra Allen Kendra Allen

#297 How Romcoms Gave Us Unrealistic Breakup Expectations

In today’s solo episode, I’m diving deep into a topic that’s come up a lot in the background of other episodes, but today I’m bringing it all together—what romcoms got wrong about breakups and relationships. I talk through five major themes that 90s and early 2000s romantic comedies sold us—like the myth of the “one that got away,” why fighting isn’t proof of love, the trope of getting back with toxic exes, finding your soulmate right after a breakup, and the classic “revenge glow-up.” I share examples from some of my all-time favorite movies, break down why these storylines gave us such unrealistic expectations, and offer my thoughts on how these narratives impact our healing after a breakup. If you grew up watching these films and ever compared your breakup story to a romcom, this episode is for you!

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Kendra Allen Kendra Allen

#296 Navigating In-Law Dynamics and Boundaries with Dr. Tracy Dalgleish

In today’s episode, I’m interviewing Dr. Tracy Dalgleish about her brand new book You, Your Husband, and His Mother. We dive into the impact of outside influences—especially in-laws—on relationships, and why these dynamics can so often lead to breakdowns. Dr. Tracy shares insights from her work as a couples therapist, including her five-step Vault Method for protecting your partnership and setting effective boundaries. We discuss the misconceptions around boundaries, the importance of getting on the same team with your partner, and specific strategies for dating with these issues in mind. This episode is a must-listen for anyone who’s struggled with in-law relationships in the past, or who wants to lay a stronger foundation in future partnerships.

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Kendra Allen Kendra Allen

#295 How Detachment Can Transform Your Breakup Recovery with Sabrina Bendory

In today’s expert episode, I’m joined by relationship and confidence coach Sabrina Bendory, host of the "You Will Be Okay" podcast and author of the new book Detached. We dive deep into the meaning of detachment—what it actually is, common misconceptions about it (hint: it’s not emotional shutdown!), and why learning to detach from outcomes is a crucial life skill, especially after heartbreak. Sabrina Bendory shares practical tips, writing exercises, and personal stories, including how to detach from an ex and ways to approach dating with a healthy, detached mindset. We also talk about how to be kind to yourself during the grief of a breakup, how to identify what needs you’re trying to fill post-breakup, and how detachment can help you build real self-worth. If you struggle with moving on or want to heal and grow after a breakup, you’ll get so much from this episode.

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Kendra Allen Kendra Allen

#294 Navigating Anxious and Avoidant Attachments with Julie Mennano

In today's expert episode, I'm interviewing Julie Mennano, who you might know from her Secure Love podcast or her super insightful Instagram account @thesecurerelationship. Julie is an attachment expert and the author of Secure Love, and in this episode we tackle all things attachment theory—especially how it relates to breakups and healing. We dive deep into the anxious-avoidant dynamic, the misconceptions so many of us have around avoidant partners, and why those relationships aren't necessarily doomed. Julie shares her unique perspective on taking accountability after heartbreak without falling into self-blame, how to build self-trust for future relationships, and explains how negative cycles erode intimacy. We also talk about why labeling attachment styles can be helpful—but sometimes overdone. If you've ever wondered how to make sense of your breakup through the lens of attachment or want to set yourself up for a healthier relationship next time, this episode is a must-listen.

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Kendra Allen Kendra Allen

#293 How to Feel Safe in Relationships with Jessica Baum

In today’s episode, I’m welcoming back Jessica Baum, licensed mental health counselor, relationship expert, and author of the new book Safe (out today!). We dive into what it truly means to feel safe in relationships, why so many of us struggle with this, and how our attachment styles play a huge role—whether we lean anxious, avoidant, or somewhere in between. Jessica breaks down the origins of our attachment styles and offers insight into how we can gradually heal, especially after heartbreak. We discuss the power of finding anchors—safe, supportive people outside of romantic relationships—and how real healing happens in connection, not isolation. This is an episode packed with hope, practical tips, and so much validation for anyone rebuilding after a breakup or looking to feel safe and secure in future relationships. To get the free gifts we talk about in the interview head to this link: https://jessicabaumlmhc.com/safe

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Kendra Allen Kendra Allen

#292 Exploring Sexual Confidence and Healing After Heartbreak with Dr. Tara

In today’s expert episode, I’m so excited to welcome back Dr. Tara, a tenured professor of relational and sexual communication, TV sexpert, and now author of the brand new book “How Do You Like It?” We dive deep into the shifting narratives around sex and relationships, especially for Gen Z, and talk about how younger generations are redefining what it means to be sexually empowered and communicative. We cover everything from the myths the media has created about “sexless” generations, to the real impact of porn on relationships (hint: it’s all about porn literacy, not porn itself), and how secrecy—not the act itself—is what really feels like betrayal in a partnership. Dr. Tara also touches on why passion and sexual communication are at the heart of lasting relationships, and shares so many tangible tips for getting to know yourself sexually—whether you’re single, going through a breakup, or in a long-term commitment. If you’re curious about healing your relationship with sex, learning how to voice your own desires, and breaking old patterns of shame and people-pleasing, this episode is for you!

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Kendra Allen Kendra Allen

#291 Is Your Breakup Story Helping or Hurting Your Recovery?

In today's solo episode I’m diving into the topic of your breakup story—what it means, why it matters, and how the way you tell it can shape your healing. I explore how sharing your breakup experience is an important part of processing, but also how we can unintentionally make our stories more painful by filling in the gaps with negative self-talk or assumptions. Whether you were cheated on, ghosted, or ended the relationship yourself, I break down practical ways to tell your story with honesty and compassion, and give tips on how to keep your narrative from holding you back. I also discuss the importance of writing out your breakup story, sticking to the facts, and allowing yourself space for your feelings without making the breakup mean something negative about you.

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Kendra Allen Kendra Allen

#290 From Self-Sabotage to Self-Regulation: Anna Runkle’s Guide to Relationship Healing

In today’s expert episode, I’m interviewing Anna Runkle, better known as the “Crappy Childhood Fairy” on YouTube, whose new book, Connectability, just launched. We talk all about what it really means to be dysregulated, how childhood trauma—not just the “big T” trauma—can play out in our adult relationships, and why so many of us find ourselves self-sabotaging or struggling to connect. Anna dives into why neglect, not being seen or cared for as a child, can have lasting neurological effects, and she shares practical steps to start re-regulating your nervous system and breaking out of old relational patterns. We also dig into why we might be drawn to emotionally unavailable people, the hidden ways we isolate ourselves, and why building multiple kinds of connection—not just romantic—is so important for healing after heartbreak. Anna offers relatable stories, super tangible advice, and hope for anyone navigating relationship wounds or looking to build a more connected, supported life.

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Kendra Allen Kendra Allen

#289 Surviving the Horrors of Dating with Rory Uphold: Mindset, Shame, and Self-Love

In today’s episode, I’m welcoming back one of my favorite guests, Rory Uphold, to talk all about her brand new book The Final Girl’s Guide to the Horrors of Dating, out tomorrow (October 1st)! Rory and I dive into what inspired her to write the book—combining her own wild relationship stories with her love for horror movies. We break down what it really means to be a “final girl” in both scary movies and in dating, how mixed messages and shame around sex impact women’s relationships, and why so many of us stay in situationships and fear being single. Rory bravely shares her personal experiences with shame, sexuality, and catching an STI, discussing what it took for her to finally reclaim her agency. We also talk through the difference between accountability and shame, what it looks like to rewrite our dating stories, and why pain can actually be the best motivator during heartbreak. This is such a validating, insightful, and hilarious conversation—I can’t wait for you all to listen, and don’t forget to grab a copy of Rory’s book at this link using our special code BREAKUP15

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Kendra Allen Kendra Allen

#288 Healing Through Letters: A Breakup Recovery Tool

In today’s solo episode, I’m diving into one of my all-time favorite tools for breakup healing—letter writing. I share why this practice has been so powerful for me, how I integrate it into my coaching sessions, and exactly why it helps with those obsessive post-breakup thoughts and the void left by no contact. I go over different types of letters you can write—to your ex, to yourself (including your younger self), to the universe, and more—and why putting pen to paper is so much more impactful than just thinking your thoughts or even journaling. I get honest about whether or not you should ever actually send these letters (the answer may surprise you!) and offer tips for making this practice your own. If you’re looking for a tangible way to process your emotions and lighten the load after heartbreak, this episode is for you.

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Kendra Allen Kendra Allen

#287 When Life Doesn’t Go as Planned with Laura Behnke

In today’s episode, I’m talking to Laura Behnke, whose story is such a powerful example of resilience, hope, and what it means to build a meaningful life regardless of the “rules” we think we need to follow. Laura shares openly about not having her first real relationship until age 35, what it felt like to reach milestones later than she expected, and how she learned to imagine a future that didn’t hinge on partnership. We dive into her experiences navigating major grief—including the losses of her father-in-law and her own father, a long, emotional journey with IVF and infertility, and eventually facing a cancer diagnosis when her daughter was just seven months old. We discuss the emotions that come up when life doesn’t go as planned, finding strength during difficult seasons, and why sharing our most vulnerable moments can be such a lifeline to others. Laura’s honesty about dating, grief, motherhood, and health is such a needed reminder that we’re not alone in life’s hardest chapters, and that it’s okay to question—and break—the “rules” we’re handed.

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