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

#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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Kendra Allen Kendra Allen

#286 Navigating the Final Stretch of Breakup Recovery

In today's solo episode, I'm diving into what I call the final 10% of breakup recovery—that last stretch where you feel mostly healed, but still find yourself thinking about your ex, feeling frustrated, or just not quite “over it” yet. I talk through why this stage can feel so uncomfortable, how it's completely normal to still have lingering curiosity or sadness, and why rushing through it doesn't actually help. I share my top tips for approaching this stage with curiosity rather than judgment, including continuing to journal, reflecting on your progress, and even considering dipping your toe back into dating—when the time is right for you. I also discuss how these lingering feelings can reveal deeper lessons and opportunities for growth. Whether you're nearing the end of your breakup journey or just want to know what to expect, this episode is all about normalizing the messy, imperfect end stages of healing and encouraging you to trust your own process.

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Kendra Allen Kendra Allen

#285 Out of the Ashes: Courtney Peppernell’s Journey Through Heartbreak and Emotional Abuse

In today’s episode, I’m joined by internationally bestselling poet and author Courtney Peppernell to talk about her deeply personal new book, Out of the Ashes. Courtney opens up about her seven-year relationship that ended in emotional abuse and infidelity, and what it was like to recognize the toxic dynamics only in hindsight. We explore how she navigated feelings of shame, guilt, and even imposter syndrome as someone whose career centers around writing about love and connection. Courtney shares how therapy, creative expression, and rebuilding trust in herself helped her heal—and why learning to embrace difficult emotions, especially anger, is essential to recovery. We also discuss the difference between healthy and emotionally abusive relationships, what it means to “rise from the ashes,” and how to reconnect with your intuition after heartbreak. This is a powerful conversation about reclaiming your voice, rebuilding self-worth, and knowing that your best days still lie ahead.

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Kendra Allen Kendra Allen

#284 Let the Truth Set You Free: Amber Rae’s Story of Leaving to Love

In today's episode, I'm joined by international best-selling author Amber Rae of the book Loveable, who shares her incredible story of breaking free from a nine-year sexless marriage after realizing she was living out a "good girl" narrative that kept her needs and desires suppressed. Amber and I dive into the difficult process of coming to terms with a relationship that looks good on paper but isn't fulfilling in reality, how meeting a soulmate became the catalyst for honesty and change, and the often-unspoken shame around discussing intimacy issues within relationships. We talk about rationalizing our way into staying, the courage it takes to leave, and the even deeper work of healing childhood wounds and learning to show up authentically in a new relationship. Amber also shares what it was like navigating others’ judgments, processing her family history, and building a partnership based on true connection and willingness. Whether you’re questioning your relationship or seeking permission to honor your own needs, this conversation is all about finding freedom and self-love on the other side of heartbreak.

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Kendra Allen Kendra Allen

#283 Listener Episode: Breaking Anxious-Avoidant Patterns with Chris

In today’s listener episode, I’m interviewing Chris, a man in his late 30s living in Arizona who is nearly two years out from a relationship that was marked by a classic anxious-avoidant dynamic. Chris opens up about navigating repeated breakup and reconciliation cycles with his ex, coming to terms with patterns of emotional unavailability, and the challenging process of finally walking away for good. We talk about what taking a full year to be single and focus on self-growth looked like for him, the deep patterns he noticed (both in his ex and himself), and how therapy and community support helped him rebuild his confidence after feeling completely lost. Chris also shares how dating again after a long break led him to a new, much healthier relationship, and what it’s been like to rewire old patterns and experience genuine emotional safety with a partner. This conversation is a refreshing look at heartbreak, healing, and growth from the male perspective, and I know so many listeners will relate to Chris’s story.

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Kendra Allen Kendra Allen

#282 The Power of Doing What You Don’t Feel Like After a Breakup

In today’s solo episode, I’m diving deep into one of my favorite—and most powerful—tools for breakup recovery: contrary action. I talk about how, in the midst of heartbreak, your thoughts and feelings can often steer you in the wrong direction, and why doing the opposite of what you feel like doing can be a true game changer. I share actionable ways to put contrary action into practice, how routines can support your healing, and why building self-trust and self-esteem really starts with showing up for yourself—especially when it feels hardest. I also discuss the tricky balance between listening to your feelings and pushing yourself just enough, providing tips for what to do when motivation is at its lowest. If you’re feeling stuck or unsure how to move forward, this episode is for you!

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Kendra Allen Kendra Allen

#281 Loneliness and the Power of Radical Listening with Dr. Robert Biswas-Diener

In today’s expert episode, I’m joined by Dr. Robert Biswas Diener, pioneer in positive psychology and co-author of the book “Radical Listening.” We dive into the power of radical listening—what it actually looks like, why it’s so hard to practice during breakups, and how improving your listening skills can radically change how you process heartbreak and receive support. Dr. Robert and I talk about why loneliness is so prevalent right now, how to coach your friends and family to be better listeners, and why so many people feel misunderstood during a split. We also dig into why it’s important to understand your motives when you’re listening—or when you’re sharing—and how to ask for the kind of support you need, whether that’s to be heard, hugged, or helped. Plus, we cover what to do when you have to listen to things you really don’t want to hear (like “I don’t want to be in this relationship anymore”) and how so much clarity actually comes from hindsight listening. This conversation is packed with practical advice for anyone navigating heartbreak, wanting to be a better support system, or looking to have healthier conversations—breakup or not.

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Kendra Allen Kendra Allen

#280 Learning to Love Better with Yung Pueblo

In today’s episode I’m joined by none other than Diego Perez—who many of you know as Yung Pueblo. This was such a pinch-me moment for me, getting to sit down with the author behind so many of my favorite books, and especially his newest release, “How To Love Better.” Diego opens up about his relationship with his wife and how their journey became the foundation for this new book. We talk about self-awareness, the idea of impermanence in relationships (and why we resist change so much), and how working on ourselves transforms the quality of our connections. Diego also shares his thoughts on how to accept breakups, when it might be time to let go, and why letting an incompatible relationship drag on can be an injustice to everyone involved. Whether you’re healing from heartbreak, looking to grow in your single life, or reflecting on what you want in your next relationship, there’s so much wisdom packed into this conversation.

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Kendra Allen Kendra Allen

#279 Stop Calling It a Discard, You Are Not Trash

In today’s solo episode, I’m diving into a term I’ve seen popping up everywhere lately—“discard”—especially in the context of avoidant attachment styles and breakups. I share how I started noticing this lingo in my Q&As on Instagram, did some research, and why the use of “discard” really doesn’t sit right with me. I break down why I believe using this term is harmful, how it can lower self-esteem, invalidate your relationship experience, and make moving forward so much harder. I also touch on the dangers of getting too wrapped up in therapy-speak and diagnostic labels instead of just allowing yourself to process the real sadness and pain of heartbreak. If you’ve felt “thrown away” in a blindsided or one-sided breakup, this episode is for you—I hope it helps you feel seen and reminds you not to tie your worth to someone else’s inability to commit.

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Kendra Allen Kendra Allen

#278 The Power of Detachment with Dr. Bob Rosen

In today’s expert episode, I’m joined by Dr. Bob Rosen—psychologist, New York Times bestselling author, and business advisor—to dive into the concept of attachment, and specifically, how our attachments can hold us back in breakups and beyond. We explore key themes from his latest book, “Detached,” including the attachment to stability, the past, control, and even perfectionism. Dr. Rosen shares how these attachments are often rooted in fear, why learning to embrace uncertainty is so critical, and how self-love plays a pivotal role in healing after heartbreak. We also discuss the importance of community, the difference between detaching and disassociating, and practical strategies for letting go of what no longer serves us. If you’ve ever felt stuck after a breakup or struggled with moving on, this episode is packed with insight, actionable advice, and a reminder that healing is a practice—not a one-time event. To take the detachment assessment you can click here.

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Kendra Allen Kendra Allen

#277 Why Your Brain Feels Stuck with Britt Frank

In today’s expert episode I’m joined by Britt Frank—author, speaker, and licensed neuropsychotherapist—who has been on my wish list for ages. We dive deep into the connection between breaking free from an addiction to substances and breaking free from an ex, and Britt so beautifully shares why our brains actually are on our side (even when it doesn’t feel like it!). We talk about why feeling “stuck” after a breakup is so common, the power of micro yeses in healing, and how to stop fighting with our own minds during heartbreak. Britt also explains how aligning different parts of our minds can help us move forward, and we get super real about grief, shame, and wiring our brains for healthier relationships. Plus, we discuss Britt’s latest book, Align Your Mind, and her previous book, The Science of Stuck, both of which are game changers for anyone struggling with breakups. This conversation is packed with compassion, actionable tools, and so many “ah-ha” moments—I can’t wait for you to listen!

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Kendra Allen Kendra Allen

#276 Listener Episode: Breaking the On and Off Cycle

In today’s listener episode, I’m talking with Dionne, a proud Gen Xer who shares her story of a six-and-a-half-year, very on-again, off-again relationship that was marked by several breakups—some lasting just a weekend, others stretching to six months. We discuss how easy and addictive the breakup-get-back-together cycle can be, especially for those with anxious attachment styles, and the emotional toll it takes over time. Dionne opens up about the moment she finally decided to choose herself and the power of sticking to no contact after their final breakup. We also touch on the importance of self-compassion, learning from past patterns, and making empowered choices as you move forward in healing. I know so many of you will resonate with Dionne’s self-awareness and reflection, and I hope this episode inspires anyone who is struggling to break free from a similar relationship cycle.

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Kendra Allen Kendra Allen

#275 The Power of Rock Bottom

In today's solo episode, I'm diving into the topic of hitting "rock bottom" after a breakup—what it really means, why it matters, and how it can actually be a catalyst for deep change and healing. I share personal stories and draw some powerful parallels to sobriety and recovery, discussing why so many of us avoid fully feeling the pain after a breakup and the ways we try to distract or numb ourselves to avoid that lowest point. We talk about the importance of allowing yourself to truly be "done," what that looks like (and doesn't look like), and why embracing the pain instead of fighting it can provide the motivation you need to start genuinely healing. If you're struggling to let go, stuck in a cycle with your ex, or afraid of facing the sadness, this episode is here to remind you that rock bottom can be a turning point—and that this, too, shall pass.

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Kendra Allen Kendra Allen

#274 Healing Heartbreak with Intuition and Action with Laura Day

In today’s expert episode, I’m joined by New York Times bestselling author Laura Day to dive into her newest book, The Prism, through the lens of heartbreak and healing. Laura and I talk about why breakups are so uniquely painful, what happens in our brains and bodies when we lose a relationship, and how intuition and ego both play a role in how we cope. We get into the seven centers of the ego, how the structures of our previous relationships can become both comfort and prison, and Laura shares practical tools for redirecting your energy after a breakup—rather than just telling yourself to “stop thinking about them.” We also cover the phenomenon of telepathic communication with exes, how to cut those invisible ties, the importance of rituals around breakups, and why action and building new routines are essential to healing. If you want real, actionable advice to rebuild after heartbreak (plus a peek into Laura’s own story), this episode is packed with wisdom and support.

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