Lost Loverboy Podcast

Send us Fan Mail For this episode, I brought in someone who knew me long before I became the Lost Loverboy: my mother. Together, we created our own Love Hall of Fame, debating the songs, movies, moments, gestures, couples, and little things that we believe represent love at its best. Some of our picks were easy. Others showed just how differently a mother and son, from two different generations, can see love. This episode is less about giving relationship advice and more about celebrating the...

Send us Fan Mail Some of the best lessons I've learned about love didn't come from romance movies. They came from an ogre who didn't believe he deserved to be loved. A man who could fast-forward through his entire life. A woman who woke up every morning without remembering the man who loved her. And a man who had everything he wanted, only to realize that loving someone sometimes means wanting what's best for them, even when it doesn't include you. In this episode of the Lost Loverboy Podcast...

Send us Fan Mail For a long time, I think I confused being willing to sacrifice for someone with what it meant to truly love them. If I could show up enough, give enough, carry enough, choose you enough… maybe eventually I’d feel chosen too. But somewhere along the way, I had to ask myself a harder question: Do I love through sacrifice because that’s how I love or because sacrifice became the way I learned to prove I was worth loving? In this episode of the Lost Loverboy Podcast, I talk ab...

Send us Fan Mail For so long, I've thought about the qualities I hoped to find in a wife. But recently, God challenged me with a different question: Am I becoming the kind of husband she's praying for? In this episode, I share a personal journal entry that unexpectedly turned into a prayer. Not a prayer asking God to bring me my future wife, but a prayer asking Him to prepare me for her. I reflect on the kind of man I hope to become, the home I hope to build, the peace I hope to protect, and ...

Send us Fan Mail At some point, almost everyone who's been disappointed in love begins asking themselves the same question: "Am I asking for too much?" But what if that's the wrong question? In this episode, we explore how loneliness, heartbreak, comparison, and time can slowly make us question our standards instead of questioning whether we're simply asking the wrong person for the right things. We talk about the difference between standards and preferences, how fear can disguise itself as...

Send us Fan Mail Being needed can feel a lot like being loved. It feels good to be the person someone depends on, leans on, or calls when life falls apart. But the two aren't always the same. In this episode, we explore why so many of us tie our worth to being useful, how people can mistake dependency for love, and what happens when our identity becomes wrapped up in fixing, rescuing, and constantly showing up for everyone else. Together, we'll unpack the difference between being valued for w...

Send us Fan Mail It's easy to blame bad judgment, ignored red flags, or poor decisions, but I don't think that's the real answer. In this episode, we explore why good people can repeatedly find themselves in unhealthy relationships, how familiarity often disguises itself as chemistry, why we fall in love with potential rather than reality, and how healing changes not only who we are but also who we're attracted to. Sometimes the wrong person doesn't feel wrong because they're exciting. Someti...

Send us Fan Mail Not every relationship that changes you is obviously toxic. Sometimes the hardest relationship to leave is the one that almost works. The one with enough love to keep you hopeful, enough chemistry to keep you attached, and just enough happiness to make you believe things will eventually get better. In this episode, I explore why "almost" can be more dangerous than "terrible," why hope can sometimes keep us stuck longer than pain, and how to recognize the difference betwee...

Send us Fan Mail There was a time when I thought all love was worth holding onto. But the older I get, the more I realize that not every kind of love is meant to last. In this episode, I open up about the kinds of love I've outgrown, the love that makes you question yourself, the love that only shows up when it's convenient, the love that asks you to become less of who you are, and the love that mistakes chemistry for compatibility. This isn't about pointing fingers or revisiting the past. I...

Send us Fan Mail We often talk about finding someone who loves us, but what if love isn't the thing we're missing? In this episode, I explore the difference between being loved and being understood—and why those two things aren't always the same. We talk about emotional safety, feeling seen, why some relationships leave you feeling lonely despite being loved, and why understanding may be one of the rarest forms of intimacy. If you've ever found yourself saying, "That's not what I meant," or...

Send us Fan Mail After my recent breakup, I've been thinking about how different dating feels now than it did ten years ago. In your 20s, chemistry can feel like enough. In your 30s, you start paying attention to things like consistency, communication, values, peace, and whether someone actually fits the life you're trying to build. This isn't dating advice. It's an honest conversation about what changes when you're no longer looking for potential and you're looking for partnership. Viewer di...

Send us Fan Mail In this deeply personal episode of Lost Lover Boy, Demetri Wiley opens up about the difficult decision to walk away from someone he loved. Addressing public speculation surrounding his recent breakup, he shares the lessons, heartbreak, and self-discovery that led him to choose peace over forcing a relationship that lacked true alignment. Demetri discusses the importance of emotional attunement, feeling supported during life's most challenging moments, and recognizing when co...

Send us Fan Mail In this episode, Demetri unpacks the quiet belief so many of us carry that we are “too much,” “not enough,” or simply hard to love. He explores the origins of that story, how past relationships and unmet needs shape our self-worth, and why believing this lie keeps us disconnected from the love we desire. This is a conversation about unlearning shame, embracing self-compassion, and allowing yourself to be loved without needing to perform or shrink. Viewer discretion is advised...

Send us Fan Mail In this special moment to close out the year and step into 2026, Demetri speaks directly to you, the listener. This episode is a heartfelt thank you for the love, support, messages, and conversations that made this journey what it is. It is a reflection on growth, consistency, and community, and a reminder that this podcast was never about perfection, just presence. No long farewell and no dramatic ending, just gratitude, perspective, and a promise to keep showing up. We are ...

Send us Fan Mail In this powerful episode of the Lost Loverboy Podcast, Demetri Wiley sits down with Trill Ace for an honest, no-dodging conversation about accountability in love and dating. From unhealed patterns to emotional avoidance, Demetri leads the discussion by asking the questions most people avoid. What part did you play? What are you still repeating? Are you truly ready to take responsibility for how you love? Together, they unpack why accountability isn’t about shame. It is about ...

Send us Fan Mail In this heartfelt episode of the Lost Loverboy Podcast, Demetri Wiley sits down with the radiant and wise Kittie J Rose for a vulnerable conversation about readiness emotionally, spiritually, and mentally for the love God has aligned for you. Together, they unpack what it really means to be prepared for a healthy relationship, how to let go of the timelines we place on ourselves, and why God’s plan often requires patience, healing, and self-awareness. Kittie shares her person...

Send us Fan Mail In this heartfelt episode of the Lost Loverboy Podcast, Demetri dives deep into the transformative power of love and the inherent risks of expressing it openly. He explores the challenges and vulnerabilities that come with loving out loud, sharing personal anecdotes and real-life stories that highlight both the beauty and the heartache that can arise when we let our love be known. Join Demetri as he encourages listeners to embrace their emotions fully, reflect on the fear of ...

Send us Fan Mail In this enlightening episode of the Lost Loverboy Podcast, Demetri dives deep into his personal journey of healing by sharing the 10 vital lessons he had to unlearn to reclaim his emotional well-being. From challenging societal expectations to letting go of limiting beliefs, Demetri opens up about the tough but necessary realizations that paved the way for his growth. Join him as he reflects on the importance of self-awareness, the power of vulnerability, and the transformati...

Send us Fan Mail In this episode of the Lost Loverboy Podcast, Demetri dives deep into the impact of social media on our understanding of relationships. He discusses how the constant influx of curated content and unsolicited advice can distort our perception of love and connection. From unrealistic expectations to comparison culture, Demetri uncovers the ways social media can poison our relationships and mental well-being. Join him as he shares insights and personal anecdotes, encouraging lis...

Send us Fan Mail In this insightful episode of the Lost Loverboy Podcast, Demetri dives deep into the complexities of modern relationships with his discussion titled "Intentions Over Interest: How to Know What They Really Want." Join him as he unpacks the essential differences between genuine intentions and fleeting interests in romantic connections. Through engaging stories and practical tips, Demetri helps listeners navigate the often murky waters of dating, offering guidance on how to disc...

Send us Fan Mail In this thought-provoking episode of the Lost Loverboy Podcast, Demetri delves into the art of detachment, examining its significance in our relationships and personal growth. Through candid reflections and insightful anecdotes, he reveals how letting go can lead to greater emotional freedom and clarity. Listeners will discover practical tips for cultivating healthy boundaries and nurturing inner peace, all while learning to embrace vulnerability without losing themselves. Jo...

Send us Fan Mail In this heartfelt episode of the Lost Loverboy Podcast, Demetri sits down with one of his closest friends for an honest and vulnerable conversation. They delve deeply into the challenges of navigating past traumas and how those experiences shape their current lives. As a single mother, his friend shares her insights on the unique struggles she faces in raising a child while trying to find love in today's dating landscape. With candid discussions on personal growth, resilience...

Send us Fan Mail In this insightful episode of the Lost Loverboy Podcast, Demetri dives deep into the complexities of loneliness within relationships. Drawing from personal experiences and psychological insights, he explores how even in partnerships, individuals can feel isolated and disconnected. Demetri shares practical strategies for fostering emotional intimacy and maintaining a strong connection with your partner. Tune in to learn how to recognize the signs of loneliness, communicate eff...

Send us Fan Mail In this heartfelt episode of the Lost Loverboy Podcast, Demetri opens up about the unique challenges and profound joys of raising a child as a single parent, specifically focusing on the dynamics of parenting a child of the opposite gender. He delves into the mindset shifts that are essential for navigating this journey, discussing the importance of empathy, communication, and understanding different perspectives. Demetri shares personal stories, insightful advice, and practi...

Send us Fan Mail In this insightful episode of “Reclaiming Inner Peace,” Demetri delves into the transformative process of reparenting ourselves after experiencing rejection. Join him as he shares personal stories and practical strategies to heal from the hurt of being overlooked or dismissed. Demetri explores the importance of self-compassion, inner dialogue, and building a nurturing relationship with ourselves. Whether you’re navigating the aftermath of a recent rejection or reflecting on p...

Send us Fan Mail In this captivating episode of the Lost Loverboy Podcast, Demetri delves deep into the enigmatic world of emotionally unavailable men. Through insightful commentary and personal anecdotes, he uncovers the underlying reasons for their behaviors and the methods they employ to navigate relationships. Listeners will gain a better understanding of the emotional barriers these men put up and learn practical strategies for recognizing red flags. Demetri also shares tips on how to co...

Send us Fan Mail In this episode of "Chasing Illusions," Demetri dives deep into the complexities of falling for potential, both in ourselves and in others. Join him as he unpacks the often-unrealistic expectations we set when we see the spark of what could be, rather than embracing the reality of what is. Through personal anecdotes, expert insights, and real-life examples, Demetri guides listeners on how to recognize when they’re idealizing potential and the potential pitfalls that come with...

Send us Fan Mail In this episode of the Lost Loverboy Podcast, Demetri takes a reflective journey into the lessons that many men, including himself, weren’t taught as boys. He opens up about the emotional truths, relationship skills, and societal pressures that often go unaddressed. Join Demetri as he shares personal stories and insights about vulnerability, communication, and self-discovery, while exploring why these lessons matter in becoming a well-rounded man. Tune in for an intimate conv...

Send us Fan Mail In this heartfelt episode of the Lost Loverboy Podcast, join us as we dive deep into the unique bond between a son and his mother. In a raw and intimate one-on-one conversation, we explore love, loss, and the lessons that shape us. With candid stories and touching reflections, we discuss everything from childhood memories to the wisdom that only a mother can impart. Tune in as we uncover the complexities of love through the eyes of a son who has always held his mother as his ...

Send us Fan Mail Join Demetri in this enlightening podcast episode as he delves into "Are We Ready for the Love We Desire?: Emotional Readiness." Together, we’ll explore what it truly means to be emotionally prepared for love and relationships. Demetri breaks down the key concepts of emotional readiness, discussing how our past experiences, self-awareness, and personal growth influence our capacity to give and receive love. Whether you’re single, in a relationship, or navigating the complexi...

Send us Fan Mail In Episode 39 of the Lost Loverboy Podcast, Demetri sits down with Shawn Brooks to explore the intricate dynamics of love and labor in long-lasting partnerships. Together, they delve into the tough truths that often accompany enduring relationships, discussing the balance between love, commitment, and the hard work required to maintain a healthy bond. Shawn shares personal anecdotes and insights, encouraging listeners to embrace the challenges of partnership while celebrating...

Send us Fan Mail On this episode of the Lost Loverboy Podcast, Demetri dives into the exciting world of relationship enhancement. He shares creative and fun ideas to help couples reignite the spark that may have faded over time. From adventurous date ideas to intimate communication techniques, Demetri explores practical ways to bring passion back into your partnership. Join him as he discusses the importance of keeping the flame alive in every love stage. Tune in for inspiration, laughs, and ...

Send us Fan Mail In this exciting episode of our podcast, join us as Demetri dives deep into another round of Q&A, tackling your burning questions and sharing his unique insights. From personal anecdotes to expert advice, Demetri's candid responses will inspire and entertain you. Whether you're curious about life lessons or career guidance or want to hear his thoughts on the latest trends, this episode is packed with valuable content. Tune in for an engaging conversation that promises to...

Send us Fan Mail Join Demetri in this thought-provoking podcast as he delves into the evolving history of general roles in America. From traditional family dynamics to the modern landscape of relationships, each episode explores how societal norms and expectations shifts have shaped our connections today. Through engaging discussions, personal anecdotes, and expert insights, Demetri uncovers the impact of these changes on friendships, partnerships, and community ties. Whether you're curious a...

Send us Fan Mail In this enlightening episode, Demetri dives deep into the fascinating world of love languages and their transformative power in relationships. He explores how understanding the five distinct love languages—words of affirmation, acts of service, receiving gifts, quality time, and physical touch—can enhance communication and deepen emotional connections. Demetri shares personal anecdotes and practical tips on identifying your love language and that of your partner, friends, or...

Send us Fan Mail In this enlightening episode of our podcast, join Demetri as he takes us on a journey of healing and self-discovery with his five transformative steps to self-forgiveness. Drawing from personal experiences and insights, Demetri shares practical strategies that can help listeners let go of guilt and shame, encouraging them to embrace compassion and acceptance. Whether you’re grappling with past mistakes or seeking a fresh start, this episode offers valuable tools and heartfelt...

Send us Fan Mail In this enlightening episode, Demetri dives deep into the intricate world of self-discovery and its profound impact on dating and relationships. Join him as he shares personal anecdotes and insights about the journey of understanding oneself—an essential foundation for building healthy, meaningful connections with others. Explore the transformative benefits of self-awareness and how it shapes our interactions, choices, and experiences in the dating landscape. Demetri discusse...

Send us Fan Mail In this heartfelt episode, Demetri sits down with his long-time friend Justice to dive into the complexities of heartbreak and the healing journey that follows. Together, they share personal stories and insights gained through their own experiences, exploring the moments of clarity and realization that often emerge in the aftermath of a breakup. Join them as they discuss the importance of self-compassion, the lessons learned from pain, and the transformative power of friendsh...

Send us Fan Mail In this episode, we dive deep into the life of Logan Wiley, the son of Demetri. Join us as we explore Logan’s unique perspective on his father, unveiling the nuances of their relationship and how it has shaped his understanding of love. We’ll discuss Logan’s thoughts on family dynamics, the bonds he shares with friends, and what love means to him in today’s world. Through heartfelt anecdotes and candid reflections, we aim to paint a vibrant picture of Logan as an individual—h...

Send us Fan Mail In this podcast, Demetri delves into the intricate world of manipulation patterns in dating and relationships. With a keen understanding of human behavior and relationships, Demetri breaks down the subtle signs of manipulation and provides valuable insights on how to recognize and navigate these patterns. Whether you're single and navigating the dating scene or in a committed relationship, this podcast offers practical advice and eye-opening perspectives to empower you in cre...

Send us Fan Mail In this podcast, Demetri delves into the intricacies of maintaining a healthy balance of masculinity and femininity in relationships. From navigating traditional gender roles to embracing individuality, he provides valuable insights on fostering harmony and understanding between partners. Tune in as Demetri shares personal experiences and expert advice on building strong, fulfilling connections. Viewer discretion is advised for this love-themed podcast. The content may contai...

Send us Fan Mail Join Demetri in this special podcast episode as he delves into questions his Instagram followers ask. Listen in as he shares his insights, experiences, and knowledge on a wide range of topics, providing valuable and entertaining answers to the questions that matter to you. Whether it's about life, career, or anything in between, Demetri's candid and engaging responses will enlighten and inspire. Tune in for an insightful and interactive journey through the world of Instagram ...

Send us Fan Mail In this podcast episode, Demetri dives into seeking a high-value partner. He shares valuable insights into the qualities to look for in a partner, the importance of mutual respect, and the benefits of being in a relationship with someone who shares your values. Whether in the dating scene or seeking to improve your existing relationship, Demetri provides practical advice for finding and maintaining a healthy, high-value partnership. Tune in to better understand what it means ...

Send us Fan Mail In this special episode, Demetri delves into the signs that indicate whether you're truly ready for love or not. Drawing from personal experiences and insights, Demetri offers a candid and introspective look at the subtle signals that can help you determine your emotional readiness for a relationship. Whether you're navigating the world of dating or simply exploring your own feelings, this episode provides practical advice and thought-provoking perspectives to help you unders...

Send us Fan Mail In this podcast, Demetri passionately shares insights and emotions surrounding his all-time favorite love movie. Join us as he delves into this cinematic masterpiece's intricate storytelling, compelling characters, and enduring impact. From analyzing key scenes to discussing the profound themes that resonate deeply with audiences, Demetri's thoughtful exploration sheds light on what makes this love movie a timeless classic. Whether you're a fellow enthusiast or curious about ...

Send us Fan Mail In this episode, we delve into the romantic deception perpetuated by movies. From grand gestures to unrealistic expectations, we explore how movies often present an idealized, exaggerated version of love that doesn't always reflect reality. Join us as we uncover the myths and misconceptions about love perpetuated by the silver screen and discuss how these portrayals can impact our real-life relationships. Viewer discretion is advised for this love-themed podcast. The content ...

Send us Fan Mail In this episode, Demetri shares his personal story of navigating the effects of generational trauma and provides practical tips for listeners who are on a journey toward healing. He discusses the importance of self-awareness, self-care, and forgiving for self. Demetri also highlights the impact of community and connection on healing from trauma and offers advice for listeners who may be struggling with feelings of isolation and disconnection. Join us as we learn from Demetri...

Send us Fan Mail In this episode, we explore the intricacies of romantic relationships and delve into the difference between loving someone and being in love with someone. Join us as we navigate the complexities of these two concepts and discuss how they impact our relationships. We'll share personal stories and expert insights to help you better understand what it means to love someone and what it means to be in love with someone. If you're looking to strengthen your relationships and deepen...

Send us Fan Mail In this episode, Demetri delves into various topics to shed light on things that women may not know about men. From communication styles and emotional expression to societal pressures and personal experiences, Demetri offers insights to help bridge the gap between the genders. Tune in to better understand the male perspective and foster better connections in your relationships. Make it persuasive Viewer discretion is advised for this love-themed podcast. The con...

Send us Fan Mail In this heartwarming episode of our podcast, we dive deep into the powerful bond between a father and his son. Join us as we explore the incredible influence that a child can have on their parent's life and how this special relationship can help us grow and evolve as individuals. Demetri shares his personal story of how his son has inspired him to become a better man and how he has learned to appreciate life's simple pleasures through the eyes of a child. This touching and ho...