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, c...

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 me...

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...

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....

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 pers...

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 con...

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...

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 "...

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 l...

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 m...

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 conv...

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 emotion...

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...

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 farewe...

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 respon...

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,...

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....

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...

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 relationsh...

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 practica...

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...

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...

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 connect...

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 und...

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...