Lost Loverboy Podcast

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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 things that made us believe in love in the first place. We share stories, disagree on a few nominations, defend our picks, and talk about how our own experiences have shaped what we consider Hall of Fame worthy.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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, I'm revisiting some of my favorite movies and unpacking the love lessons I didn't fully understand when I first watched them. We talk about Shrek, Click, 50 First Dates, Bruce Almighty, and the moments that hit completely differently once you've actually experienced love, heartbreak, sacrifice, fatherhood, and growing up. 

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 about my own relationship with being picked, the ways our earliest experiences with love can follow us into adulthood, and what I’m beginning to unlearn about the kind of love I’ve spent my life looking for.

Maybe love isn’t supposed to require me to constantly prove what I’m willing to lose for it.

Maybe the unlearning is realizing I don’t have to sacrifice myself to finally feel chosen.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 the love I hope she'll never have to question. This isn't a conversation about finding the right person. It's about becoming the right person.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 compromise, and why healthy love should never require you to abandon what matters most to you.

If you've ever wondered whether your expectations are unrealistic or if you've just been settling for less than you deserve, this conversation is for you.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 what you provide and being cherished for who you are. Because real love doesn't disappear the moment you have nothing left to give.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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. Sometimes they feel right because they feel familiar. If you've ever looked back at a relationship and wondered, "How did I end up here?" this conversation is for you.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 between fighting for a relationship and fighting against reality. If you've ever struggled to walk away from someone who wasn't all bad, but still wasn't right for you, this conversation is for you.

New episodes of the Lost Loverboy Podcast explore love, relationships, healing, and the conversations we don't have often enough, but probably should.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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. It's about recognizing how life, heartbreak, and experience can redefine what we should, and shouldn't, accept in our relationships.

If you've ever looked back at a relationship and thought, "I'll never settle for that again," this conversation is for you.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop

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 feeling like someone cared about you but never truly got you, this conversation is for you.

New episodes of the Lost Loverboy Podcast explore love, relationships, and the conversations we don't have often enough, but probably should.

Viewer discretion is advised for this love-themed podcast. The content may contain discussions of sensitive topics related to relationships, dating, and love. Some content may not be suitable for all listeners, especially those uncomfortable with open and vulnerable conversations. We encourage our listeners to practice self-care and to reach out to a trusted friend or professional if they need support. If you have no friends, you have me! Welcome to the Lost Loverboy Podcast!

Support the show

Join the Lover's House Discord to connect with Demetri Wiley and fellow enthusiasts! Share your experiences, seek advice, and celebrate romance within a welcoming community. Don't miss out—join us today: https://discord.com/servers/the-lovers-house-1345240227538538617

You can also purchase Lost Loverboy merchandise at https://demetriwiley.com/shop