Growing up different can leave a lasting impact on how we see ourselves, our relationships, and our sense of belonging. Even years later, many gay men still carry the feeling of being on the outside looking in—surrounded by people, yet not truly known. In this episode, we're exploring the roots of belonging, why so many gay men struggle with deep loneliness, and what it actually takes to find meaningful connection. We get into: The difference between fitting in and truly belonging Why you can have friends and still feel profoundly lonely How shame and abandonment wounds shape our relationships The role authenticity plays in creating real connection Why belonging isn't about everyone agreeing with you—and what it actually requires Practical ways to cultivate a deeper sense of belonging in your life If you've ever felt like you don't quite fit, this conversation is a reminder that belonging isn't about becoming someone else—it's about finding the courage to let yourself be known. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Apps are a huge part of modern gay life. We delete them, reinstall them, swear them off, go back on, and keep trying to figure out whether they’re helping us connect or quietly getting in the way. In this episode, we’re talking about app seasonality: that on-again, off-again relationship many gay men have with the apps, and the skill of knowing when they’re serving you, when they’re draining you, when to use them…and when to lose them. We’re getting into: Why apps can be the right choice in one season and the wrong choice in another How to know when it’s time for a break or hiatus When getting back on the apps can actually be the healthy choice The difference between using apps intentionally vs. compulsively How the apps can reveal your patterns around rejection, desire, sex, dating, and self-worth Whether you’re on the apps, off the apps, or currently “just checking who’s nearby,” this conversation will help you bring more honesty, agency, and self-trust to the way you use them. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Why do the guys who are a little distant, a little edgy, and a little hard to get feel so magnetic? Is it actually attraction…or is a deeper pattern being activated? In this episode, we unpack what’s going on underneath the pull toward “bad boys” and why it can feel so intense, compelling, and hard to walk away from. We talk about: What exactly is it about “bad boys” that makes them so attractive What we’re really responding to beneath the surface  Why intensity can feel like chemistry, but isn’t always compatibility What “bad boys” do well that “nice guys” can learn from How to take those traits into your own dating life—without the chaos If you’ve ever found yourself drawn to someone who felt exciting but hard to reach, this episode will help you understand why—and what to do differently. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Intimacy sounds like something we all want, but being truly seen can feel terrifying. In this episode, we talk about why fantasy often feels safer than reality, why vulnerability can feel exposing, and how the fear of rejection keeps many gay men hiding behind performance.  We also get personal about our own struggles with being seen, how this shows up in dating. This episode is about the fear beneath the fantasy: the part of us that wants closeness, but panics when closeness asks us to be honest, visible, and emotionally available. We talk about: Why intimacy can feel unsafe even when we crave it The fear of being fully seen, known, and rejected Why fantasy feels easier than real connection How to feel safer, more grounded, and more open to intimacy A deep, honest conversation for gay men who want connection, but sometimes find themselves pulling away when it starts to get real. Link: Matt’s Secure Attachment Handbook  Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Seeking validation isn’t just about chasing likes. It’s the part of us that needs approval, wants to belong, and feel accepted. But does it come at a cost? In this episode, we unpack the subtle ways validation-seeking still shows up in our everyday lives, especially as gay men who learned early to scan, adapt, perform, and manage how we’re perceived. We talk about the difference between healthy feedback and outsourcing your self-worth, and what it actually looks like to build self-trust in real life. In this episode, we discuss: What validation-seeking actually looks like The difference between caring what people think and letting their opinion become a verdict on your worth Why self-trust requires tolerating discomfort, disappointment, and disapproval How we’re each still learning to come back to ourselves in more honest, grounded ways Self-trust doesn’t mean you stop caring what people think- it means their reaction no longer gets to decide who you are. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Feeling bad is not a flaw in the human experience. It’s an essential life skill for anyone who wants a life of love, growth, satisfaction, and intimacy— all of it requires the capacity to feel discomfort without running from it. In this episode, Michael and Matt make the case for feeling bad on purpose: when to sit with an emotion, when to change your mindset, and why emotional avoidance often costs us more than the original pain. We get into: Why feeling bad is a skill, not a personal failure The difference between allowing an emotion and reframing your thoughts How men are often taught to avoid, repress, intellectualize, or act out emotions The ways we numb and escape through food, alcohol, sex, porn, productivity, scrolling, and distraction Why building emotional capacity makes you braver, more honest, and more willing to live a bigger life The goal isn’t to be happy all the time — it’s to become someone who can feel bad without abandoning yourself or shrinking your future. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

A lot of gay men pride themselves on being “nice”— easygoing, agreeable, low-drama. But what if that’s exactly why you’re not getting what you want? In this episode, we break down the difference between being kind and being “nice,” and how approval-seeking, conflict avoidance, and over-accommodating are quietly killing attraction, respect, and real connection.  We talk about: Why “nice” is often a strategy, not a personality The hidden cost of being liked by everyone How this shows up in dating and relationships The difference between being chosen vs. being liked How to shift from approval-seeking to self-respecting If you’ve ever felt overlooked, under-appreciated, or stuck in the friend-zone, this one will hit. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Hookups get a bad rap as shallow, transactional, or disconnected. But what if they could actually become a space for growth, awareness, and real connection? In this episode, we’re advocating for shift from default, unconscious hookups  to something more intentional, honest, and grounded. We explore how hookup culture can either reinforce negative patterns or become a powerful mirror for your patterns, desires, boundaries, and capacity for intimacy. We talk about: Why hookups aren’t the problem—but how we show up in them can be The difference between unconscious vs. intentional hookups How to bring honesty, communication, and authenticity into casual sex How our own hookups have evolved over time Practical ways to make hookups more enjoyable, respectful, and connected—for everyone involved This isn’t about judging hookup culture or pretending it should be something it’s not. It’s about raising the standard of how you show up—so even casual encounters can feel aligned, present, and real. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

For many gay men, our relationship with our dad is one of the most defining- and least talked about. In this episode, we explore the nuances of our relationships with our fathers through three core questions: How did your dad react when you came out? How do you express your gayness around him today? Does being gay impact the level of intimacy you have with your dad? From there, we go deeper into family dynamics, cultural expectations, and the different expressions of love and acceptance between fathers and their gay sons. We get into physical affection between fathers and sons, how much access we give them into our lives, and the boundaries we set as adults. We also explore how these early relationships can shape the kinds of men we’re attracted to… and the patterns we carry into dating and relationships. This is a grounded, honest conversation about the often complex and layered relationship between fathers and sons.  Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

A lot of gay men take pride in being independent, self-sufficient and in control. But is there a shadow side? When the time comes to let someone in, ask for support, or even rely on others—it feels uncomfortable, exposing, even threatening. In this episode, we explore the spectrum between dependence, co-dependence, independence, hyper-independence, and interdependence—and why so many gay men get stuck at the far end of doing life alone. We talk about:  What hyper-independence actually is (and why it’s so common) The fear of losing yourself, your freedom, or your identity Why intimacy feels harder than being alone How this shows up in dating, relationships, and asking for support What it looks like to move toward interdependence (secure attachment)  This isn’t about becoming dependent. It’s about learning how to find a happy middle ground where you can let someone in without losing yourself or pulling further away.  Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.