Gay Men Going Deeper

300 episodes over six years. A lot has changed.

For our 300th episode, Michael, Matt, and Reno are back together at the mic for the first time in three months to look back at where Gay Men Going Deeper started, how we’ve changed along the way, and what we’re still figuring out.

We’re revisiting some of those early days (including the things that make us cringe now), sharing beliefs we once held strongly that we see very differently today, and getting honest about the areas in our own lives where we’re still learning and growing.

Whether you’ve been with us since the beginning or this is your first episode, thanks for going deeper with us.

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 http://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.

Growing up gay shapes you. Even if you had a relatively good experience, many of us learned to hide parts of ourselves, seek approval, stay guarded, or adapt in order to feel safe, accepted, or lovable. Over time, those survival strategies can quietly shape our relationships, confidence, intimacy, and sense of self.

In this episode, we’re talking about the “inner work” many gay men find themselves doing as adults: unpacking old conditioning, unlearning shame, building self-trust, and learning how to live more honestly and fully as ourselves. We also share parts of our own journeys, the patterns we see in our clients, and what real growth actually looks like in practice.

We get into:

• How growing up gay can shape your self-esteem, relationships, and identity
• The difference between healing, self-awareness, and staying stuck in the past
• Common coping strategies gay men develop to feel safe, desired, or accepted
• What meaningful personal growth actually looks like in everyday life
• The balance between understanding your past without making it your identity

This is a grounded conversation about growth, self-awareness, and becoming more fully yourself — not perfectly healed, but more conscious, honest, and free.

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 http://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.

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 http://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 http://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 http://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 http://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 http://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 http://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 http://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 http://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 http://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 http://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.

There’s something unique about friendships between gay and straight men. They often feel easy, natural, and unexpectedly intimate.

In this episode, we explore the unique reasons why gay and straight men are drawn towards each other. From male bonding and emotional intimacy to validation, and the freedom to drop the “rules” of being a man, these friendships often offer something both sides aren’t getting elsewhere.

We unpack:

• Why gay men are drawn to straight men… and what they represent
• Why straight men feel safe, open, and even curious around gay men
• How masculinity is shifting in 2026… and where these friendships fit
• What each side gives the other and how we balance each other out

This isn’t about hookups or labels. It’s about what men are craving, and what that reveals about modern masculinity.

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 http://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.

We’ve all dealt with them. And maybe we’ve probably been one too…

In this episode, we unpack what’s really going on beneath hate. Not just online trolls or obvious critics, but the subtle ways judgment, resentment, and animosity show up in everyday life.

We explore:

• Why people hate in the first place (and why it’s rarely about you)
• The difference between healthy disagreement and actual hate
• How hate often masks insecurity, unmet expectations, or avoidance
• What it actually costs you to be a hater
• And how to deal with haters without shrinking, proving, or losing yourself

This isn’t about pretending to be positive or “above it.” It’s about understanding psychology so you don’t get pulled into it, or unconsciously become part of it.

️ Connection Circle: Your Coming Out Process

If this episode resonates, join Matt for a live Connection Circle. This is an opportunity to share your story, be witnessed without judgment, and begin releasing the parts of you that learned it wasn’t safe to be fully authentic. You don’t have to carry it alone anymore.

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 http://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.

What if the things you turn to for fun, pleasure, and productivity are also the ways you avoid your life?

In this episode, we explore escapism through a grounded, real-world lens. Not necessarily as a clinical issue, but as a pattern most of us fall into without realizing it.

From constant busyness and social plans to sex, substances, and scrolling, it’s never been easier to stay stimulated- and disconnected at the same time. We break down:

• Why escapism is so common (and why it makes sense)
• The difference between enjoyment and avoidance
• How to recognize when it shifts from choice to compulsion
• The hidden costs of always staying “on”
• Why a full life can still feel empty

Join us for an eye-opening episode about understanding the spectrum of escapism… and what it might be helping you avoid.

️ Connection Circle: Slowing Down Without Falling Behind

If this episode resonates, join Michael for a live Connection Circle where we explore how to slow down, be more intentional, and stay connected to your life… without feeling like you’re falling behind. http://www.gaymensbrotherhood.com/events

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 http://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.

At what point did life stop being fun?

As kids, play came naturally. We were curious, spontaneous, and fully present. But for many adults, especially gay men who grew up navigating shame and self-consciousness, play slowly disappears.

Responsibility takes over. Image matters more. We try to be cool. And somewhere along the way, joy gets replaced with pressure, performance, and productivity.

In this episode, we explore why so many adults lose their playful side and why reconnecting with it can be one of the most powerful ways to reclaim joy, authenticity, and connection.

Some of the things we cover in this conversation are:

• How shame and self-consciousness disconnect us from play
• The difference between authentic play and performative fun
• How western culture slowly erodes our inner child
• Why playfulness is connected to vulnerability and authenticity
• The role of play in intimacy, connection, and great sex
• How play can protect against burnout and bring us back to life
• Why joy and appreciation are skills worth intentionally developing

If life has started to feel heavy, serious, or overly effortful, this episode is a reminder that play is not childish. It may be one of the most important ingredients in a meaningful life.

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 http://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.

When a gay man says he’s attracted to masculine men, is that simply preference… or could internalized homophobia be part of the story?

In this episode, we unpack one of the most volatile conversations in the gay community. We explore what people actually mean when they say “masculine,” the masc and fem archetypes that shape gay culture, and how social conditioning around masculinity and femininity can influence attraction and identity.

Most importantly, we tackle the question at the center of the debate: where is the line between genuine preference and internalized bias?

In this episode we discuss:

• What people really mean when they say “masculine”
• Masculine and feminine archetypes
• How conditioning around masculinity shapes attraction
• What internalized homophobia can look like in everyday life
• The difference between preference and hierarchy
• Where the line may exist between preference and prejudice

Join us for a nuanced conversation about masculinity, attraction, and the cultural forces that shape how gay men see themselves and each other.

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 http://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.

The guy who constantly cancels plans, keeps things vague, or disappears when something better comes along — that’s flakiness: a pattern of not following through.

In a culture of endless options and shifting feelings, has unreliability quietly become normal? And what does that actually say about us?

In this off-the-cuff episode, we talk about:

• What flakiness actually is — and what it isn’t
• The difference between boundaries and excuses
• Common avoidance patterns in dating and friendships
• Why keeping your word is about more than just social plans
• What it really means to be a reliable man

This isn’t just about the inconvenience of canceled plans. It’s about self-trust, stronger relationships, and the kind of man you’re practicing becoming.

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 http://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.

What does it actually mean to identify as gay?

For many of us, claiming the word “gay” was liberating. It gave us language, belonging, community, and pride. It helped us make sense of our experiences and find people who understood us. But is there a point where identification turns into over-identification?

In this episode, we unpack some big questions:

• What is identity, really?
• In what ways is identifying as gay empowering?
• How does it foster belonging and inclusion?
• When does it start to create division, hierarchy, or limitation?
• Is “gay” a culture — and if so, what does that even mean?
• Where’s the line between healthy pride and rigid attachment?

We explore the benefits and the drawbacks of tying ourselves closely to any identity — and how over-identifying can sometimes shrink us rather than expand us.

This conversation isn’t about minimizing being gay. It’s about integrating it. About moving from performance to embodiment. From label to lived experience.

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 http://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.

In a world of swipes, situationships, and high-intensity connections, romance can start to feel obsolete — replaced by sexual energy, emotional guardedness, or the safety of detachment.

And yet many of us still long for thoughtfulness, depth, being chosen and choosing in return.

In this episode, we explore why that part of us often gets buried under performance, fear of rejection, and modern dating norms — and what it actually takes to lead with romance instead of intensity.

We talk about:

• What romance really looks and feels like in dating
• Why intensity is so often mistaken for intimacy
• What it means to actively bring romance into your dating life
• How love languages and attachment styles shape our romantic expression
• And what truly sweeps us off our feet

This conversation is both a reality check and an ode to the intentional, courageous, thoughtful part of ourselves that still believes in romance.

Today's Hosts:

• Michael DiIorio - Take the 360° Self-Review for Gay Men
• Matt Landsiedel
• 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 http://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.