Gay Men Going Deeper

Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood

Gay Men Going Deeper is a podcast about gay relationships, identity, sexuality, and personal growth for gay men navigating modern life.

Hosted by Matt Landsiedel and Michael DiIorio, the show dives into topics like dating, shame, masculinity, confidence, emotional intimacy, and the pressures of modern gay culture.

Expect raw conversations, psychological insight, and the kind of honest discussions that challenge assumptions and invite deeper reflection about what it means to live authentically as a gay man.

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293 episodes
Updated July 23
Explicit

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Episodes293

Newest first

Aug 21, 2025 · 35 min
The Problem With Self-Love
We all know self-love is important, but what happens when it goes too far in the wrong direction? In this episode, Michael DiIorio is joined by therapist Michael Pezzullo for an honest conversation about the shadow side of self-love. Together, they explore: The difference between self-comforting and self-coddling How emotional sensitivity can become emotional fragility Why self-bulldozing is just as harmful as avoidance The four zones of the Self-Love Spectrum How trauma impac
Aug 14, 2025 · 49 min
Lone Wolf Energy
Some of us didn’t choose to become lone wolves—we were shaped into them. Many gay men have learned to rely only on themselves, and while that self-sufficiency can feel empowering, it often comes at the cost of connection and intimacy. In this personal and vulnerable episode, Michael and Matt open up about their own lone wolf energy—where it comes from, how it’s served them, and the moments when it became more isolating than empowering. Together, we’re unpacking: The origin stories of o
Aug 7, 2025 · 58 min
Why Do I Keep Attracting Unavailable Men?
In this episode, Matt speaks with queer relationship coach Lonay Halloum about why we attract unavailable men. This episode will provide you with a deeper understanding of your relationship patterns and why you might be attracting unavailable men. This episode was inspired by a deep desire to help you heal the subconscious programs that lead to self-abandonment so you can end this exhausting cycle and finally attract available men. The concepts and questions we explore in this episode are:
Jul 31, 2025 · 1 hr
Rejection Sensitivity
Why do so many gay men struggle with deep fears of rejection—whether in dating, friendships, or even at work? In this episode, we’re unpacking rejection sensitivity: where it comes from, how it shows up in everyday life, and why it can feel so intense for us. Some of the topics we cover: The early roots of rejection sensitivity (hint: it starts young) How social norms, internalized homophobia, and shame wire us for hypervigilance The impact of dating app culture and body-focused rej
Jul 24, 2025 · 38 min
Overcoming Uncertainty: A Special Solo Episode with Reno
How would you, your life, and your experience be if you were free from uncertainty, instability, and insecurity? While it can’t be promised you won’t have to experience these again, in this special solo episode, Reno shares personal experiences, perspectives, anecdotes, and practices to help you relate to them in ways that do create more freedom, creativity, resourcefulness, resilience, discernment, enthusiasm and lightness in the face of them. He also demonstrates some ways he has personall
Jul 17, 2025 · 53 min
Claiming Your Power
We may be adults, but a lot of us are still living in emotional childhood—blaming others for how we feel and how we act. When you give other people control over your emotions, you give away your power. In this episode, we're breaking down what it means to take responsibility for your emotions and why it is fundamental if you want true freedom, stronger relationships, and genuine self-confidence. We’ll share personal stories of when we were stuck in emotional immaturity and how we learned to t
Jul 10, 2025 · 1 hr 5 min
How to Soften the Inner Critic
In this episode, Matt speaks with author and love advocate, Scott Stabile. Together, they break down the psycho-spiritual aspects of the inner critic and how to best work with it from a place of love. If you are someone who is hard on yourself and has a tough time finding self-love and self-compassion, this episode will help you develop greater awareness of your inner critic, where self-judgment originates, and how you can start practicing more acceptance of yourself and others through presence,
Jul 3, 2025 · 1 hr
Feeling Your Emotions
What happens when we avoid feeling our emotions? In this episode, we explore the importance of emotional awareness: tuning in instead of checking out. We share what happens when we suppress our feelings, and how to navigate the tough ones with compassion and care. We also explore: The link between emotional avoidance and things like addiction, depression, and burnout What blocks us from feeling our emotions Practical ways to process emotions that feel overwhelming or uncomfortable
Jun 26, 2025 · 46 min
Pride Panel Discussion
It’s Pride Month, and with everything going on in the world right now, it feels especially important to pause and reflect. In this special panel discussion episode, Reno Johnston is joined by three incredible guests—Mark Fleming, Keone Wales, and Jordan Layne—for a candid panel discussion on the meaning of Pride: where it began, how it’s evolved, and what it means to each of us today. Together, they explore questions like: What does Pride mean to you? What was your first Pride experien
Jun 19, 2025 · 49 min
Are LGBTQ Rights Under Attack?
In 2025, LGBTQ rights are facing renewed challenges- from the rise of far-right populism to legislative rollbacks and the rise of hate sweeping across the globe. But how serious is the threat? And if the fight is back on… are we ready? This week, Michael is joined by author and longtime activist, Tim McCaskell, who’s been on the front lines of LGBTQ+ resistance for over five decades. From the bathhouse raids to the fight for AIDS treatment and beyond, Tim brings deep historical context and li
Jun 12, 2025 · 49 min
Has Pride Lost Its Meaning?
In today’s episode, we’re diving into a question many in our community have been quietly (or loudly) asking: Has Pride lost its meaning? In this wide-ranging conversation, we reflect on how Pride has evolved from its radical roots in activism to its present-day celebratory scene shaped by media, politics, and corporate sponsorships. We talk about what’s been gained, what’s been lost, and what still needs to be reclaimed. Some topics we explore: The impact of corporatization and rainbow
Jun 5, 2025 · 1 hr 13 min
Dating as a Demisexual
In this episode, Matt speaks with a panel of demisexual gay men about their experiences dating as demisexuals. What we want you to get out of this episode is greater awareness of yourself if you are demisexual, and to know you are not alone. We want to share our own experiences in the hope that you can learn ways to thrive as a demisexual. If you are not demisexual, this episode will offer you a greater understanding of demisexual men you might come across in dating. We also share helpful, prac
May 29, 2025 · 53 min
Why Are Gay Friendships So Hard?
For many gay men, friendship is complicated, performative, and sometimes downright painful. We crave genuine connection but end up navigating cliques, comparison, and quiet loneliness. In this episode, Michael and Pepper are doing an exposé on gay friendships to unpack what’s really going on beneath the surface and why so many gay friendships fall short of the depth and safety we actually want. We’re breaking it down in three parts: The Pretty Lies: Performative friendship, superficia
May 22, 2025 · 53 min
The Reparenting Process
How do the unmet needs of our childhood shape who we are today? And more importantly, how do we learn to meet those needs for ourselves as adults? In this deeply personal and eye-opening episode of Gay Men Going Deeper, we explore the re-parenting process—a therapeutic model that helps us heal old wounds, develop self-compassion, and rewrite the internal narratives we inherited from childhood. We’ll be getting personal as we reflect on on three powerful questions: 1️⃣ What needs went un
May 15, 2025 · 53 min
How to Not Lose Yourself in Your Relationships
In this episode, Matt speaks with therapist and author, Tom Bruett, about how to avoid losing yourself in your relationships. By balancing connection and autonomy in our relationships, we can foster more secure relationships that allow us to maintain our sense of self while allowing our partner to do the same. If you easily lose yourself in your relationships or you’re having a hard time establishing intimacy, this episode will offer a refreshing perspective and tangible takeaways to help yo
May 8, 2025 · 44 min
Why Gay Men Love Divas
From Madonna to Mariah, Beyoncé to Barbra— throughout the generations, gay men have been obsessed with divas. But why? In this episode of Gay Men Going Deeper, we’re diving into the deep connection between gay men and our beloved divas, exploring: Who are the divas and what do they have in common? Why divas resonate so deeply with gay men How these women inspire us The diva anthems that have become the soundtrack of self-confidence What it means to channel your inner diva in
May 1, 2025 · 46 min
The Women in Our Lives
The women in our lives have influenced us in ways we don’t always recognize, but when we take a step back, their impact is undeniable. In this heartfelt episode, we’re celebrating the uniquely beautiful relationships gay men have with women—from mothers and grandmothers to besties, sisters, and beyond. We’re showing love to all the women who have supported us, shaped us, and often modeled the traits that helped us become who we are today. Some of the topics we’ll explore: How our child
Apr 24, 2025 · 52 min
People Pleasing, Boundaries, and Fear of Conflict
Do you find yourself putting other people’s needs ahead of your own? Struggle to set boundaries? Feel responsible for keeping the peace even when it costs you your authenticity? In this episode, gay therapist Michael Pezzullo joins Michael to go deeper into the roots of people pleasing—especially why so many gay men fall into this pattern. We’ll explore how people pleasing shows up in everyday life, why it’s so hard to stop, and how the fear of conflict and rejection keeps us from showing up
Apr 17, 2025 · 44 min
The Power of No
Many gay men struggle with saying no, setting boundaries, or engaging in difficult conversations due to deep-seated people-pleasing tendencies and fear of conflict. But staying silent often leads to resentment, burnout, or feeling disconnected from your true self. As recovering people-pleasers themselves, Matt and Michael have plenty to share about their own journeys toward becoming more assertive in their boundaries. In this episode, we dive into: The difference between people-pleasin
Apr 10, 2025 · 53 min
Eroticizing Shame - Turning Pain Into Pleasure
In this episode, Matt speaks with Psychotherapist, Merle Yost, about how shame may influence sexual desire and arousal by eroticizing shame as a way of coping with it. Merle shares his story about being sexually molested by his father and the impact this had on his sexual development. Join us for this interesting topic that is often not talked about but deeply impacts many of us. The concepts and questions we explore in this episode are: What does it mean to eroticize shame? How do sh