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:

This episode is your invitation to shift from followers to friendship, and from competition to collaboration—and start building real connection.

Related Episodes:

Today's Guest: Pepper Rojas

Today's Host: Michael DiIorio

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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 unmet for you as a child?

From loneliness and perfectionism to people-pleasing and self-expression, we dive into the real-life stories and coping strategies that shaped our past and the lessons we’ve learned to become the men we are today. 

Tune in for an honest, vulnerable, and inspiring discussion on how we can become the loving, supportive parents we always needed—for ourselves.

Related Link: Inner Child Work

Today's Hosts:

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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 you improve your relationship with yourself and others. 

The concepts and questions we explore in this episode are:

Book by Tom Bruett:

The Go-To Relationship Guide for Gay Men: From Honeymoon to Lasting

Today's Guest: Tom Bruett

Today's Host: Matt Landsiedel

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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:

This isn’t just about pop culture—it’s a conversation about power, identity, and how divas have given generations of gay men comfort and strength.

Today's Hosts:

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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:

Join us for a deep conversation about the power of women and how these relationships continue to shape us—today and always.

Today's Hosts:

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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 fully in our relationships.

We’ll also discuss:

If you’re ready to stop performing for approval and start living with more authenticity, this episode is for you.

Today's Guest: Michael Pezzullo

Today's Host: Michael DiIorio

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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:

If you’ve ever found yourself saying “yes” when you really meant “no” or avoiding confrontation at the cost of your own needs, this conversation is for you!

Today's Hosts:

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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:

Today's Guest: Merle Yost

Today's Host: Matt Landsiedel

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Communication is at the heart of every relationship—whether it’s with friends, partners, colleagues, or even yourself. But what does it actually mean to be a strong communicator? In this episode, we’re diving into the key skills that make conversations more effective, engaging, and authentic.

Join us as we discuss:

Whether you want to deepen your connections, set clearer boundaries, or simply get your point across without second-guessing yourself, this episode will give you insights to help you communicate with more clarity and impact.

Related Link: Authentic Relating and Empowerment for Gay Men

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They didn’t teach us about gay sex in school… so we had to teach ourselves. From porn to awkward trial-and-error hookups, most of us pieced together our own “education”—for better or worse.

In this episode, Michael is joined by porn star turned sex educator, Patrick Marano, to talk about the sex ed we should have had, how we’ve had to create it for ourselves, and why stigma and censorship still keep gay men in the dark. Some of the topics covered in this episode:

🔹 How conventional sex education fails gay men

Plus: Our favourite resources, communities, and channels for the sex education we actually deserve.

Join Michael’s Sexual Empowerment Men’s Group

🎟 Use code GMGD to get 25% off!

Today's Guest: Patrick Marano

Today's Host: Michael DiIorio

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