Gay Men Going Deeper

This episode of Gay Men Going Deeper is less of a casual conversation and more of a confidence masterclass . One you’ll likely want to come back to again and again. We break down what real, unshakeable confidence actually is (and what it isn’t). Not the loud, performative kind, but the grounded confidence that comes from self-trust, self-compassion, and emotional regulation. We talk honestly about...

In this episode, we’re breaking down one of the biggest dating myths gay men love to repeat: “My standards are too high.” But sometimes the problem isn’t what you want, it’s what you allow. We get into the real difference between standards and boundaries, why attraction wipes our memory clean, and how low boundaries quietly reveal your level of self-worth. If you’ve ever said you want emotional ma...

In this episode, Michael and Matt get personal about what we love about being single, how we knew we were ready to start dating again, and what we want to experience differently this time around. We talk about flirting on apps, dating in 2026, and all the messy, exciting parts of putting yourself back out there when you’re ready to mingle.  Some of the topics we cover in this episode are: • Gettin...

Why does attraction fade… and what can we do about it?  In this episode we get real about attraction in long-term relationships. The spark doesn’t always burn forever, and losing sexual interest doesn’t mean the relationship is doomed. We talk about why attraction naturally shifts over time and how couples can ignite intimacy. We explore: Why attraction fades in relationships The 4 types of intima...

After unpacking our culture’s obsession with “perfect” bodies, this week we’re flipping the script. In this episode, we’re celebrating what’s actually hot: the things that don’t get enough love in the gay world. We’re talking dad bods, wrinkles, kindness, confidence, awkward charm, conversational skills, and all the real stuff that makes someone magnetic.  Some of the things we’re talking about: H...

From the gym to social media, gay men are constantly surrounded by images of the “ideal” body. But what does all this perfection chasing actually cost us? In this episode, we explore how body perfection culture impacts gay men on a deeper level: from belonging and self-worth to intimacy and identity. We open up about our own journeys with body image— how we’ve moved from obsession to acceptance, w...

In this episode, we dive into what radical honesty really means- not the brutally blunt “telling it like it is” version, but the deeper, more vulnerable kind that lets you actually be known. We explore why being honest is both terrifying and liberating, the subtle ways we still avoid it, and how honesty differs from harsh truth-telling. We share our own struggles with showing up honestly in dating...

Today we’re diving into one of the most iconic (and hilarious) parts of gay culture: labels. In this episode, we unpack why gay men are so obsessed with categories like “twink,” “daddy,” “masc,” “otter,” “guy next door,” and every micro-label in between… and how these identities shape the way we date, belong, and see ourselves. We explore: Why labels can feel empowering (and sometimes limiting) Ho...

Today we’re talking about The Slow Fade :  that slow, quiet drifting apart where the messages get shorter, the replies slower, and the energy shifts until one day…it’s just silence. In this episode, we’re unpacking: Why we quietly quit people instead of having real conversations What’s actually happening beneath the surface for both sides — the Fader and the Fadee Who deserves an explanation and w...

What we want you to gain from this episode is the importance of non-sexualized, safe, and brave spaces for gay men to heal and grow together. By the end of this episode, you will be able to identify what a nest is, how you could benefit from one, and where to find or create one if you are interested in nesting. The concepts and questions we explore in this episode are: What is “nesting” and why is...

We all say we want love… but are we actually open to receiving it? In this episode, we’re going deeper into what it really means to open your heart. From the subtle subconscious programming that keeps love at arm’s length to the sneaky ways we self-sabotage, we’re unpacking the hidden barriers that make intimacy feel unsafe (even when we crave it most). You’ll learn: Why receiving love can feel ha...

Some of us don’t fall in love with people, we fall in love with an idea of them. The story, the potential, the fantasy of the perfect boyfriend who finally makes everything click. But that idealized version of love often keeps us chasing what looks right instead of what feels real. In this episode, Michael DiIorio and therapist, Michael Pezzullo , explore how fantasy, perfectionism, and external v...

Why does joy feel so hard to hold onto? In this episode of Gay Men Going Deeper, we’re revealing the joy killers : those sneaky ways we sabotage happiness even when life is going well. We explore: The difference between chasing pleasure and cultivating joy Foreboding joy (a.k.a. waiting for the other shoe to drop) and how it robs us of the present. How trauma and disappointment condition us to exp...

What would your day, your week, your next year, or even your life look like if you spent it following your joy? What if joy became your North Star? Your guiding light? Your compass? What is in the way of you experiencing more joy in your life?  What if you could find joy in how you dress, what you eat, how you exercise, where you live, what you do for work, who you spend time with, and how you nav...

Joy isn’t just fireworks and big milestones; it’s in the ordinary, everyday moments we often overlook. Yet for many of us, joy feels slippery and hard to find.  In this episode of Gay Men Going Deeper, we’re diving into what joy really feels like, how it shifts as we evolve and age, and why it’s less about chasing highs and more about cultivating presence. We’ll explore: The difference between joy...

You know the type — ambitious, perfectionistic, and always striving to do more and be more… yet secretly fuelled by pressure, anxiety, and fear.   In this episode, Michael is joined by special guest Scott Stirrett as they share their own stories of hustling for achievement and how they’ve learned to stay ambitious without destroying themselves in the process. Together, they unpack how perfectionis...

In this final installment of our 4-part series on grief, we explore the powerful practice of Radical Acceptance —what it means, why it’s so difficult, and how it becomes the turning point in your healing journey. Whether you're grieving the person you used to be, mourning a friendship that faded, or facing the slow heartbreak of watching your parents age, grief often leaves us wrestling with reali...

As our parents get older, many of us are faced with a new kind of grief- the quiet, ongoing loss that comes not from death, but from watching the people who once raised us begin to slow down and need us in ways they never did before. In this deeply personal episode, we open up about the emotional complexity of witnessing our parents age. From role reversals and unresolved wounds, to meaningful mom...

Not all grief is about death. Sometimes, the hardest losses are the people (or pets) who are still alive—but no longer in our lives. In this episode, we’re talking about the heartbreak of losing relationships: romantic breakups, friendship fallouts, and the deep sadness that comes with saying goodbye to a beloved pet. We explore how grief shows up emotionally, mentally, and even physically—and the...

Grief isn’t just about death—it’s also about the quiet losses we carry as we grow and evolve. In this episode, we’re kicking off a 4-part series on grief by exploring what it means to grieve your past. Whether it’s a version of yourself that felt more confident, more desirable, or more socially “relevant,” we often feel a deep emotional pull toward who we used to be. From aging and identity shifts...

Most of us want to be seen, heard, and understood, but the fear of judgment can stop us from doing so. Whether it’s being more social, speaking your feelings, or sharing creative work, putting yourself out there can feel risky, especially when we’ve been conditioned to play it safe due to past hurt or rejection.  In this episode, we’re sharing: Our personal journeys from shy and self-conscious to...

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...

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...

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...

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, an...