Gay Men Going Deeper

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, an...

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.
• H...

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,...

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:

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...

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 wrestlin...

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 m...

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 physi...

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 id...

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...

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 em...

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 mo...

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 exhaus...

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)
• ...