Gay Men Going Deeper

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 h...

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 validation shape the way we love- ...

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 ...

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 navigate your day to day li...

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 betwe...

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 perfectionism, internalized shame,...

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 reality. Radical acceptance is what al...

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 moments and surprising lessons, we ...

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 unique challenges of letting go...

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 to the grief of letting go of o...

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 being more visible 👉 Th...

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 j...

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 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....

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.

How would you, your life, and your experience be if you were free from uncertainty, instability, and insecurity?

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, 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 pr...

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.