Gay Men Going Deeper
by 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 Michael DiIorio and Matt Landsiedel, 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.
Episodes
-
300 Episodes Later: Growing, Changing & Still Figuring It Out
300 episodes over six years. A lot has changed. For our 300th episode, Michael, Matt, and Reno are back together at the mic for the first time in three months to look back at where Gay Men Going Deeper started, how we’ve changed along the way, and what we’re still figuring out. We’re revisiting...
-
The Gay Man’s Healing Journey: What Is The Inner Work And How Do We Actually Do It
Growing up gay shapes you. Even if you had a relatively good experience, many of us learned to hide parts of ourselves, seek approval, stay guarded, or adapt in order to feel safe, accepted, or lovable. Over time, those survival strategies can quietly shape our relationships, confidence…
more -
Growing Up Different: The Impact on Belonging
Growing up different can leave a lasting impact on how we see ourselves, our relationships, and our sense of belonging. Even years later, many gay men still carry the feeling of being on the outside looking in—surrounded by people, yet not truly known. In this episode, we're exploring the roots…
more -
When To Get Off the Apps (And When to Go Back On)
Apps are a huge part of modern gay life. We delete them, reinstall them, swear them off, go back on, and keep trying to figure out whether they’re helping us connect or quietly getting in the way. In this episode, we’re talking about app seasonality: that on-again, off-again relationship many gay...
-
Why Bad Boys Feel So Good
Why do the guys who are a little distant, a little edgy, and a little hard to get feel so magnetic? Is it actually attraction…or is a deeper pattern being activated? In this episode, we unpack what’s going on underneath the pull toward “bad boys” and why it can feel so intense, compelling, and…
more -
Why Gay Men Struggle with Intimacy
Intimacy sounds like something we all want, but being truly seen can feel terrifying. In this episode, we talk about why fantasy often feels safer than reality, why vulnerability can feel exposing, and how the fear of rejection keeps many gay men hiding behind performance. We also get personal...
-
From Validation-Seeking to Self-Trust
Seeking validation isn’t just about chasing likes. It’s the part of us that needs approval, wants to belong, and feel accepted. But does it come at a cost? In this episode, we unpack the subtle ways validation-seeking still shows up in our everyday lives, especially as gay men who learned early…
more -
When Feeling Bad Is Good For You
Feeling bad is not a flaw in the human experience. It’s an essential life skill for anyone who wants a life of love, growth, satisfaction, and intimacy— all of it requires the capacity to feel discomfort without running from it. In this episode, Michael and Matt make the case for feeling bad on...
-
Liked by Everyone, Chosen by No One: The Nice Guy Trap
A lot of gay men pride themselves on being “nice”— easygoing, agreeable, low-drama. But what if that’s exactly why you’re not getting what you want? In this episode, we break down the difference between being kind and being “nice,” and how approval-seeking, conflict avoidance, and...
-
How to Elevate Your Hookups
Hookups get a bad rap as shallow, transactional, or disconnected. But what if they could actually become a space for growth, awareness, and real connection? In this episode, we’re advocating for shift from default, unconscious hookups to something more intentional, honest, and grounded. We…
more -
The Daddy Issue: Our Relationships With Our Dads
For many gay men, our relationship with our dad is one of the most defining- and least talked about. In this episode, we explore the nuances of our relationships with our fathers through three core questions: How did your dad react when you came out? How do you express your gayness around him...
-
“I Don’t Need Anyone”: Why Gay Men Struggle to Let Someone In
A lot of gay men take pride in being independent, self-sufficient and in control. But is there a shadow side? When the time comes to let someone in, ask for support, or even rely on others—it feels uncomfortable, exposing, even threatening. In this episode, we explore the spectrum between...
-
Gay–Straight Bromance: Why We’re Drawn to Each Other
There’s something unique about friendships between gay and straight men. They often feel easy, natural, and unexpectedly intimate. In this episode, we explore the unique reasons why gay and straight men are drawn towards each other. From male bonding and emotional intimacy to validation, and the...
-
How To Deal With Haters (Without Getting Defensive)
We’ve all dealt with them. And maybe we’ve probably been one too… In this episode, we unpack what’s really going on beneath hate. Not just online trolls or obvious critics, but the subtle ways judgment, resentment, and animosity show up in everyday life. We explore: Why people hate in the first...
-
Busy, Stimulated, and Disconnected: Gay Men & Escapism
What if the things you turn to for fun, pleasure, and productivity are also the ways you avoid your life? In this episode, we explore escapism through a grounded, real-world lens. Not necessarily as a clinical issue, but as a pattern most of us fall into without realizing it. From constant…
more -
Let’s Play! When Did Life Stop Being Fun?
At what point did life stop being fun? As kids, play came naturally. We were curious, spontaneous, and fully present. But for many adults, especially gay men who grew up navigating shame and self-consciousness, play slowly disappears. Responsibility takes over. Image matters more. We try to be...
-
Masc for Masc: Preference or Internalized Homophobia?
When a gay man says he’s attracted to masculine men, is that simply preference… or could internalized homophobia be part of the story? In this episode, we unpack one of the most volatile conversations in the gay community. We explore what people actually mean when they say “masculine,” the masc…
more -
Flakey Gays: Why is Follow-Through So Hard?
The guy who constantly cancels plans, keeps things vague, or disappears when something better comes along — that’s flakiness: a pattern of not following through. In a culture of endless options and shifting feelings, has unreliability quietly become normal? And what does that actually say about…
more -
Is Being Gay Your Entire Identity? (The Hidden Cost of Over-Identification)
What does it actually mean to identify as gay? For many of us, claiming the word “gay” was liberating. It gave us language, belonging, community, and pride. It helped us make sense of our experiences and find people who understood us. But is there a point where identification turns into...
-
Is Romance Dead in Gay Culture?
In a world of swipes, situationships, and high-intensity connections, romance can start to feel obsolete — replaced by sexual energy, emotional guardedness, or the safety of detachment. And yet many of us still long for thoughtfulness, depth, being chosen and choosing in return. In this episode…
more -
Sexual Authenticity: Owning Your Desires
Being sexually open isn’t the same as being sexually honest. In a culture that celebrates sex, many gay men still struggle to feel aligned with what they truly want, without shame or pressure. In this off-the-cuff conversation, we explore what it really looks like to own your desires without…
more -
The Body Count Dilemma: Why Gay Men Can’t Win
In gay culture, “body count” refers to how many people you’ve slept with. And whether it’s high or low, it often feels like a no-win situation. Have a low body count and you risk being seen as repressed, inexperienced, or undesirable. Have a high one and you’re either celebrated… or slut shamed.…
more -
Why So Many “Confident” Guys Are Secretly Insecure
Gay culture rewards visibility, desirability, and dominance, so a lot of what looks like confidence is actually performance under pressure. In this episode, we unpack the myths of self-confidence gay men inherit and what real confidence looks like when no one’s watching. In this conversation, we...
-
The Slow Build in Romantic Relationships
Everyone says they want a “slow build” in dating… right up until chemistry hits and judgement leaves the building. In this off-the-cuff episode, we talk about why moving fast feels so intoxicating, what actually happens in your nervous system when you do, and how speed can quietly hijack...
-
Why Gay Men Are Talking About Heated Rivalry
Gay Men Going Deeper has never done an episode about a TV show before. There’s a reason we did this one. Heated Rivalry isn’t just popular. It landed at a very specific cultural moment for gay men, and the response to it points to something bigger than whether people liked the plot. In this...
-
Will I Be Single Forever?
It’s a question many gay men quietly carry… especially after heartbreak, disappointment, or years of trying. In this episode of Gay Men Going Deeper, we put on our coach hats and unpack why this belief takes hold, how shame and self-protection can block love without us realizing it, and what...
-
How to Build Unshakeable Confidence
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...
-
Standards vs. Boundaries in Dating
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…
more -
Single and Ready to Mingle
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...
-
When Attraction Fades
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…
more -
What’s Really Sexy (and Nobody Talks About It)
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...
-
How to Thrive in the Culture of Body Perfection
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...
-
Radical Honesty: Letting Yourself Be Known
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...
-
Twinks, Jocks, and Bears, Oh My! The Obsession with Gay Labels
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...
-
The Slow Fade: When We Ghost Without Ghosting
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...
-
Nesting: Creating Platonic Spaces for Healing and Authentic Connection in the Gay Community
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...
-
How to Open Your Heart to Receive Love
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…
more -
Falling in Love With The Fantasy
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…
more -
Joy Killers: How and Why We Sabotage Joy
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...
-
Following Your Joy: A Special Solo Episode with Reno
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...
-
How to Find More Joy in Your Life
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...
-
Perfectionism, Pressure, and the Gay Overachiever
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…
more -
Radical Acceptance: Grief’s Final Lesson
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…
more -
Aging Parents and Pre-Grief
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...
-
Grieving Relationships
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...
-
Grieving Your Past
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...
-
How to Put Yourself Out There
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…
more -
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...
-
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...
-
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…
more
About this show
Gay Men Going Deeper is a podcast about gay relationships, identity, sexuality, and personal growth for gay men navigating modern life.Hosted by Michael DiIorio and Matt Landsiedel, 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.
Hosted by
Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood