Gay Men Going Deeper

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 Matt Landsiedel and Michael DiIorio, 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.

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293 episodes
Updated July 23
Explicit

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Episodes293

Newest first

July 23 · 36 min
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 purpose: when to sit with an emotion, when to change your mindset, and why emotional avoidance often costs us more than the original pain. We get into: Why feeling bad is a skill, not a personal
July 9 · 49 min
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 over-accommodating are quietly killing attraction, respect, and real connection. We talk about: Why “nice” is often a strategy, not a personality The hidden cost of being liked by everyone How this sho
June 25 · 31 min
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 explore how hookup culture can either reinforce negative patterns or become a powerful mirror for your patterns, desires, boundaries, and capacity for intimacy. We talk about: Why hookups aren’t the
June 11 · 52 min
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 today? Does being gay impact the level of intimacy you have with your dad? From there, we go deeper into family dynamics, cultural expectations, and the different expressions of love and accep
May 28 · 36 min
“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 dependence, co-dependence, independence, hyper-independence, and interdependence—and why so many gay men get stuck at the far end of doing life alone. We talk about: What hyper-independence actually is
May 14 · 43 min
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 freedom to drop the “rules” of being a man, these friendships often offer something both sides aren’t getting elsewhere. We unpack: Why gay men are drawn to straight men… and what they represen
April 30 · 31 min
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 place (and why it’s rarely about you) The difference between healthy disagreement and actual hate How hate often masks insecurity, unmet expectations, or avoidance What it actually cost
April 16 · 31 min
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 busyness and social plans to sex, substances, and scrolling, it’s never been easier to stay stimulated- and disconnected at the same time. We break down: Why escapism is so common (and why it makes sense) The
April 2 · 53 min
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 cool. And somewhere along the way, joy gets replaced with pressure, performance, and productivity. In this episode, we explore why so many adults lose their playful side and why reconnecting with
March 26 · 51 min
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 and fem archetypes that shape gay culture, and how social conditioning around masculinity and femininity can influence attraction and identity. Most importantly, we tackle the question at the center
March 19 · 31 min
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 us? In this off-the-cuff episode, we talk about: What flakiness actually is — and what it isn’t The difference between boundaries and excuses Common avoidance patterns in dating and friend
March 12 · 25 min
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 over-identification? In this episode, we unpack some big questions: What is identity, really? In what ways is identifying as gay empowering? How does it foster belonging and inclusion? When doe
March 5 · 51 min
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, we explore why that part of us often gets buried under performance, fear of rejection, and modern dating norms — and what it actually takes to lead with romance instead of intensity. We talk abo
February 26 · 24 min
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 shame, performance, or pressure. We unpack how conditioning, fear, and expectations can quietly pull us away from what we genuinely want, and why many gay men feel disconnected from their evolving desires ov
February 19 · 24 min
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. In this off-the-cuff conversation, we unpack why gay men are stuck between purity culture and performance culture, and how both distort our relationship to sex, desire, and self-worth. We explore:
February 12 · 48 min
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 explore: What traits often get mistaken for confidence in gay culture How social media amplifies performative confidence and quietly fuels insecurity Why confidence built on validation, desi
February 5 · 31 min
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 discernment, attachment, and self-trust. We share personal stories, name the difference between excitement and regulation, and break down how slowing down isn’t about playing games, withholding sex, or killin
January 29 · 22 min
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 off-the-cuff conversation, Michael and Matt explore why this story resonated so strongly, what emotional needs it taps into, and why certain depictions of gay love, sex, courage, and intimacy feel especial
January 22 · 49 min
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 actually helps us become more open to connection again. This conversation isn’t about forcing positivity or dating tactics. It’s about understanding the patterns that keep us guarded, how we sabotage l
January 15 · 53 min
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 confidence that comes from self-trust, self-compassion, and emotional regulation. We talk honestly about why confidence can feel harder for gay men, how minority stress and shame shape a harsh inner