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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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24 episodes
fortnightly
Avg 38 min
English

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Episodes 24

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#297
Thursday · 35 min
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 men have with the apps, and the skill of knowing when they’re serving you, when they’re draining you, when to use them…and when to lose them. We’re getting into: Why apps can be the right choi
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#296
September 3 · 33 min
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 hard to walk away from. We talk about: What exactly is it about “bad boys” that makes them so attractive What we’re really responding to beneath the surface Why intensity can feel like chemistry, but isn
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#295
August 20 · 28 min
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 about our own struggles with being seen, how this shows up in dating. This episode is about the fear beneath the fantasy: the part of us that wants closeness, but panics when closeness asks us to be
- Chapters
#294
August 6 · 48 min
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 to scan, adapt, perform, and manage how we’re perceived. We talk about the difference between healthy feedback and outsourcing your self-worth, and what it actually looks like to build self-trust in real
- Chapters
#293
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
- Chapters
#292
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
- Chapters
#291
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
- Chapters
#290
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
- Chapters
#289
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
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#288
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
- Chapters
#287
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
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#286
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
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#285
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
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#284
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
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#283
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
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#282
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
- Chapters
#281
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
- Chapters
#280
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
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#279
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:
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#278
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
- Chapters

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