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Gay Men Going Deeper

Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood
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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.

  1. Busy, Stimulated, and Disconnected: Gay Men & Escapism

    16 APR • EARLY ACCESS EARLY ACCESS

    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 difference between enjoyment and avoidance - How to recognize when it shifts from choice to compulsion - The hidden costs of always staying “on” - Why a full life can still feel empty Join us for an eye-opening episode about understanding the spectrum of escapism… and what it might be helping you avoid.

    31 min
  2. Let’s Play! When Did Life Stop Being Fun?

    1 HR AGO

    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 it can be one of the most powerful ways to reclaim joy, authenticity, and connection. Some of the things we cover in this conversation are: How shame and self-consciousness disconnect us from play The difference between authentic play and performative fun How western culture slowly erodes our inner child Why playfulness is connected to vulnerability and authenticity The role of play in intimacy, connection, and great sex How play can protect against burnout and bring us back to life Why joy and appreciation are skills worth intentionally developing If life has started to feel heavy, serious, or overly effortful, this episode is a reminder that play is not childish. It may be one of the most important ingredients in a meaningful life. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop seri... Chapters (00:00:05) - Let's Play(00:02:05) - Why Do Gay Men Stop Playing?(00:04:19) - What Did You Play For As A Child?(00:07:15) - When Did You Start Playing Solo?(00:13:20) - What Would You Get Out Of Play?(00:18:10) - How I Used To Play Both Girls And Boys(00:21:05) - Gay Men Talk About Childhood Play(00:23:32) - Have Your Relationships to Play Changed As You Get Older?(00:29:03) - The Importance of Play(00:31:01) - The Role of Play in Me(00:36:39) - What Does Playing Bring Up For You?(00:37:00) - What Are The Ways That You Play?(00:40:02) - The Importance of Travel(00:42:20) - Matt the Filmmaker on Play(00:47:33) - Michael's Secret To Fun And Play(00:50:39) - Play Will Save Your Life!

    54 min
  3. Masc for Masc: Preference or Internalized Homophobia?

    26 MAR

    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 of the debate: where is the line between genuine preference and internalized bias? In this episode we discuss: What people really mean when they say “masculine” Masculine and feminine archetypes  How conditioning around masculinity shapes attraction What internalized homophobia can look like in everyday life The difference between preference and hierarchy Where the line may exist between preference and prejudice Join us for a nuanced conversation about masculinity, attraction, and the cultural forces that shape how gay men see themselves and each other. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your... Chapters (00:00:00) - Gay Men Going Deep(00:01:00) - Gay Men's Issues With Masculinity(00:03:16) - What is Internalized Homophobia?(00:05:26) - Are You Attracted To Masculine Men?(00:10:26) - Tom Brokaw on Masculinity(00:11:40) - Masculinity and the Gay Community(00:14:31) - On Masculinity and Sexuality(00:17:39) - Gayman's Brotherhood Connection Circles(00:18:29) - Internalized Homophobia(00:23:06) - Gay Men's Brotherhood: Femininity and Gay Life(00:29:44) - Queens Talk About Their Gay Culture(00:32:15) - Outing My Own Phobia(00:36:08) - Gay Men Go Deep Coaching(00:36:50) - Where Is the Line Between Real Sexual Desire and Internalized Homophobia(00:39:58) - I Used To Be Attracted To Performative Masculinity(00:45:24) - Reno On Gay Men's Sexualities(00:49:08) - Blind Dating on Grindr(00:50:14) - A Very Long Goodbye

    51 min
  4. Flakey Gays: Why is Follow-Through So Hard?

    19 MAR

    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 friendships Why keeping your word is about more than just social plans What it really means to be a reliable man This isn’t just about the inconvenience of canceled plans. It’s about self-trust, stronger relationships, and the kind of man you’re practicing becoming. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report. Chapters (00:00:00) - Gay Men Going Deep: FlAKY Gays(00:03:24) - Gay Men Talk About Flakiness(00:07:37) - How to run a group(00:08:45) - Flaky Gay Men vs Avoidant Gay Men(00:13:03) - Being Candid With People(00:16:34) - Gay Men Talk About When They Don't Want To Connect With Me(00:20:13) - How to Get More Out of Your Friendships(00:21:10) - Lack of Follow Through(00:25:50) - Matt On His Love Life(00:29:04) - In the Elevator With Flakiness(00:30:25) - Gaming Going Deep

    31 min
  5. Is Being Gay Your Entire Identity? (The Hidden Cost of Over-Identification)

    12 MAR

    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 does it start to create division, hierarchy, or limitation? Is “gay” a culture — and if so, what does that even mean? Where’s the line between healthy pride and rigid attachment? We explore the benefits and the drawbacks of tying ourselves closely to any identity — and how over-identifying can sometimes shrink us rather than expand us. This conversation isn’t about minimizing being gay. It’s about integrating it. About moving from performance to embodiment. From label to lived experience. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report. Chapters (00:00:00) - Gay Men Going Deep: Over Identifying With Being Gay(00:00:50) - Being gay in the quest for enlightenment(00:03:29) - Michael Buble On Over Identifying With Being Gay(00:08:55) - On Loss of Identity(00:13:26) - Gay Men's Brotherhood: The Gay Community(00:18:03) - Coming Out Has Helped People(00:21:17) - How Over Identifying Can Be a Hindrance(00:23:05) - Is Pride Helpful or a hindrance for Gay Men?

    25 min
  6. Is Romance Dead in Gay Culture?

    5 MAR

    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 about: What romance really looks and feels like in dating  Why intensity is so often mistaken for intimacy What it means to actively bring romance into your dating life How love languages and attachment styles shape our romantic expression And what truly sweeps us off our feet This conversation is both a reality check and an ode to the intentional, courageous, thoughtful part of ourselves that still believes in romance. Today's Hosts: Michael DiIorio - Take the 360° Self-Review for Gay Men Matt Landsiedel Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report. Chapters (00:00:05) - Gay Men Going Deeper: The Romantic Gay Man(00:00:53) - How To Bring Romance Into Your Dating & Relationships(00:01:56) - How To Be Romantic In Gay Culture(00:03:47) - Michael on Romance in Gay Culture(00:07:34) - Gay Men Talk About Romance(00:12:44) - "I Don't Think Romance Is Romantic"(00:18:00) - How To Start A Romance: Setting the Tone(00:20:25) - The Gay Men's Brotherhood(00:21:09) - How Do You Bring Romance Into Dating?(00:25:48) - How Do I Bring Romance Into Dating?(00:29:03) - What's The Most Romantic Thing You've Ever Done For Someone?(00:33:40) - How To Get Out Of Your Attractor's Grip(00:34:51) - The Most Romantic Thing Someone's Done For Me(00:36:47) - What Do You Need To Know To Be Swept Off Your Feet(00:39:04) - Toronto Guy Problems(00:43:11) - Saved Off My Feet(00:47:10) - "If I'm a 10, I'll Keep Dating"(00:50:05) - Don't Be Afraid To Be Romantic With Your Gay Guy Friends

    52 min
  7. Sexual Authenticity: Owning Your Desires

    26 FEB

    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 over time. We talk about: What sexual authenticity actually means (and what it doesn’t) The subtle ways we learn to edit or override our desires How shame, fear, and social expectations shape what we allow ourselves to want How desire changes across seasons of life, relationships, and identity Why authenticity, not experience or performance, is the foundation of sexual empowerment This episode isn’t about labelling “right” or “wrong” desires. It’s about building an honest, compassionate relationship with yourself so your choices around sex feel grounded, intentional, and aligned. Join Michael's Sexual Empowerment 101 7-week men’s group starting in April. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report. Chapters (00:00:00) - Gay Men Going Deeper: Unpacking Sexual Authenticity(00:01:30) - What Does It Mean To Be Sexual Authentic?(00:04:32) - Kinky and Vanilla Sexual Shamers(00:06:02) - How to Exploit Your Sexual Desire in Your 40s(00:08:09) - Tom Brokoe on His Sexual Authenticity(00:09:08) - Demisexuals on Being More Sexual in Their 40s(00:12:28) - The Importance of Authenticity in Relationships(00:15:28) - Geminis Talk Sexually(00:18:04) - Gemini Talk About Vocal Play(00:19:06) - Gay Men Talk Sex(00:22:21) - Gay Mens Brotherhood: Sexual Authenticity

    24 min
  8. The Body Count Dilemma: Why Gay Men Can’t Win

    19 FEB

    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: Why body count became a stand-in for confidence and masculinity How sex gets turned into proof of worth instead of a personal choice The difference between sexual freedom and sexual pressure Why sex positivity isn’t about having more sex, or less sex What sexual empowerment actually looks like when shame isn’t running the show This episode isn’t about judging how much sex you’ve had. It’s about reclaiming choice, agency, and a healthier relationship to desire. Join the Sexual Empowerment 101 7-week men’s group Link Today's Hosts: Michael DiIorio - Take the 360° Self-Review for Gay Men Matt Landsiedel Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report. Chapters (00:00:00) - Gay Culture: Perpetual Sexual Hygiene(00:02:00) - Body Count in Our Culture(00:05:48) - Purity Culture and Performance Culture(00:06:42) - Who Are The People Shaming Gay People Having Sex?(00:08:29) - "Purity Culture" Is Full of Shame For Gay Men(00:09:52) - What Is the Story You Tell Yourself About People Who Have A Lot(00:10:18) - Demisexual Man on His Sexual Preoccupation(00:13:55) - Is Demisexual Love The Same As Sex?(00:16:09) - Straight Guys Think They're More Hot Than Girls(00:18:14) - Sexual Empowerment(00:21:57) - Sexual Empowerment Group and Connection Circle(00:23:31) - Oh My Goodness(00:23:40) - Gay Men's Brotherhood: Connections Circles

    24 min
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About

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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