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

    MAR 19 • EARLY ACCESS EARLY ACCESS

    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.

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

    1D AGO

    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
  3. Is Romance Dead in Gay Culture?

    MAR 5

    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
  4. Sexual Authenticity: Owning Your Desires

    FEB 26

    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
  5. The Body Count Dilemma: Why Gay Men Can’t Win

    FEB 19

    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
  6. Why So Many “Confident” Guys Are Secretly Insecure

    FEB 12

    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, desirability, or status is inherently fragile How childhood experiences and early coping strategies shape what confidence feels safe to express The difference between looking confident and being confident Why real confidence isn’t the absence of insecurity and why it naturally shifts over time This episode isn’t about fixing yourself or learning how to project confidence. It’s about understanding why the version you were taught to chase often feels exhausting, and what a quieter, more grounded confidence actually looks like in real life. 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 fr... Chapters (00:00:05) - Gays Go Deep: Why So Many Confident Gay Men Are(00:00:59) - How Confidence For Gay Men Is Decoded(00:04:32) - What Are The Traits That Get Mistaken for Confidence in(00:09:03) - The Gay Gay Male Hypothesis(00:10:39) - Gay Men Reveal How Much Confidence They Have(00:15:52) - The Need for Codependence(00:16:48) - What Makes a Confident Person?(00:21:58) - Is Your Confidence Dependent on Social Media?(00:23:11) - The Need for Self-Confidence(00:25:15) - Want to Attend a Connection Circle? Here!(00:26:10) - What Does Real Confidence Look Like In Real Life?(00:29:16) - What Does Real Confidence Look Like In Real Life?(00:33:28) - Is There A Difference Between Confidence And Heart-centered Confidence(00:35:59) - What does real confidence look like in real life?(00:36:24) - How to Handle Failure and Defeat(00:38:01) - Who Is The Most Confident Person That You Know?(00:41:55) - What Is It That Gay People Get From Being Confident?(00:47:03) - How to Build a Confidence(00:48:20) - Thank You!!

    49 min
  7. The Slow Build in Romantic Relationships

    FEB 5

    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 killing the spark… it’s about letting something real have a chance to form. If you’ve ever confused intensity for intimacy, this one’s for you. 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) - Gaiman Going Deeper: Slow Build In Relationships(00:00:39) - What is the Slow Build?(00:02:29) - How to Control the Pace of a Relationship(00:02:50) - Falling In Love Too Fast(00:05:57) - How To Manage Your Relationships(00:07:43) - Why Do We Do This?(00:11:06) - What Is A Healthy Pace For A Romantic Relationship?(00:14:13) - What Happens to People Who Go Too Fast?(00:15:13) - What is the Healthy Pace for a Romantic Relationship?(00:17:01) - "We're Going Too Fast For My Own Natural System"(00:19:23) - Knowledge Is Key to Secure Relationships(00:23:01) - How To Slow Down Your Love Life(00:25:02) - How To Control the Pace of Your Relationship(00:29:48) - How To Manage Your Attachment Style(00:30:56) - Podcast

    32 min
  8. Why Gay Men Are Talking About Heated Rivalry

    JAN 29

    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 especially potent right now. This isn’t a recap or a review. It’s a conversation about why some stories carry more weight than others, and how paying attention to your reaction can become an opportunity to understand yourself more deeply. 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 Men Going Deep: The Rivalry(00:00:47) - Heated Rival: Gay Men's Brotherhood Comments(00:01:49) - "The Disappointment"(00:02:55) - "Love Yourself"(00:07:04) - Bait & Switch: The Gay Men's Episode 3(00:10:53) - Pushing the Gay Culture(00:12:53) - Coming Out: Gay People in the Closet(00:13:36) - Matt Cooke on Coming Out In The Hockey League(00:17:49) - The Gay Love Story(00:21:06) - Neil Gaiman: The Book Review, Part 2

    23 min
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4.5
out of 5
372 Ratings

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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