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Gay Men Going Deeper

Gay Men's Brotherhood
  • 4.5 (369)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective. Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time. This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between. Visit us at www.GayMenGoingDeeper.com Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN

  1. FEB 19 • EARLY ACCESS EARLY ACCESS

    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: https://learn.wellismo.com/courses/sexual-empowerment-101

    24 min

  2. FEB 12 • EARLY ACCESS EARLY ACCESS

    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.

    49 min

  3. 5D AGO

    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 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

  4. 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 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

  5. JAN 22

    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 love unintentionally, and how to restore hope without lowering your standards or abandoning yourself. In this episode, we explore: Where the belief “I’ll be single forever” comes from The most common blocks to love we see in gay men How shame quietly shapes dating and relationships The difference between protection and emotional availability How to let love in while staying grounded, discerning, and self-respecting If you want real connection but feel tired, guarded, or discouraged, this episode offers clarity, reassurance, and a grounded way forward. Listen now and go deeper. Today's Hosts: Matt Landsiedel Michael DiIorio: Take the 360 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) - Going Deeper(00:00:34) - Gaming Gay Men's Brotherhood(00:02:05) - Will I Be Single Forever?(00:04:42) - Lack of role models for gay couples(00:05:31) - Open Relationships(00:06:19) - I'll Be Single 'Forever'(00:12:48) - This 67-Year-Old Gay Man Found Love For the First(00:14:47) - How To Get Out Of The Single Trap(00:15:38) - Common Shame Blocks in Gay Men's Love Life(00:22:07) - Gay Men Need To Heal Their Love Lives(00:28:27) - Healing Your Shame For Dating & Relationships(00:30:04) - How to Overcome the Blocks to Love(00:33:26) - "My Protector Parts Are Slowly Breaking My Own Heart"(00:36:53) - How to Love Yourself(00:42:17) - How To Heal Your Heart From Heartbreak(00:44:38) - Are You Ready for Your Relationship?(00:45:58) - Gay Men's Brotherhood Podcast

    49 min

  6. JAN 15

    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 critic, and how we deal with setbacks. In this episode, we cover: How confidence is built through action, discomfort, self-compassion How shame and the inner critic quietly undermine self-trust Whether “fake it till you make it” actually works… and where it falls apart Why taking action builds confidence (and how inaction erodes it) How self-compassion keeps confidence intact when things go wrong What to do when confidence wobbles after rejection, embarrassment, or insecurity If you’ve ever looked confident on the outside but felt shaky on the inside, this episode will help you understand why, and give you a clear, grounded path forward. Save this one. It’s the kind of episode you’ll get something new from every time you listen. 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 Qui... Chapters (00:00:05) - Gay Men Going Deeper: How to Build Confidence(00:01:05) - How to Build Unshakable Confidence(00:04:35) - What Actually Build Unshakable Confidence?(00:11:14) - How Do You Build Unshakable Self Confidence?(00:15:18) - How to Build Confidence(00:19:02) - Self-Compassion vs. Boastful(00:20:16) - What helps you build confidence? Join our Connection Circles(00:21:06) - Faking It Till It Actually Works(00:24:55) - "Faking It" Has It Work For You?(00:29:26) - Kinda Like Fake It Till You Make It(00:33:30) - You Should Be More Frumpy On The Podcast(00:33:48) - Gay Men: Unshakable Self Confidence(00:34:53) - How To Deal With Confirmations(00:39:15) - Reno on Being Confident(00:41:55) - How Do You Deal With Confidence(00:47:48) - Queens Talk About Self-Compassion(00:52:33) - Gayman's Brotherhood: Connection Circle

    54 min

  7. JAN 8

    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, and how low boundaries quietly reveal your level of self-worth. If you’ve ever said you want emotional maturity but keep entertaining sexy chaos, this episode is going to sting a little (in a good way). Some of the topics we cover in this episode are: A clear explanation of standards vs boundaries (with examples) Why our standards collapse the second a hot man gives you attention How boundaries are actually a self-worth and self-respect practice The “crumb diet” too many gay men settle for Join us for this honest, relatable, and painfully accurate episode that might be the reset your dating life has been waiting for. Today's Hosts: Michael DiIorio - Take the 360° Self-Review for Gay Men Matt Landsiedel Come to our Monthy Community Events  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's Dating: Standards and Boundaries(00:02:54) - What's The Difference Between Standards and Boundaries(00:04:52) - Gay Women Talk About Boundaries(00:09:14) - How To Give Care To Your Partner(00:12:34) - Why High Standards Don't Matter If Your Boundaries Are Low(00:16:22) - When do you find your boundaries collapsing fastest?(00:18:58) - What Makes You Feel Valid? Validation and Control(00:23:13) - What Poor Boundaries Look Like(00:27:08) - Standards vs Boundaries(00:27:23) - Gay Men's Brotherhood: Donor-funded Podcast

    28 min

  8. JAN 1

    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 back out there when you’re ready to mingle.  Some of the topics we cover in this episode are: • Getting back into the dating world • When your nervous system tries to hijack your dating life • Red flags and green flags • What we’re actually looking for in a man now (and how that has changed)  It’s cheeky, honest, and surprisingly insightful. If you’re single (or single-ish), you’ll feel right at home. Today's Hosts: Matt Landsiedel Michael DiIorio 360° Self-Review for the New Year 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) - Gamin Going Deeper: Being Single & Ready To Mingle(00:01:46) - What Is Single and Ready To Mingle?(00:02:27) - What Do You Love About Being Single?(00:05:02) - Mixed Messages on Dating and Singling(00:06:02) - What's Your Favorite Stage Of A Relationship? The Honeymoon Phase(00:10:22) - Matt on Conflicts In His Relationships(00:12:06) - Single People Talk About The Best Things About Being Single(00:16:13) - What I Need In A Good Relationship(00:17:50) - What's The Non-Negotiable Item In A Relationship?(00:20:43) - Gay Men's Brotherhood(00:21:22) - When Are You Ready to Mingle?(00:24:31) - Gay Men on Matching Apps(00:28:26) - "Does It Mean I Attract a Polyamorous Partner?"(00:31:49) - Are You Dating Gay People?(00:33:28) - Gaiman's Going Deep: Relationships and Dating(00:34:25) - What Would You Like To Experience The This Time Around?(00:39:17) - What You Need To Know About Chasing(00:43:10) - What I Want In A Relationship(00:43:52) - Matt on His Sexual Life(00:46:14) - I Should've Knew That My Best Friend Had Sex With Her(00:49:28) - "That's Off-limits" For Gay People(00:49:47) - Gay Men's Brotherhood: Connection Circle

    51 min
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4.5
out of 5
369 Ratings

About

Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective. Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time. This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between. Visit us at www.GayMenGoingDeeper.com Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN

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