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Gay Men Going Deeper
Gay Men Going Deeper
Author: Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood
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© 2020 Gay Men's Brotherhood
Description
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.
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.
281 Episodes
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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?
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
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
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
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!!
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
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
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° 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) - 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
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...
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
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
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
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 - 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
(00:00:05) - 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
Why does attraction fade… and what can we do about it? In this episode we get real about attraction in long-term relationships. The spark doesn’t always burn forever, and losing sexual interest doesn’t mean the relationship is doomed. We talk about why attraction naturally shifts over time and how couples can ignite intimacy.
We explore:
Why attraction fades in relationships
The 4 types of intimacy (and why they matter)
Sexless marriages and normalizing libido changes
What erodes desire over time
How to bring spark, novelty, and connection back
Join us for a real conversation on attraction, intimacy, and what keeps the spark alive over time.
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) - When Attraction Fades in Gay Relationships(00:04:24) - 4 Types of Intimate Relationship(00:10:11) - How To Keep The Fire In Your Relationships(00:15:06) - What Causes Attraction To Fizzle For You(00:18:01) - How to Keep the Sex Fire Alive in Your Marriage(00:21:21) - 3 Tips For Keeping Intimate Relationships Alive(00:23:47) - Gay Men's Brotherhood: Sparking Your Love Life
After unpacking our culture’s obsession with “perfect” bodies, this week we’re flipping the script. In this episode, we’re celebrating what’s actually hot: the things that don’t get enough love in the gay world. We’re talking dad bods, wrinkles, kindness, confidence, awkward charm, conversational skills, and all the real stuff that makes someone magnetic.
Some of the things we’re talking about:
How social media perpetuates social norms that don’t fit
The traits we find sexy that don’t get enough love
Stories of when we’ve fallen for people outside our type
The roles of dating apps in attraction and rejection
How our types have changed (and how they haven’t)
This is our love letter to all the guys out there who feel they aren’t sexy because they don’t fit the mold. It’s time to expand our definition of sexy and give some overdue appreciation where it’s due.
Today's Hosts:
Michael DiIorio - Take the 360° Self-Review for Gay Men
Matt Landsiedel
Reno Johnston
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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: What's Really Sexy?(00:01:15) - How To Survive A Culture of Body Perfection(00:03:42) - The Real Sexy, Unmarketed(00:04:42) - Celebrating What's Real(00:05:09) - What Is Something That You Think Is Sexy About Your Guy?(00:06:02) - 5 Things That Make A Guy Sexy(00:08:03) - What's The Sexiest Walk?(00:08:55) - Michael's Signature Walk(00:09:45) - Alexandra On Being Hot For Quirkies(00:12:44) - People Compare Their Feet To Hands(00:14:58) - What's The Non Physical Attraction Of Gay People?(00:18:37) - Dad Bods and Big Nose(00:21:23) - Oh, Lisps and Accents(00:21:58) - Connection Circle(00:22:58) - My Types Are Different(00:27:06) - I Should've Swiped On Grindr Instead Of Dating(00:31:10) - Are You My Type?(00:34:44) - Matt Reno And Chris Hemsworth On Being Unorthodox(00:37:34) - Michael Jackson On His Hotness(00:39:37) - Thank You!!!
From the gym to social media, gay men are constantly surrounded by images of the “ideal” body. But what does all this perfection chasing actually cost us?
In this episode, we explore how body perfection culture impacts gay men on a deeper level: from belonging and self-worth to intimacy and identity.
We open up about our own journeys with body image— how we’ve moved from obsession to acceptance, where it still sneaks in today, and what we’ve learned along the way.
You’ll hear us unpack:
Why body image matters more for gay men
How fitness and self-worth often get mixed up
The difference between caring for your body and obsessing over it
How to stop letting your reflection decide your mood
Practical ways to reclaim confidence and self-respect
If you’ve ever felt like a “perfect” body will earn you love, attention, or belonging, this one’s for you.
Today's Hosts:
Matt Landsiedel
Michael DiIorio - Join my weekly newsletter for deeper reflections and practical tools
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
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Get on our email list to get access to our monthly Zoom calls
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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 Deep: The Culture of Body Perfection(00:01:52) - How to Love Your Body (Without Perfection)(00:05:50) - Does the Culture of Body Perfection Impact You?(00:09:07) - The Help I Learned To Love My Body(00:13:40) - What Do You Think You Need To Look To Be Attractive?(00:16:08) - November 6: The Culture of Body Perfection(00:16:55) - Letting Go Of Body Perfection(00:22:08) - "Self-worth is not solely based on your body"(00:24:42) - Body Positivity(00:26:33) - What Have We Done To Mitigate Body Perfection Culture?(00:30:41) - What Have I Done To Prevent Body Perfection Pressure?(00:35:43) - Neil Gaiman on The Gay Brotherhood(00:36:53) - The Hard Work of Being Gay(00:37:30) - Gay People Go To the Gym(00:41:27) - Gay culture's need for belonging(00:43:13) - Gay Men's Brotherhood Podcast
In this episode, we dive into what radical honesty really means- not the brutally blunt “telling it like it is” version, but the deeper, more vulnerable kind that lets you actually be known.
We explore why being honest is both terrifying and liberating, the subtle ways we still avoid it, and how honesty differs from harsh truth-telling. We share our own struggles with showing up honestly in dating, friendships, and community, and why the outcome isn’t always pretty… but is always worth it.
If honesty is one of your personal values (or you want it to be) this episode will give you plenty to reflect on. And if you’re enjoying these more relaxed, conversational episodes, let us know. We’ve been loving creating them.
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
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Get on our email list to get access to our monthly Zoom calls
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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) - Game & Going Deeper: The Gaiman Brothers Podcast(00:00:26) - What is Radical HONOR?(00:04:35) - Being Candid With My Partner(00:06:25) - How To Talk About Jealousy In Relationships(00:10:04) - Radical honesty can be a beautiful tool to heal intimacy(00:14:36) - Radical Alignment: The Benefits of Real Love(00:20:06) - Radical Honesty and the Relationship(00:22:38) - What are some other things that you need to practice radical honesty in(00:27:51) - Slices With Matt Maher(00:28:20) - What's Hard for You to Share?
Today we’re diving into one of the most iconic (and hilarious) parts of gay culture: labels.
In this episode, we unpack why gay men are so obsessed with categories like “twink,” “daddy,” “masc,” “otter,” “guy next door,” and every micro-label in between… and how these identities shape the way we date, belong, and see ourselves.
We explore:
Why labels can feel empowering (and sometimes limiting)
How they create tribe, shorthand, and community
When they become boxes we get stuck in
How attraction, identity, and insecurity get wrapped into these roles
What happens when you “grow out” of a label or never fit one at all
It’s a fun, honest look at the ways we use labels to navigate gay life: where they help, where they fall short, and why they matter more than most of us want to admit.
If you enjoy these more conversational episodes, let us know… we’re trying something new.
Today's Hosts:
Matt Landsiedel
Michael DiIorio - Join my weekly newsletter for deeper reflections and practical tools
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: A Short Talk(00:01:02) - What Gay Labels Do You Use?(00:05:21) - Gay People Don't Like Labels(00:08:40) - In the Gay Community's Elite Communities(00:11:56) - Gay Men Let Go Of Their Identities(00:17:07) - The Negative Connotations of Labels(00:21:34) - Gay People Play With Their Identities(00:24:54) - Spontaneous Conversation With The Gaiman's Brotherhood
Today we’re talking about The Slow Fade: that slow, quiet drifting apart where the messages get shorter, the replies slower, and the energy shifts until one day…it’s just silence.
In this episode, we’re unpacking:
Why we quietly quit people instead of having real conversations
What’s actually happening beneath the surface for both sides — the Fader and the Fadee
Who deserves an explanation and who doesn’t
What can we do instead of fading away
If you’ve ever been on either side of The Slow Fade, this conversation will help you see what’s really going on underneath, and how to move through it with more clarity, courage, and integrity.
Today's Hosts:
Michael DiIorio - Join my weekly newsletter for deeper reflections and practical tools
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 Slow Fade(00:01:12) - Why We're Always Ghosting(00:01:53) - What Is The Slow Fade?(00:03:17) - How To Deal With An Uncomfortable Relationship(00:08:02) - What To Do About A faded Love Letter(00:10:20) - What's The Slow Fade?(00:14:06) - Gay Men Talk About Dating Apps(00:15:05) - Matt on Slow Fade(00:19:17) - In the Elevator With Real People(00:20:38) - A Sense of Community With Neil Gaiman(00:21:42) - The Fader and the Fade(00:22:42) - The Signs That Someone Is Starting To Distance From You(00:26:51) - When You're Not Enough, Do You Lash Out?(00:28:44) - Fader: Being Honest With My Friends(00:30:34) - The Slow Fade(00:34:52) - Reno on His Heartbreak(00:36:16) - Slow Fling(00:37:44) - The Gay Men's Brotherhood(00:41:30) - How to Deal With An Avoidant Partner(00:45:32) - You Can't Force People To Tell You Things(00:46:52) - Gaiman's Brotherhood
What we want you to gain from this episode is the importance of non-sexualized, safe, and brave spaces for gay men to heal and grow together. By the end of this episode, you will be able to identify what a nest is, how you could benefit from one, and where to find or create one if you are interested in nesting.
The concepts and questions we explore in this episode are:
What is “nesting” and why is it important for gay men?
What moments in our lives require the need for nesting?
How do we know when we’re “nested” — or when we’re not?
What makes a nest truly safe?
How do you tend and protect a nest once it’s formed?
What could gay culture look like if nesting became normal?
What’s one small way you can begin nesting today?
Today's Guest: Nigel Pedlingham
Gay Men's Retreat
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Today's Host: Matt Landsiedel
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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
Chapters
(00:00:05) - Gaiman Going Deeper: The Need for Gay Sexual Spaces(00:01:44) - The Nested Experience(00:07:27) - The Neve of Gay Men(00:10:48) - Are Gay Nests Sexual?(00:17:38) - The Need for Self-Compassion(00:23:32) - Exploring the Body in Gay Groups(00:26:36) - Why are these spaces so important for gay and queer men?(00:29:15) - How to help lone wolves(00:31:51) - What Makes You Feel Like You're a Real Person?(00:33:58) - What Makes Gay Men Feel Like They Deserve Their Love?(00:39:06) - How to Connect with Others(00:40:53) - Finding a nest(00:44:34) - An offering to the sacred men(00:46:52) - Let's Nest
We all say we want love… but are we actually open to receiving it?
In this episode, we’re going deeper into what it really means to open your heart. From the subtle subconscious programming that keeps love at arm’s length to the sneaky ways we self-sabotage, we’re unpacking the hidden barriers that make intimacy feel unsafe (even when we crave it most).
You’ll learn:
Why receiving love can feel harder than giving it
How old conditioning teaches us to block love without realizing it
The difference between performing for love and allowing it in
Practical ways to build safety, self-trust, and openness in all forms of love—romantic, platonic, and self
If you find yourself pushing love away, deflecting compliments, or find yourself stuck in patterns that keep intimacy just out of reach—this one’s for you.
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
(00:00:02) - Gaiman Going Deeper: How to Open Your Heart to Love(00:02:43) - The Secret to Feeling Love(00:05:36) - When I Can't Receive Love(00:10:25) - Navy Green and The Beauty of Technology(00:10:41) - Why It's So Hard To Receive Love(00:15:35) - What I'm Most Afraid Of(00:18:18) - In What Ways Has It Been Difficult to Receive Love From(00:19:33) - What Does It Look Like To Receive Love?(00:23:04) - Letting Yourself Receive Love(00:24:07) - Receiving Love From Others(00:29:03) - How to Learn How to Receive Love(00:30:35) - 5 Tips for Open Your Heart to Love(00:34:51) - How to Open Your Heart to Love(00:41:03) - Gay Men Talking About Love(00:44:04) - Gayman's Brotherhood: Unpacking Love
Some of us don’t fall in love with people, we fall in love with an idea of them. The story, the potential, the fantasy of the perfect boyfriend who finally makes everything click. But that idealized version of love often keeps us chasing what looks right instead of what feels real.
In this episode, Michael DiIorio and therapist, Michael Pezzullo, explore how fantasy, perfectionism, and external validation shape the way we love- and why chasing the ideal often keeps us from the real thing.
We’ll unpack:
What it looks like to fall in love with potential - and why we do it
How to tell the difference between healthy excitement and mental storytelling
How seeking the “perfect” partner keeps us single or dissatisfied
How to stop chasing the ideal and let love be more organic and human
Whether letting go of the fantasy means “settling for less”
If you’ve ever been in love with potential or the picture-perfect relationship, this conversation will help you come back to reality…where real connection actually happens.
Today's Guest: Michael Pezzullo
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Today's Host: Michael DiIorio
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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.
Ta...
Chapters
(00:00:00) - Gay Men Going Deeper: Falling In Love With The Fantasy(00:01:47) - What Is Love And The Perfect Relationship?(00:04:03) - Falling In Love With Potential(00:05:02) - Have You Ever Fall In Love With Potential?(00:07:47) - How To Tell When You're Falling In Love With a Potential Partner(00:10:15) - What I Learned From Falling In Love With Fantasy(00:14:17) - What I Wish I Knew About Falling For My Guy(00:17:11) - Chasing A Single Guy(00:19:25) - Gay Men's Brotherhood Connection Circles(00:20:31) - The Perfect Boyfriend Myth(00:22:19) - What Are Some Standards That Gay People Have For Their Love Relationships(00:27:09) - "And It's Proof To Who?"(00:27:18) - Michael on Dating and Being Single(00:32:08) - Michael: Don't Have A List Of Qualities For Dating(00:34:41) - What Advice Would You Give Someone Who's Chasing Perfection(00:40:05) - "The More Perfect My Relationship, the More Lovable I Am(00:43:06) - How to Connect with People(00:43:16) - Gaming Going Deeper: Falling In Love With The Fantasy




























this was deep i think this is my problem also ive been so hurt for so long that now i dont trust myself so i hide n stay hidden from life
Amazing episode guys! I learned so much about myself. Thank you! ❤️🏳️🌈❤️ Mark