Gay Men Going Deeper

At what point did life stop being fun?

As kids, play came naturally. We were curious, spontaneous, and fully present. But for many adults, especially gay men who grew up navigating shame and self-consciousness, play slowly disappears.

Responsibility takes over. Image matters more. We try to be cool. And somewhere along the way, joy gets replaced with pressure, performance, and productivity.

In this episode, we explore why so many adults lose their playful side and why reconnecting with it can be one of the most powerful ways to reclaim joy, authenticity, and connection.

Some of the things we cover in this conversation are:

How shame and self-consciousness disconnect us from play

The difference between authentic play and performative fun

How western culture slowly erodes our inner child

Why playfulness is connected to vulnerability and authenticity

The role of play in intimacy, connection, and great sex

How play can protect against burnout and bring us back to life

Why joy and appreciation are skills worth intentionally developing

If life has started to feel heavy, serious, or overly effortful, this episode is a reminder that play is not childish. It may be one of the most important ingredients in a meaningful life.

Today's Hosts:

Matt Landsiedel

Michael DiIorio - Take the 360° Self-Review for Gay Men

Reno Johnston

Support the Show - viewer and listener support helps us to continue making episodes

- CONNECT WITH US -

Watch podcast episodes on YouTube

Join the Gay Men's Brotherhood Facebook community

Get on our email list to get access to our monthly Zoom calls

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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 seri...

Chapters

(00:00:05) - Let's Play
(00:02:05) - Why Do Gay Men Stop Playing?
(00:04:19) - What Did You Play For As A Child?
(00:07:15) - When Did You Start Playing Solo?
(00:13:20) - What Would You Get Out Of Play?
(00:18:10) - How I Used To Play Both Girls And Boys
(00:21:05) - Gay Men Talk About Childhood Play
(00:23:32) - Have Your Relationships to Play Changed As You Get Older?
(00:29:03) - The Importance of Play
(00:31:01) - The Role of Play in Me
(00:36:39) - What Does Playing Bring Up For You?
(00:37:00) - What Are The Ways That You Play?
(00:40:02) - The Importance of Travel
(00:42:20) - Matt the Filmmaker on Play
(00:47:33) - Michael's Secret To Fun And Play
(00:50:39) - Play Will Save Your Life!

When a gay man says he’s attracted to masculine men, is that simply preference… or could internalized homophobia be part of the story?

In this episode, we unpack one of the most volatile conversations in the gay community. We explore what people actually mean when they say “masculine,” the masc and fem archetypes that shape gay culture, and how social conditioning around masculinity and femininity can influence attraction and identity.

Most importantly, we tackle the question at the center of the debate: where is the line between genuine preference and internalized bias?

In this episode we discuss:

What people really mean when they say “masculine”

Masculine and feminine archetypes 

How conditioning around masculinity shapes attraction

What internalized homophobia can look like in everyday life

The difference between preference and hierarchy

Where the line may exist between preference and prejudice

Join us for a nuanced conversation about masculinity, attraction, and the cultural forces that shape how gay men see themselves and each other.

Today's Hosts:

Matt Landsiedel

Michael DiIorio - Take the 360° Self-Review for Gay Men

Reno Johnston

Support the Show - viewer and listener support helps us to continue making episodes

- CONNECT WITH US -

Watch podcast episodes on YouTube

Join the Gay Men's Brotherhood Facebook community

Get on our email list to get access to our monthly Zoom calls

Follow us on Instagram | TikTok

Learn more about our community at GayMenGoingDeeper.com

- LEARN WITH US -

Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.

Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.

Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.

Take the Attachment Style Quiz to determine your...

Chapters

(00:00:00) - Gay Men Going Deep
(00:01:00) - Gay Men's Issues With Masculinity
(00:03:16) - What is Internalized Homophobia?
(00:05:26) - Are You Attracted To Masculine Men?
(00:10:26) - Tom Brokaw on Masculinity
(00:11:40) - Masculinity and the Gay Community
(00:14:31) - On Masculinity and Sexuality
(00:17:39) - Gayman's Brotherhood Connection Circles
(00:18:29) - Internalized Homophobia
(00:23:06) - Gay Men's Brotherhood: Femininity and Gay Life
(00:29:44) - Queens Talk About Their Gay Culture
(00:32:15) - Outing My Own Phobia
(00:36:08) - Gay Men Go Deep Coaching
(00:36:50) - Where Is the Line Between Real Sexual Desire and Internalized Homophobia
(00:39:58) - I Used To Be Attracted To Performative Masculinity
(00:45:24) - Reno On Gay Men's Sexualities
(00:49:08) - Blind Dating on Grindr
(00:50:14) - A Very Long Goodbye

The guy who constantly cancels plans, keeps things vague, or disappears when something better comes along — that’s flakiness: a pattern of not following through.

In a culture of endless options and shifting feelings, has unreliability quietly become normal? And what does that actually say about us?

In this off-the-cuff episode, we talk about:

What flakiness actually is — and what it isn’t

The difference between boundaries and excuses

Common avoidance patterns in dating and friendships

Why keeping your word is about more than just social plans

What it really means to be a reliable man

This isn’t just about the inconvenience of canceled plans. It’s about self-trust, stronger relationships, and the kind of man you’re practicing becoming.

Today's Hosts:

Matt Landsiedel

Michael DiIorio - Take the 360° Self-Review for Gay Men

Support the Show - viewer and listener support helps us to continue making episodes

- CONNECT WITH US -

Watch podcast episodes on YouTube

Join the Gay Men's Brotherhood Facebook community

Get on our email list to get access to our monthly Zoom calls

Follow us on Instagram | TikTok

Learn more about our community at GayMenGoingDeeper.com

- LEARN WITH US -

Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.

Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.

Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.

Take the Attachment Style Quiz to determine your attachment style and get a free report.

Chapters

(00:00:00) - Gay Men Going Deep: FlAKY Gays
(00:03:24) - Gay Men Talk About Flakiness
(00:07:37) - How to run a group
(00:08:45) - Flaky Gay Men vs Avoidant Gay Men
(00:13:03) - Being Candid With People
(00:16:34) - Gay Men Talk About When They Don't Want To Connect With Me
(00:20:13) - How to Get More Out of Your Friendships
(00:21:10) - Lack of Follow Through
(00:25:50) - Matt On His Love Life
(00:29:04) - In the Elevator With Flakiness
(00:30:25) - Gaming Going Deep

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