Gay Men Going Deeper

Growing up different can leave a lasting impact on how we see ourselves, our relationships, and our sense of belonging. Even years later, many gay men still carry the feeling of being on the outside looking in—surrounded by people, yet not truly known.

In this episode, we're exploring the roots of belonging, why so many gay men struggle with deep loneliness, and what it actually takes to find meaningful connection.

We get into:

The difference between fitting in and truly belonging

Why you can have friends and still feel profoundly lonely

How shame and abandonment wounds shape our relationships

The role authenticity plays in creating real connection

Why belonging isn't about everyone agreeing with you—and what it actually requires

Practical ways to cultivate a deeper sense of belonging in your life

If you've ever felt like you don't quite fit, this conversation is a reminder that belonging isn't about becoming someone else—it's about finding the courage to let yourself be known.

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 attachment style and get a free report.

Chapters

(00:00:00) - Gay Men Going Deep: How Did Growing Up Gay Affect My Sense
(00:04:52) - How Growing Gay Affected My Sense of Belonging Today
(00:10:57) - Gay Men Talking About Being Gay
(00:15:28) - Michael on Being Gay and Growing Up
(00:18:56) - How to Belong as a Child
(00:20:50) - The Shame of Being Gay
(00:24:31) - What It's Like To Be Gay
(00:28:32) - How Did Growing Up Gay Affect My Sense of Belonging?
(00:29:22) - What Does Belonging Mean to You?
(00:31:26) - You Talk About Belonging To Your Sexual Pleasure
(00:35:42) - The Importance of Belonging
(00:37:57) - What Does Belonging Mean To You? Part 2
(00:39:30) - How do you find belonging in your life?
(00:42:24) - Are Gay Spaces Necessary For Dating?
(00:46:36) - A Couple's Surprise
(00:47:28) - What Does Belonging Mean To You?
(00:48:57) - Michael On The Importance Of Self-
(00:51:25) - What's the space that you feel most comfortable being yourself in?
(00:52:36) - Gay Men's Brotherhood: The Coaching Collection

Apps are a huge part of modern gay life. We delete them, reinstall them, swear them off, go back on, and keep trying to figure out whether they’re helping us connect or quietly getting in the way.

In this episode, we’re talking about app seasonality: that on-again, off-again relationship many gay men have with the apps, and the skill of knowing when they’re serving you, when they’re draining you, when to use them…and when to lose them.

We’re getting into:

Why apps can be the right choice in one season and the wrong choice in another

How to know when it’s time for a break or hiatus

When getting back on the apps can actually be the healthy choice

The difference between using apps intentionally vs. compulsively

How the apps can reveal your patterns around rejection, desire, sex, dating, and self-worth

Whether you’re on the apps, off the apps, or currently “just checking who’s nearby,” this conversation will help you bring more honesty, agency, and self-trust to the way you use them.

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: Grindr On-Off-Again
(00:01:31) - Apps' On-Again, Off-Again Cycle
(00:02:14) - Matt on Why He Joined Grindr
(00:06:03) - Michael Jackson on 'Both'
(00:06:14) - On The Difference Between Grindr and Hinge
(00:08:28) - Gay Dating: Compulsivity vs Intentionality
(00:11:37) - Scruff's 'What's Behind the Paywall'
(00:13:10) - When It's Time To Take a Break From Grindr
(00:16:59) - Marriage on Grindr When You're Traveling
(00:19:23) - Gay Men on Dating Apps
(00:22:48) - Both Apps and No Apps
(00:23:17) - "No Response Is a Response" on Grindr, Hinge
(00:26:45) - When Do You Know You're Ready to Go Back On?
(00:28:15) - What Are You Looking To Experience With Your Gay Guy?
(00:32:16) - What is Your Ideal Pace of Connection?
(00:34:07) - Amino and Matt on Gay Men's Brotherhood

Why do the guys who are a little distant, a little edgy, and a little hard to get feel so magnetic? Is it actually attraction…or is a deeper pattern being activated?

In this episode, we unpack what’s going on underneath the pull toward “bad boys” and why it can feel so intense, compelling, and hard to walk away from.

We talk about:

What exactly is it about “bad boys” that makes them so attractive

What we’re really responding to beneath the surface 

Why intensity can feel like chemistry, but isn’t always compatibility

What “bad boys” do well that “nice guys” can learn from

How to take those traits into your own dating life—without the chaos

If you’ve ever found yourself drawn to someone who felt exciting but hard to reach, this episode will help you understand why—and what to do differently.

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 attachment style and get a free report.

Chapters

(00:00:00) - Why Bad Boys Feel So Good
(00:01:38) - Are Bad Boy Guys Hot?
(00:03:19) - What Are We Actually Attracting To Bad Boys?
(00:07:24) - Good Boy vs Bad Boy
(00:11:08) - Good Boy Or Bad Boy?
(00:15:05) - Queer as Folk on Michael
(00:16:00) - A Neil Gaiman's Brotherhood
(00:16:43) - What Can We Learn From Bad Boys?
(00:20:36) - Is Your Bad Boy Unafraid Of Getting Cancelled?
(00:22:00) - Do Bad Boys Get Attracted To Women?
(00:24:28) - I'm The Bad Boy
(00:27:39) - Good Boy vs. Bad Boy
(00:30:45) - Good Boy vs. Nice Guy
(00:32:13) - The Gay Man Going Deeper: Nice Guys

Intimacy sounds like something we all want, but being truly seen can feel terrifying.

In this episode, we talk about why fantasy often feels safer than reality, why vulnerability can feel exposing, and how the fear of rejection keeps many gay men hiding behind performance. 

We also get personal about our own struggles with being seen, how this shows up in dating. This episode is about the fear beneath the fantasy: the part of us that wants closeness, but panics when closeness asks us to be honest, visible, and emotionally available.

We talk about:

Why intimacy can feel unsafe even when we crave it

The fear of being fully seen, known, and rejected

Why fantasy feels easier than real connection

How to feel safer, more grounded, and more open to intimacy

A deep, honest conversation for gay men who want connection, but sometimes find themselves pulling away when it starts to get real.

Link: Matt’s Secure Attachment Handbook 

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: Why Intimacy Feels Safer
(00:02:16) - What Is Intimacy Really Like?
(00:06:15) - Married People Say They're Not Attracted To Perfect People
(00:09:17) - What Are You Afraid Of Being Proactively Rejected For?
(00:12:38) - Geminis Have A Fear Of Intimacy
(00:13:24) - What Am I Afraid Of In A Relationship?
(00:17:03) - When Did You Start Naked With Your Girlfriend?
(00:17:31) - How to Love Yourself (No Fear of Intimacy)
(00:22:15) - How to Develop Secure Attachment
(00:23:50) - "I Get Scared in Intimacy"
(00:26:51) - The Gay Men's Brotherhood

Seeking validation isn’t just about chasing likes. It’s the part of us that needs approval, wants to belong, and feel accepted. But does it come at a cost?

In this episode, we unpack the subtle ways validation-seeking still shows up in our everyday lives, especially as gay men who learned early to scan, adapt, perform, and manage how we’re perceived. We talk about the difference between healthy feedback and outsourcing your self-worth, and what it actually looks like to build self-trust in real life.

In this episode, we discuss:

What validation-seeking actually looks like

The difference between caring what people think and letting their opinion become a verdict on your worth

Why self-trust requires tolerating discomfort, disappointment, and disapproval

How we’re each still learning to come back to ourselves in more honest, grounded ways

Self-trust doesn’t mean you stop caring what people think- it means their reaction no longer gets to decide who you are.

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 attachment style and get a free report.

Chapters

(00:00:00) - Coming Home To Yourself
(00:01:56) - Why Do Gay Men Seek Validation?
(00:03:43) - What Does Validation Seeking Actually Look Like?
(00:05:51) - What Does It Look Like to Be Overcomfortable?
(00:07:20) - Michael Buble on Being Validated
(00:07:57) - Michael Says He Feels Good About Himself
(00:08:45) - Validation Seeking and How It Affects Your Life
(00:13:53) - How to Stop Seeking External Validation
(00:18:10) - What does validation seeking look like in your life?
(00:18:35) - Why Is Self-Trust So Difficult For Gay People?
(00:23:26) - "People Plead"
(00:27:58) - What Makes Self Trust So Difficult?
(00:31:43) - The Importance Of Identity
(00:33:28) - Self-Trust Coaching
(00:34:08) - Michael on Coming Home To Himself
(00:35:38) - What Would I Do If I Wasn't Trying To Be Like
(00:39:35) - Coming Home to Yourself
(00:43:20) - Getting Back Home to Yourself
(00:46:26) - Why I Don't Need To Explain My Time
(00:48:06) - Coming Back Home To Yourself