Gay Men Going Deeper

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

Feeling bad is not a flaw in the human experience. It’s an essential life skill for anyone who wants a life of love, growth, satisfaction, and intimacy— all of it requires the capacity to feel discomfort without running from it.

In this episode, Michael and Matt make the case for feeling bad on purpose: when to sit with an emotion, when to change your mindset, and why emotional avoidance often costs us more than the original pain.

We get into:

Why feeling bad is a skill, not a personal failure

The difference between allowing an emotion and reframing your thoughts

How men are often taught to avoid, repress, intellectualize, or act out emotions

The ways we numb and escape through food, alcohol, sex, porn, productivity, scrolling, and distraction

Why building emotional capacity makes you braver, more honest, and more willing to live a bigger life

The goal isn’t to be happy all the time — it’s to become someone who can feel bad without abandoning yourself or shrinking your future.

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) - Why Feeling Bad Is Good For You
(00:01:46) - Why Are People So Bad at Feeling Bad?
(00:06:06) - How to Win with Emotions
(00:08:13) - How to Love Yourself
(00:13:16) - How to Get Through Trauma
(00:16:52) - What Emotion Is The Hardest To Deal With?
(00:20:05) - How To Live A Fully Feeling Life
(00:20:54) - How to Deal With Feeling Bad
(00:23:48) - The ego takes over the body
(00:24:32) - Gay Men's Ways To Cope With Feeling Bad
(00:25:45) - How to Stop Feeling Bad
(00:29:31) - How to Love Yourself Through Fear
(00:30:38) - How to Handle Negative Emotions
(00:34:37) - People Cope With Crying
(00:35:29) - Gay Men's Brotherhood

A lot of gay men pride themselves on being “nice”— easygoing, agreeable, low-drama. But what if that’s exactly why you’re not getting what you want?

In this episode, we break down the difference between being kind and being “nice,” and how approval-seeking, conflict avoidance, and over-accommodating are quietly killing attraction, respect, and real connection. 

We talk about:

Why “nice” is often a strategy, not a personality

The hidden cost of being liked by everyone

How this shows up in dating and relationships

The difference between being chosen vs. being liked

How to shift from approval-seeking to self-respecting

If you’ve ever felt overlooked, under-appreciated, or stuck in the friend-zone, this one will hit.

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 Deeper: The Nice Guy Trap
(00:01:04) - Being Nice
(00:03:16) - What Does Being A Nice Guy Actually Mean To You?
(00:05:46) - Matt on Being A Nice Guy
(00:09:49) - Have You Ever Been The Nice Guy?
(00:13:30) - Is Your Friend Think You're A Nice Guy?
(00:17:16) - What Is Niceness In Your Relationships?
(00:20:09) - Gayman's Brotherhood: Connection Circles
(00:20:54) - Why Being a Nice Guy Backfires in Dating
(00:23:16) - Matt Says Being Honest In Dating Backfires
(00:28:19) - In the Elevator With Michael
(00:29:38) - Gay Men on Dating and Relationships
(00:30:19) - How to Shift From Being Nice to Being Chosen
(00:35:02) - How To Be With Yourself
(00:39:06) - Be Candid With Yourself
(00:42:15) - Michael Jackson on Not Being Like Everyone
(00:45:34) - Matt on Not Being the Nice Guy
(00:48:20) - Thank You!