Gay Men Going Deeper

Hookups get a bad rap as shallow, transactional, or disconnected. But what if they could actually become a space for growth, awareness, and real connection?

In this episode, we’re advocating for shift from default, unconscious hookups  to something more intentional, honest, and grounded. We explore how hookup culture can either reinforce negative patterns or become a powerful mirror for your patterns, desires, boundaries, and capacity for intimacy.

We talk about:

Why hookups aren’t the problem—but how we show up in them can be

The difference between unconscious vs. intentional hookups

How to bring honesty, communication, and authenticity into casual sex

How our own hookups have evolved over time

Practical ways to make hookups more enjoyable, respectful, and connected—for everyone involved

This isn’t about judging hookup culture or pretending it should be something it’s not. It’s about raising the standard of how you show up—so even casual encounters can feel aligned, present, and real.

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) - How To Elevate Your Hookup Culture
(00:02:22) - The Pros and Cons of Hookup Culture
(00:05:50) - What are the cons of hookup culture?
(00:07:12) - How Gay Men View Their Hookups
(00:11:36) - No More Sex: We Need Love
(00:13:34) - What Makes A Hookup Good For You?
(00:17:38) - "Honesty Is What Makes A Hookup Good"
(00:21:15) - Demisexual Guy On Grindr
(00:25:31) - Demisexual People Talk About Their Sexualities
(00:26:00) - Michael On His Hookups...
(00:29:59) - Elevating Your Hookups
(00:31:16) - PODCAST: Please support the community

For many gay men, our relationship with our dad is one of the most defining- and least talked about. In this episode, we explore the nuances of our relationships with our fathers through three core questions:

How did your dad react when you came out?

How do you express your gayness around him today?

Does being gay impact the level of intimacy you have with your dad?

From there, we go deeper into family dynamics, cultural expectations, and the different expressions of love and acceptance between fathers and their gay sons. We get into physical affection between fathers and sons, how much access we give them into our lives, and the boundaries we set as adults.

We also explore how these early relationships can shape the kinds of men we’re attracted to… and the patterns we carry into dating and relationships.

This is a grounded, honest conversation about the often complex and layered relationship between fathers and sons. 

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) - Going Deeper: The Daddy Issue
(00:01:47) - Did Gay Men Need Daddies?
(00:03:20) - How Did My Dad React To My Coming Out?
(00:07:49) - How Did My Dad React To My Coming Out?
(00:10:18) - Reno On Not Bringing Up Gay Issues With His Father
(00:14:24) - When My Gay Friend Comes Out
(00:14:43) - How Did My Dad React To Coming Out?
(00:18:53) - Coming Out To My Dad
(00:20:52) - How Do You Describe Your Gayness To Your Dad?
(00:27:38) - How Do I Feel Representing My Gayness To My Dad?
(00:31:14) - How My Parents Accept My Gay Love Life
(00:33:37) - Do You Hold Back Your Gayness When You're Around Your Dad
(00:37:56) - Adam Levine on Father-Son Conferences
(00:42:40) - Does Being Gay Impact How You Experience Intimate Touch With Your Dad
(00:45:32) - Does Being Gay Impact How I Experience Intimate With My Dad?
(00:47:52) - Michael Jackson on His Dad's Love
(00:51:09) - We Love You, Dads

A lot of gay men take pride in being independent, self-sufficient and in control. But is there a shadow side? When the time comes to let someone in, ask for support, or even rely on others—it feels uncomfortable, exposing, even threatening.

In this episode, we explore the spectrum between dependence, co-dependence, independence, hyper-independence, and interdependence—and why so many gay men get stuck at the far end of doing life alone. We talk about: 

What hyper-independence actually is (and why it’s so common)

The fear of losing yourself, your freedom, or your identity

Why intimacy feels harder than being alone

How this shows up in dating, relationships, and asking for support

What it looks like to move toward interdependence (secure attachment) 

This isn’t about becoming dependent. It’s about learning how to find a happy middle ground where you can let someone in without losing yourself or pulling further away. 

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: How to Let People In
(00:01:14) - What is Dependency and Independence?
(00:03:34) - Guys Who Are Hyper Independent or Codependent
(00:04:54) - Cocodependent and Secure Attachment: How Do You Know
(00:08:04) - How to Grow Up With Someone (Gay Men)
(00:10:49) - Insecure Attachment and The Fear That
(00:13:38) - What Are Some Boundaries That You Have For Yourself?
(00:15:23) - What's the Hardest Part of Learning To Trust Again?
(00:17:06) - How Anxious Attachers Get Out Of Conflict
(00:18:45) - How To Start Moving Toward Interdependence
(00:20:21) - Can An Avoidant Attachment Style Overcorrect Into Becoming Cod
(00:24:59) - How to Cope With Anxious Partner
(00:27:54) - The Importance of Living With Your Partner
(00:30:44) - How To Overcome The Fear Of Disappointment During Relationships
(00:34:35) - Gay Men Talk About Being Independent

There’s something unique about friendships between gay and straight men. They often feel easy, natural, and unexpectedly intimate.

In this episode, we explore the unique reasons why gay and straight men are drawn towards each other. From male bonding and emotional intimacy to validation, and the freedom to drop the “rules” of being a man, these friendships often offer something both sides aren’t getting elsewhere.

We unpack:

Why gay men are drawn to straight men… and what they represent

Why straight men feel safe, open, and even curious around gay men

How masculinity is shifting in 2026… and where these friendships fit

What each side gives the other and how we balance each other out 

This isn’t about hookups or labels. It’s about what men are craving, and what that reveals about modern masculinity.

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) - Gaming Going Deeper
(00:00:59) - Gay Men On Straight Men's Friendship
(00:04:43) - Why Do Gay Men Are Attracted To Straight Men?
(00:06:55) - Gay Hockey Players Play With Straight Guys
(00:08:41) - Why Are You Attracted To Straight Male Friends?
(00:13:32) - Straight Men On The Gay Men's Brotherhood
(00:17:46) - Gay Men's Brotherhood Connection Circles
(00:18:28) - Why Are Straight Men Drawn To Gay Men?
(00:22:43) - Damon on Why Gay Men Are Drawn to Him
(00:23:50) - Straight Men Are Desperate For Sex
(00:26:45) - Broke Male Podcast: Permission To Be You
(00:31:41) - "It's Okay to Hug Your Gay Father"
(00:33:11) - Gay Men Going Deep
(00:33:48) - Gay Men Want More Sexual Closeness
(00:39:15) - Straight Men Talk About Gay Bars
(00:41:46) - Set Free Your Gay Men!
(00:43:12) - Going Deep: Gay Men's Brotherhood

There’s something unique about friendships between gay and straight men. They often feel easy, natural, and unexpectedly intimate.

In this episode, we explore the unique reasons why gay and straight men are drawn towards each other. From male bonding and emotional intimacy to validation, and the freedom to drop the “rules” of being a man, these friendships often offer something both sides aren’t getting elsewhere.

We unpack:

Why gay men are drawn to straight men… and what they represent

Why straight men feel safe, open, and even curious around gay men

How masculinity is shifting in 2026… and where these friendships fit

What each side gives the other and how we balance each other out 

This isn’t about hookups or labels. It’s about what men are craving, and what that reveals about modern masculinity.

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) - Gaming Going Deeper
(00:00:59) - Gay Men On Straight Men's Friendship
(00:04:43) - Why Do Gay Men Are Attracted To Straight Men?
(00:06:55) - Gay Hockey Players Play With Straight Guys
(00:08:41) - Why Are You Attracted To Straight Male Friends?
(00:13:32) - Straight Men On The Gay Men's Brotherhood
(00:17:46) - Gay Men's Brotherhood Connection Circles
(00:18:28) - Why Are Straight Men Drawn To Gay Men?
(00:22:43) - Damon on Why Gay Men Are Drawn to Him
(00:23:50) - Straight Men Are Desperate For Sex
(00:26:45) - Broke Male Podcast: Permission To Be You
(00:31:41) - "It's Okay to Hug Your Gay Father"
(00:33:11) - Gay Men Going Deep
(00:33:48) - Gay Men Want More Sexual Closeness
(00:39:15) - Straight Men Talk About Gay Bars
(00:41:46) - Set Free Your Gay Men!
(00:43:12) - Going Deep: Gay Men's Brotherhood