

Gay Men Going Deeper
Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood
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.
Episodes
Mentioned books

Jul 27, 2023 • 52min
Aging
Aging is an inevitable part of life, but we each have a unique relationship with it.
Some of us embrace it with open arms and don't buy into the idea of a "gay death" at a certain age.
Others struggle with aging and cling to our youth and relevance as each year passes.
In this episode of Gay Men Going Deeper, we’re talking about our own relationship to aging and what it means to “age well.”
Some of the questions we’ll be unpacking are:
What has been your relationship to aging?
What do you like and dislike about aging?
Where do your ideas/beliefs about aging come from?
How would you define “aging well” on your own terms?
Who is someone who you perceive to have “aged well”?
Watch this ep on YouTube
Gay Men Going Deeper: The Coaching Collection
Take the Attachment Style Quiz!
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take our "Healing Your Shame" course
Instagram
GayMenGoingDeeper.com
Support the Show

Jul 20, 2023 • 1h 1min
The Core Wound of Growing Up Gay
In this episode, Matt Landsiedel and Theo Bill have a heartfelt conversation about the struggles and joys of being a gay man. They discuss the core wounds of growing up gay, the impact this has on the gay community, and what we can do to start to heal these wounds.
We explore these topics in the episode:
The wounds gay men may experience in their development
Toxic Shame
Attachment trauma
Gay men and spirituality
What advantages do we have as gay men
Some things we can do to start healing our wounds
Sensitivity
The GoHigher Summit (hosted by Theo) is about elevating the rainbow community by finding the gift of growth and healing that resides within each of us. 30+ speakers shared their life stories, lessons and experiences – all to empower, elevate, and educate! It is a place to celebrate our diversity and unique culture, but also to learn how we can more easily expand our identity beyond our wounds.
Connect with Theo:
www.gohighersummit.com
Instagram
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take our "Healing Your Shame" course
Coaching Collection
Instagram
GayMenGoingDeeper.com
Support the Show

Jul 13, 2023 • 1h 22min
Age Discrimination Panel
It’s a sad reality that older gay men face stereotypes about their attractiveness, desirability, or relevance as they age.
Age discrimination, or ageism, can result in feeling isolated, undervalued, and even invisible.
In today’s episode, we are having a panel discussion about age discrimination with 3 of our community members.
We’ll cover topics such as:
Being judged by younger gay men
The discomfort around revealing your age around to others
Dating and aging
What advice they have for younger gay men
The importance of intergenerational relationships
How the gay community has changed or remained the same over the decades?
Listen to this episode to recognize and challenge ageism so that we can foster a more accepting and inclusive community.
Watch this episode on YouTube
Today's Panelists:
Steven Band
Jon Carl Lewis
Miguel Diaz
Today's Host: Michael DiIorio
Resources
Gay Men Going Deeper Coaching Collection
Building Better Relationships course
Healing Your Shame course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

Jul 6, 2023 • 53min
Friends with Benefits
Friends with benefits (FWB) is a type of relationship where you can enjoy the sexual benefits of a relationship without the expectation of long-term commitment.
Navigating the blurred lines between friendship and sexual intimacy is a complex and potentially risky endeavour.
In this episode, Michael DiIorio and Pepper of The Gay Good discuss the nuances of having Friends With Benefits. They’ll discuss topics such as:
The pros and cons of FWB
Why this is common with gay guys
When FWB works and when it doesn't
Dos and don'ts for a satisfying FWB relationship
Join in for this revealing discussion that will give you greater clarity and understanding of this common relationship structure.
Watch this episode on YouTube
Find us on Instagram:
Today's Guest: Pepper
Today's Host: Michael DiIorio
Related Episode: Being Kindr on Grindr
Resources
Gay Men Going Deeper Coaching Collection
Building Better Relationships course
Healing Your Shame course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

Jun 29, 2023 • 1h 9min
Unconscious Bias
Unconscious bias refers to the internal biases or attitudes that influence our interactions and behaviour towards others.
We all have these deeply ingrained biases that unfortunately can hinder our efforts to build a more diverse and inclusive community.
In today's episode, we are sharing our experience with Unconscious Bias in hopes that it will help contribute to embracing greater acceptance and belonging. Some of the questions we'll be unpacking:
What are some unconscious biases you currently have or have had in the past? Where did they come from?
How do you discern between preferences and prejudices?
How can we become aware of these biases and change them to be more inclusive?
By acknowledging unconscious bias and working to mitigate its impact, we can celebrate a more inclusive queer community that values the diverse experiences of all individuals.
Watch this episode on YouTube
Your Hosts
Michael DiIorio
Matt Landsiedel
Reno Johnston
Resources
Gay Men Going Deeper Coaching Collection
Building Better Relationships course
Healing Your Shame course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

Jun 22, 2023 • 1h 6min
Creating Authentic Connection
In this episode, Matt Landsiedel and Jamaal Wesley talk about authentic connection and the importance of having relationships in our lives where we can be completely ourselves. They share their own personal challenges with being authentic and how they have overcome these challenges. Come spend an hour learning how to bring your most authentic self into connection and reap the reward of being seen, understood and getting your needs met.
The questions we explored in this episode are:
What does authentic connection mean to you?
In what ways do you hold yourself back from belonging and connecting?
What does it feel like for you when you have authentic connection?
What can people do to have more authentic connection in their lives?
Connect with Jamaal:
www.myauthenticbook.com
Instagram
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take our "Healing Your Shame" course
Coaching Collection
Instagram
GayMenGoingDeeper.com
Support the Show

Jun 15, 2023 • 45min
Acceptance and Belonging
One of the goals of the Gay Men’s Brotherhood and this podcast is to help foster a deeper sense of community and connection for queer people all over the world.
But how do you learn to belong to a community that does not accept you as you are? This is the crux of today’s episode on Acceptance and Belonging.
We’re answering some tough questions such as:
What do you think is responsible for the lack of acceptance and belonging within the gay community?
What parts of yourself do you struggle to accept?
How can we begin to cultivate more acceptance and belonging within ourselves and the gay community?
Join us for this important episode about what it means to take up your fair share of space as a queer person in the queer community.
Watch this episode on YouTube
Your Hosts
Michael DiIorio
Matt Landsiedel
Reno Johnston
Resources
Gay Men Going Deeper Coaching Collection
Building Better Relationships course
Healing Your Shame course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

Jun 8, 2023 • 41min
Being a Dad
Being a dad can be one of the most rewarding experiences of a man’s life. Historically, gay men have not had adequate opportunities to be parents, but the tide is turning.
In this episode, Joseph Tito of The Dad Diaries stops by to talk to Michael about his journey from surrogacy to fatherhood, including:
The decision to be a parent
The challenges and rewards of being a parent
Dealing with homophobia
Advice for anyone considering parenthood
Whether you’re a dad yourself or have ever considered what it’s like to be one, this episode is for you.
Today's Guest: Joseph Tito of The Dad Diaries
The Dad Diaries
YouTube Channel
Instagram
Your Host
Michael DiIorio
Instagram
Resources
Gay Men Going Deeper Coaching Collection
Healing Your Shame course
Building Better Relationships course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

Jun 1, 2023 • 52min
Celebrating Diversity
Pride is celebration of the progress we've made as a community and a reminder that there is still much work to do. Unfortunately, many people don't feel like part of the community- and we want to help change that.
In today’s episode, we’re not just celebrating our queerness, but also the diverse range of people, experiences, and interests our community has to offer.
In this episode, we’ll be talking about:
How we have felt included in the gay community
How we have felt excluded
How we can create space for more diversity
How we can learn to belong
Join us for this episode that kicks off Pride month by celebrating ALL of the beautiful flavours of the queer rainbow.
Watch this episode on YouTube
Your Hosts
Michael DiIorio
Matt Landsiedel
Reno Johnston
Resources
Gay Men Going Deeper Coaching Collection
Building Better Relationships course
Healing Your Shame course
Take the Attachment Style Quiz!
Connect With Us
Join the Facebook community and monthly Group Zoom call
You can also follow us on Instagram and TikTok
Support the Show

May 25, 2023 • 1h 17min
Heterophobia
In this episode, Matt Landsiedel and Andre-Lee Wills talk about their experiences with heterophobia. They share what it was like growing up gay in a heteronormative world and how this created fear and anger towards heterosexual people. They also unpack the relationship between internalized homophobia and heterophobia and how taking responsibility for ourselves in new ways can help us overcome these fears.
The questions we explored in this episode are:
What was life like for you as a young gay boy?
When did you first realize that it was not acceptable to be gay? How did you cope with that?
In what ways did you/do you fear heterosexual people?
How can we overcome heterophobia?
Connect with Andre:
www.raisingvibrationscoaching.com
Linkedin
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take our "Healing Your Shame" course
Coaching Collection
Instagram
GayMenGoingDeeper.com
Support the Show


