

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

Jan 5, 2023 • 1h 28min
Healing From Sexual Trauma
In this episode, Matt Landsiedel and Tirrell Cherry talk intimately about healing sexual trauma. They share their own personal experiences with sexual abuse and how they have moved through their own trauma healing journeys. If you have experienced sexual trauma, you are not alone. This episode was created with the intention to normalize having these difficult conversations that can lead to deep connection, authenticity and healing.
Connect with Tirrell:
Website link: https://tirrellcherry.life
Instagram: @tirrellcherry
TikTok: https://vm.tiktok.com/TTPdMKxrbN/
Today's episode is sponsored by The Silva Ultramind System
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
Instagram
GayMenGoingDeeper.com
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Dec 29, 2022 • 1h 11min
Making Friends
Research has shown that quality friendships are fundamental to the mental and emotional well-being of 2SLGBTQ+ individuals.
A close-knit circle of friends can help us feel less alone, affirm our identity, and alleviate the stressors that come with being part of a stigmatized minority group.
But making friends can be challenging for many reasons.
In this episode, we're exploring the topic of making friends, and answering these questions:
What is the hardest part about making new friendships and how do you deal with it?
How can you become more “likable” to others and still honour your individuality?
What steps can you take to expand your social network?
Whether you want to make more friends or improve the friendships you already have, this episode will give you plenty of tips and insights that will help you improve your social circle.
Today's episode is sponsored by The Silva Ultramind System
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
Patreon

Dec 22, 2022 • 42min
Conflict Transformation
The holiday season can be a triggering one for a lot of people, especially those of us from the LGBTQ+ community.
In today's episode, host Calan Breckon speaks with guest Jeremy Long about how we can navigate conflict during this holiday season. Together they share their personal tips and tricks for those difficult interactions in hopes that it can make your holiday season a little more jolly.
Jeremy Long is the founder of the Conscious Queer Community where he leads Queer Men's groups. He’s also the owner of Enhance Leadership where he coaches about Leadership and Relationship Systems. Jeremy’s personal struggle with self-esteem and acceptance of his sexuality inspired him to support other queer men on their journeys. He now applies his experience in facilitation, emotional intelligence, and relationship systems to support queer and emerging leaders and teams who are ready to reach the next level in their development.
Jeremy on IG
The Conscious Queer Community IG
In this episode, we’re exploring conflict transformation and ways you can go about navigating the holiday season with family and friends.
We’ll be answering questions like:
How can people best navigate conflict during the holidays?
Why is it so hard to admit when we’re wrong? and why must we be willing to admit it if we are?
What are some tips and tools you use to navigate conflict when it comes up for you?
Join us to get a few tips and ideas on how you can survive this holiday season.
Today's episode is sponsored by Manscaped: Get 20% OFF on all items + Free Shipping with promo code GMGD at MANSCAPED.com!
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
Instagram
GayMenGoingDeeper.com
Patreon

Dec 15, 2022 • 49min
Lonely vs Being Alone
Being alone does not necessarily mean that you’re feeling lonely. Some people quite enjoy the experience of solitude and prefer it over being in large groups. But over time, does that disconnection lead to chronic loneliness?
In this episode, we’re exploring the difference between being alone and the feeling of loneliness. We’ll cover topics such as:
What’s the difference between loneliness and being alone?
What roles does introversion or extroversion play in feeling lonely?
How do you know when you’ve had too much alone time?
How do you come back to connection if the feelings of loneliness start to creep up?
Join us to get a deeper understanding of how your introversion or extroversion can impact your experience of loneliness.
Today's episode is sponsored by The Silva Ultramind System
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
Instagram
GayMenGoingDeeper.com
Patreon

Dec 8, 2022 • 1h 5min
Bathhouses and Cruising
Long before the days of Grindr and the internet, the gay scene was largely underground. Gay and bi men had to find creative ways to connect in discreet, yet relatively safe spaces.
For many, the locals baths - or bathhouses- were a sanctuary where you could be yourself and meet other guys who were interested in both sexual and friendly connection.
Meanwhile, cruising spots were known public spaces where men met for casual encounters.
Yet for decades, the baths were routinely raided and became a battleground for the fight for queer rights and the gay liberation movement.
In today’s episode of #GayMenGoingDeeper, Michael is talking with long-time writer, activist, and educator Tim McCaskell about bathhouses and cruising. Together they’ll share personal stories while exploring topics such as:
What really goes on in a bathhouse?
Why are they important to our history and culture?
Are they still relevant today?
What are the risks?
Tips for making the most of your visit
Whether you enjoy the bathhouse scene or not, this episode will shed light on the sociological and historical significance of these queer spaces from the perspective of two men of two different generations.
Today's Guest
Tim McCaskell is a long-time writer, activist and educator. In addition to being a collective member of The Body Politic from 1974 to 1986, he was a leader in the fight back against police raids on the gay baths in the 80s. He was also a member of AIDS ACTION NOW! where he fought for funding for AIDS treatment and medication. He has published two books: "Queer Progress" and "Race to Equity".
Today's Host
Michael DiIorio is a certified life and wellness coach specializing in self-confidence, sexuality, and relationships. You can find Michael at www.wellismo.com and at in the Sexual Empowerment Group. You can also follow him on Instagram @wellismo_coach.
Read: 10 Tips for Making the Most of Your Bathhouse Experience
Today's episode is sponsored by The Silva Ultramind System
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
Instagram
GayMenGoingDeeper.com
Patreon

Dec 1, 2022 • 1h 17min
Dealing with Loneliness
Loneliness is extremely common among gay men of all ages and backgrounds. In fact, some mental health professionals refer to loneliness as an epidemic for our times.
In this episode, we are sharing our own struggles with loneliness and how we have dealt with it.
The questions we’re answering today are:
How has loneliness impacted your life?
What relational fears do you have when it comes to connection? How do you deal with these fears?
What have you done to deal with loneliness in your life?
By the end of this episode, our hope is that you will feel less lonely and have some strategies for the next time this feeling shows up for you.
Today's episode is sponsored by The Silva Ultramind System
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
Instagram
GayMenGoingDeeper.com
Patreon

Nov 24, 2022 • 1h 2min
Leadership in the Gay Community
In this episode, Matt Landsiedel interviews Peter DeWitt from Gaywellness.com and they explore the topic of leadership in the gay community. Both Matt and Peter have been in leadership positions within the gay community over the last several years and they wanted to share what their experience has been like and how we can all be a leader in our own right. Come join us to learn what makes a great leader and how you can step into your power through leadership.
These are the questions that were explored in today’s episode:
What does leadership mean to you?
What makes a good leader?
What are the needs you see in the gay/queer community?
How can we develop more culture of connection in the gay/queer community?
What can people focus on to become great leaders in gay/queer spaces?
Connect with Peter:
Website link: www.gaywellness.com
Instagram: @gay.wellness
Today's episode is sponsored by Manscaped: Get 20% OFF on all items + Free Shipping with promo code GMGD at MANSCAPED.com!
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Instagram
GayMenGoingDeeper.com
Patreon

Nov 17, 2022 • 1h 4min
Having Difficult Conversations
A difficult conversation is often the one thing standing in the way between you and greater connection. Many of us have a hard time with these conversations because we don't have the tools to navigate all of the emotions that arise when we feel vulnerable.
In this episode, we're discussing how to have these prickly conversations
Join us as we discuss how to navigate a conversation when you need to talk about topics charged with negative emotions.
Today's episode is sponsored by The Silva Ultramind System
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
Instagram
GayMenGoingDeeper.com
Patreon

Nov 10, 2022 • 55min
Intersectionality & Mental Health
In this episode, host Calan Breckon unpacks some of the questions around intersectionality with guest Owin Pierson and the work he does as a mental health and Asian American Pacific Islander advocate.
Intersectionality is the acknowledgement that everyone has their own unique experiences of discrimination and oppression and we must consider everything and anything that can marginalise people ranging from gender, race, class, sexual orientation, physical ability, etc.
Today's episode is sponsored by The Silva Ultramind System
Follow Owin: @owinpierson
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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GayMenGoingDeeper.com
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Nov 3, 2022 • 55min
Crying
Researchers have established that crying releases oxytocin and endogenous opioids, also known as endorphins. These feel-good chemicals help ease both physical and emotional pain.
There are 3 different types of tears that we cry:
Basal: The tear ducts constantly secrete basal tears, which are a protein-rich antibacterial liquid that help to keep the eyes moist every time a person blinks.
Reflex: These are tears triggered by irritants such as wind, smoke, or onions. They are released to flush out these irritants and protect the eye.
Emotional: Humans shed tears in response to a range of emotions. These tears contain a higher level of stress hormones than other types of tears.
In today's episode, we're talking all about crying and its multiple benefits.
Specifically, we'll be talking about...
What has your journey with crying been like?
What benefits have you experienced from crying?
Do you practice crying?
How can the people out there listening learn to cry in a supportive and healthy way?
How can we support others to cry more?
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
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GayMenGoingDeeper.com
Patreon
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