

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

Aug 18, 2022 • 1h 17min
Pretty Privilege
In this episode, Matt Landsiedel and Andre-Lee Wills unpack the hot topic of pretty privilege.
Pretty privilege works on the principle that people who are deemed more attractive—based on accepted societal beauty standards—have an upper hand in the world and are afforded many opportunities that less “attractive” people don't have. Yet, it's not often that people are willing to admit it—or even talk about it—especially if they’re on the receiving end of its benefits.
Here is what Matt and Andre-Lee explored in this episode:
What is pretty privilege?What is your personal experience with pretty privilege?Why is this topic important for gay men to discuss?What does it mean to be attractive?Why does our culture place so much emphasis on attractiveness?How does pretty privilege relate to ageism, racism or sexism?How can we start to deconstruct the system that is conditioning us to be so limited in our definition of attractive?
Connect with Andre-Lee:
Andre-Lee Wills is an Empowerment Coach. He uses his unique gifts and talents to offer guidance, support, and assistance to others in being an expression of their truest and highest self. He is adept in career coaching, life and relationship coaching, communication, team building, and organizational management.
mrandreleewills@gmail.com
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Join the private Facebook community
Take the "Healing Your Shame" course
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Aug 11, 2022 • 1h 5min
Open and Closed Relationships (Vol. 2)
As more people are choosing to explore non-monogamous relationships, the discussion about open and closed relationships can be divisive and unhelpful.
In today's episode, we are having an open conversation about open and closed relationships that will enrich your understanding of the many different types of relationships out there and help you figure out what's right for you. We will cover questions such as:
What is the ideal relationship structure for you?How do you handle jealousy in your relationships?Which of your needs do you expect your primary partner to meet and which needs can be met outside the relationship?What tips will help someone decide which relationship structure works for them?
Listen to this episode to get some fresh and insightful perspectives on this hot topic.
Watch this ep on YouTube
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Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Aug 4, 2022 • 36min
Community Inclusion
Recognizing and understanding privilege can be a hard pill to swallow for some. It means admitting you’re not perfect and possibly “looking bad,” which we were all taught growing up not to do.
In today’s episode, host Calan Breckon unpacks some of the hard questions around community inclusion with guest Raymond Jordan Johnson-Brown and the work they do as an indigenous wellness leader. Raymond, who uses they/them pronouns, is passionate about creating connections for marginalized groups and having courageous conversations around these sometimes hard topics.
Together they explore questions like...
How do you think people are “missing the mark” when it comes to inclusivity for racialized folks?How has your lived experience inspired your work?What is intersectionality?What are some of the ways the queer community has contributed/participated in systems of harm?What could a path forward look like to create an equitable world?
By the end of this episode, you’ll have a better understanding of how you can be more courageous about getting uncomfortable and having those sometimes difficult conversations around inclusivity.
Follow Raymond on Instagram: @TheOnlyRJJB
Foundry BC
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Take the Attachment Style Quiz!
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Jul 28, 2022 • 1h 4min
Sexual Empowerment
Sex is a natural part of the human experience yet many people sense a lot of shame and insecurity around the topic.
In this episode of Gay Men Going Deeper, we want to help you become more sexually empowered. We will be discussing things like…
What does sexual empowerment mean to you?What makes you feel sexually empowered?What makes you feel sexually disempowered?What is one tip you can share with the audience to feel more sexually empowered?
By the end of this episode, you’ll be able to improve your own unique relationship with sex and sexuality so that you can enjoy the sex you want on your terms.
Watch this ep on YouTube
VOTE FOR US FOR THE PODCAST AWARDS!
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Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Jul 21, 2022 • 54min
Shiny Object Syndrome
Shiny Object Syndrome (SOS) is the tendency chase after things that are new and exciting, keeping you in a state of perpetually looking for “the next best thing”.
In this episode of Gay Men Going Deeper, Michael invites psychiatrist Dr. Hector Rodriguez to discuss how Shiny Object Syndrome affects gay men in life and in relationships. They’ll cover topics such as:
SOS in dating apps
The link between perfectionism and SOS
The role of social media
The fear of genuine intimacy
The impact on mental health
How you can overcome SOS
By the end of this episode, you’ll be able to recognize where SOS is showing up in your life and how you can overcome it.
Connect with Dr. Hector
Website: https://www.doctorhector.com/
Instagram: https://www.instagram.com/drhector511/
Today's Host: Michael DiIorio
Website: https://www.wellismo.com
Instagram: https://instagram.com/wellismo_coach/
Sexual Empowerment: Sexual Empowerment 101
"The Rise of the A-Gay" - GQ Magazine article referenced in today's episode
Watch this ep on YouTube
VOTE FOR US FOR THE PODCAST AWARDS!
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Jul 14, 2022 • 51min
Bottom Shaming
One of the most common forms of sexual shaming we see in the gay community is towards bottoming. The closed-minded narratives that are perpetuated around receptive anal sex reflect a patriarchal belief system that inhibits our growth as a community.
In this episode, we're tackling the topic of bottom shaming and exploring questions like...
Where do you think bottom shaming stems from?Why do you think bottom shaming keeps being perpetuated in the community?How do you think we as a community can start moving away from bottom shaming and start empowering ourselves?
Join us as we unpack the causes and effects of sexual shaming and understand how we all play a role in elevating the dialogue around sex and sexuality.
Watch this ep on YouTube
VOTE FOR US FOR THE PODCAST AWARDS!
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Jul 7, 2022 • 1h 44min
Introduction to Breathwork
In this episode, Matt Landsiedel speaks with certified SOMA Breath breathwork instructor Jason Samadhi.
Jason takes us on a journey into the power of breathwork and how consciously connecting with your breath can be one of the most potent tools for healing. By sharing the science of breathwork, Jason teaches us about the health benefits of working with your breath and how it can be used to improve performance both in and out of the bedroom.
Jason then takes us on an hour long breathwork journey that will leave you feeling expansive and blissful. You do not want to miss this episode!
What is explored in this episode:
BREATHWORK DISCLAIMER
Breathwork is NOT advised if you have a known cardiac arrhythmia (including very slow heart rate), a history of heart block, or are taking certain antipsychotic medications. Please review and acknowledge the Breathwork Liability Waiver
Recommended Book: “Multi-Orgasmic Man” by Mantak Chia
Connect with Jason:
@samadhibreath & www.samadhibreath.com
3-Day Gay Men’s Tantra Breathwork Journey:
Promo Code: GMB10
Gay Men's Brotherhood 10% Off Discount on the 3-Day Gay Men's Tantra Breathwork Journey (Valid Jul 1, 2022 - Aug 28, 2022)
Watch this ep on YouTube
VOTE FOR US FOR THE PODCAST AWARDS!
- Connect with us -
Join the private Facebook community
Take the "Healing Your Shame" course
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Patreon
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Jun 30, 2022 • 1h 4min
Ego
One of the greatest obstacles along the spiritual path is an overactive ego - that fear-based part of you that needs to control outcomes and win at all costs.
But having an ego is necessary to the human experience, so how can we reconcile both the ego self and spiritual self?
In this episode, we’re explaining how understanding your ego can actually benefit your spiritual practice. We’re answering questions such as:
How do you distinguish between your ego self and spiritual self?How do you regulate your ego?How can you develop a greater connection to the Spiritual Self?
Join us for this thought-provoking episode as we go deeper into the concepts of spirit and ego.
Watch this ep on YouTube
VOTE FOR US FOR THE PODCAST AWARDS!
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Jun 23, 2022 • 45min
Navigating Non-Binary
Change can be scary. And in today’s world of ever-evolving language around gender and identity, it can make it hard for someone to ask questions without feeling judged or misunderstood.
In today’s episode, host Calan Breckon opens up the conversation around navigating non-binary with genderqueer author Jason June and what his journey was like and how it now informs his work as a writer.
Together they explore questions like…
What is Non-Binary and what does it mean to be non-binary?What’s the most important thing people need to know about Non-binary and genderqueer people?Why do you think we’re experiencing more of a conversation around gender and gender identities in recent years?and much more!
After this episode, you'll have a better understanding of the term Non-Binary and how you can navigate this ever-evolving and growing landscape around gender and identity.
Watch this ep on YouTube
About today’s Guest: Jason June (it's a two-name first name, like Mary-Kate without the hyphen or the Olsen twin) is a genderqueer writer mermaid who loves to create picture books that mix the flamboyantly whacky with the slightly dark, and young adult contemporary rom-coms full of love and lust and hijinks.
When not writing, JJ zips about Austin, Texas. He loves dinosaurs, unicorns, Pomeranians, and anything magical that takes you to a different world or time. JJ is a tried and true Laura Dern stan, and he is actively looking for an Andalite friend.
Connect with Jason June:
Website: https://www.heyjasonjune.com/Instagram: https://www.instagram.com/heyjasonjune/Books: https://www.heyjasonjune.com/books.html
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Jun 16, 2022 • 1h 3min
Spirituality
Spirituality is an umbrella term that means many different things to many people. In this episode, we’re revealing our own experience with spirituality and spiritual practices by exploring these questions:
What does spirituality mean to you?What in your life brought you to spirituality?What does your spiritual practice involve?Where can someone start if they want to develop a spiritual practice?
Whether you’re spiritual or religious or neither, this episode will give you much to think about when it comes to nurturing that deeper connection to something greater.
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Toronto PRIDE EVENT
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