

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

21 snips
Oct 27, 2022 • 50min
Masturbation
Masturbation is a perfectly natural and healthy sexual activity that has many physical and mental benefits.
However, some question whether it is a harmful habit that leads to negative consequences in their personal life and relationships.
In this provocative and educational episode, Michael and Sex Coach, Craig Cassey answer your burning questions about masturbation, including topics such as:
The benefits of masturbation
When is it too much?
Masturbation while in a relationship
Is porn helpful or harmful?
Feeling guilty
Tips for mindful masturbation
Join Michael and Craig as they share their own experiences and provide their best coaching tips for more mindful masturbation..
Today's Guest
Craig Cassey is a professional life, executive, and sex coach. You can find Craig at www.craigcassey.com or on Instagram @craigcasseyjr
Today's Host
Michael DiIorio is a certified life and wellness coach. You can find Michael at www.wellismo.com or on Instagram @wellismo_coach. You can also join Michael's Sexual Empowerment Group.
The link between masturbation & risk of prostate cancer (2004 study)
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Oct 20, 2022 • 50min
Lack of Trust in the Gay Community
Trust takes a long time to build and only seconds to break. In this episode, we’re talking about how our trust issues impact our ability to connect with others. Specifically, we’ll be exploring questions such as:
What do you think has led to trust issues in the gay community?How have trust issues impacted your relationships?How can we begin to heal trust issues amongst gay men?
Join us to learn some practical tips on relating more authentically with others, especially if you’ve had a hard time trusting others in the gay community.
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Oct 13, 2022 • 1h 6min
The Psychological Impact of Conversion Therapy
In this episode Matt Landsiedel interviews Dr. Lucas Wilson about the psychological impact of conversion therapy. They explore how shame and internalized homophobia are typically precursors to making someone susceptible to agreeing to do conversion therapy. Dr. Wilson shares his own personal experience with conversion therapy and how this experience has impacted his life. Both Matt and Dr. Wilson share how they have approached their own healing journey through shame and internalized homophobia and how to move through the trauma caused by conversion therapy.
These are the questions that were explored in this episode:
What is conversion therapy?What is your personal experience with conversion therapy?What impact did conversion therapy have on your psychology?How is conversion therapy connected to religion?What is affect theory and how does it relate to conversion therapy?How can someone who has gone through conversion therapy begin to heal?
Born and raised in Toronto, Dr. Lucas Wilson is the Justice, Equity, and Transformation Postdoctoral Fellow at University of Calgary. He holds graduate degrees from McMaster University, Vanderbilt University, and Florida Atlantic University. He has authored several peer-reviewed articles and book chapters, and his public-facing work has appeared in The Advocate, Queerty, LGBTQ Nation, and Religion Dispatches, among other venues.
Connect with Dr. Lucas Wilson:
Website link: https://ucalgary.academia.edu/LucasWilsonInstagram: @lukeslamdunkwilsonTwitter: @wilson_fwFacebook: https://www.facebook.com/luke.wilson.96
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Oct 6, 2022 • 50min
Trusting Yourself
We often talk about trust in the context of trusting others, but in this episode, we’re focusing on how to build an internal sense of trust.
We’re exploring questions such as:
How do you know if you trust yourself? What gets in the way of trusting yourself?What is one thing you can do to build greater self-trust?
Join us for this informative conversation that will help you develop your relationship to self, and ultimately your relationship with others.
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Sep 29, 2022 • 53min
Making Space for Being Uncomfortable
In today’s episode, host Calan Breckon and guest Drummond Fulcher dive into the uncomfortable for a conversation that revolves around cancel culture, the "either you’re with me or against me (or us)" mentality, giving space for the in-between where conversation happens, how bridges are where understanding is born, and where we need to go in order to work through the uncomfortable feelings in order to learn and grow.
Together they unpack questions like:
Why do people avoid being uncomfortable?How do you think cancel culture affects our community?How do we make space in our lives for being uncomfortable and having hard conversations?
Take a listen to find out how you can better navigate uncomfortable conversations and begin building more bridges of understanding and compassion in your life today.
More on Drummond:
@DrummondCultureWebsite
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Sep 22, 2022 • 54min
Your Questions Answered
You asked and we answered!
In this episode, we're answering some of the juiciest questions from our community such as…
How to let go of the past?Why can’t gay men find love?How to get unstuck and move forward?
Join us as we cover topics such as shame, gay dating, self-confidence, and trust in this Q & A style discussion.
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Sep 15, 2022 • 1h 11min
Behind the Scenes of the Gay Men's Brotherhood
In this very special

Sep 8, 2022 • 48min
Our Community
From the outside looking in, the queer community is seen as an inclusive space that celebrates diversity. Yet for many people, it feels quite exclusive and lonely.
In this episode, we are sharing our vision for the gay community and the different ways we are implementing this vision.
We’re talking about...
What exactly is our vision?What are the different parts of our community?Why is building this community important to each of us?How we’ve changed from the beginning to today?What is one thing we’re excited about co-creating for our community in the future?
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Sep 1, 2022 • 56min
The Dark Night of the Soul
Dark periods are an inevitable part of life that can happen at any moment and in any number of ways:
The death of a loved one
A terminal diagnosis
Job loss
Relationship breakdown
But what is the spiritual and psychological significance of this pain?
In this episode of Gay Men Going Deeper, Michael is joined by LGBTQ+ affirmative psychotherapist Justin Oberste to discuss the concept of the Dark Night of the Soul, including:
The 4 phases of a dark night of the soul
Sharing personal, real-life examples
The spiritual significance of dark periods
Tips for finding hope within the darkness
The 4 Phases of a Dark Night of the Soul - blog post referenced in today's episode
Connect with Justin
Website: www.justinoberste.com
Instagram: www.instagram.com/justinoberste
Today's Host: Michael DiIorio
Website: https://www.wellismo.com
Instagram: https://instagram.com/wellismo_coach/
Courses: learn.wellismo.com
Watch this ep on YouTube
Take the Attachment Style Quiz!
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Aug 25, 2022 • 43min
Mindset
Your mind is a powerful tool that you can use to create a life that you love. Your mindset is your overall outlook on life and it will determine whether you remain stuck spinning your wheels or moving towards your goals and dreams.
In this episode, we’re looking specifically at the difference between the Fixed and Growth Mindsets. We will be discussing questions such as….
What type of mindset were you raised with (growth of fixed)? And what mindset do you have today?How do you cultivate more of a growth mindset for yourself? What did you have to transform to become a more growth mindset-oriented?What is your internal dialogue in a fixed mindset say to you vs. when you’re in a growth mindset?What has helped you on your growth journey that may help our listeners?
By the end of this episode, you’ll feel motivated and inspired to leave behind the fixed mindset and shift into a growth mindset.
Watch this ep on YouTube
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