

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

Jun 24, 2021 • 1h 19min
Demisexuality
About Today’s Show
In this episode, Matt explores the topic of Demisexuality with fellow brothers Carlos, Ron and Andre.
All 4 men identify as demisexual and they candidly break down what it’s like to be demisexual in the gay community and the benefits and challenges of honouring this truth.
Here are some of the questions explored in the episode:
-What does it mean to be demisexual?
-In what ways do you find it difficult to fit into the gay community being demisexual?
-How has it been communicating with non-demisexual men your desire to develop intimacy prior to having sex?
-The benefits of dating a demisexual?
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Jun 17, 2021 • 60min
Celebrating Our Gayness
About Today’s Show
On this episode honouring Pride Month, we’re celebrating what it means to be gay. We speak out about the challenges we've faced and the valuable life lessons they have provided us. Pride has a unique meaning for everyone and this episode is about celebrating who you are in a way that feels authentic to you.
Watch this ep on YouTube
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Jun 10, 2021 • 55min
Interview with Brita Filter from RuPaul's Drag Race Season 12
About Today’s Show
On today’s episode, Calan has a sit down with RuPaul’s Drag Race season 12 contestant Brita Filter (aka Jesse Havea) to talk about mental health and the experience of being on a show like RPDR. Jesse was very open, honest and candid with Calan as he shared his journey with depression, toxic social media, alcoholism, being painted as “the villain” on his season of RPDR, hitting rock bottom and attempting suicide. He also shared how he’s now on a healing journey, recovering, re-focusing his energies and learning how to navigate life in the public eye.
Get Social with Brita:
Instagram | Twitter
www.thebritafilter.com
Watch this ep on YouTube
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Jun 3, 2021 • 59min
Lone Wolf Syndrome
About Today’s Show
The Lone Wolf mentality can feel safe and serve us in some ways, but as we share in this episode, it's also one of the common blocks that prevent us from belonging and connecting in community. We'll also share some tips on how you can allow more connection in your life.
Watch this ep on YouTube
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May 27, 2021 • 56min
Evolution of the Gay Community with Tim McCaskell
About Today’s Show
As Pride Month celebrations begin, Michael turns back the clock and takes a glimpse into the evolution of the gay community with long-time activist, author, and educator, Tim McCaskell. Tim shares his unique experience living through those watershed moments of our shared history including the fight for gay liberation and the AIDS crisis.
Together they discuss how the gay community has evolved through the last 50 years. They also take stock of where we are today and explore whether the notion of community is as relevant or necessary as it was in the past.
Connect with Tim: Tim_mccaskell@hotmaill.com
Tim’s Facebook
Tim’s books, Race to Equity and Queer Progress can be found at your favourite bookshop or directly from the publisher by clicking here.
Watch this ep on YouTube
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May 20, 2021 • 58min
Fear of Judgment
About Today’s Show
Fear of judgment often prevents us from showing up as our authentic selves. Not only do we fear judgment and criticism of others, but we also have to contend with our self-judgment and self-criticism. In this episode, we're sharing our experiences with this deep-seated fear and the lessons we've learned on how to deal with it.
Watch this ep on YouTube
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May 13, 2021 • 48min
Gender and Sexual Identity with Christiano Green
About Today’s Show
In this episode, Matt Speaks with Identity & Mindset Coach, Speaker, Trainer, Author, Podcast Host, Thought Leader, & Entrepreneur Christiano Green about Gender & Sexual Identity.
These two coaches candidly breakdown the difference between gender and sexuality and how it is a spectrum, not a construct. Further concepts that are unpacked in this episode are gender fluidity, gender energies, rising of the feminine, topping and bottoming and how we view them as masculine and feminine, and gender stereotypes that are holding us back due to shame and patriarchal conditioning.
Connect with Christiano
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May 6, 2021 • 56min
The Power of Vulnerability
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About Today’s Show
We tend to avoid vulnerability but when we use it to our advantage, it can be a potent source of personal power and a means of establishing authentic connections with others. In this episode, we're sharing how vulnerability has actually helped us along our respective journeys to become more self-confident, more rooted in authenticity, and develop deeper relationships.
Watch this ep on YouTube
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Apr 29, 2021 • 1h 15min
Talking Relationships with Jordan Bach
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About Today’s Show
Relationships! Always such a hot topic in the gay community (and in all communities really). In today’s episode, Calan Breckon invites guest speaker, writer and Life Coach Jordan Bach back for a chat about gays and relationships.
Covering things like resentment after a rejection, conscious uncoupling, clearness is kindness, confidently asking someone out and what “pretty privilege” is and how it affects us are just a few of the topics that came up in today’s chat.
Jordan’s Instagram
thebachbook.com
Watch this ep on YouTube
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Apr 22, 2021 • 1h 5min
Romantic Relationships
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About Today’s Show
Romantic relationships give us a perfect opportunity to learn more about ourselves and how we relate with others. In this episode, we're sharing our perspectives and lessons learned in love, dating & relationships.
Watch this ep on YouTube
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