

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 26, 2025 • 46min
Pride Panel Discussion
It’s Pride Month, and with everything going on in the world right now, it feels especially important to pause and reflect.
In this special panel discussion episode, Reno Johnston is joined by three incredible guests—Mark Fleming, Keone Wales, and Jordan Layne—for a candid panel discussion on the meaning of Pride: where it began, how it’s evolved, and what it means to each of us today. Together, they explore questions like:
What does Pride mean to you?
What was your first Pride experience?
How has Pride changed since then?
What would you like Pride to become?
This conversation isn’t a history lesson or a debate. It's an open, honest sharing of lived experience. Whether you’re a seasoned activist or celebrating your first Pride, we invite you to reflect alongside us and consider what Pride means to you, not just this month, but all year round.
Today's Guests:
Mark Fleming
Facebook
Keone Wales
Instagram
Jordan Layne
Instagram
Today's Host: Reno Johnston
Instagram
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
Join the Gay Men's Brotherhood Facebook community
Get on our email list to get access to our monthly Zoom calls
Follow us on Instagram | TikTok
Learn more about our community at GayMenGoingDeeper.com
- LEARN WITH US -
Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.
Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
Take the Attachment Style Quiz to determine your attachment style and get a free report.

Jun 19, 2025 • 49min
Are LGBTQ Rights Under Attack?
In 2025, LGBTQ rights are facing renewed challenges- from the rise of far-right populism to legislative rollbacks and the rise of hate sweeping across the globe. But how serious is the threat? And if the fight is back on… are we ready?
This week, Michael is joined by author and longtime activist, Tim McCaskell, who’s been on the front lines of LGBTQ+ resistance for over five decades. From the bathhouse raids to the fight for AIDS treatment and beyond, Tim brings deep historical context and lived experience to the conversation.
Together, they explore what activism looks like in 2025, whether we’ve grown too comfortable, how activism has changed over the decades, and most importantly, what we need to do to show up and fight for our future.
Today's Guest: Tim McCaskell
Facebook
LinkedIn
Books
Today's Host: Michael DiIorio
Instagram
TikTok
YouTube
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
Join the Gay Men's Brotherhood Facebook community
Get on our email list to get access to our monthly Zoom calls
Follow us on Instagram | TikTok
Learn more about our community at GayMenGoingDeeper.com
- LEARN WITH US -
Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.
Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
Take the Attachment Style Quiz to determine your attachment style and get a free report.

Jun 12, 2025 • 49min
Has Pride Lost Its Meaning?
In today’s episode, we’re diving into a question many in our community have been quietly (or loudly) asking: Has Pride lost its meaning?
In this wide-ranging conversation, we reflect on how Pride has evolved from its radical roots in activism to its present-day celebratory scene shaped by media, politics, and corporate sponsorships. We talk about what’s been gained, what’s been lost, and what still needs to be reclaimed.
Some topics we explore:
The impact of corporatization and rainbow capitalism
How we’d reimagine Pride moving forward
The meaning Pride has for us personally
The importance of making Pride more inclusive for those still on the margins
The role media plays in shaping what Pride looks and feels like
How far our rights have come… and how fragile they still are
Whether you love Pride, feel disconnected from it, or land somewhere in between, this episode is an invitation to reflect, reimagine, and reconnect with what Pride means to you in 2025.
Today's Hosts:
Michael DiIorio
Matt Landsiedel
Reno Johnston
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
Join the Gay Men's Brotherhood Facebook community
Get on our email list to get access to our monthly Zoom calls
Follow us on Instagram | TikTok
Learn more about our community at GayMenGoingDeeper.com
- LEARN WITH US -
Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.
Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
Take the Attachment Style Quiz to determine your attachment style and get a free report.

7 snips
Jun 5, 2025 • 1h 14min
Dating as a Demisexual
Ron Fisher, a gay man who emerged from a long heterosexual marriage, shares insights on dating as a demisexual and the challenges of age gaps. Kasey Cromer reflects on celibacy, relationship dynamics, and the importance of pacing and building trust. Meanwhile, Andre-Lee Wills discusses his spiritual awakening during quarantine and how it shifted his understanding of intimacy. Together, they provide practical dating advice and emphasize the value of friendships and vulnerability in navigating the demisexual experience.

May 29, 2025 • 54min
Why Are Gay Friendships So Hard?
Pepper Rojas, creator of The Gay Good and queer culture commentator, shares candid reflections on building nourishing gay friendships. They unpack performative dynamics, shame-driven survival habits, social media’s influence, and how to practice vulnerability. Short, honest conversations about boundaries, scarcity, and creating chosen family.

6 snips
May 22, 2025 • 54min
The Reparenting Process
Dive into the transformative journey of reparenting as hosts unpack childhood unmet needs. They share real stories of coping strategies like perfectionism and escapism. Explore how skills like self-compassion and boundary-setting can help heal old wounds. The discussion turns personal as they reflect on loneliness, trust issues, and the impact of parental expectations. Learn how to turn past challenges into strengths for healthier relationships and ultimately become the supportive parent you always needed.

20 snips
May 15, 2025 • 54min
How to Not Lose Yourself in Your Relationships
Tom Bruett, therapist and founder of the Queer Relationship Institute, offers concise guidance on keeping your identity in relationships. He explores codependency, enmeshment, and their roots. The conversation covers healing through differentiation, practical self-regulation and journaling, and building interdependence that balances autonomy and closeness.

May 8, 2025 • 44min
Why Gay Men Love Divas
From Madonna to Mariah, Beyoncé to Barbra— throughout the generations, gay men have been obsessed with divas. But why?
In this episode of Gay Men Going Deeper, we’re diving into the deep connection between gay men and our beloved divas, exploring:
Who are the divas and what do they have in common?
Why divas resonate so deeply with gay men
How these women inspire us
The diva anthems that have become the soundtrack of self-confidence
What it means to channel your inner diva in everyday life.
Who are today’s divas?
This isn’t just about pop culture—it’s a conversation about power, identity, and how divas have given generations of gay men comfort and strength.
Today's Hosts:
Michael DiIorio
Matt Landsiedel
Reno Johnston
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
Join the Gay Men's Brotherhood Facebook community
Get on our email list to get access to our monthly Zoom calls
Follow us on Instagram | TikTok
Learn more about our community at GayMenGoingDeeper.com
- LEARN WITH US -
Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.
Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
Take the Attachment Style Quiz to determine your attachment style and get a free report.

May 1, 2025 • 46min
The Women in Our Lives
The women in our lives have influenced us in ways we don’t always recognize, but when we take a step back, their impact is undeniable.
In this heartfelt episode, we’re celebrating the uniquely beautiful relationships gay men have with women—from mothers and grandmothers to besties, sisters, and beyond. We’re showing love to all the women who have supported us, shaped us, and often modeled the traits that helped us become who we are today.
Some of the topics we’ll explore:
How our childhoods were shaped by the women around us
The unique love and support between gay men and women
What makes female friendships different from male friendships
The role of empathy and emotional intelligence in these relationships
How friendships evolve over the years
Join us for a deep conversation about the power of women and how these relationships continue to shape us—today and always.
Today's Hosts:
Michael DiIorio
Matt Landsiedel
Reno Johnston
Support the Show - viewer and listener support helps us to continue making episodes
- CONNECT WITH US -
Watch podcast episodes on YouTube
Join the Gay Men's Brotherhood Facebook community
Get on our email list to get access to our monthly Zoom calls
Follow us on Instagram | TikTok
Learn more about our community at GayMenGoingDeeper.com
- LEARN WITH US -
Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame.
Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
Take the Attachment Style Quiz to determine your attachment style and get a free report.

6 snips
Apr 24, 2025 • 53min
People Pleasing, Boundaries, and Fear of Conflict
In this insightful conversation, therapist Michael Pezzullo brings his expertise on relationships, codependency, and emotional health, particularly in the context of the gay experience. He delves into the challenges of people-pleasing, distinguishing it from genuine kindness. The duo explores how shame and family dynamics contribute to this pattern and discusses the emotional toll it takes, including loneliness and disconnection. Michael offers tips on setting boundaries and emphasizes the importance of embracing discomfort to break free from the cycle of seeking approval.


