

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

Mar 9, 2023 • 1h 23min
Body Representation
Mainstream and social media influence the norms of what is an attractive or acceptable body within our community.
Buying into this narrow definition is easy, but it can be detrimental to your self-image and self-esteem.
Body representation is the practice of celebrating a diverse range of body types and unlearning the conditioning that only some bodies are worth showing.
In this juicy episode, we’re answering questions such as:
What has been your experience around body representation and body image in the media?
How did that translate into your experience in the gay community?
Do you actively work at changing your relationship with media/social media and how it affects you?
What (if any) are the things you try to do to be part of the change around body representation?
Join us for this spirited discussion about body positivity, self-image, and what you can do to support more diverse body representation in the media.
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
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Matt Landsiedel's Website
Michael DiIorio's Website
Calan Breckon's Website

Mar 2, 2023 • 56min
Being Kinder on Grindr
There’s no doubt that Grindr has cemented itself as part of the gay culture. For an entire generation, an app has shaped what it means to be gay - for better or worse.
In this episode, Michael invites special guest, Pepper, to make a case for engaging on Grindr with more respect, kindness, and humanity.
They are talking candidly about such things as:
What to write in your bio
Kinder communication
Ghosting
Respectful rejection
Setting expectations
Hook ups
Dealing with unsolicited pics
Stating preferences politely
Knowing when to take a break
Today’s Guest: Pepper
Instagram
The Gay Good
Today’s Host: Michael DiIorio
Instagram
Sexual Empowerment 101 Workshops
Wellismo Coaching
Take the 5 Love Languages Quiz
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
--
Matt Landsiedel's Website
Michael DiIorio's Website
Calan Breckon's Website

Feb 23, 2023 • 1h 8min
Love Languages
There are countless ways to give and receive love. We each have unique preferences can change over time.
Our "love languages" are influenced by factors such as our upbringing, attachment traumas, and relationship history.
In this episode, we're going deeper into the Love Languages, specifically answering questions such as:
❤️ What are your love languages?
❤️ What makes you feel loved? What influenced this?
❤️ How do you like to give love? What influenced this?
❤️ What would be your 6th love language?
Take the 5 Love Languages Quiz
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
--
Matt Landsiedel's Website
Michael DiIorio's Website
Calan Breckon's Website

Feb 16, 2023 • 1h 10min
The Practice of Empathy & Being an Empath
In this episode, Matt Landsiedel and Dr. Michael R. Smith talk about empathy and what it’s like being an empath and sensitive gay man in a world that isn’t designed for us. We share our own personal experiences being empathic/intuitive and how this can be beneficial but also challenging. We also discuss how relationships and sex can be different for empaths and how we have learned to best navigate this dynamic terrain.
The concepts we explored in this episode are:
What is empathy?
What is an empath?
Why is empathy important?
Challenges of having high empathy
Benefits of having high empathy
The science of empathy
What is it like being an empath in relationships?
What is it like to have sex as an empath?
Connect with Michael:
Website link: www.empathconnection.com
Instagram: @michael_robert_smith
Facebook: Empath Connection
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
GayMenGoingDeeper.com
Patreon

Feb 9, 2023 • 51min
Unconditional Love
Unconditional love sounds romantic, but is it realistic or even healthy? There are a lot of factors at play when we talk about this type of love, and it’s not as simple as it sounds.
In this episode, we're diving deeper into unconditional love asking some important questions such as:
❤️ What does unconditional love mean?
❤️ What gets in the way of unconditional love?
❤️ How do you move towards loving someone unconditionally?
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
--
Matt Landsiedel's Website
Michael DiIorio's Website
Calan Breckon's Website

Feb 2, 2023 • 47min
Dating Intentionally
Dating is still one of the greatest mysteries in the world some might say. And with over 1,500 dating apps out there it’s only getting more confusing on how to “figure it out” and find someone who is compatible.
In today’s episode, host Calan Breckon unpacks some of the mysteries around dating intentionally with guest Michael Kaye.
Michael is the Head of Global Communications at OkCupid, one of the world's largest dating apps, where he leads public relations programming, influencer marketing, and social media.
Michael has been a leading voice in dating and relationships and has been featured in many news outlets such as ABC News, Cosmopolitan, The New York Times, and The Washington Post as well as many others.
Together they unpack questions like…
Where do you think we’re going wrong with dating on all these different apps these days?
What do you think the difference is between just dating and dating intentionally?
How can someone be more intentional when they’re looking to seriously date?
...as well as some insider information from behind the curtain of what those dating apps know about us as daters, and you may be surprised to find that it’s not what you’d think!
Be sure to listen to the full episode as there is a surprise waiting at the end for those who make it there.
Michael on IG: @michaelkayepr
Twitter: @MichaelKayePR
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

Jan 26, 2023 • 43min
Zero F**ks Given
What is holding you back from doing everything you want to do and being whoever you want to be?
For a lot of people, worrying about what others will say or how they’ll be perceived gets in the way of living a truly authentic life.
In this episode, we’re looking at what it means to give zero f**ks. We’ll be answering questions such as…
If you gave zero fucks and could do anything, what would it be and why?
What’s the fear holding you back from doing it now?
Where’s the line between being true to yourself and honouring your needs but not hurting other people by being unapologetic?
What’s something you’re going to work on this year and be unapologetic about?
Whether you give too many fucks, not enough, or just the right amount, you’ll find valuable insights and laughs in this fun-filled conversation.
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

Jan 19, 2023 • 56min
Intergenerational Relationships
In a youth-obsessed culture, it’s easy to overlook the benefits of aging and the wisdom that only comes with lived experience.
Including people of different generations in your social circle helps enrich our community and improves quality of life for everyone involved.
Yet there are many stigmas attached to intergenerational (or “age-gap”) relationships, especially the romantic variety.
In this episode, Michael invites psychiatrist Dr. Hector Rodriguez to talk about platonic and romantic intergenerational relationships. This episode covers a variety of topics such as:
Benefits of intergenerational relationships to our community and at the individual level
Common stigmas in romantic relationships
Ageism in the gay community
Fetishizing older/younger men
The unique challenges of romantic intergenerational relationships and how to overcome them
Join us for this episode that is ultimately about connection and community - regardless of age.
Today's Guest: Dr. Hector Rodriguez
https://www.doctorhector.com
Instagram
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 follow him on Instagram @wellismo_coach.
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

Jan 12, 2023 • 1h 31min
Reinventing Yourself
One of the most exciting things about life is being able to transform your identity whenever you want.
For most people, transformation happens naturally and gradually over time. But sometimes you can purposefully and intentionally undergo a process of personal reinvention to become a new version of yourself.
In this episode, we’re talking about Reinventing Yourself and answering questions such as…
What has contributed to defining your self-image?
How have you let go of old versions of yourself?
How have you gone about reinventing yourself?
How do you perceive yourself now? How much of that perception comes from how others respond to you?
Join us as we share our own reinventions of the past, and present, and how we’re reinventing ourselves for the future.
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
Coaching Collection
Instagram
Patreon

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
Patreon


