Not all grief is about death. Sometimes, the hardest losses are the people (or pets) who are still alive—but no longer in our lives.
In this episode, we’re talking about the heartbreak of losing relationships: romantic breakups, friendship fallouts, and the deep sadness that comes with saying goodbye to a beloved pet. We explore how grief shows up emotionally, mentally, and even physically—and the unique challenges of letting go of someone who once meant everything to you.
Together, we share personal experiences of:
The stages of grief
Grieving people who are still alive
Letting go of “what could’ve been”
Healing after a breakup
Losing chosen family or long-time friends
Learning how to let go without lingering
This conversation shines a light on the many ways we experience loss and how to move through the grief with compassion, courage, and clarity.
Related Episodes:
Grieving Your Past
When It's Time to Say Goodbye
Grappling with Grief: Addison Brasil
Today's Hosts:
Michael DiIorio
Matt Landsiedel
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
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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.
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49:32
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49:32
Grieving Your Past
Grief isn’t just about death—it’s also about the quiet losses we carry as we grow and evolve. In this episode, we’re kicking off a 4-part series on grief by exploring what it means to grieve your past.
Whether it’s a version of yourself that felt more confident, more desirable, or more socially “relevant,” we often feel a deep emotional pull toward who we used to be. From aging and identity shifts to the grief of letting go of our dreams, we’re diving into the invisible grief that comes with change.
We discuss:
What grieving your past looks like
How grief can show up as you grow and evolve
Letting go of your youth, body, or social capital as a gay man
The bittersweet nostalgia of past chapters—even ones you chose to leave behind
How to know when it’s time to move on, and how to do it with self-compassion
This conversation is about honoring who you were while embracing who you’re becoming.
Related Episode:
Grappling with Grief: Addison Brasil
Today's Hosts:
Michael DiIorio
Matt Landsiedel
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.
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39:54
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39:54
How to Put Yourself Out There
Most of us want to be seen, heard, and understood, but the fear of judgment can stop us from doing so. Whether it’s being more social, speaking your feelings, or sharing creative work, putting yourself out there can feel risky, especially when we’ve been conditioned to play it safe due to past hurt or rejection.
In this episode, we’re sharing:
👉 Our personal journeys from shy and self-conscious to being more visible
👉 The fears that held us back, and sometimes still do
👉 How we want to be perceived vs. showing up authentically
👉 What helps us keep showing up, even when it’s uncomfortable
If you’ve ever held back because you’re scared of what people might think, this episode is for you.
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.
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56:31
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56:31
The Problem With Self-Love
We all know self-love is important, but what happens when it goes too far in the wrong direction?
In this episode, Michael DiIorio is joined by therapist Michael Pezzullo for an honest conversation about the shadow side of self-love. Together, they explore:
The difference between self-comforting and self-coddling
How emotional sensitivity can become emotional fragility
Why self-bulldozing is just as harmful as avoidance
The four zones of the Self-Love Spectrum
How trauma impacts the way we “love” ourselves
How to tell if you're truly healing…or just hiding.
You’ll learn about the Self-Love Spectrum, the signs of self-coddling and self-bulldozing, and how to practice a more empowering, growth-oriented version of self-love- without abandoning your need for care and compassion.
Join us for an episode that will help you get honest about how you love yourself, and what real self-love actually looks like.
Today's Guest: Michael Pezzullo
Website
Instagram
Today's Host: Michael DiIorio
Website
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.
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35:11
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35:11
Lone Wolf Energy
Some of us didn’t choose to become lone wolves—we were shaped into them. Many gay men have learned to rely only on themselves, and while that self-sufficiency can feel empowering, it often comes at the cost of connection and intimacy.
In this personal and vulnerable episode, Michael and Matt open up about their own lone wolf energy—where it comes from, how it’s served them, and the moments when it became more isolating than empowering.
Together, we’re unpacking:
The origin stories of our lone wolf instincts
The protective thoughts that sound strong but hide deeper wounds
What makes us want to cut people off—and what’s really underneath that urge
How this energy shows up in dating and relationships
And how to honour your need for space without shutting people out
Whether you identify as a lone wolf or love someone who does, this episode will help you navigate the delicate balance between fierce independence and meaningful connection.
Today's Hosts:
Michael DiIorio
Matt Landsiedel
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.
Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective.
Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time.
This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between.
Visit us at www.GayMenGoingDeeper.com
Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN