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
• 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.

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.

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.