Gay Men Going Deeper
Gay Men Going Deeper
Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood
Grieving Your Past
39 minutes Posted Sep 4, 2025 at 11:00 am.
0:00
39:54
Download MP3
Show notes
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.