Liked by Everyone, Chosen by No One: The Nice Guy Trap

300 episodes over six years. A lot has changed. For our 300th episode, Michael, Matt, and Reno are back together at the mic for the first time in three months to look back at where Gay Men Going Deeper started, how we’ve changed along the way, and what we’re still figuring out. We’re revisiting some of those early days (including the things that make us cringe now), sharing beliefs we once held strongly that we see very differently today, and getting honest about the areas in our own lives where we’re still learning and growing. Whether you’ve been with us since the beginning or this is your first episode, thanks for going deeper with us. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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.

Growing up gay shapes you. Even if you had a relatively good experience, many of us learned to hide parts of ourselves, seek approval, stay guarded, or adapt in order to feel safe, accepted, or lovable. Over time, those survival strategies can quietly shape our relationships, confidence, intimacy, and sense of self. In this episode, we’re talking about the “inner work” many gay men find themselves doing as adults: unpacking old conditioning, unlearning shame, building self-trust, and learning how to live more honestly and fully as ourselves. We also share parts of our own journeys, the patterns we see in our clients, and what real growth actually looks like in practice. We get into: How growing up gay can shape your self-esteem, relationships, and identity The difference between healing, self-awareness, and staying stuck in the past Common coping strategies gay men develop to feel safe, desired, or accepted What meaningful personal growth actually looks like in everyday life The balance between understanding your past without making it your identity This is a grounded conversation about growth, self-awareness, and becoming more fully yourself — not perfectly healed, but more conscious, honest, and free. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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: Lifeti... Chapters (00:00:00) - Gay Men Going Deep: The Gay Man's Healing Journey(00:03:47) - Unlearning the Shame of Being Gay(00:09:34) - The inner work of shame(00:10:50) - Healing Emotional Wounds and Protective Strategies(00:13:41) - Why Does Being Gay Need to Be Healed?(00:16:01) - What are the pain points people come to you for?(00:17:38) - What is Self-Confidence and Self Worth?(00:22:10) - Six things we're actually healing in our gay relationships(00:26:53) - How to Heal From Trauma (Gay Men)(00:32:04) - How to Get Back On Your Path(00:32:27) - What's The Secret to Being the Man You Want to Be(00:33:44) - How To Become The Man You Want To Be(00:37:30) - Gay Men's Brotherhood

Growing up different can leave a lasting impact on how we see ourselves, our relationships, and our sense of belonging. Even years later, many gay men still carry the feeling of being on the outside looking in—surrounded by people, yet not truly known. In this episode, we're exploring the roots of belonging, why so many gay men struggle with deep loneliness, and what it actually takes to find meaningful connection. We get into: The difference between fitting in and truly belonging Why you can have friends and still feel profoundly lonely How shame and abandonment wounds shape our relationships The role authenticity plays in creating real connection Why belonging isn't about everyone agreeing with you—and what it actually requires Practical ways to cultivate a deeper sense of belonging in your life If you've ever felt like you don't quite fit, this conversation is a reminder that belonging isn't about becoming someone else—it's about finding the courage to let yourself be known. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Gay Men Going Deep: How Did Growing Up Gay Affect My Sense(00:04:52) - How Growing Gay Affected My Sense of Belonging Today(00:10:57) - Gay Men Talking About Being Gay(00:15:28) - Michael on Being Gay and Growing Up(00:18:56) - How to Belong as a Child(00:20:50) - The Shame of Being Gay(00:24:31) - What It's Like To Be Gay(00:28:32) - How Did Growing Up Gay Affect My Sense of Belonging?(00:29:22) - What Does Belonging Mean to You?(00:31:26) - You Talk About Belonging To Your Sexual Pleasure(00:35:42) - The Importance of Belonging(00:37:57) - What Does Belonging Mean To You? Part 2(00:39:30) - How do you find belonging in your life?(00:42:24) - Are Gay Spaces Necessary For Dating?(00:46:36) - A Couple's Surprise(00:47:28) - What Does Belonging Mean To You?(00:48:57) - Michael On The Importance Of Self-(00:51:25) - What's the space that you feel most comfortable being yourself in?(00:52:36) - Gay Men's Brotherhood: The Coaching Collection

Apps are a huge part of modern gay life. We delete them, reinstall them, swear them off, go back on, and keep trying to figure out whether they’re helping us connect or quietly getting in the way. In this episode, we’re talking about app seasonality: that on-again, off-again relationship many gay men have with the apps, and the skill of knowing when they’re serving you, when they’re draining you, when to use them…and when to lose them. We’re getting into: Why apps can be the right choice in one season and the wrong choice in another How to know when it’s time for a break or hiatus When getting back on the apps can actually be the healthy choice The difference between using apps intentionally vs. compulsively How the apps can reveal your patterns around rejection, desire, sex, dating, and self-worth Whether you’re on the apps, off the apps, or currently “just checking who’s nearby,” this conversation will help you bring more honesty, agency, and self-trust to the way you use them. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Gay Men Going Deep: Grindr On-Off-Again(00:01:31) - Apps' On-Again, Off-Again Cycle(00:02:14) - Matt on Why He Joined Grindr(00:06:03) - Michael Jackson on 'Both'(00:06:14) - On The Difference Between Grindr and Hinge(00:08:28) - Gay Dating: Compulsivity vs Intentionality(00:11:37) - Scruff's 'What's Behind the Paywall'(00:13:10) - When It's Time To Take a Break From Grindr(00:16:59) - Marriage on Grindr When You're Traveling(00:19:23) - Gay Men on Dating Apps(00:22:48) - Both Apps and No Apps(00:23:17) - "No Response Is a Response" on Grindr, Hinge(00:26:45) - When Do You Know You're Ready to Go Back On?(00:28:15) - What Are You Looking To Experience With Your Gay Guy?(00:32:16) - What is Your Ideal Pace of Connection?(00:34:07) - Amino and Matt on Gay Men's Brotherhood

Why do the guys who are a little distant, a little edgy, and a little hard to get feel so magnetic? Is it actually attraction…or is a deeper pattern being activated? In this episode, we unpack what’s going on underneath the pull toward “bad boys” and why it can feel so intense, compelling, and hard to walk away from. We talk about: What exactly is it about “bad boys” that makes them so attractive What we’re really responding to beneath the surface  Why intensity can feel like chemistry, but isn’t always compatibility What “bad boys” do well that “nice guys” can learn from How to take those traits into your own dating life—without the chaos If you’ve ever found yourself drawn to someone who felt exciting but hard to reach, this episode will help you understand why—and what to do differently. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Why Bad Boys Feel So Good(00:01:38) - Are Bad Boy Guys Hot?(00:03:19) - What Are We Actually Attracting To Bad Boys?(00:07:24) - Good Boy vs Bad Boy(00:11:08) - Good Boy Or Bad Boy?(00:15:05) - Queer as Folk on Michael(00:16:00) - A Neil Gaiman's Brotherhood(00:16:43) - What Can We Learn From Bad Boys?(00:20:36) - Is Your Bad Boy Unafraid Of Getting Cancelled?(00:22:00) - Do Bad Boys Get Attracted To Women?(00:24:28) - I'm The Bad Boy(00:27:39) - Good Boy vs. Bad Boy(00:30:45) - Good Boy vs. Nice Guy(00:32:13) - The Gay Man Going Deeper: Nice Guys

Intimacy sounds like something we all want, but being truly seen can feel terrifying. In this episode, we talk about why fantasy often feels safer than reality, why vulnerability can feel exposing, and how the fear of rejection keeps many gay men hiding behind performance.  We also get personal about our own struggles with being seen, how this shows up in dating. This episode is about the fear beneath the fantasy: the part of us that wants closeness, but panics when closeness asks us to be honest, visible, and emotionally available. We talk about: Why intimacy can feel unsafe even when we crave it The fear of being fully seen, known, and rejected Why fantasy feels easier than real connection How to feel safer, more grounded, and more open to intimacy A deep, honest conversation for gay men who want connection, but sometimes find themselves pulling away when it starts to get real. Link: Matt’s Secure Attachment Handbook  Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Gay Men Going Deep: Why Intimacy Feels Safer(00:02:16) - What Is Intimacy Really Like?(00:06:15) - Married People Say They're Not Attracted To Perfect People(00:09:17) - What Are You Afraid Of Being Proactively Rejected For?(00:12:38) - Geminis Have A Fear Of Intimacy(00:13:24) - What Am I Afraid Of In A Relationship?(00:17:03) - When Did You Start Naked With Your Girlfriend?(00:17:31) - How to Love Yourself (No Fear of Intimacy)(00:22:15) - How to Develop Secure Attachment(00:23:50) - "I Get Scared in Intimacy"(00:26:51) - The Gay Men's Brotherhood

Seeking validation isn’t just about chasing likes. It’s the part of us that needs approval, wants to belong, and feel accepted. But does it come at a cost? In this episode, we unpack the subtle ways validation-seeking still shows up in our everyday lives, especially as gay men who learned early to scan, adapt, perform, and manage how we’re perceived. We talk about the difference between healthy feedback and outsourcing your self-worth, and what it actually looks like to build self-trust in real life. In this episode, we discuss: What validation-seeking actually looks like The difference between caring what people think and letting their opinion become a verdict on your worth Why self-trust requires tolerating discomfort, disappointment, and disapproval How we’re each still learning to come back to ourselves in more honest, grounded ways Self-trust doesn’t mean you stop caring what people think- it means their reaction no longer gets to decide who you are. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Coming Home To Yourself(00:01:56) - Why Do Gay Men Seek Validation?(00:03:43) - What Does Validation Seeking Actually Look Like?(00:05:51) - What Does It Look Like to Be Overcomfortable?(00:07:20) - Michael Buble on Being Validated(00:07:57) - Michael Says He Feels Good About Himself(00:08:45) - Validation Seeking and How It Affects Your Life(00:13:53) - How to Stop Seeking External Validation(00:18:10) - What does validation seeking look like in your life?(00:18:35) - Why Is Self-Trust So Difficult For Gay People?(00:23:26) - "People Plead"(00:27:58) - What Makes Self Trust So Difficult?(00:31:43) - The Importance Of Identity(00:33:28) - Self-Trust Coaching(00:34:08) - Michael on Coming Home To Himself(00:35:38) - What Would I Do If I Wasn't Trying To Be Like(00:39:35) - Coming Home to Yourself(00:43:20) - Getting Back Home to Yourself(00:46:26) - Why I Don't Need To Explain My Time(00:48:06) - Coming Back Home To Yourself

Feeling bad is not a flaw in the human experience. It’s an essential life skill for anyone who wants a life of love, growth, satisfaction, and intimacy— all of it requires the capacity to feel discomfort without running from it. In this episode, Michael and Matt make the case for feeling bad on purpose: when to sit with an emotion, when to change your mindset, and why emotional avoidance often costs us more than the original pain. We get into: Why feeling bad is a skill, not a personal failure The difference between allowing an emotion and reframing your thoughts How men are often taught to avoid, repress, intellectualize, or act out emotions The ways we numb and escape through food, alcohol, sex, porn, productivity, scrolling, and distraction Why building emotional capacity makes you braver, more honest, and more willing to live a bigger life The goal isn’t to be happy all the time — it’s to become someone who can feel bad without abandoning yourself or shrinking your future. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Why Feeling Bad Is Good For You(00:01:46) - Why Are People So Bad at Feeling Bad?(00:06:06) - How to Win with Emotions(00:08:13) - How to Love Yourself(00:13:16) - How to Get Through Trauma(00:16:52) - What Emotion Is The Hardest To Deal With?(00:20:05) - How To Live A Fully Feeling Life(00:20:54) - How to Deal With Feeling Bad(00:23:48) - The ego takes over the body(00:24:32) - Gay Men's Ways To Cope With Feeling Bad(00:25:45) - How to Stop Feeling Bad(00:29:31) - How to Love Yourself Through Fear(00:30:38) - How to Handle Negative Emotions(00:34:37) - People Cope With Crying(00:35:29) - Gay Men's Brotherhood

A lot of gay men pride themselves on being “nice”— easygoing, agreeable, low-drama. But what if that’s exactly why you’re not getting what you want? In this episode, we break down the difference between being kind and being “nice,” and how approval-seeking, conflict avoidance, and over-accommodating are quietly killing attraction, respect, and real connection.  We talk about: Why “nice” is often a strategy, not a personality The hidden cost of being liked by everyone How this shows up in dating and relationships The difference between being chosen vs. being liked How to shift from approval-seeking to self-respecting If you’ve ever felt overlooked, under-appreciated, or stuck in the friend-zone, this one will hit. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - Gay Men Going Deeper: The Nice Guy Trap(00:01:04) - Being Nice(00:03:16) - What Does Being A Nice Guy Actually Mean To You?(00:05:46) - Matt on Being A Nice Guy(00:09:49) - Have You Ever Been The Nice Guy?(00:13:30) - Is Your Friend Think You're A Nice Guy?(00:17:16) - What Is Niceness In Your Relationships?(00:20:09) - Gayman's Brotherhood: Connection Circles(00:20:54) - Why Being a Nice Guy Backfires in Dating(00:23:16) - Matt Says Being Honest In Dating Backfires(00:28:19) - In the Elevator With Michael(00:29:38) - Gay Men on Dating and Relationships(00:30:19) - How to Shift From Being Nice to Being Chosen(00:35:02) - How To Be With Yourself(00:39:06) - Be Candid With Yourself(00:42:15) - Michael Jackson on Not Being Like Everyone(00:45:34) - Matt on Not Being the Nice Guy(00:48:20) - Thank You!

Hookups get a bad rap as shallow, transactional, or disconnected. But what if they could actually become a space for growth, awareness, and real connection? In this episode, we’re advocating for shift from default, unconscious hookups  to something more intentional, honest, and grounded. We explore how hookup culture can either reinforce negative patterns or become a powerful mirror for your patterns, desires, boundaries, and capacity for intimacy. We talk about: Why hookups aren’t the problem—but how we show up in them can be The difference between unconscious vs. intentional hookups How to bring honesty, communication, and authenticity into casual sex How our own hookups have evolved over time Practical ways to make hookups more enjoyable, respectful, and connected—for everyone involved This isn’t about judging hookup culture or pretending it should be something it’s not. It’s about raising the standard of how you show up—so even casual encounters can feel aligned, present, and real. Today's Hosts: Matt Landsiedel Michael DiIorio - Take the 360° Self-Review for Gay Men 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. Chapters (00:00:00) - How To Elevate Your Hookup Culture(00:02:22) - The Pros and Cons of Hookup Culture(00:05:50) - What are the cons of hookup culture?(00:07:12) - How Gay Men View Their Hookups(00:11:36) - No More Sex: We Need Love(00:13:34) - What Makes A Hookup Good For You?(00:17:38) - "Honesty Is What Makes A Hookup Good"(00:21:15) - Demisexual Guy On Grindr(00:25:31) - Demisexual People Talk About Their Sexualities(00:26:00) - Michael On His Hookups...(00:29:59) - Elevating Your Hookups(00:31:16) - PODCAST: Please support the community