gay dating

How to Elevate Your Hookups

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: 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: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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The Daddy Issue: Our Relationships With Our Dads

For many gay men, our relationship with our dad is one of the most defining- and least talked about. In this episode, we explore the nuances of our relationships with our fathers through three core questions: From there, we go deeper into family dynamics, cultural expectations, and the different expressions of love and acceptance between fathers and their gay sons. We get into physical affection between fathers and sons, how much access we give them into our lives, and the boundaries we set as adults. We also explore how these early relationships can shape the kinds of men we’re attracted to… and the patterns we carry into dating and relationships. This is a grounded, honest conversation about the often complex and layered relationship between fathers and sons.  Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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“I Don’t Need Anyone”: Why Gay Men Struggle to Let Someone In

A lot of gay men take pride in being independent, self-sufficient and in control. But is there a shadow side? When the time comes to let someone in, ask for support, or even rely on others—it feels uncomfortable, exposing, even threatening. In this episode, we explore the spectrum between dependence, co-dependence, independence, hyper-independence, and interdependence—and why so many gay men get stuck at the far end of doing life alone. We talk about:  This isn’t about becoming dependent. It’s about learning how to find a happy middle ground where you can let someone in without losing yourself or pulling further away.  Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Masc for Masc: Preference or Internalized Homophobia?

When a gay man says he’s attracted to masculine men, is that simply preference… or could internalized homophobia be part of the story? In this episode, we unpack one of the most volatile conversations in the gay community. We explore what people actually mean when they say “masculine,” the masc and fem archetypes that shape gay culture, and how social conditioning around masculinity and femininity can influence attraction and identity. Most importantly, we tackle the question at the center of the debate: where is the line between genuine preference and internalized bias? In this episode we discuss: Join us for a nuanced conversation about masculinity, attraction, and the cultural forces that shape how gay men see themselves and each other. Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Flakey Gays: Why is Follow-Through So Hard?

The guy who constantly cancels plans, keeps things vague, or disappears when something better comes along — that’s flakiness: a pattern of not following through. In a culture of endless options and shifting feelings, has unreliability quietly become normal? And what does that actually say about us? In this off-the-cuff episode, we talk about: This isn’t just about the inconvenience of canceled plans. It’s about self-trust, stronger relationships, and the kind of man you’re practicing becoming. Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Is Romance Dead in Gay Culture?

In a world of swipes, situationships, and high-intensity connections, romance can start to feel obsolete — replaced by sexual energy, emotional guardedness, or the safety of detachment. And yet many of us still long for thoughtfulness, depth, being chosen and choosing in return. In this episode, we explore why that part of us often gets buried under performance, fear of rejection, and modern dating norms — and what it actually takes to lead with romance instead of intensity. We talk about: This conversation is both a reality check and an ode to the intentional, courageous, thoughtful part of ourselves that still believes in romance. Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Courting

Courting

In a world where swiping on apps and instant gratification dominates, is there still room for the timeless art of courtship? Join us on this episode of Gay Men Going Deeper as we explore the concept of courtship in the digital age. Some of the topics we’re covering in this episode include:  Join us as we discover an age-old approach to fostering intimacy, trust, and emotional connection. We’re sharing personal anecdotes, insights, and tips for slowing down your approach. Whether you’re a hopeless romantic or a skeptic, get ready to shake up your understanding of romance, connection, and the pursuit of love. Today’s Hosts: Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Another “Failed” Relationship (Navigating Gay Dating)

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In this episode Matt speaks with Indie Author and Counselor, Jonathan Lee about dating as a gay man. Jonathan wrote his debut book 40 Single Gay where he over-shares his experience in the hostile gay dating world and what he learned about himself through the process. Matt and Jonathan unpack everything from hookup culture and non-monogamy, to intimacy and how to get our emotional needs met as gay men.  Here are some of the concepts they explored in this episode: If you find yourself lonely and frustrated with the gay dating scene and hook up apps, this episode may be just what you need. Don’t miss this episode!🎙️📺 Today’s Hosts: Jonathan Lee:Instagram Matt Landsiedel:InstagramWebsite Watch this ep on YouTube – Connect with us – Join the private Facebook community including access to monthly group Zoom calls Take our “Building Better Relationships” course Take our “Healing Your Shame” course Coaching Collection – Get lifetime access to 2 courses, 45 coaching videos, and 2 workshop series Follow us on Instagram GayMenGoingDeeper.com Support the Show – viewer and listener support helps us to continue making episodes

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Sharing NSFW Pics

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In this provocative episode of Gay Men Going Deeper, Michael DiIorio and Pepper pushing boundaries, sparking discussion, and providing helpful tips on sharing NSFW pics. Some of the topics we’ll be covering today are: Join us for this entertaining episode where we celebrate sexuality and self-expression while also considering the very real risks and drawbacks of the world NSFW pics.  Don’t forget to share with your friends – this episode is not to be missed! 🔞🏳️‍🌈📸 Connect with Pepper: Connect with Michael: Related episode: Being Kindr on Grindr 📺 Watch this ep on YouTube Take the Attachment Style Quiz! – Connect with us – Join the private Facebook community including access to monthly group Zoom calls Take our “Building Better Relationships” course Take our “Healing Your Shame” course Coaching Collection – Our 2 courses + 45 coaching videos, and 2 workshop series Follow us on Instagram GayMenGoingDeeper.com Support the Show – viewer and listener support helps us to continue making episodes

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Friends with Benefits

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Friends with benefits (FWB) is a type of relationship where you can enjoy the sexual benefits of a relationship without the expectation of long-term commitment.  Navigating the blurred lines between friendship and sexual intimacy is a complex and potentially risky endeavour.  In this episode, Michael DiIorio and Pepper of The Gay Good discuss the nuances of having Friends With Benefits. They’ll discuss topics such as: Join in for this revealing discussion that will give you greater clarity and understanding of this common relationship structure.  Watch this episode on YouTube Find us on Instagram: Resources Gay Men Going Deeper Coaching Collection Building Better Relationships course Healing Your Shame course Take the Attachment Style Quiz! Connect With Us Join the Facebook community and monthly Group Zoom call You can also follow us on Instagram and TikTok Support the Show

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