Gay Men Going Deeper

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.

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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:

This is a grounded conversation about growth, self-awareness, and becoming more fully yourself — not perfectly healed, but more conscious, honest, and free.

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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:

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.

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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:

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.

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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:

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.

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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:

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 

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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:

Self-trust doesn’t mean you stop caring what people think- it means their reaction no longer gets to decide who you are.

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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:

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.

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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:

If you’ve ever felt overlooked, under-appreciated, or stuck in the friend-zone, this one will hit.

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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.

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