Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective. Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time. This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between. Visit us at www.GayMenGoingDeeper.com Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN
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, ...
Being sexually open isn’t the same as being sexually honest. In a culture that celebrates sex, many gay men still struggle to feel aligned with what they truly want, without shame or pressure.
In this off-the-cuff conversation, we explore what it really looks like to own your desires without shame, performance, or pressure. We unpack how conditioning, fear, and expectations can quietl...
In gay culture, “body count” refers to how many people you’ve slept with. And whether it’s high or low, it often feels like a no-win situation. Have a low body count and you risk being seen as repressed, inexperienced, or undesirable. Have a high one and you’re either celebrated… or slut shamed.
In this off-the-cuff conversation, we unpack why gay men are stuck between purity culture and...
Gay culture rewards visibility, desirability, and dominance, so a lot of what looks like confidence is actually performance under pressure. In this episode, we unpack the myths of self-confidence gay men inherit and what real confidence looks like when no one’s watching.
In this conversation, we explore:
Everyone says they want a “slow build” in dating… right up until chemistry hits and judgement leaves the building.
In this off-the-cuff episode, we talk about why moving fast feels so intoxicating, what actually happens in your nervous system when you do, and how speed can quietly hijack discernment, attachment, and self-trust. We share personal stories, name the difference between ex...
Gay Men Going Deeper has never done an episode about a TV show before. There’s a reason we did this one. Heated Rivalry isn’t just popular. It landed at a very specific cultural moment for gay men, and the response to it points to something bigger than whether people liked the plot.
In this off-the-cuff conversation, Michael and Matt explore why this story resonated so strongly, what ...
It’s a question many gay men quietly carry… especially after heartbreak, disappointment, or years of trying.
In this episode of Gay Men Going Deeper, we put on our coach hats and unpack why this belief takes hold, how shame and self-protection can block love without us realizing it, and what actually helps us become more open to connection again.
This conversation isn’t about forcing pos...
This episode of Gay Men Going Deeper is less of a casual conversation and more of a confidence masterclass. One you’ll likely want to come back to again and again.
We break down what real, unshakeable confidence actually is (and what it isn’t). Not the loud, performative kind, but the grounded confidence that comes from self-trust, self-compassion, and emotional regulation.
We talk hones...
In this episode, we’re breaking down one of the biggest dating myths gay men love to repeat: “My standards are too high.” But sometimes the problem isn’t what you want, it’s what you allow.
We get into the real difference between standards and boundaries, why attraction wipes our memory clean, and how low boundaries quietly reveal your level of self-worth. If you’ve ever said you want em...
In this episode, Michael and Matt get personal about what we love about being single, how we knew we were ready to start dating again, and what we want to experience differently this time around. We talk about flirting on apps, dating in 2026, and all the messy, exciting parts of putting yourself back out there when you’re ready to mingle.
Some of the topics we cover in this episode are...
Why does attraction fade- and what can we do about it? In this episode, we get real about attraction in long-term relationships. The spark doesn’t always burn forever, and losing sexual interest doesn’t mean the relationship is doomed. We talk about why attraction naturally shifts over time and how couples can ignite intimacy.
We explore:
After unpacking our culture’s obsession with “perfect” bodies, this week we’re flipping the script. In this episode, we’re celebrating what’s actually hot: the things that don’t get enough love in the gay world. We’re talking dad bods, wrinkles, kindness, confidence, awkward charm, conversational skills, and all the real stuff that makes someone magnetic.
Some of the things we’re talkin...
From the gym to social media, gay men are constantly surrounded by images of the “ideal” body. But what does all this perfection chasing actually cost us?
In this episode, we explore how body perfection culture impacts gay men on a deeper level: from belonging and self-worth to intimacy and identity.
We open up about our own journeys with body image— how we’ve moved from obsession t...
In this episode, we dive into what radical honesty really means- not the brutally blunt “telling it like it is” version, but the deeper, more vulnerable kind that lets you actually be known.
We explore why being honest is both terrifying and liberating, the subtle ways we still avoid it, and how honesty differs from harsh truth-telling. We share our own struggles with showing up hones...
Today we’re diving into one of the most iconic (and hilarious) parts of gay culture: labels.
In this episode, we unpack why gay men are so obsessed with categories like “twink,” “daddy,” “masc,” “otter,” “guy next door,” and every micro-label in between… and how these identities shape the way we date, belong, and see ourselves.
We explore:
Today we’re talking about The Slow Fade: that slow, quiet drifting apart where the messages get shorter, the replies slower, and the energy shifts until one day…it’s just silence.
In this episode, we’re unpacking:
What we want you to gain from this episode is the importance of non-sexualized, safe, and brave spaces for gay men to heal and grow together. By the end of this episode, you will be able to identify what a nest is, how you could benefit from one, and where to find or create one if you are interested in nesting.
The concepts and questions we explore in this episode are:
We all say we want love… but are we actually open to receiving it?
In this episode, we’re going deeper into what it really means to open your heart. From the subtle subconscious programming that keeps love at arm’s length to the sneaky ways we self-sabotage, we’re unpacking the hidden barriers that make intimacy feel unsafe (even when we crave it most).
You’ll learn:
Some of us don’t fall in love with people, we fall in love with an idea of them. The story, the potential, the fantasy of the perfect boyfriend who finally makes everything click. But that idealized version of love often keeps us chasing what looks right instead of what feels real.
In this episode, Michael DiIorio and therapist, Michael Pezzullo, explore how fantasy, perfectionism, an...
Why does joy feel so hard to hold onto? In this episode of Gay Men Going Deeper, we’re revealing the joy killers: those sneaky ways we sabotage happiness even when life is going well.
We explore:
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
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