confidence

Perfectionism, Pressure, and the Gay Overachiever

You know the type — ambitious, perfectionistic, and always striving to do more and be more… yet secretly fuelled by pressure, anxiety, and fear. In this episode, Michael is joined by special guest Scott Stirrett as they share their own stories of hustling for achievement and how they’ve learned to stay ambitious without destroying themselves in the process. Together, they unpack how perfectionism, internalized shame, and the need for external validation can be ways we attempt to outrun our insecurities — and pivot toward ambition that’s healthy, sustainable, and soul-driven. Topics covered in this episode: By the end of this episode, you’ll be inspired to pursue success in a way that keeps you driven and impactful — without burning yourself out — and to start measuring your worth from the inside out. Today’s Guest: Scott Stirrett Today’s Host: Michael DiIorio Support the Show – viewer and listener support helps us to continue making episodes – CONNECT WITH US – – LEARN WITH US –

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Feeling Your Emotions

Matt Landsiedel

What happens when we avoid feeling our emotions? In this episode, we explore the importance of emotional awareness: tuning in instead of checking out. We share what happens when we suppress our feelings, and how to navigate the tough ones with compassion and care. We also explore: Whether you’re someone who bottles it all up or someone who feels everything all at once, this conversation will give you insight and tools to better understand yourself and others. 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 Power of No

Michael DiIorio

Many gay men struggle with saying no, setting boundaries, or engaging in difficult conversations due to deep-seated people-pleasing tendencies and fear of conflict. But staying silent often leads to resentment, burnout, or feeling disconnected from your true self. As recovering people-pleasers themselves, Matt and Michael have plenty to share about their own journeys toward becoming more assertive in their boundaries. In this episode, we dive into: If you’ve ever found yourself saying “yes” when you really meant “no” or avoiding confrontation at the cost of your own needs, this conversation is for you! 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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Level Up Your Dating Profile

Michael DiIorio

Is your dating profile truly showing the best version of you? In this episode of Gay Men Going Deeper, we’re diving into the do’s and don’ts of crafting a profile that is aligned with what you’re truly looking for. On the apps, your profile is the first impression that counts so whether you’re looking for love, fun, or meaningful connections, it matters. Some topics we’ll discuss: Tune in for tips, insights, and takeaways to help you create a profile that attracts the right matches and reflects the real you. Join Michael’s FREE one-time workshop where we’ll give your dating profile a glow up: The Dating App Glow Up 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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Hookup Culture and Self-Discovery

Michael DiIorio

Whether you love it or hate it, hookup culture is a part of gay culture—and if you look a little closer, it just might be a powerful tool for self-discovery. In this episode, we’re diving into the real-life lessons our casual hookups taught us about confidence, boundaries, and self-love. We’re going beyond the benefits and drawbacks of hookup culture, and sharing how these experiences have shaped who we are This episode is for anyone curious about navigating hookup culture with more clarity and intentionality. Some of the topics we’ll be covering: Join us as we break down the skills that casual sex can build (yes, they’re easily transferable to other areas of life!) and how you can approach hookups in a way that feels empowered, intentional, and true to yourself. Reflection Questions in the Show: Michael’s 3 Questions (listen to the episode to learn when and how to use these!) 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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Perfectionism, Pressure, and the Gay Overachiever

Feeling Your Emotions

The Power of No

Level Up Your Dating Profile

Hookup Culture and Self-Discovery

Sex Positivity

Fake vs. Real Confidence

Self-Acceptance