Cool Conversations with Pressley
Welcome to Cool Conversations! On this show, me and my famous friends are going to get real, raw, and talk about some hard truths and "uncool" things that we all go through, because we need a space for us, by us, and where we can connect on things affecting our generation. Make sure to check me out on all socials @pressley and get more clips and BTS content at @coolconvospod and let me know what you want to hear us chat about!
Episodes
May 21, 2026 • 47 mins
In this episode of Cool Conversations, Griffin McIntyre joins us to talk about what it’s really like chasing a dream before the world sees the hard work behind it. From self-doubt and staying motivated to making music and trusting the process, we dive into the highs, lows, and reality of pursuing a passion while still figuring it all out.
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May 7, 2026 • 38 mins
In this episode of Cool Conversations, we are sitting down with athlete and entrepreneur Hercy Miller and diving into what it really means to “find your why” as a teen or young adult. From feeling lost and overwhelmed to discovering passions, purpose, and personal growth, we’re talking about the pressure to have life figured out—and why it’s okay if you don’t. Join us for an honest conversation about identity, comparison, chasing d...
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April 9, 2026 • 42 mins
In this episode of Cool Convos, we sit down with Janice Brown to talk about what it really means to grow up outside of what people call “normal.” From navigating an unconventional childhood to feeling caught between two worlds, Janice opens up about the moments that shaped her, the pressures people don’t always see, and how she’s learned to redefine “normal” on her own terms. It’s an honest conversation about identity, perspective,...
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March 26, 2026 • 40 mins
In this episode of Cool Convos, Raphael Luce joins us for “The Plot Twist Years”—a real, unfiltered conversation about navigating unexpected turns, redefining identity, and growing through the moments that don’t go as planned. From career shifts to personal evolution, it’s all about embracing the chaos and finding meaning in the in-between.
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March 12, 2026 • 49 mins
In this episode of Cool Convos, Ava Jean dives into the idea that different people experience different sides of us. She talks about boundaries, growth, and why it’s okay that not everyone gets the same version of who you are. Through honest reflections and real-life moments, the conversation explores authenticity, self-respect, and how evolving as a person can change the way others see you.
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February 19, 2026 • 44 mins
In this honest and heartfelt episode of Cool Convos, Preslee Faith opens up about the gap between the life she imagined and the person she’s growing into. From childhood dreams to unexpected detours, she shares the lessons, identity shifts, and quiet realizations that shaped her journey. It’s a real conversation about letting go of who you thought you had to be—and embracing who you’re becoming instead.
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February 5, 2026 • 34 mins
In this episode, Brooklyn talks about growth that happens offline. We talk about healing in private, letting change be slow and unseen, and choosing real peace over performative progress—proving that the most meaningful glow-ups don’t need an audience.
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January 22, 2026 • 51 mins
Why We Feel Everything So Deeply is a real, honest Cool Convos episode with Dylan Hoffman about sensitivity, emotions, and feeling everything at full volume. Together, we unpack why some of us feel so deeply, how that affects creativity and growing up, and why being emotional isn’t a weakness—it’s a superpower.
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January 8, 2026 • 37 mins
In this episode of Cool Convos, Pressley and actor Lumi Pollack talk about chasing big dreams without burning out. From navigating pressure in the entertainment industry to choosing rest, patience, and presence, they explore why slowing down doesn’t mean giving up — it means moving with intention. A refreshing conversation about balance, timing, and trusting your own pace.
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December 18, 2025 • 36 mins
In this episode of Cool Conversations, Pressley sits down with Julian Lerner, a fast-rising talent whose charm and screen presence is taking over film, television, and stage. Lerner talks chasing dreams, exploring passions, and of Broadway debuts.
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November 27, 2025 • 48 mins
In this episode, Pressley talks to Kenzi Richardson about her experience as a child actor working in the entertainment industry. From booking her titular role on Vampirina: Teenage Vampire (2025) to the hardships of growing up under the scrutiny of the public eye. Kenzi opens up about her journey with self confidence and staying true to herself. Pressley and Kenzi give advice on how to take failures in stride and use them as an ...
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November 20, 2025 • 51 mins
In this episode, Pressley talks to Raegan Revord about growing up a child actor and navigating life under a spotlight. Raegan dives deep into her personal experience working on the set of a hit TV show as a kid and the people she has met along the way who have left a lasting impression on her. Pressley and Raegan offer heartfelt stories and guidance on discovering who you are, all while the world is watching.
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November 6, 2025 • 47 mins
In a world that moves fast and compares even faster, it’s easy to feel like you’re falling behind. But what if your path isn’t meant to look like anyone else’s? In this episode, Pressley sits down with actor and artist Jadah Marie to talk about slowing down, trusting your own pace, and finding peace in the in-between.
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October 30, 2025 • 28 mins
In this episode, Pressley chats with Deja Clark for an honest, down-to-earth conversation about what it really means to grow into yourself. Deja opens up about navigating identity, purpose, and the pressure to have it all figured out. She talks about the moments that shaped her, the lessons she’s still learning, and the importance of staying true to who you are—on and off the screen.
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October 23, 2025 • 45 mins
Today we are joined by actress and performer Carmen Sanchez for a conversation about why working together always wins over tearing each other down. They dive into what collaboration really looks like in the entertainment industry, how to celebrate other people’s wins without losing your own shine, and the power of building genuine relationships. Carmen also shares her own experiences, behind-the-scenes lessons, and why she believes...
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October 16, 2025 • 63 mins
This week we sit down with actress and singer Jenna Davis to talk about the side of social media most people don’t see. Jenna opens up about the pressure to appear perfect online while juggling the realities of her career, friendships, and growing up in the public eye. She shares behind-the-scenes stories from her work, what her real life looks like off camera, and how she’s learning to separate her true self from the highlight ree...
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October 9, 2025 • 42 mins
Today we got real with creator Markell Washington for an unfiltered conversation about life beyond the screen. Markell opens up about who he really is behind the viral videos, sharing stories and struggles that fans don’t always see online. From the pressure of likes and followers to discovering his true self outside of social media, he talks about growth, vulnerability, and what it means to be authentically you. This episode is ab...
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October 2, 2025 • 31 mins
Today we sat down with singer Liamani to talk about what it really feels like to grow up in the spotlight—the in-between stages, the pressure to figure things out, and why no one really talks about the awkward middle. They also dive into Liamani’s new projects, her creative process, and how chasing passions while growing up comes with its own challenges and breakthroughs. This episode is all about embracing change, owning your grow...
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September 25, 2025 • 56 mins
In this week's episode, we chatted with singer-songwriter Haven Madison about the truth behind “having it all together.” From navigating self-doubt to the pressure of looking perfect online, they open up about the messy, unfiltered side of chasing dreams. Haven shares how she balances confidence with vulnerability, and why admitting we’re all just figuring it out might be the most freeing thing of all.
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September 18, 2025 • 40 mins
Welcome back to Season 2! To kick things off, we sit down with actress Catherine Bradley to talk about finding beauty in the everyday. From making the most of ordinary moments to shifting your perspective when life feels routine, they dive into how “romanticizing real life” can change the way you see yourself and the world around you. Catherine shares personal stories, simple mindset shifts, and why slowing down to notice the littl...
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