Pretty Likkle Jacket

What happens when your father is more myth than memory? In this emotionally charged episode, we shift gears as Richard vulnerably opens up about his fragmented relationship with his dad—a man known more for his absences than his presence. From childhood consequences tied to inherited trauma, to silent reunions and unexpected moments of grace, Richard recounts the complexity of seeking love from a man who was never fully there.

As Fa...

In this vibrant episode of Pretty Little Jacket, we’re live from Antigua with Senator Michael Freeland, Deputy Chairman of the Festivals Commission—and the heartbeat behind a bold new era of politics and culture in the Caribbean. From restoring community representation in St. George to redefining what it means to truly serve the people, Senator Freeland shares a powerful grassroots vision rooted in empowerment, pride, and unity.

But...

What happens when two people share decades of inside jokes, emotional intimacy, late-night hotel room talks, and unwavering support — but never cross the romantic line? In this episode, Richard and Kathy peel back the curtain on a friendship that’s confused strangers, shocked friends, and even made spouses raise an eyebrow. From college days and VHS film projects to tearful hospital visits and luxury getaways, their journey is full...

What happens when you finally visit your best friend’s hometown after 30 years? In this laugh-filled and unexpectedly touching episode of Pretty Likkle Jacket, Richard takes his first trip to Antigua—and everything from the infamous “titty bread” to a goat with bodybuilder muscles becomes part of the adventure.

Between the jokes, beach bloopers, and flirtatious locals, a deeper story unfolds—one of friendship, family, and seeing whe...

What happens when the man you thought was just a family friend turns out to be your father? In this powerful and soul-stirring episode of Pretty Likkle Jacket, we’re in Antigua celebrating a 50th birthday and unpacking a lifetime of hidden truths. Host Kathy is joined by her father Sean—whom she only officially met in her 20s—and friend Richard, as they peel back the layers of growing up as “outside child” in a culture that draws s...

In this deeply moving episode of Pretty Likkle Jacket, Kathy shares a courageous story from her youth—a 13-year-old girl's solo journey across the sea to find her estranged father. What started as a fact-finding mission became a profound moment of discovery, emotional reckoning, and unanswered questions. Hosts Kathy and Richard dive into the impact of generational silence, the weight of childhood trauma, and the cultural dynam...

In the very first episode of Pretty Likkle Jacket, Kathy and Richard take you on a rollercoaster ride of laughs, love, and life’s unexpected truths. From their hilariously unforgettable first meeting (spoiler: it involves stolen Ray-Bans and an elevator) to the raw and emotional journey of discovering one’s true paternity, this episode lays the foundation for a podcast that’s as real as it gets.

Kathy opens up about what it means to...

Hey everyone, I'm Kathy Wint and welcome to Pretty Little Jacket. Richard and I have been friends for nearly 30 years, so we've shared a lot. He knows all my skeletons and have actually helped me bury a few. 

So we're here to dive deep into the secrets, betrayals, and hidden truths that so many of us carry. We've both experienced firsthand how these discoveries can reshape who we are. And we want to create a spac...