In part one of this conversation on Pretty Likkle Jacket,, Kathy sits down with her longtime friend Ricardo, with Arlene in the studio too, for a raw, funny, and heavy look at the backstory behind the guy everyone thinks has it all together. Ricardo shares what it was like growing up in the British Virgin Islands with roots in St. Kitts and Nevis, where fighting at school felt like survival and responsibility started young.

He talks about a complicated father, harsh discipline, and the family dynamics that shaped his work ethic, his outlook on relationships, and his need to protect his energy. Ricardo also opens up about witnessing abuse at home, the promises his mother asked him to keep, and how those lessons carried into adulthood, including fatherhood and caring for his mom today.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

In Part 2 of our conversation with Gwen, we go even deeper into the truth of family patterns, emotional wounds, and what it really takes to heal from the inside out. Kathy and Richard sit with Gwen as she opens up about her complicated relationship with her father, the pain of feeling unwanted, and the lifelong impact of growing up without affection.

Gwen shares raw, powerful stories about breaking generational trauma, rebuilding her emotional health, walking away from alcohol, and choosing herself after years of carrying the weight of other people’s choices. She talks about the courage it takes to forgive without forgetting, the importance of real hugs and real connection, and why energy and intention matter so much in every relationship.

This episode is a reminder that healing is messy, choosing yourself is necessary, and your story can help someone else find their way. If you’ve ever struggled with family disconnect, feeling unseen, or learning how to set boundaries that protect your peace, Gwen’s honesty will meet you right where you are.

Listen in as we explore growth, heartbreak, resilience, and the beauty of reclaiming your own life.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

In Part 1 of this deeply moving two part series on Pretty Likkle Jacket, Kathy and Richard sit down with their friend Gwen as she begins sharing the story behind her strength, her humor, and the walls she learned to build early in life.

Gwen opens up about her childhood in Panama, growing up with a single mother, and the complicated relationship with a father who was present in name but absent in love. She reflects on waiting at the door with her backpack for a dad who never came, witnessing infidelity at only three years old, and the emotional weight she carried long before she understood it.

She also speaks about the cultural dynamics she grew up with, her mother’s resilience, the family patterns she later recognized, and the early experiences that shaped her understanding of love, trust, and belonging.

This episode sets the stage for a powerful continuation in Part 2 as Gwen opens up about immigration, trauma, survival, and the adult decisions that changed her life.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

This Thanksgiving week, Pretty Likkle Jacket revisits one of our most powerful and revealing conversations. In this re-air of Episode 8, Kathy shares the story that changed everything she thought she knew about family — the truth about Chester Ramsey, the man who spent Sundays with her family, and the secret that shaped her life without her knowing.

As many of us gather with family (or choose not to), this episode reminds us that togetherness isn’t always simple. In Caribbean households, secrets can run deep, loyalties can twist, and the truth has a way of showing up when we’re finally ready — or when tragedy forces it to the surface.

Kathy walks us through the shock, the grief, the subtle signs she missed, and the profound healing that followed. This Thanksgiving, we’re reflecting on the families we’re born into, the families we build, and the courage it takes to claim your own story.

Grab your leftovers, settle in, and re-experience one of our most unforgettable episodes.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

Kathy and Richard open the inbox and let it fly in a no holds barred Q and A that swings from playful to profound. What first drew them together and why the infamous sunglasses mattered. How their emotional bond works inside long term friendship and why vulnerability with the right person is not emotional cheating. Jealousy myths debunked and the truth about boundaries when you never cross the line. The hotel room question, the kiss question, and whether marriage would ever be on the table. Richard addresses his past marriage and confirms the girlfriend is very real while Kathy shares why she would only ever consider marriage under the right conditions.

Then the energy turns tender as they tackle letters about absent fathers finding biological family forgiveness fear and caregiving burnout. Richard reflects on his own dad and unseen battles while Kathy speaks to healing childhood wounds and choosing self care. They close with a quick glow up moment featuring Kathy’s simple skincare routine: water, exfoliate, moisturize, mind your business - plus a laser shoutout. Real talk, real laughs, real life said out loud.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

In this heartfelt and hilarious episode of Pretty Likkle Jacket, Kathy and Richard welcome Kathy’s sister, Kandy James, for an unforgettable conversation about family, secrets, and the surprising way they discovered their shared father. From summers in Antigua to unexpected introductions and messy aunts who spill the tea, Kandy opens up about finding out the truth at sixteen, meeting her dad, and the unbreakable bond she shares with her siblings—especially Kathy. Together they reflect on love, loss, laughter, and the healing power of family stories told out loud.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

Kathy and Richard return with Harria and Kathleen for part two of this unforgettable family story. What begins with one suitcase and a messy kitchen turns into a journey through dishes hidden under a bed, the three sister dress that fit everyone, five kids in one room, and a father torn between love and obligation. There’s laughter, tears, and the day the cutlass came out—marking a turning point for the whole family. Together they revisit the pain, the healing, and how faith and friendship helped them move from resentment to forgiveness.

If you’ve ever held on too long or loved someone from a distance, this conversation will remind you that it’s never too late to make space for love.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com

Kathy and Richard welcome two of their dearest friends, Harria and Kathleen, for a raw and riveting story that starts in the countryside of Clarendon, Jamaica and winds all the way to a Florida sugar cane village. They share what it meant to walk miles to school barefoot, wash feet at the river to save the one pair of shoes, stretch shop profits to feed seven kids, and carry the kind of resilience that only struggle can shape.

You will hear the real family history, from the father who worked in America, the second household, the long wait for papers, and the day five siblings landed in Miami expecting city lights and found themselves surrounded by endless cane and a commissary. There is culture shock, hard conversations about resentment and love, and the strength of a mother who did what she had to do.

It is laughter, side eyes, and truth telling in equal measure as Harria and Kathleen describe those first weeks in the camp, the messy kitchen they cleaned, and how they began to find their footing. Stay tuned for part two where the story continues with curtains and cutlass and even more lessons on family, grit, and grace.

Contact Kathy:
Instagram: @thekathywint
TikTok: @the.kathy.wint

Contact Richard:
Instagram: @dmellothe1
TikTok: @melltheirish
Website: www.blacktriadentertainment.com

Podcast Instagram:
@prettylikklejacket

Website:
www.prettylikklejacket.com