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

Kathy and Richard kick off with laughter and a jacket that will not cooperate, then dive into a real talk conversation about the difference between sex, intimacy, and chemistry. They unpack why intimacy is about trust, honesty, and being fully yourself, while chemistry is the spark and sex is only one expression of connection. They revisit the early days, complicated circumstances, separate beds, payphone calls, and the letters that still live in a time capsule. Rumors get addressed with love and clarity, and the friendship at the center of it all stands tall. If you have ever been told that a deep platonic bond is impossible, this one is for you. Come for the jokes, stay for the heart, and get ready for the troupe and Kathy’s sister in upcoming 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

In part two of our conversation with Curtis Anthony, Kathy and Richard continue an honest and powerful journey through the experiences that shaped his life. Curtis opens up about hidden struggles behind academic success, the turning point that led him to seek healing, and the lasting impact of his mother’s sacrifices.

He shares deeply about reconnecting with his father, breaking generational cycles, and the importance of creating safe spaces for men to embrace vulnerability and growth. This heartfelt continuation of Curtis’s story is filled with wisdom, courage, and the reminder that true strength comes from doing the work to heal.

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 a very special guest and childhood friend, Curtis Anthony, for a heartfelt trip down memory lane. From growing up in Antigua, sharing classrooms, choirs, and competitions, to navigating life changes, separation, and the challenges of reuniting with family, Curtis opens up about the moments that shaped him. Together they share stories of friendship, resilience, and the unexpected lessons learned along the way.

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

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

Podcast Instagram
@prettylikklejacket

Website
https://www.buzzsprout.com/2464335/about