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January felt like eight months long but we’re finally back with another episode.

The episode kicks things off with weekend recaps, Caribbean pop culture moments, Bad Bunny’s Grammy win, and the madness of modern dating — from misunderstood “karaoke dates” to financial red flags and Valentine’s Day expectations.

Episode Sponsor: CINICO

This episode is proudly sponsored by CINICO – Cayman Islands National Insurance Company, providing quality health insurance coverage and peace of mind for Caymanians and residents alike.

Your health matters — and CINICO is here to support you every step of the way.

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On this episode: The crew returns with unfiltered conversation—covering everything from fashion and cereal debates to work permits, politics, relationships, and ageing. Friend of the podcast Lana joins the table as the discussion jumps from Cayman issues to global headlines and social media drama, leading to heated takes on policy, scooters/insurance, U.S. politics, and the now-iconic “Mr. Earl” moment.
Plus, a special word from Cinco Insurance, reminding you why peace of mind matters on Cayman’s roads.

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00:00 – Opening Chat
01:00 – Food talk, cereal cravings
02:40 – 🎯 Cinco Insurance promo
03:18 – Welcome to Episode 154 & intro to the panel
05:00 – OG Lana joins the conversation
06:30 – Weekend recaps & everyday Cayman life
08:30 – Food safety debates & leftovers controversy
10:45 – Online bills vs old-school payments
14:00 – Work permits, population growth & the Cayman economy
18:00 – Jobs Caymanians won’t do & labour realities
21:00 – AFCON drama & football controversies
24:00 – Global politics, media narratives & the U.S.
29:00 – Immigration, human rights & border discussions
33:00 – Cost of living, food security & supply chains
36:30 – Desmond and Kristy breakup & public relationships
41:00 – Cheating, marriage, and public perception
46:00 – 💀 The “Mr. Earl” conversation
52:00 – Ageing, intimacy & relationship expectations
58:00 – E-scooters, insurance & government rollout issues
01:04:00 – Public transport, enforcement & road safety
01:10:00 – Parking chaos, urban planning & frustration
01:18:00 – Comedy, culture & social commentary
01:22:30 – Final thoughts & wrap-up

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On this episode: The crew kicks things off with fashion jokes that quickly turn into the birth of a new nickname, Eggplant Papi - setting the tone for a wide-ranging, unapologetic conversation.

From generational debates and “expert” culture to Starlink officially landing in the Cayman Islands, e-bike and scooter legislation, rising food costs, public transport frustrations, and the realities of living and working in Cayman.

The episode also features a deep and insightful conversation with Alyssa Gilbert, Caymanian creative and founder of WIK Magazine, as she shares her journey through fashion, media, creativity, mental health, and why so many Cayman creatives feel the need to leave in order to grow, with hopes of one day returning home.

The discussion closes with powerful commentary on financial literacy, money mules, online scams, social systems, and why common sense isn’t always common.

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