"She felt empathy for him..." Inside Princess Diana’s Secret NY Encounter with JFK Jr. episode artwork

EPISODE · Jul 24, 2026 · 12 MIN

"She felt empathy for him..." Inside Princess Diana’s Secret NY Encounter with JFK Jr.

from A Right Royal Podcast · host Hello! Magazine Ltd

How did Princess Diana and JFK Jr. manage to meet in secret at the Carlyle Hotel without a single paparazzi finding out? 🤫 In this special live recording of the Right Roll Podcast from the Moxy Hotel in Chelsea, NYC, Andrea, Emmy, and Emily dive deep into Princess Diana’s profound, glamorous, and emotional relationship with New York City. From her historic first solo trip at age 27 to her groundbreaking visit to Harlem Hospital's AIDS unit, we trace the fashion, the philanthropy, and the moments that defined her American legacy. Plus, we are joined by an incredible insider who shares the never-before-heard, behind-the-scenes story of planning a top-secret meeting between the world's most famous princess and John F. Kennedy Jr. For a magazine cover pitch. Hear about the ridiculous disguise ideas, the paparazzi evasion tactics, and exactly what JFK Jr. Said about Diana when he walked out of that hotel room. 👑✨| ✨ WANT TO WATCH THE FULL EPISODE? ✨ This is a shortened preview of our live recording! Access the complete, uncut episode right now by signing up for Hello VIP here: https://www.hellomagazine.com/subscribe/ Chapters: 0:00 - Welcome to the Right Roll Podcast Live from NYC! 0:33 - Princess Diana’s First Solo Trip to New York (Age 27) 1:35 - Fashion, Philanthropy, and Breaking Stigmas at Harlem Hospital 2:27 - The $5.7M Dress Auction & William’s Brilliant Idea 3:15 - Icon Meets Icon: Meeting Mother Teresa & The Wet-Look Hair Trend 4:30 - Planning the Ultimate Secret Meeting: JFK Jr. & Princess Diana 5:34 - Evading the Paparazzi: The Carlyle Hotel Caper 7:34 - What Happened in the Room? JFK Jr.’s First Impressions of Diana 8:55 - Why Diana Said No to the Magazine Cover (and Madonna's Outrageous Pitch!) 10:38 - Watch the Full Episode on Hello VIP Don't forget to LIKE, COMMENT with your favorite Princess Diana fashion moment, and SUBSCRIBE for more deep dives into royal history! #PrincessDiana #JFKJr #RoyalHistory #NewYorkCity #TheCarlyle #DianaInNewYork #Podcast Learn more about your ad choices. Visit megaphone.fm/adchoices

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"She felt empathy for him..." Inside Princess Diana’s Secret NY Encounter with JFK Jr.

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