{"id":4943,"date":"2026-06-06T22:04:56","date_gmt":"2026-06-06T22:04:56","guid":{"rendered":"https:\/\/login9ja.com\/global\/how-jfk-jr-once-propositioned-princess-diana-and-the-part-of-her-body-he-admired-most\/"},"modified":"2026-06-06T22:04:56","modified_gmt":"2026-06-06T22:04:56","slug":"how-jfk-jr-once-propositioned-princess-diana-and-the-part-of-her-body-he-admired-most","status":"publish","type":"post","link":"https:\/\/login9ja.com\/global\/how-jfk-jr-once-propositioned-princess-diana-and-the-part-of-her-body-he-admired-most\/","title":{"rendered":"How JFK Jr. once propositioned Princess Diana &#8212; and the part of her body he admired most"},"content":{"rendered":"<p><img decoding=\"async\" src=\"https:\/\/pagesix.com\/wp-content%2Fuploads%2Fsites%2F3%2F2026%2F06%2F130012036.jpg?quality%3D90%26strip%3Dall\" \/><\/p>\n<div>\n<p>John F. Kennedy Jr. once propositioned Princess Diana at a private meeting held at the Carlyle Hotel in December 1995, but the meeting was anything but romantic.<\/p>\n<p>The late political scion reached out to Diana to ask her if she would be a cover star of his new political lifestyle magazine, George.<\/p>\n<p>\u201cJohn had brought along with him several ideas for the cover shoot,\u201d writes Caroline Hallemann in her new book, \u201cThe Kennedys and the Windsors,\u201d <a href=\"https:\/\/www.dailymail.com\/news\/article-15877399\/jfk-jr-kennedy-princess-diana-propositioned-body-carolyn-bessette.html\" target=\"_blank\" rel=\"noopener\">per Daily Mail<\/a>. <\/p>\n<p>\u201cOne featured her wearing a three-corner hat like one from the Revolutionary War, another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers.\u201d <\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>John F. Kennedy Jr.(seen here attending an American Jewish Committee gala in 1997)  once propositioned Princess Diana in a top secret meeting to be the cover star of his political lifestyle magazine George, according to a new book.   <span class=\"credit\">Ron Galella Collection via Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>But Diana (seen here attending a A Gala Evening In Aid Of Cancer Research At Bridgewater House) wasn\u2019t interested in being featured in the new venture.   <span class=\"credit\">Tim Graham Photo Library via Getty Images<\/span><\/figcaption><\/figure>\n<aside class=\"single__inline-module aligncenter wp-block-nypost-editor-primary-tag\">\n<\/aside>\n<p>But unfortunately for Kennedy, the princess \u2014 who tragically died in a car accident the following year \u2014 had already decided she was uninterested in being featured in the magazine before even hearing his ideas.  <\/p>\n<p>\u201cShe needed the magazine to be a success before she\u2019d publicly front it,\u201d writes Hallemann, \u201cand even with a Kennedy at the helm of the publication, that was hardly a guaranteed prospect.\u201d<\/p>\n<p>Halleman claims Diana told Kennedy: \u2018Well, you know, this is all very nice, John. Thank you. But I hope you\u2019ll forgive me if I don\u2019t take up the opportunity this time, but would love to maybe for your 50th or your 100th issue or something.\u201d<\/p>\n<p>When Kennedy got back to the George offices, he allegedly told employees of Diana\u2019s shut down but admitted he was still taken by her this feature on the princess. <\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>The royal (pictured here sitting on a step at her home at Highgrove House in 1986) allegedly told Kennedy, she would \u201clove to maybe for your 50th or your 100th issue or something.\u201d <span class=\"credit\">Tim Graham Photo Library via Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>After being turned down, Kennedy allegedly told staffers Diana (seen here wearing a short black cocktail dress attending a gala in 1994) \u201csaid no,\u201d but \u201cshe had a great pair of legs.\u201d  <span class=\"credit\">Getty Images<\/span><\/figcaption><\/figure>\n<p>\u201cWell, she said no,\u201d Kennedy told them. \u201cBut she had a great pair of legs.\u201d<\/p>\n<p>As for why she still chose to take the meeting with Kennedy, one theory is because Diana greatly admired Kennedy for the way he carried himself in the public eye and hoped her eldest son, William \u2014 who was just barely a teenager at the time \u2014 would adopt some of his admirable qualities. <\/p>\n<p>\u201cI\u2019m hoping he\u2019ll grow up to be as smart about it as John Kennedy Jr,\u201d Diana told magazine editor Tina Brown \u2014 who interviewed the princess just weeks before her death \u2014 of William, according to her former assistant Patrick Jephson.<\/p>\n<p>\u201cI want William to be able to handle things as well as John does.\u201d<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>The late royal (pictured above at a meeting with  Paula Dos Santos) is said to have to taken the meeting likely because she admired Kennedy\u2019s handling of the press.  <span class=\"credit\">Tim Graham Photo Library via Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>At one point, Diana told a reporter she hoped Prince William (seen here with his mother and brother Prince Harry on their first day of school) would \u201cgrow up to be as smart about it as John Kennedy Jr.\u201d  <span class=\"credit\">Tim Graham Photo Library via Getty Images<\/span><\/figcaption><\/figure>\n<p>Another reason she allegedly wanted to meet with Kennedy \u2014 who had been recently named the Sexiest Man Alive at the time \u2014 was to make her <a href=\"https:\/\/pagesix.com\/2026\/05\/28\/royal-family\/why-princess-diana-and-sarah-ferguson-had-a-falling-out\/\">sister-in-law Sarah Ferguson jealous<\/a>. <\/p>\n<p>\u201cThe princess\u2019s wish to meet America\u2019s most eligible bachelor owed more than a bit to the fact that he was at the time a particular pin-up of Fergie\u2019s,\u201d Jephson later wrote.<\/p>\n<p>The late royal isn\u2019t the only celebrity once woo\u2019d by the political charmer. <\/p>\n<p>Just last month, Madonna named JFK Jr. as <a href=\"https:\/\/pagesix.com\/2026\/05\/28\/celebrity-news\/madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat\/\">her \u201cbest d\u2013k down\u201d<\/a> during her conversation with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez and ID\u2019s Marcello Gutierrez. The stars briefly dated in the 1980s. <\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>Though it wasn\u2019t a romantic meeting, John famously settled down with Carolyn Bessette Kennedy (both pictured above holding hands).  <span class=\"credit\">Ron Galella Collection via Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-large\"><figcaption>They were married from 1996 until they tragically died in a plane accident in 1999. (Seen here is JFK Jr. giving Carolyn a smooch on the cheek).  <span class=\"credit\">Getty Images<\/span><\/figcaption><\/figure>\n<p>One of Kennedy\u2019s former close pals described the short-lived romance as \u201ctotally a fling\u201d in \u201cJFK Jr.: An Intimate Oral Biography\u201d by RoseMarie Terenzio and Liz McNeil, which came out in 2024. \u201cNothing more. Barely a fling at that.\u201d<\/p>\n<p>Kennedy famously ended up with his wife Carolyn Bessette Kennedy, whom he married in 1996. Their <a href=\"https:\/\/pagesix.com\/2026\/02\/13\/entertainment\/real-story-behind-jfk-jr-and-carolyn-bessette-love-story-show-passion-for-danger\/\">tumultuous love story <\/a>was most recently depicted on the silver screen with FX\u2019s \u201cLove Story,\u201d which premiered in February. <\/p>\n<p>Tragically, John and Carolyn died in 1999 when John lost control of their small plane. <\/p>\n<\/p><\/div>\n<p><a href=\"https:\/\/pagesix.com\/2026\/06\/06\/royal-family\/how-jfk-jr-once-propositioned-princess-diana-and-the-part-of-her-body-he-admired-most\/\" target=\"_blank\">Source link<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>John F. Kennedy Jr. once propositioned Princess Diana at a private meeting held at the<\/p>\n","protected":false},"author":1,"featured_media":4944,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[3],"tags":[],"class_list":["post-4943","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-entertainment"],"jetpack_featured_media_url":"https:\/\/login9ja.com\/global\/wp-content\/uploads\/2026\/06\/130012036.jpg","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/4943","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/comments?post=4943"}],"version-history":[{"count":0,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/4943\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media\/4944"}],"wp:attachment":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media?parent=4943"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/categories?post=4943"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/tags?post=4943"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}