{"id":3851,"date":"2026-05-28T17:43:59","date_gmt":"2026-05-28T17:43:59","guid":{"rendered":"https:\/\/login9ja.com\/global\/madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat\/"},"modified":"2026-05-28T17:43:59","modified_gmt":"2026-05-28T17:43:59","slug":"madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat","status":"publish","type":"post","link":"https:\/\/login9ja.com\/global\/madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat\/","title":{"rendered":"Madonna says JFK Jr. was the best sex of her life&#8230; with a caveat"},"content":{"rendered":"<p><img decoding=\"async\" src=\"https:\/\/pagesix.com\/wp-content%2Fuploads%2Fsites%2F3%2F2026%2F05%2F128824471.jpg?quality%3D90%26strip%3Dall\" \/><\/p>\n<div>\n<p>Stiff competition!<\/p>\n<p>Asked recently to name her best-ever lay, Madonna said she was prepared only to rank the dead ones. But of all her extinct exes, she picked John F. Kennedy Jr.<\/p>\n<p>The Material Girl is promoting her new album, \u201cConfessions II,\u201d by working with Grindr. And instead of doing the usual press tour, she made a video with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID\u2019s Marcello Gutierrez asking the questions.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>Madonna said in a video for Grindr that the best sex of her life was with John F. Kennedy Jr. She was snapped with him at an event in Las Vegas in 1997. <span class=\"credit\">GTRES \/ Shutterstock<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>She was married to Sean Penn \u2014 shown here in New York in 1986 \u2014 during her fling with Kennedy. <span class=\"credit\">Getty Images<\/span><\/figcaption><\/figure>\n<aside class=\"single__inline-module aligncenter wp-block-nypost-editor-primary-tag\">\n<\/aside>\n<p>\u201cI\u2019m only going to name dead people,\u201d says the \u201cPapa Don\u2019t Preach\u201d superstar, before covering her mouth and whispering, \u201cJohn Kennedy Jr.\u201d \u2014 inciting a choral \u201cShut upppppppp!\u201d from the group so loud that the late scion may well have heard it.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>Raul Lopez, here at  the Fashion Scholarship Fund annual gala at the Glasshouse in March, asked who her best sex was with. <span class=\"credit\">Getty Images for Fashion Scholarship Fund<\/span><\/figcaption><\/figure>\n<p>Lending valuable journalistic context, Lopez adds, \u201cEveryone says his d**k was crazy and he was a good f**k.\u201d<\/p>\n<p>\u201cMmm hmm,\u201d Madonna confirms, with a inescapable degree of satisfaction.<\/p>\n<p>\u201cYou\u2019re the third person I\u2019ve heard say that,\u201d Lopez, who should perhaps be considered as Anderson Cooper\u2019s replacement on \u201c60 Minutes,\u201d said.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>JFK Jr .was dating model Christina Haag when they met. <span class=\"credit\">Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>\u201cSlave Play\u201d writer Jeremy O. Harris was among the group quizzing Madonna in the video. <span class=\"credit\">Getty Images for Vanity Fair<\/span><\/figcaption><\/figure>\n<p>The pair dated very briefly in the late 1980s.<\/p>\n<p>\u201cMadonna was totally a fling,\u201d one of Kennedy\u2019s close pals said in \u201c<a href=\"https:\/\/r.pagesixlink.com\/?btn_ref=org-282f0dd399864b44&amp;btn_url=https%3A%2F%2Fwww.amazon.com%2FJFK-Jr-Intimate-Oral-Biography%2Fdp%2F1668018519%3Ftag%3Dpagesix-20%26asc_refurl%3Dhttps%3A%2F%2Fpagesix.com%2F2024%2F07%2F16%2Fcelebrity-news%2Fwhy-jfk-jr-didnt-sleep-with-madonna-or-brooke-shields%2F%26asc_source%3Dweb\" target=\"_blank\" rel=\"noreferrer noopener\">JFK Jr.: An Intimate Oral Biography<\/a>\u201d by Rosemarie Terenzio and Liz McNeil, which came out in 2024. \u201cNothing more. Barely a fling at that<\/p>\n<p>The book claims they met\u00a0while he was dating actress Christina Haag and she was married to Sean Penn.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>Needless to say, Kennedy went on to marry Carolyn Bessette, seen together heading to Bubby\u2019s in 1997. <span class=\"credit\">Lawrence Schwartzwald<\/span><\/figcaption><\/figure>\n<p>The unnamed Kennedy friend says that Madonna came on to JFK Jr., \u201cand it was flattery \u2014 she was at the top of her game.\u201d<\/p>\n<p>It was \u201call about physical attraction, it wasn\u2019t going to be anything beyond that,\u201d the source claimed.<\/p>\n<p>Rather impressively \u2014 if the book is to be believed \u2014 Jon Jon won Madonna\u2019s boudoir blue ribbon (deceased category) without all the, er, usual tools at his disposal.<\/p>\n<p>\u201cThey didn\u2019t have the protection measures and she was very on top of HIV prevention,\u201d the pal explains.<\/p>\n<p>That didn\u2019t stop the couple from having \u201cfun in other ways\u201d and Kennedy remarking that the \u201cVogue\u201d singer had \u201cone of the most beautiful bodies he had ever seen.\u201d<\/p>\n<p>According to the book, many years later, Penn appeared on the December 1998 cover of Kennedy\u2019s George magazine, and the two had dinner.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>She currently dating Akeem Morris. They attended the Met Gala together earlier this month. <span class=\"credit\">Kevin Mazur\/Getty Images for The Met Museum\/Vogue<\/span><\/figcaption><\/figure>\n<p>The friend says that JFK Jr. assured Penn that \u201che never knew Madonna in the biblical sense.\u201d<\/p>\n<p>And, proving that he was from a family of lawyers, that may <em>very<\/em> <em>technically<\/em> have been true.<\/p>\n<p>Kennedy\u2019s competition amongst late lovers include Jean Michel Basquiat, Luke Perry and Tupac Shakur. Stiff competition!<\/p>\n<p>We\u2019re told the video will be available on Grindr\u2019s in-app media hub \u201cGrindr Presents\u201d and on its YouTube and Instagram accounts.<\/p>\n<p>The app company is also putting out limited-editon, picture-disc vinyl copies of the new record.<\/p>\n<\/p><\/div>\n<p><a href=\"https:\/\/pagesix.com\/2026\/05\/28\/celebrity-news\/madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat\/\" target=\"_blank\">Source link<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Stiff competition! Asked recently to name her best-ever lay, Madonna said she was prepared only<\/p>\n","protected":false},"author":1,"featured_media":3852,"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-3851","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\/05\/128824471.jpg","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/3851","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=3851"}],"version-history":[{"count":0,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/3851\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media\/3852"}],"wp:attachment":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media?parent=3851"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/categories?post=3851"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/tags?post=3851"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}