{"id":508388,"date":"2026-05-29T09:02:21","date_gmt":"2026-05-29T09:02:21","guid":{"rendered":"https:\/\/www.europesays.com\/ie\/508388\/"},"modified":"2026-05-29T09:02:21","modified_gmt":"2026-05-29T09:02:21","slug":"madonna-says-jfk-jr-was-the-best-sex-of-her-life-with-a-caveat","status":"publish","type":"post","link":"https:\/\/www.europesays.com\/ie\/508388\/","title":{"rendered":"Madonna says JFK Jr. was the best sex of her life \u2014 with a caveat"},"content":{"rendered":"<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, who was asking the questions.<\/p>\n<p>Madonna said in a video for Grindr that the best sex of her life was with John F. Kennedy Jr. (She is seen above with him at an event in Las Vegas in 1997.) GTRES \/ Shutterstock<\/p>\n<p>She was married to Sean Penn (shown here in New York in 1986) during her fling with Kennedy. Getty Images<\/p>\n<p>Page Six got hold of the video before its release, and in one especially memorable moment, Lopez asks, \u201cWho was your best d\u2013k down?\u201d<\/p>\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<p>Raul Lopez (seen above at the Fashion Scholarship Fund annual gala in March) asked whom she had the best sex with. Getty Images for Fashion Scholarship Fund<\/p>\n<p>Lending valuable journalistic context, Lopez adds, \u201cEveryone says his d\u2013k was crazy and he was a good f\u2013k.\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<p>The pair dated very briefly in the late 1980s.<\/p>\n<p>JFK Jr .was dating model Christina Haag when he and Madonna met. Getty Images<\/p>\n<p>\u201cSlave Play\u201d writer Jeremy O. Harris was among the group quizzing Madonna in the video. Getty Images for Vanity Fair<\/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 nofollow\">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.\u201d<\/p>\n<p>The book claims they met\u00a0while he was dating actress Christina Haag and Madonna was married to Sean Penn.<\/p>\n<p>The unnamed Kennedy friend says that the pop icon 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>Needless to say, Kennedy went on to marry Carolyn Bessette (seen together above heading to Bubby\u2019s in 1997). Lawrence Schwartzwald<\/p>\n<p>Rather impressively \u2014 if the book is to be believed \u2014 John-John 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<p>The friend says that JFK Jr. assured Penn that \u201che never knew Madonna in the biblical sense.\u201d<\/p>\n<p>Madonna is currently dating Akeem Morris. They attended the Met Gala together earlier this month. Kevin Mazur\/Getty Images for The Met Museum\/Vogue<\/p>\n<p>And, proving that he was from a family of lawyers, that may very technically have been true.<\/p>\n<p>Kennedy\u2019s competition amongst late lovers include Jean-Michel Basquiat, Luke Perry and Tupac Shakur.<\/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","protected":false},"excerpt":{"rendered":"Stiff competition! Asked recently to name her best-ever lay, Madonna said she was prepared only to rank the&hellip;\n","protected":false},"author":2,"featured_media":508389,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":"","_share_on_mastodon":"0"},"categories":[268],"tags":[434,1955,35984,2110,18,117,4500,27940,19,17,133507,7250,437],"class_list":["post-508388","post","type-post","status-publish","format-standard","has-post-thumbnail","category-celebrities","tag-celebrities","tag-celebrity-couples","tag-celebrity-exes","tag-celebrity-news","tag-eire","tag-entertainment","tag-exclusive","tag-grindr","tag-ie","tag-ireland","tag-john-f-kennedy-jr","tag-madonna","tag-sex-and-relationships"],"share_on_mastodon":{"url":"https:\/\/pubeurope.com\/@ie\/116657058600119148","error":""},"_links":{"self":[{"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/posts\/508388","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/comments?post=508388"}],"version-history":[{"count":0,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/posts\/508388\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/media\/508389"}],"wp:attachment":[{"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/media?parent=508388"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/categories?post=508388"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.europesays.com\/ie\/wp-json\/wp\/v2\/tags?post=508388"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}