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JFK Jr. romanced Brooke Shields and Madonna — but here’s why he didn’t sleep with either of them

  2024-07-31 pagesixNicki Gostin9820
Introduction

John F. Kennedy Jr. had high-profile romances with Madonna and Brooke Shields — but the alleged playboy didn’t actually

JFK Jr. romanced Brooke Shields and Mado<i></i>nna — but here’s why he didn’t sleep with either of them

John F. Kennedy Jr. had high-profile romances with Madonna and Brooke Shields — but the alleged playboy didn’t actually sleep with either of them, according to a new book.

“Madonna was totally a fling,” one of Kennedy’s close pals says in “JFK Jr.: An Intimate Oral Biography” by Rosemarie Terenzio and Liz McNeil, out Tuesday. “Nothing more. Barely a fling at that.”

The political scion met the pop star in the 1980s while he was dating actress Christina Haag and she was married to Sean Penn.

The unnamed Kennedy friend says that Madonna came on to JFK Jr., “and it was flattery — she was at the top of her game.”

It was “all about physical attraction, it wasn’t going to be anything beyond that,” the source claims.

John F. Kennedy Jr. had high-profile romances with Madonna and Brooke Shields — but the alleged playboy didn’t actually sleep with either of them, according to a new book. Getty Images

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 Mado<i></i>nna and JFK JR.
A pal of Kennedy’s says the political scion’s fling with Madonna was very brief — and all about physical attraction. MEGA

Despite the heat between them, though, they never actually had sex.

“On one occasion when she was on tour, they didn’t have the protection measures and she was very on top of HIV prevention,” the pal explains.

That didn’t stop the couple from having “fun in other ways” and Kennedy remarking that the “Vogue” singer had “one of the most beautiful bodies he had ever seen.”

Mado<i></i>nna and Sean Penn.
Madonna was still married to Sean Penn (above) when she first met JFK Jr. — something the two men later talked about. Getty Images

Many years later, Penn appeared on the December 1998 cover of Kennedy’s George magazine, and the two had dinner.

The friend says that JFK Jr. assured Penn that “he never knew Madonna in the biblical sense.”

Kennedy also had an unusual interlude with Brooke Shields around 1984 or 1985.

Brooke Shields posed in a red chair, with her legs kicked up
Brooke Shields says she and Kennedy kissed, but she stopped things before they went any further. NBCUniversal via Getty Images

The “Suddenly Susan” alum, 59, says in the book that she was in Aspen for a wedding when Kennedy’s paternal grandmother, Rose, invited her to a cocktail party. JFK Jr. kept telling the actress that “I looked like his mother. And I was thinking, ‘Okay, is that weird?'”

Funnily enough, when Shields was a toddler, her mother showed her a photo of the young Kennedy and told her: “See that boy, that’s going to be your husband one day.”

The two ended up leaving the party for an outdoor smooch.

John F. Kennedy Jr. shirtless and outdoors
Shields says Kennedy was a great kisser. Ron Galella Collection via Getty Images

“He was a delicious kisser,” Shields recalls. “He tasted like … pillow lips. Very sweet … The lips were just ridiculous. Just full, beautiful — so edible.”

However, the “Blue Lagoon” star was 19 or 20 and still a virgin.

“You so do not want me to lose my virginity to you because in my world, that means we’re married,” Shields recalls telling Kennedy. “So do yourself a favor, back off.”

Brooke Shields posed in a chair
Shilds says she told Kennedy she would become too attached if they slept together. NBCUniversal via Getty Images

She admits that, at first, he was incredulous.

“It’s like, I’m America’s sweetheart,” she explained. “You do not want to have that on your head. You might not even care, but I will make your life miserable … I would love to, but I’ll just cry. And then you might not talk to me the next day, and then I’ll really cry.

“It’s easier for all of us if you just let me go.”

Shields added that if she slept with him, she was bound to “fall in love with you. And I’m just going to get hurt.”

John F. Kennedy Jr. shirtless and outdoors
Kennedy, according to Shields, was surprised she wouldn’t sleep with him. Getty Images

The pair ended up being snowed in together the following night — with Kennedy taking the couch before they finally flew back to New York City.

“We dropped him off at his mom’s,” Shields recalls. “That was the last time I saw him.”

(By/Nicki Gostin)
 
 
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