JFK Jr. Reportedly Broke Up With Madonna Because She Tried to Channel This Controversial Figure to the Family

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It seems like John F Kennedy Jr’s dating history is a who’s who of A-listers that people still can’t get enough of to this day. We know all about his phone call with Pamela Anderson that left her “blushing” and his highly publicized marriage to Carolyn Bessette. But did you know he reportedly had a steamy relationship with none other than Madonna back in the late 1980s?! Well, they seem like a perfect match made in Hollywood, Kennedy reportedly broke it off for one rather concerning reason.

In Christopher Anderson’s book entitled The Good Son: JFK Jr. and the Mother He Loved, that “the same year JFK Jr. was named the Sexiest Man Alive by People magazine, he and the Material Girl began a steamy affair.” (For those that don’t know, it was in 1988!)

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Andersen claimed in his book that “the only place the superstar couple could let their guard down was in Hyannis Port, where they bundled up in sweaters and jackets and jogged on the beach. Inside the compound, they curled up by the fire, sipping daiquiris from Waterford crystal glasses.”

In an article by the Irish Central, which used excerpts from the book, it’s said the two had an affair while Kennedy was still with his girlfriend of five years Christina Haag, and when Madonna and Sean Penn split up.

And in the same outlet, they used an excerpt from the book that claimed Madonna’s actions and image were the reason Kennedy called it off.

It reportedly started with the fact that when he took Madonna to his mother Jackie Kennedy’s NYC apartment, she allegedly signed in as “Mrs. Sean Penn,” and Jackie allegedly didn’t approve of her use of Catholic symbolism in her performances.

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But the biggest reason is that Andersen claimed that John felt uncomfortable with the fact that Madonna tried to channel Marilyn Monroe. Andersen wrote, “One unwelcome reminder of JFK’s torrid affair with Marilyn — the affair that most troubled Jackie — arrived on her doorstep in the form of another blond bombshell by the name of Madonna. Already a pop icon, Madonna was best known at the time for her ‘Material Girl’ video, an homage to Monroe’s ‘Diamonds Are a Girl’s Best Friend’ number from the film Gentlemen Prefer Blondes.”

For those that don’t know, Monroe was allegedly entangled in an affair with John’s father John F. Kennedy.

And Madonna has claimed for years that Monroe has been a source of inspiration for her. Most recently, she did a photoshoot with V Magazine, where she channeled Monroe for the cover in Oct. 2021.

Before you go, click here to see everyone Madonna has been linked to: