Jackie Kennedy Reportedly Once Went to Great Lengths to Vet Her Son JFK Jr's Partner

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It’s no secret that John F. Kennedy Jr. had some dalliances with the most recognized women in Hollywood, from Pamela Anderson to Madonna. Speaking of Madonna, do you remember when Kennedy and Madonna had a brief fling in the late 1980s? Well, it seems things got serious quickly because Kennedy allegedly wanted his mom Jackie Kennedy to meet her, but Jackie had her own, unique way of doing so (and going about the vetting process for her son).

The story goes that John wanted Jackie to attend one of Madonna’s performances, but Jackie would only go in disguise because “she didn’t want to validate the relationship,” according to Jackie: Public, Private, Secret by J. Randy Taraborrelli.

In Taraborrelli’s book, he claimed he spoke to someone who helped Jackie get into disguise. “I interviewed somebody who worked with Jackie at Doubleday, who said that she went with Jackie to the show; that Jackie wore a red wig so that she wouldn’t be recognized,” he said. “She put the wig on, and she asked this woman, ‘How do I look?’ And the woman said, ‘You look just like Jackie Onassis in a red wig.’”

She allegedly wanted to vet Madonna for her son, but when offered to meet her backstage, she denied the offer quickly. Taraborrelli said, “She thought Madonna was good in the show. But she also felt like she didn’t want to validate the relationship that John had with Madonna by being photographed.”

John and Madonna’s affair though didn’t last long. In Christopher Anderson’s book entitled The Good Son: JFK Jr. and the Mother He Loved, he claimed that John felt uncomfortable with the fact that Madonna tried to channel Marilyn Monroe. “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,” he said. “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.”

However, that wasn’t the reason Jackie didn’t end up approving of the Four Rooms star. Taraborrelli says she didn’t like the fact that Madonna was still technically married to Sean Penn when she was with John. “[Jackie’s] problem with [Madonna] was that she was married,” Taraborrelli said. She was “confounded by Madonna’s penchant for attention. Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn’t understand any of that.”