I remember being a kid and hearing about John F. Kennedy Jr. in NYC. I remember vague stories, gossip about his glamorous New York life as a bachelor. I remember hearing about his relationship with Daryl Hannah and I remember rumors about John-John and Sarah Jessica Parker back in the day too. My mom had a subscription to People Magazine, and back in those days, it was all about Princess Diana, JFK Jr. and, like, Dynasty. Anyway, I’m trying to put this in context in my own mind – there’s a new tabloidy kind of book about John-John called The Good Son: JFK Jr. and the Mother He Loved. It’s all about John and Jackie’s relationship, obviously, but it’s also about the women John dated in his New York Years and how Jackie rarely approved. Apparently, John had a thing with Madonna in the late ‘80s. Sure. I’ll buy that. Some highlights via NYDN:

Bob Littell recalled the day six-foot-tall Sports Illustrated cover model Ashley Richardson showed up at their 86th Street apartment looking for John, wearing nothing but a mink coat and Prada booties. On another occasion during this period between serious girlfriends, John failed to hang up the phone properly when he was in bed with one girl, giving an earful of noisy sex to another. The girl on the phone remained on the line long enough to scream at John, but forgave him the very next day. John was “sleeping with every hot chick on the planet,” Billy Noonan said.

John liked to call his best friend and leave a taunting message. “Check out the cover of People (or Vogue or Vanity Fair),” John would say. “I banged her last night. Just thought you might like to know.” Later, Noonan would get all the juicy particulars from John over the phone. “The possibilities were limitless,” he said, “and John played them out.”

The temptation to draw parallels between the Sexiest Man Alive and his womanizing dad was irresistible. Ever since the revelations about JFK’s affairs began to emerge in the late 1970s — with Marilyn Monroe, Judith Campbell Exner, and others — Jackie and John just looked the other way. “Obviously,” Gore Vidal said, “it’s not the kind of thing a boy brings up to his mother. They just pretended none of it ever really happened. All the Kennedys are very good at that.” 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.

The Material Girl and JFK Jr. met briefly at a party following one of her concerts at Madison Square Garden in 1985. Three years later, after the breakup of her stormy marriage to Sean Penn, she went after John. Beyond the obvious — stories of her sexual escapades abounded — Madonna was convinced that destiny was taking a hand in bringing together the undisputed heiress to Monroe’s platinum persona with the son of JFK. She told friends she believed that her affair with JFK Jr. would be nothing less than “cosmic.” Like his mother, John was perfectly capable of being starstruck. “You could see it in his eyes that first time they met,” said dancer Erika Belle, one of Madonna’s closest friends at the time. “John was totally in awe.”

In a clumsy effort to avoid detection, the couple rendezvoused at the health club where they both worked out and shared the same trainer, venturing outside together only for a quick morning jog through Central Park. She quickly came up with her own handles for John; Madonna called him either “Johnny,” or just “Kennedy.” It wasn’t long before John took Madonna to meet his mother.

At 1040, Madonna stepped off the elevator and signed the guestbook “Mrs. Sean Penn” (technically, she still was). Not surprisingly, Jackie was anything but thrilled with this particular liaison. There were many things about Madonna that rubbed Jackie the wrong way, not the least of which was her habit of thumbing her nose at Roman Catholic rituals. Madonna’s use of crucifixes and other Catholic images was deemed sacrilegious by the Vatican, and across the globe she was being condemned as a heretic. Nor did it help when Jackie picked up a copy of Life only to see Madonna dolled up as Marilyn on the cover. “I imagine it was all hitting a bit close to home,” Vidal said. …

One day while he was staying with Billy Noonan in Hyannis Port, John phoned New York to check his messages. On the other end, a woman with a familiar voice was calling from Rome. “Kennedy,” she began, “I’m drunk and when I see you next I’m going to take your …” The rest was decidedly X-rated, and after John played it for Noonan, his friend asked to hear it again. Unable to quite place the voice, Noonan begged John to tell him who it was. “Madonna,” John answered matter-of-factly. Noonan was speechless. “You are banging Madonna?” Noonan asked. “How do I not know this until now?” So what was it like sleeping with Madonna? “Let me tell you,” Kennedy replied, “she’s a sexual dynamo.”

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 marked “Caroline” and “John-John” — souvenirs from the family’s first trip to Ireland after the assassination.

[From The NYDN]

There are more details in there, like the fact that Madonna was still technically married to Sean Penn and he was still very possessive of her. When John tried to introduce himself to Sean, Sean was super-pissed because he knew all about their affair. John also had a steady girlfriend at the time too, plus he was seeing other women. There’s a possibility that John might have been sleeping with Madonna around the same time he had a fling (that lasted a few months) with Sarah Jessica Parker.

Here’s why I question the extent of this alleged affair though: I think Madonna would have talked about it more. She would have dropped some info about John to Vanity Fair years ago or she would have mentioned it in some documentary. But hey, maybe I should give her more credit for being able to keep a secret?

Photos courtesy of WENN.