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John F. Kennedy Jr. often found himself managing multiple romantic interests simultaneously, but this was a deliberate tactic on his part.
While some friends portrayed him as more monogamous and tabloids painted him as highly promiscuous, his reality was somewhere in between.
Kennedy understood the importance of appearing to be in a relationship; being perceived as single would lead to an overwhelming influx of dating proposals.
Barbara Vaughn, a friend, reminisced about how John would receive introductions from people linked to his father’s political circle and from members of distant noble families, which he politely declined.
He would commit to one partner for extended periods, but as soon as he sensed the relationship losing its spark, he would discreetly seek another romantic interest before officially ending things.
Unfortunately, that meant there was often overlap, which could lead to awkward moments.
One evening he was in bed with a woman when the phone started ringing. He waited for it to stop and then took the phone off the hook, resting it on the table to avoid being interrupted again.
He then rolled over and continued what he had been doing.
Kennedy rolled over and continued what he had been doing – unaware his other girlfriend was listening on the other end of the phone line
Kennedy had a well-publicized on-off relationship with the actress Daryl Hannah
Kennedy with his wife Carolyn Bessette Kennedy in May 1999 – the couple died in a plane crash two months later
What he did not realize, however, was that he had lifted the receiver prematurely and ended up answering the call. The girlfriend on the other end of the phone listened while John made love to someone else.
She started yelling into the receiver. After a few minutes, John realized his mistake and quickly hung up the phone.
For most cheating men, that moment would have marked the end of both relationships. But people rarely held John accountable for his actions, and both women forgave him.
In 1985 John started a serious relationship with actress Christina Haag.
The two had met as teenagers on New York’s Upper East Side, attended Brown together, and even lived in the same Benefit Street house.
They did not become romantically involved until they both moved to New York and appeared together onstage in six invitation-only performances of Brian Friel’s Winners at Manhattan’s Irish Arts Center, which was directed by fellow Brown graduate Robin Saex.
John thought it would be fun to perform in a play with Christina, and he tamped down any speculation that he would become a professional actor.
‘This is definitely not a professional acting debut by any means,’ he told reporters. ‘It’s just a hobby.’
Previous girlfriends of Kennedy include Sally Munro (left), during his college years, and Meg Azzoni (right), who he dated in 1977
Kennedy with Haag in 1991 – friends say he was smitten and intended to marry her
Kennedy gets a hug from Haag in 1988 – just outside his mother’s Fifth Avenue apartment. He was on crutches after tearing several ligaments in his ankle while riding his bike
But the romance with Christina was real. While rehearsing for the play, they traveled to Jackie Onassis’s country estate in New Jersey, where John kissed Christina for the first time.
‘I’ve been waiting to do that for a long time,’ he told her.
John was smitten. ‘I’m obsessed with you,’ he told her at one point. ‘You make me an emotional person, and I’m not.’
He told Rob Littell, a close friend and confidant also from his Brown days, that Haag was ‘the girl I’m going to marry.’
And Christina was equally enamored of John. ‘He had his faults, like anyone,’ she admitted, ‘but never arrogance, never meanness, never snobbery. What he aimed for, and succeeded some days entertaining, was a remarkable equipoise of humility and confidence that is grace.’
She introduced John to Cumberland Island off the coast of Georgia, where they stayed at the same inn where, ironically, John would hold his wedding to a different woman a few years later.
It was here that John professed his love for Christina for the first time.
Christina also got a taste of John’s attraction to danger when they took a kayak trip near Treasure Beach while vacationing in Jamaica. They set out on the two-person kayak with three sandwiches, a mango, and a liter of water.
The water seemed calm, so they kept paddling farther. They then moved through a stiff current to reach Pedro Bluff, where they stopped, ate lunch, and watched the dolphins frolicking nearby.
John insisted on testing their limits by paddling even farther out in search of a secluded beach. As they inched closer, the gentle swells had turned into angry waves that were breaking on a coral reef just off the shoreline.
John spotted a possible opening in the coral just wide enough for the kayak. ‘If we are going to do this, I need you with me,’ he pleaded. ‘And I need you to paddle hard, so we can pull ahead of the break. I can’t do it alone. What do you say: Are you game?’
Christina nodded. They were only a few yards from the beach when they saw a large boulder blocking the narrow entrance to dry land. She was convinced they would hit it and get thrown into the jagged coral. But just as they approached, a wave lifted them up above the boulder and carried them safely to shore.
The encounter left both John and Christina shaken and too scared to speak. John, who rarely showed fear, paced the beach muttering: ‘Don’t tell Mummy, don’t tell Mummy.’
Christina said that he appeared to be in a trance. His hands were shaking. ‘I had never seen him like this – not skiing down the chute during a whiteout in Jackson Hole or nearly colliding with a gray whale in Baja.’
Just as with other dangerous situations John had put himself into, he managed to extricate himself and walk away unscathed. Maybe that was one of the reasons that John remained so careless until the end. He always managed to survive.
Haag got a taste of her boyfriend’s attraction to danger when they took a risky kayak trip in JamaicaÂ
‘Don’t tell Mummy,’ Kennedy told Haag once they were out of dangerÂ
Christina Haag photographed in 2014
In 1989, his old college roommate Pat Manocchia, an avid mountain climber, invited John to join him with a few others to scale Mount Rainier in Washington State.
Although John had completed Outward Bound, he had no climbing experience. But, as usual, he threw himself into the adventure.
They went with a group of hard-core climbers who worried about having a novice climber in their ranks and had to be convinced to allow John to join them.
On the first day, they reached 10,000 feet and decided to camp for the night. The next morning, the party woke up early hoping to reach the summit.
They eventually made it to a ridge of solid ice positioned at a 45-degree angle and a 3,000-foot drop to the bottom.
As they started making their way across the ridge, the wind picked up, and the guide decided that it was too dangerous to proceed.
‘We’re going back,’ he announced.
John, though the least experienced, exploded.
‘I didn’t come all the way here not to climb the mountain!’ he screamed.
Pat, who usually delighted in poking fun at John, was not impressed by his temper tantrum.
‘OK, Mr People Magazine, get the f*** back to the camp!’
As they descended the mountain, events took another unexpected turn.
They came across a young girl sitting on a bench in the middle of nowhere. ‘I knew you were coming here, so I came up because my prom is tonight,’ she told John.
John sent the others down to the camp and spent a few minutes talking to her. When he returned, he told them that the girl had climbed halfway up Mount Rainier just for the opportunity to meet him.
The story did not end there. The next day, they boarded a plane from Seattle to New York for the trip home.
As usual, John went wandering around the airport and had to rush to get on the plane before the doors closed.
He was supposed to sit in the aisle seat in front of Pat but spied two empty seats farther back and plopped down there. A few seconds later, a woman boarded the plane, saw John, and asked if she could sit in the empty seat beside him.
About 45 minutes into the flight, John signaled to Pat that he needed to talk. They went to the back of the plane near the bathrooms.
‘You gotta rescue me,’ John begged. ‘She is a flight attendant who is from New York. She found out my itinerary and flew today from New York to Seattle to be in the seat next to me for the flight back to New York. When she saw that I had switched seats, she followed me.’
John told him that the first words out of her mouth were: ‘You know, my ex-boyfriend said you would not even talk to me.’
Pat got a huge laugh out of the situation and told John that he was on his own. John returned briefly to his seat, told the woman that he needed to talk with his friends, and then maneuvered back to his original seat.
After arriving in New York, they headed to the baggage claim, where they found a well-known actress in a full-length mink coat (and nothing else) waiting for him.
Manocchia refused to name the actress, but other sources identified her as Sarah Jessica Parker. It was not the first time that Parker had appeared in a similar outfit while waiting for John to retrieve his luggage.
Kennedy with Bessette and their dog in 1997 – he was neither as monogamous as some friends claimed nor as promiscuous as the tabloids suggested
Haag introduced Kennedy to Cumberland Island – where, ironically, he would marry Carolyn Bessette a few years later (photographed: Sarah Pidgeon and Paul Anthony Kelly play the couple in the TV series Love Story)
At baggage claim, they found a well-known actress in a full-length mink coat (and nothing else) waiting for him
She scooped up John, and the two jumped into the backseat of a waiting limousine.
Later, John told Pat that he had gone mountain climbing to escape the constant dating and women seeking his attention.
‘That really worked out for you,’ Manocchia wisecracked.
Adapted from America’s Reluctant Prince by Steven M. Gillon, published in 2019 by Dutton, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2019 by Steven M. Gillon