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Very few noted individuals garnered America’s intense interest quite like John F. Kennedy Jr. In his time, JFK Jr. was broadly viewed as one of the world’s most sought-after single men. Prior to his sorrowful passing in a 1999 air disaster alongside his spouse, Carolyn Bessette-Kennedy, the offspring of President John F. Kennedy and Jacqueline Kennedy Onassis drew focus wherever he appeared.
Good-looking, magnetic, and constantly in the spotlight, he even earned People magazine’s “Sexiest Man Alive” distinction in 1988 — an honor that simply amplified the popular curiosity surrounding his romantic entanglements. As he fashioned his personal path as a legal professional, writer, and the creative force behind George magazine, his relationships with performers, socialites, and renowned figures consistently dominated media coverage.
From initial flings to the woman he eventually wed, journey back through time to observe the women who captured JFK Jr.’s affections.
Julie Baker
The politician’s offspring, who departed at 38 years of age, went out with Julie Baker for a two-year span after they first met back in 1989. The model admitted to Liz McNeil and RoseMarie Terenzio – who penned JFK Jr: An Intimate Oral Biography – that the attractive man extended an invitation for her to accompany him to a poetry performance, however she turned it down as she considered it too “boring.”
She expressed on The Last Days of JKF Jr., “I was just fond of the fact that he was somewhat goofy, peculiar, forgetful, enjoyable, and daring.” They later ended up dating at other locations but their involvement led to a friendly acquaintance.
Christina Haag to Madonna
American attorney John F Kennedy Jr (1960 – 1999) (dark jacket, back to camera) and Pop singer Madonna (born Madonna Ciccone) talk together at the MGM Grand Garden Arena, Paradise, Nevada, June 28, 1997. They were there to attend the WBA Heavyweight Championship, a rematch between boxers Mike Tyson & Evander Holyfield. (Photo by Michael Brennan/Getty Images)
During the year of 1988 John Fitzgerald Kennedy Jr. engaged in a five-year bond with actress Christina Haag. Though they were engaged in their busy lives alongside each other and appeared to possess a sturdy connection, it reached its conclusion when he embarked on a brief romance with the recording artist Madonna.
According to Christopher Anderson who mentioned in The Good Son: JFK Jr. and the Mother He Loved, the pair delighted in spending time together, but his mother Jackie was disapproving of their relationship which caused their split.
Sarah Jessica Parker
Sarah Jessica Parker during 1997 VH1 Vogue Fashion Awards at Madison Square Garden in New York City, New York, United States. (Photo by Ke.Mazur/WireImage)
The Sex and the City leading lady shared a romantic relationship with John for about six months – 1991 to 1992. Their connection was such a talking point that the 59-year-old performer felt that her public persona would only be associated with dating him – she conveyed to The New York Times in 1992.
“We would visit spots where no one was to be found, and subsequently I would observe photographs of us in those same spots in the tabloids…He’s a kind man, but honestly, I believe I owe people an apology for seeing him. It has morphed into the defining trait of my identity. It’s somewhat sad.”
Brooke Shields
Brooke Shields at the 1998 Golden Globe Awards in Los Angeles. (Photo by Jeff Kravitz/FilmMagic, Inc)
The 59-year-old actress revealed on The Howard Stern Show that she had an encounter with the beloved gentleman, considering him her “best kiss”. She remembered being intensely smitten with him, with her mother having signaled from a tender age that she would someday be his wife.
Brooke recounted, “He continuously pointed out my likeness to his mother, which was certainly noteworthy and a compliment, [yet] I was also somewhat hesitant on ‘how to process this.’ We eventually did go on an official date. But I declined any romantic involvement due to the intense amount of affection I had for him.”
Daryl Hannah
Daryl Hannah during “Love Ride” 7 to Benefit Muscular Dystrophy at Glendale Harley Davidson in Glendale, California, United States. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
The pair had a romantic relationship over a span of a few years but their status developed into a committed relationship in 1992. Since they had an acquaintance from their teenage years, they bonded after both had separated from their respective partners. Their connection was turbulent as his mother “did not warm up” to her, as per John’s statement, which created difficulties for their relationship.
The roster carried on with more women who captured his heart such as Xuxa, Meg Azzoni, including whispered sentiments with Cindy Crawford. To conclude, he joined in matrimony with his departed partner Carolyn Bessette in 1996.