Back in the 1980s and early '90s, John F. Kennedy Jr. wasn’t just any guy—he was America’s golden boy, the ultimate bachelor everyone wanted to know. Standing tall at 6-foot-1 with a face that could light up a room, John, the son of the late President John F. Kennedy and the iconic Jackie Kennedy Onassis, had the whole world at his feet. Before he tied the knot with fashion publicist Carolyn Bessette in 1996, John was living life to the fullest, dating some of the most beautiful women in Hollywood. But it wasn’t just about good looks and charm; John had a heart of gold and a story that captivated everyone around him.
John, a Brown University graduate, tragically lost his life at the young age of 38, alongside his wife and her sister, in a plane crash on the way to a family wedding in Martha’s Vineyard, Massachusetts, in July 1999. During his lifetime, he had an impressive list of romances, including stars like Sarah Jessica Parker, Daryl Hannah, Brooke Shields, Sharon Stone, and even Madonna. Now, let’s dive deeper into what it was really like to date the charismatic political heir, straight from the words of those who knew him best.
Remembering JFK Jr.: The Ladies’ Man Who Stole Hearts
John was more than just a pretty face—he was a lawyer turned magazine publisher with a knack for making women feel like they were the only ones in the room. Take Sex and the City star Sarah Jessica Parker, for example. After her breakup with Robert Downey Jr. in 1991, John swept her off her feet. SJP was so excited about their first date that she couldn’t contain herself. As her friend and director Adam Shankman once revealed, she called him screaming, “You’re not going to believe who asked me out!”
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Sarah wasn’t the only one who felt special. Christina Haag, John’s girlfriend of four years from 1985 to 1989, described him as an “adventurous and romantic” lover in her memoir, Come to the Edge. She shared a story about how John once left two dozen red roses tied to her bicycle with a note that read, “You rule my world.” Haag called kissing John “magical” and even mentioned his curiosity about tantric sex, bringing a book about it on vacation.
Then there’s Brooke Shields, who, during a 2023 interview with Howard Stern, recalled sharing “the best kiss I’ve ever had in my life” with John in the 1980s. She gushed, “It was beyond not-disappointing. The lips are beautiful, and the face is amazing, and the body.” Meanwhile, Sharon Stone reportedly had a steamy two-night fling with John in Martha’s Vineyard in 1995. An insider told Closer that although it was short-lived, Sharon considered it one of the most romantic encounters of her life.
But not everyone was swept off their feet. Madonna, who hooked up with John in 1988, reportedly found him too traditional for her uninhibited tastes. A friend of the singer revealed, “He was far too straight for her sexually.”
Jackie Kennedy Onassis: The Mother Who Meddled
Before her passing in 1994, Jackie Kennedy Onassis was deeply involved in her son’s love life, often setting him up with women she thought were suitable matches. For instance, she introduced him to Brooke Shields. But not everyone passed Jackie’s test. Stunning actress Daryl Hannah, despite her undeniable charm, didn’t quite fit into Jackie’s high-society world. A source told Closer, “Daryl was an actress, and people in Jackie’s circle didn’t want to associate themselves with those types of people.”
John and Daryl’s on/off relationship eventually came to an end in 1994, partly because she struggled with the intense media attention and felt frustrated by John’s reluctance to propose. Daryl once said, “I get asked about [marriage] all the time. Even my plumber asks me. I’m just trying to get my pipes fixed. Why can’t people talk about something else?”
John F. Kennedy Jr.: A Man Who Left Lasting Impressions
Despite his reputation as a ladies’ man, John was known for being kind-hearted and respectful to the women in his life. Model and ex-girlfriend Julie Baker summed it up perfectly: “John was a normal, humble, great guy.” Even years after their relationships ended, John remained on good terms with most of his exes, proving that he wasn’t just a heartthrob but also a genuinely nice person.
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