Back in the '80s and early '90s, John F. Kennedy Jr. was the guy everyone wanted to meet. With his striking good looks, charm, and impressive height of 6-foot-1, he was the crown jewel of the Kennedy dynasty. As the son of the late President John F. Kennedy and the iconic Jacqueline Kennedy Onassis, he could've had his pick of anyone. And, let’s be honest, he did. From high-profile celebrities like Sarah Jessica Parker, Daryl Hannah, Brooke Shields, Sharon Stone, and Madonna, to his eventual wife, fashion publicist Carolyn Bessette, John Jr.'s dating life was as much a tabloid staple as it was a personal journey. Tragically, his life was cut short when, at the age of 38, he, his wife, and her sister lost their lives in a plane crash in 1999. Today, we’re diving into the stories behind the romances of this beloved public figure, as told by those who knew him best.
John Jr., a graduate of Brown University, wasn’t just a pretty face. He was a lawyer-turned-magazine publisher who used his charm to sweep women off their feet. His story is one of love, heartbreak, and a life lived with passion. Let's take a closer look at what it was like to be with the man who captured the hearts of so many.
Charming and Adventurous: JFK Jr.'s Romantic Reputation
John Jr. had a knack for making women feel special, and his romantic escapades were legendary. Remember Sarah Jessica Parker, the star of "Sex and the City"? She had a whirlwind romance with John Jr. after her split with Robert Downey Jr. in 1991. Parker was so excited when he asked her out that she reportedly called her friend, director Adam Shankman, screaming with joy. A source close to Parker revealed to Closer that John treated her with care and attention, making her feel like the only woman in the world. One unforgettable night, she even exited a limo wearing nothing but a coat—a bold and daring move that spoke to the intensity of their connection.
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Then there was Christina Haag, his girlfriend of four years. In her memoir, Come to the Edge, Haag paints a vivid picture of John Jr. as an adventurous and romantic partner. She recounts a time when he surprised her by tying red roses to her bicycle with an unsigned card that read, "You rule my world." Haag described kissing him as "magical" and shared that he was curious about tantric sex, even bringing a book on the subject with him on vacation. These stories paint a picture of a man who was both passionate and open-minded in his relationships.
Brooke Shields also had a memorable encounter with John Jr. During a 2023 interview with Howard Stern, Shields revealed that she shared what she called "the best kiss I’ve ever had in my life" with him in the '80s. She described it as "beyond not-disappointing," adding that his lips, face, and body were all part of what made the moment unforgettable. Meanwhile, Sharon Stone reportedly had a steamy two-night fling with John in Martha’s Vineyard in 1995. Though brief, it was a romantic encounter she still holds dear. On the other hand, Madonna and John Jr. didn’t quite click in the bedroom. A friend of the singer told Closer that John was "far too straight" for Madonna’s uninhibited sexual preferences when they hooked up in 1988.
Mom Knows Best: Jackie Kennedy Onassis and Her Son's Love Life
Before her passing in 1994, Jackie Kennedy Onassis was deeply invested in her son's romantic adventures. She wasn’t shy about meddling in his love life, often playing matchmaker. It was Jackie who introduced John Jr. to Brooke Shields. However, not everyone passed her test. J. Randy Taraborrelli, in his book The Kennedy Heirs, noted that it was challenging for John Jr.'s girlfriends to meet Jackie's approval. Daryl Hannah, the star of Splash, didn’t quite fit into Jackie’s high-society world. A source told Closer that people in Jackie’s circle weren’t keen on associating with actresses, which made things difficult for Hannah. Ultimately, their on/off relationship ended in 1994, partly because Hannah couldn’t handle the media scrutiny and felt let down by John’s reluctance to propose.
A Gentleman Through and Through
Despite his reputation as a ladies’ man, John Jr. was known for being kind and respectful to his exes. Model Julie Baker, one of his former partners, described him as "a normal, humble, great guy." This sentiment echoes throughout the stories of those who knew him, painting a picture of a man who valued relationships beyond just romance. His charm and grace made him unforgettable to all who crossed his path.
