From the moment John F. Kennedy Jr. entered the world, he was destined for fame. In November 1960, just months before his parents, John and Jacqueline Kennedy, moved into the White House, a press secretary described the newborn as "wonderful." "His eyes were closed," the secretary recalled, "but I think he had a tiny bit of dark hair." It was the start of a life lived in the spotlight, one that would captivate the nation and the world.

The World's Favorite Son

From his earliest days, John Jr. was a public figure, belonging not just to his family but to the world at large. Over the years, he formed deep connections with several women, each of whom offers a glimpse into the life of a man who was as charming and kind as he was famous. Their stories paint a picture of a man trying to navigate the complexities of fame and personal relationships, until his tragic death in a plane crash at the age of 38 in July 1999.

Julie Baker: The Quirky Love

Model Julie Baker remembers her time with John in the late 1980s fondly. "I just loved that he was kind of silly, quirky, forgetful, fun, and adventurous," she says. "He was like a normal and humble great guy." Their relationship showcased a side of John that few got to see—a man who could be both playful and down-to-earth, even while living in the glare of the public eye.

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Christina Haag: The Long-Term Love

One of John's longest relationships was with actress Christina Haag, a childhood friend from his New York upbringing. During their five-year courtship, John affectionately called her nicknames like "Puppy," "Chief," and "Sweet Frog." In her 2011 memoir, Come to the Edge, Christina shares a harrowing tale of nearly drowning on a kayak trip with John in Jamaica. "He pushed me to go further," she writes, highlighting their adventurous spirit. However, the couple parted ways in 1990 when Christina grew weary of John's wandering eye. "It wasn't lack of love," she explains. "It was timing."

JFK Jr.'s Former Lovers Recall Sweet Memories 22 Years After His Death — Susan Walsh/AP/Shutterstock

Sarah Jessica Parker: The Starry-Eyed Encounter

Sarah Jessica Parker, the future star of Sex and the City, met John in New York. "He had exquisite hair, it was like a paintbrush," she recalls. Yet, the intense scrutiny that came with John's fame left her uneasy. "I never had any idea what real fame was until I met John," she says. "We would go places where there wasn’t a soul around, and the next day I’d see pictures of us there in the tabloids." Their relationship was brief but memorable, highlighting the challenges of dating a public figure.

Daryl Hannah and Madonna: The Controversial Connections

Actress Daryl Hannah was better equipped to handle the spotlight. "I get asked about [marrying John] all the time," she said in 1993. "This morning, I call up my plumber, and even he asks me." Despite sharing an apartment for a time, John's mother, Jackie, reportedly disapproved of the relationship, and they parted ways shortly after her death. Similarly, John's flirtation with Madonna drew Jackie's disapproval, as singer Carly Simon recalls. "Jackie was very consumed with getting him on the right path," she says.

Carolyn Bessette: The Final Chapter

John's 1996 marriage to Carolyn Bessette seemed to align with Jackie's vision for her son's future. "John didn’t need anyone else who was going to say yes. So she said no," says Kennedy’s cousin Carole Radziwill. "He loved her. And she loved him. And they drove each other crazy." Their union was tragically cut short in 1999 when they, along with Carolyn's sister Lauren, perished in a plane crash. Friends and former lovers often wonder what might have been. "He was an ordinary boy in extraordinary circumstances," says CNN’s Christiane Amanpour, a college pal. "And he lived his life with grace."

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