It was the kind of New York morning that feels like a movie set. A neighbor, looking out across an Upper West Side rooftop in 1993, saw something that most people would pay a year's rent to witness. There was John F. Kennedy Jr., the most famous man in America, shirtless in boxer shorts, dancing with a barefoot Daryl Hannah in a short nightgown. They were laughing. He was tickled her, she was running away, and then they’d catch each other and sway.
To the world, they were the ultimate power couple: the Prince of Camelot and the blonde mermaid from Splash. But behind that sun-drenched rooftop scene was a relationship that was, honestly, kinda messy.
They dated for over five years. That’s a long time in celebrity years. People forget that Daryl Hannah and John F. Kennedy Jr. weren't just a brief fling; they were a serious, live-in couple that almost ended in marriage. Yet, by the time they split in 1994, the "fairytale" had curdled into a series of public arguments and deep-seated resentments involving everything from Jackie Kennedy’s disapproval to the ashes of a family dog.
How It All Began (The St. Martin Meet-Cute)
Most people think they met at a glamorous Hollywood party. Not really.
The first time they locked eyes was in the early 1980s. Both families were vacationing on the Caribbean island of St. Martin. John reportedly found Daryl fascinating, even if he did think it was a bit weird that she carried a teddy bear everywhere she went. It wasn't a romance then—just two kids from famous families crossing paths.
The real spark didn't happen until 1988. They were both at the wedding of John’s aunt, Lee Radziwill, to director Herb Ross. Herb had just worked with Daryl on Steel Magnolias.
🔗 Read more: The Fifth Wheel Kim Kardashian: What Really Happened with the Netflix Comedy
At the time, they were both "taken." John was with Christina Haag, and Daryl was in a long-term, ten-year relationship with singer Jackson Browne. But the chemistry was undeniable. John’s friend Robbie Littell eventually wrote in his memoir, The Men We Became, that Daryl was "as beautiful as a sunrise."
The Turbulence Nobody Saw Coming
By the early 90s, the two were officially a thing. John even moved into Daryl’s Upper West Side apartment. This was the peak of their public visibility. They were seen everywhere: rollerblading through Central Park, making out in the back of taxis, and attending high-profile events.
But their dynamic was described by friends as "on-again, off-again."
A lot of the friction came from their personalities. They were both "flowers"—naturally beautiful, a bit spoiled, and used to being the center of attention. When you have two flowers and no "gardener" to do the emotional weeding, things get tangled. They would have these massive, loud blowouts on street corners. Once, in 1992, they were spotted screaming at each other on a Manhattan corner at dawn. John was heard yelling, "Then why did you come back?"
The Jackie Factor
Then there was Jackie.
💡 You might also like: Erik Menendez Height: What Most People Get Wrong
It's long been rumored that Jacqueline Kennedy Onassis didn't approve of the match. While some family members, like Daryl’s stepmother Sue Wexler, claimed Jackie was "warm," other accounts are much colder.
In the book The Good Son, author Christopher Andersen claims Jackie would avoid Daryl when she came over for dinner, choosing to eat on a tray in a different room. Jackie apparently worried that Daryl lacked the "social prestige" for a man who might one day enter politics. John, being John, sometimes became even more attached to Daryl specifically because his mother didn't like her.
The Dog Incident and the Final Break
If you want to know why Daryl Hannah and John F. Kennedy Jr. finally ended, you have to talk about the dog. It sounds like a bad tabloid plot, but it was the literal turning point.
In May 1994, John was walking Daryl’s dog in Central Park. He lost control of the leash, and the dog was hit and killed by a car.
John was devastated, but Daryl was inconsolable. She organized a funeral for the dog in Los Angeles and expected John to be there. This happened exactly as Jackie Kennedy’s health was failing. Jackie was dying of non-Hodgkin’s lymphoma in New York.
📖 Related: Old pics of Lady Gaga: Why we’re still obsessed with Stefani Germanotta
John flew to LA to attend the dog’s funeral and bring the ashes back. But things got weird. Daryl reportedly got angry with him because he hadn't chosen a nice enough box for the ashes. John, meanwhile, felt a deep sense of guilt and resentment. He was in California for a pet while his mother was taking her last breaths in New York.
Jackie died on May 19, 1994.
After the funeral, John and Daryl staged one last "happy" rollerblading date for the cameras to keep the press off the scent of a split during a time of mourning. But it was over. By August, they had officially called it quits.
What We Can Learn From the "Mermaid and the Prince"
Their relationship was a masterclass in the pressure of public expectation. People wanted them to be a fairytale, so they performed like one, even when they were bickering over Blockbuster late fees or where to go for dinner.
- Public vs. Private: Their rooftop dancing was real, but so were the street-corner screaming matches. A relationship isn't just its highlight reel.
- Family Influence: Even as a grown man, John was heavily influenced by his mother’s silent (and not-so-silent) judgments.
- The "Flower" Dynamic: Relationships usually need a balance of roles. Two people who are both used to being the "star" can struggle to find common ground when the spotlight dims.
Shortly after the breakup, John met Carolyn Bessette. Daryl eventually found her long-term partner in Neil Young. They both moved on, but for five years, they were the center of the New York universe.
If you're looking for more details on this era, you should check out Steven M. Gillon’s biography America’s Reluctant Prince. It gives a very honest, non-sugarcoated look at how John viewed Daryl—and why he eventually felt he had to walk away to become the man he wanted to be.
To dig deeper into this history, you can look for archived copies of People from August 1993, which captured the height of their romance before the 1994 collapse.