JFK Jr. and Daryl Hannah's Relationship Timeline: A Look Back

After reportedly meeting in the Caribbean in the early '80s, late political heir John F. Kennedy Jr. and model and actress Daryl Hannah crossed paths again in 1988 at a family wedding. Soon after, they began dating. Apart from looking good together — Kennedy earned the title of People's Sexiest Man Alive in 1988 (despite his "sloppy" style), while Hannah made Empire magazine's list of "100 Sexiest Stars in Film History" in 1995 — these two jibed well. 

For someone as famous and publicly hounded as Kennedy, it was probably comforting to be with a fellow celebrity who wasn't blindsided by the demands of the press and also understood that you sometimes need to stage a rollerblading date for the sake of appearances (more on that, below). However, their relationship was far from perfect, especially in the eyes of "helicopter mom" Jackie Kennedy. As a result, the pair called it quits in 1994 after being romantically linked for over five years.  

Here's a look back at John F. Kennedy Jr. and Daryl Hannah's relationship.

Early 1980s: Daryl Hannah and JFK Jr. first meet

According to Steven M. Gillon's biography America's Reluctant Prince: The Life of John F. Kennedy Jr., Kennedy and Hannah first met in the early '80s while on respective family vacations in Saint Martin.

"John found it odd that Daryl seemed to carry a teddy bear with her wherever she went, but also found her fascinating," Gillon wrote of their initial meeting. 

They were introduced by Hannah's billionaire stepfather Jerrold Wexler, who'd made large contributions to the presidential campaign of Ted Kennedy. However, it wasn't until a few years later that the two started dating.

October 1992: Daryl Hannah and JFK Jr. are first spotted together

Hannah and Kennedy met again at the wedding of his aunt, Lee Radziwill, to director Herb Ross in 1988. At the time, both parties were in relationships with other people — Hannah had spent the last 10 years with singer-songwriter Jackson Browne, while Kennedy had been dating actress Christina Haag since 1985. Shortly after, they began seeing each other.

The Wall Street actress and Kennedy remained non-exclusive until 1992 when the latter flew to Los Angeles after Hannah had a domestic incident with Browne at the time, reported People.

1993: Daryl Hannah denies she and JFK Jr. are getting married

Although the couple never wed, that didn't keep the marriage rumors from circulating. 

"It's getting really annoying. I get asked about it all the time," Hannah told Entertainment Weekly in 1993, per People, about speculation that she and Kennedy were going to tie the knot. "This morning, I call up my plumber, and even he asks me. Oh, brother, I'm just trying to get my pipes fixed. Why can't people talk about something else?"

August 1994: Daryl Hannah and JFK Jr. break up

Gillon, a historian and friend of Kennedy's, told InStyle exclusively that he thought "John just found Daryl so self-absorbed." 

In America's Reluctant Prince, he wrote that while Kennedy's mom, Jackie, was in the hospital in New York just days before she died in 1994, Kennedy was in L.A. for the funeral of Hannah's dog. 

Fueling the story's absurdity, Hannah got angry with Kennedy because he hadn't chosen a more elaborate box for the dog's ashes. 

"That just infuriated him," Gillon said. "And even after [Jackie] died, Daryl had another dog that was sick, and John was up in Martha's Vineyard or Hyannis Port, and Daryl's on the phone talking about her dog all the time, and John is there in the kitchen with [his longtime friend] Sasha Chermayeff, and he says, 'Can you believe this. I just lost my mom, and all she wants to talk about is her sick dog.'"

Though "in his mind, the relationship had already ended," Kennedy knew he couldn't let a public breakup take away from his mother's passing, so he did what any grieving child who was protective of their parent would do: stage a rollerblading outing with Hannah to distract the media and quell any rumors about a split.

No doubt, adding to the mounting tension between them through the years, the former First Lady had not been a fan of Hannah. According to Christopher Andersen, who wrote The Good Son: JFK Jr. and the Mother He Loved, while his mom never directly confronted him about Hannah, whenever the actress came over to her apartment for dinner, she would manage to eat on a tray in another room.

In the book The Kennedy Heirs, author J. Randy Taraborrelli wrote that Jackie had never fully given her son her blessing regarding Hannah as his girlfriend. 

"John had measured most of the women in his life by Jackie's opinion of them," wrote Taraborrelli. "If his mother approved, John would decide he wasn't sure. However, if his mother disapproved, as she did with actress Daryl Hannah, John became even more attached." Nevertheless, by August 1994, about three months after his mom's death, Kennedy and Hannah had broken up for good, according to United Press Internal (UPI).

Following the split, Hannah took a break from getting involved in high-profile relationships. By 2001, however, she was romantically linked with actor Val Kilmer, though it didn't last. In 2018, People reported the Splash star married musician Neil Young, who she had been dating since 2014.

Kennedy went on to date and later married Calvin Klein publicist Carolyn Bessette in 1996. Kennedy, Bessette, and her sister Lauren, died on July 16, 1999, in a plane crash off Martha's Vineyard that Kennedy piloted.