Who: The late businessman, editor, and political heir, John F. Kennedy Jr., and model and actress Daryl Hannah, 58.

How They Met: According to Steven M. Gillon’s recent 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 writes 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, John's uncle. However, it wasn’t until they met again at the wedding of John's aunt, Lee Radziwill, to director Herb Ross in 1988, that they began dating.

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. Hannah and Kennedy remained non-exclusive until 1992 when John flew to L.A. after Daryl had a reported domestic incident with now ex-boyfriend Browne.

When They Peaked: If Mr. & Mrs. Smith had come out 15 years earlier, we would’ve campaigned for Hannah and Kennedy in the title roles. I mean, LOOK AT THEM:

Why We Loved Them: For someone as famous and publicly hounded as John, 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 roller blading date for the sake of appearances — which he did soon after his mother Jackie Kennedy’s death in order to distract the media from breakup rumors.

The Breakup: Gillon, a friend to John as well as a historian, told InStyle exclusively that he thought “John just found Daryl so self-absorbed.” In America’s Reluctant Prince he writes that while Jackie was in the hospital in New York, just days ahead of her death in 1994, John was in L.A. for the funeral of Hannah’s dog — yep. Fueling the absurdity of the story, Hannah then got angry with John because he hadn’t chosen a more elaborate box for the dog’s ashes. “That just infuriated him,” Gillon told us. “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 distract from Jackie’s passing, hence the aforementioned roller blading outing.

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

By August of 1994, about three months after Jackie’s death, Kennedy and Hannah had split for good.

Where They Are Now: Hannah wed singer Neil Young in 2018, whom she’s been dating since 2014. The Splash star recently appeared in Netflix’s Sense8 and will ironically be in an upcoming comedy called Undateable John.

Kennedy went on to date and later marry Calvin Klein publicist Carolyn Bessette in 1996. In his final years, he started political-cultural hybrid George Magazine.

Both John, Carolyn, and Carolyn’s sister Lauren died on July 16, 1999 in a flight to Martha's Vineyard that Kennedy piloted.

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