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John F. Kennedy, Jr. was one of the world’s most eligible bachelors in the ’80s and ’90s. A striking man with good looks, he dated a slew of women, including Sarah Jessica Parker and Cindy Crawford, before he married his wife, Carolyn Bessette in 1996.

He also had a relationship with actor Daryl Hannah, but he broke things off with her because of her dog.

John F. Kennedy Jr. and Daryl Hannah on their way to wedding
John F. Kennedy Jr. and Daryl Hannah on their way to wedding | Brian Quigley/The LIFE Images Collection via Getty Images/Getty Images

John F. Kennedy, Jr. and Daryl Hannah met on vacation in St. Martin

The late political heir and The Fury star initially met it in the early ’80s while they were each vacationing with their families in St. Martin. According to Steven M. Gillon’s biography America’s Reluctant Prince: The Life of John F. Kennedy Jr., Kennedy via InStyle was immediately intrigued by Hannah. “John found it odd that Daryl seemed to carry a teddy bear with her wherever she went but also found her fascinating,” Gillion wrote.

However, the pair did not begin dating until 1988 and they were not an exclusive couple until 1992 when Hannah finally ended things with her reportedly abuse ex-boyfriend, singer-songwriter, Jackson Browne.

The media was immediately obsessed with Daryl Hannah and John F. Kennedy, Jr.

The media was immediately obsessed with Hannah and Kennedy together. The Splash star was used to being publically hounded and harassed. Therefore, being with a Kennedy was nothing out of the ordinary for her.

She was even up for staging at a roller-blading date dating with him following his mother, Jackie Kennedy’s death to distract the media from their constant gossip about their relationship and breakup rumors.

However, the truth was, Kennedy was over his relationship with Hannah by the time his mother died.


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John F. Kennedy, Jr. ended his relationship with Daryl Hannah because of her dog

Despite being fascinated by Steel Magnolias star, Kennedy could not cope with some of Hannah’s quirks. “John just found Daryl so self-absorbed,” Gillon told InStyle. The late businessman’s final straw in the relationship all boiled down to Hannah’s dogs.

In America’s Reluctant Prince, he explains that just days before Jackie Kennedy’s death, the editor found himself across the country in L.A. at a funeral for Hannah’s dog. The couple fought because Hannah was angry that Kennedy did not choose 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 Kennedy stuck things out for four more months following his mother’s death, the breakup was a very long time coming.