Jackie Kennedy Was ‘Concerned’ Over JFK Jr.’s Romance With Daryl Hannah

John F. Kennedy Jr.’s family and friends opened up about his complicated five-year romance with Daryl Hannah in the new CNN documentary American Prince.

“His mom did have concerns with Daryl Hannah, the movie star,” Kennedy biographer Dr. Joseph Ponterotto revealed in the episode airing Saturday, August 9. “It was once said, to love John, you need the approval of his mom first.”

John Jr. and Hannah, now 64, reportedly originally met on vacation in Saint Martin in the early 1980s, with the two going on to have a highly publicized and often tumultuous relationship starting in 1988. Carole Radziwill — who was married to John Jr.’s first cousin Anthony Radziwill — opened up about the Kennedy family heir’s “pretty long relationship” with the Kill Bill actress in the first installment of CNN’s three-part docuseries American Prince.

The George Magazine editor started casually seeing future wife Carolyn Bessette during one of several breakups with the Splash actress in the early 1990s, yet he tried to save his relationship with Hannah prior to a life-changing event.

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“He said that Daryl decided to move back to New York. … She was living in L.A. or something and that he felt like he owed it to her to see if it could work [now] that they were both living on the same coast,” Carole, 61, recalled.

She went on, “I’m sure he loved Daryl. They stayed together for a couple of years until his mother got sick.”

Jackie was diagnosed with non-Hodgkin lymphoma in December 1993, and while her prognosis initially seemed positive, the cancer spread to her spinal cord, brain and liver by the following March. The former first lady died in May 1994, around the same time as John Jr.’s first cousin Anthony had a recurrence of testicular cancer that eventually claimed his life.

Amid a frenzy of media coverage, John Jr. briefly cut things off with Bessette to avoid having to hard-launch a new relationship in the wake of Jackie’s death.

“This is John’s life. His mom dies, he’s mourning his mom but he’s afraid that if the people know that he’s broken up with Daryl Hannah, the media is going to focus on that, not on his mom’s life,” John Jr.’s close friend Steve Gillon explained in American Prince. “So, he went through the pretense of still being together [with Daryl] … just so everybody could see them together. That’s the kind of calculation that John has to make that most of us don’t have to make.”

Once the media coverage settled down, Carole recalled that John Jr. felt freer to be his authentic self in public without worrying about disappointing his family.

“John and Jackie, they were really close,” Carole recalled. “He was heartbroken, and it was a very hard time for him, but there was almost, I would say, an emancipation [after Jackie’s death]. I think, for the first time, he felt free to do what he wanted to do in a way that he wouldn’t have when his mom was alive. A lot of good came out of that.”

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John Jr. broke things off with Hannah for good in the mid-1990s before marrying Bessette in Cumberland Island, Georgia, in September 1996. Tragically, John Jr., Carolyn and her sister Lauren Bessette were killed in a plane crash near Martha’s Vineyard in July 1999.

Meanwhile, Hannah was involved with singer Jackson Browne prior to getting together with John Jr. and later married rock legend Neil Young in 2018.

American Prince premieres on CNN Saturday, August 9, at 9 p.m. ET, with new episodes continuing each Saturday through August 23.