John F. Kennedy Jr.’s past romance with Daryl Hannah has resurfaced in discussions amid the February 12, 2026, premiere of the FX/Hulu series, Love Story: John F. Kennedy Jr. & Carolyn Bessette.The couple had a high-profile romantic relationship beginning in the 1980s and ending in the early 1990s. It was marked by intense media scrutiny. They met as teenagers while vacationing with their families on the Caribbean island of St. Martin and reconnected at the wedding of Kennedy’s aunt, Lee Radziwill, to director Herb Ross.Their romance lasted more than five years, and they broke up in 1994 due to several factors. One of which was the death of Hannah’s dog when Kennedy Jr. was walking him in Central Park. She was devastated and insisted that Kennedy Jr. fly out to Los Angeles to carry her dog’s ashes for his funeral, which was organized by her.This reportedly happened around the time John F. Kennedy Jr.’s mother, Jackie Kennedy, was in the hospital in New York with her condition worsening rapidly.Continue to read for more details.What led to the split of John F. Kennedy Jr. and Daryl Hannah?Before John F. Kennedy Jr. fell deeply in love with Carolyn Bessette, he was involved in a long and tumultuous romantic relationship with actress Daryl Hannah that lasted more than five years.Their love story didn’t begin at their first encounter during a family vacation on the Caribbean island of St. Martin. At that time, the duo were young and were involved in their own lives.They reconnected at the wedding of Kennedy’s aunt, but at that time they were in other relationships—John F. Kennedy was dating Christina Haag, and Hannah was with musician Jackson Browne. The spark that led to their romance ignited in 1989, when they met through Hannah’s businessman stepfather, Jerrod Wexler.As the romance deepened between Hannah and Kennedy Jr., their relationship became strained over the course of time. Some reports describe “aggressive” arguments, with Hannah sometimes kicking Kennedy Jr. out of shared apartments. Kennedy’s friends described Hannah as a “sweetheart” but also “needy” at the same time.2006 Sundance Film Festival - Volkswagen Lounge Produced by Backstage Creations - Day 3 - Source: GettyA friend noted:“You never saw them look each other in the eye, you know, lovingly. Ultimately, they didn't see eye to eye on much.”There were also reports that Kennedy Jr.’s mother, Jackie, never approved of his relationship with Hannah. Author J. Randy Taraborrelli wrote in his book, The Kennedy Heirs:"John had measured most of the women in his life by Jackie's opinion of them. 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.”According to Steven M. Gillon, the author of America's Reluctant Prince: The Life of John F. Kennedy Jr. Hannah’s focus on her pet’s death left Kennedy Jr. feeling infuriated and unsupported amid his profound grief. The author said:“That just infuriated him. 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.'”By the time his mother died, the relationship between John F. Kennedy Jr. and his mother was already over in his mind due to escalating frustrations. Three months after Jackie’s death, the pair broke up.Following the split, the couple moved on to new relationships, with Kennedy dating Carolyn Bessette, whom he married in 1996. Hannah relatively kept a low profile. In 2014, she reportedly started dating legendary musician Neil Young and married him in a private ceremony in 2018.