Carolyn Bessette-Kennedy and JFK Jr.’s Real-Life Relationship Timeline

Radziwill recalls Kennedy bringing Bessette on a weekend trip with them in the documentary JFK JR: The Final Year. “We were sharing a summer house, Anthony and I and John, and he brought her for Memorial Day weekend,” said Radziwill. “They had been seeing each other for a few months, super on the DL. And that’s when I first met her.” She added, “And then, he broke up with her a few weeks later because he got back with his ex-girlfriend Daryl Hannah.”

RoseMarie Terenzio, Kennedy’s chief of staff, shared in the same documentary: “He just kind of went off the radar. And then she opened up the newspaper, and there he was at a movie premiere with Daryl. And her mom, who is hilarious, sent her the article in the mail: ‘Carolyn, please get on with your life, love mom.’ With a sad face.” However, Kennedy and Hannah did finally split that summer, and he began dating Bessette seriously.

The Middle: The Proposal, a Fight, and a Wedding

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July 4, 1995: On Fourth of July weekend, about a year after they began dating, Kennedy proposed to Bassette in Martha’s Vineyard on a fishing boat. “He went into this thing about how everything’s better with a partner, not just fishing but life,” Terenzio told People. “He said, ‘I want you to be my partner.’”

However, it was not an automatic “yes.” The fashion publicist took three weeks before agreeing to marry Kennedy. “She understood that the formality meant something, especially to John and his lifestyle. He was pretty old-fashioned, and given his place in the world, he couldn’t be single forever,” Terenzio said in her book Fairy Tale Interrupted. “I actually think that made John even more eager to marry her.”