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

Radziwill recalled how Kennedy took Bassett on a weekend trip in the documentary KENNEDY JR: Final year. “We, Anthony, John and I shared a summer house, and he brought her over for Memorial Day weekend,” Radziwill said. “They had been seeing each other on the DL for a few months. That’s when I first met her.” She added, “He broke up with her a few weeks later because he got back with his ex-girlfriend Daryl Hannah.”

“He just disappeared,” Kennedy’s chief of staff RoseMarie Terenzio shared in the same documentary. “Then she opened the paper and saw him at a movie premiere with Daryl. Her mom, who was hilarious, sent her an article: ‘Caroline, please move on with your life, love mom.'” There was a look of sadness on her face. However, Kennedy and Hannah eventually broke up that summer, and he began dating Bessette in earnest.

Middle Part: Proposal, Quarrel, and Wedding

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July 4, 1995: Kennedy proposed to Bassett on a fishing boat on Martha’s Vineyard over the Fourth of July weekend, about a year after they started dating. “He talked about how having a partner makes everything better, not just fishing but life,” Terenzio told people. “He said, ‘I want you to be my partner.'”

However, this is not an automatic “yes.” It took the fashion publicist three weeks to agree to marry Kennedy. Terenzio said in her book: “She understood that this reserve meant something, especially to John and his way of life. He was very conservative and, given his place in the world, he could not remain single forever.” Fairy tale interrupted. “I actually think it made John even more eager to marry her.”

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Photo: New York Daily News Archives/Getty Images

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