Note: This story contains spoilers for Love Story: John F. Kennedy Jr. and Carolyn Bessette-Kennedy episode five.
Love Story’s fifth episode, “Battery Park,” focuses on two major moments in Carolyn Bessette and John F. Kennedy Jr.’s relationship: the proposal and the highly publicized fight the couple had in a New York City park. The famously private couple kept most of their engagement details under wraps from the press. In fact, they never even announced anything about their relationship until their wedding day and flatly denied an engagement when one had actually occurred. But later interviews with members of their inner circle revealed some of what actually happened when the Kennedy heir proposed to Calvin Klein’s chic “VIP whisperer.”
Bessette and Kennedy first connected in 1992 through Calvin Klein. The fashionable Bessette helped the assistant district attorney at the company’s showroom when he came in for a fitting. While Kennedy gave her his number, a real romance did not begin until spring 1994. Kennedy first had to break up with actress Daryl Hannah, with whom he had an on-and-off relationship for years. In the 2019 A&E documentary JFK Jr.: The Final Year, Carole Radziwill—the widow of Kennedy’s cousin Anthony Radziwill—recalled, “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.”
A year later, in 1995, Kennedy and Bessette were together in Martha’s Vineyard over the Fourth of July weekend when he proposed. Similar to what was depicted in Love Story, his former assistant RoseMarie Terenzio revealed that Kennedy took Bessette out on a fishing boat to pop the question. “He went into this thing about how everything’s better with a partner, not just fishing but life,” Terenzio told People in 2022. “He said, ‘I want you to be my partner.’”
For the engagement ring, Kennedy gave Bessette a diamond and sapphire eternity band—a design similar to one worn by his mother, Jacqueline Kennedy Onassis. Radziwill wrote in her book What Remains that Bessette later told her it was “a copy of a ring [John’s] mother wore.” The original ring was a diamond and emerald eternity band that Kennedy Onassis called her “swimming ring.” It likely was a gift from her long-time companion, diamond dealer Maurice Tempelsman.
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