Carolyn Bessette Kennedy Would Be 55 Today: Her Glamorous Life and Love Story with JFK Jr.

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An enamored John F. Kennedy Jr. proposed to Carolyn Bessette during a weekend on Martha’s Vineyard in July 1995. Kennedy popped the question while fishing on a boat off the island’s coast: “He went into this thing about how everything’s better with a partner, not just fishing but life,” his former assistant, RoseMarie Terenzio, tells PEOPLE. “He said, ‘I want you to be my partner.’ “

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It wasn’t an instant yes for Bessette Kennedy. A close friend reveals that she waited three weeks to accept his proposal, which made Kennedy “all the more intent on marrying her.”

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Kennedy was captivated by Bessette Kennedy from the start: “He was a guy who could never stand to be bored, and with her he was never bored,” the close friend tells PEOPLE.

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She did, of course, accept — and the couple wed in an intimate, secret ceremony on Sept. 21, 1996, on Cumberland Island in Georgia.

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Despite the high-profile nature of their relationship (seen here attending a White House dinner in February 1998) Kennedy was determined for the couple to remain a sense of normalcy. They declined security at his insistence, which made Bessette Kennedy uneasy. “John wasn’t sensitive to the fact that this had been his life since he was born, but it was not Carolyn’s,” Terenzio tells PEOPLE.

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Despite their intense bond, they had their ups and downs. “They would love hard, and fight hard,” Ariel Paredes, the granddaughter of Jacqueline Kennedy’s former assistant Providencia Paredes (and a good friend of couple), tells PEOPLE. “But they were very much in love.”

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The couple attended public events both together and separately (here, Bessette-Kennedy posed at the the Fire and Ice Ball in 1998 with Kennedy’s cousin Maria Shriver). But after Princess Diana died in a car crash after a paparazzi chase in 1997, she was unsettled by the constant presence of photographers. “Carolyn was rattled by the fact that she and John were just as vulnerable,” Terenzio says.

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Although they were talking about starting a family, Kennedy was more ready than his wife, who wanted to wait until they found a home outside New York. She had concerns about the omnipresent paparazzi outside of their downtown Manhattan loft.

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The Carolyn that her friends knew was “quite a loveable person,” says Carole Radziwill, the widow of Kennedy cousin Anthony Radziwill, who was close to Bessette Kennedy. “She was clever, she was naughty, and she had that balance of being able to be really serious and deep yet funny.”

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Bessette Kennedy considered skipping the July 1999 Cape Cod wedding of Kennedy cousin Rory Kennedy. “I said, ‘You have to go — this is a family wedding,'” Terenzio tells PEOPLE. Kennedy piloted the small plane carrying Bessette Kennedy and her older sister Lauren Bessette (pictured here), which plunged into the dark waters near Martha’s Vineyard, killing all onboard.

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