The Complicated Reality of John F. Kennedy Jr. and Carolyn Bessette’s Tragic, Legendary Love Story

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Carolyn Bessette didn't say yes when John F. Kennedy Jr. first proposed to her.

She didn't say no, either, but remarkably the 29-year-old Calvin Klein publicist, who had been dating the eligible bachelor for about a year, wasn't yet sure that she was ready for what marrying him would entail. Namely, a merging of lives that would come with a host of perks but also require a daunting amount of self-sacrifice, not even including the matter-of-fact assault on her privacy.

Carolyn had spent enough time at the Kennedy family compound in Hyannis Port to know that there was no exaggerating the legend behind the larger-than-life name, a family technically made up of flesh and blood just like any other but which had embedded itself in the very fabric of American culture over the greater part of the 20th century.

And she wasn't bowled over by the Kennedy bond. Rather, the clannishness turned her off.

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Carolyn loved John, but in what would become a point of contention for the rest of their lives, she didn't particularly enjoy going to spend holidays and weekends with his sprawling family on the Cape, where their comings and goings were rather formally presided over by reigning matriarch Ethel Kennedy, Robert F. Kennedy's widow, and the Kennedy men, who with their touch football games and clambakes seemed lifted from a Ralph Lauren ad.

She wasn't exactly culturally adrift, having been born in White Plains, N.Y., and raised in posh Greenwich, Conn., by her mother and orthopedic surgeon stepfather, but she still felt like an outsider. And on the beach of Hyannis Port, Carolyn witnessed John being a cog in the Kennedy machine, rather than the dashing man about town he was in New York. Independent and confident on her own, being around the Kennedys made the 5-foot-10 beauty feel small and insecure.

"We don't do insecurity very well," John told his childhood friend Gustavo Peredes, whose mother, longtime Jacqueline Kennedy Onassis aide Providencia Paredes, was close to the couple. "That's definitely not on the Kennedy menu."

Red flags aside, though, he was still JFK Jr.

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So, about three weeks after People's Sexiest Man Alive in 1988 first popped the question over Fourth of July weekend on Martha's Vineyard, she did finally accept.

"I actually think that made John even more eager to marry her," RoseMarie Terenzio, John's executive assistant starting in 1994, told The Kennedy Heirs author J. Randy Taraborrelli.

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