Carolyn Bessette had a magnetism about her that she possessed her entire life. It's that casual magnetism that won the heart of one of the country's most desired bachelors, John F. Kennedy Jr. He wasn't her first high-profile love, but he would tragically be her last.
The love story between Carolyn and JFK Jr. has been told time and time again since their tragic deaths on July 16, 1999. Much of those stories focus on their years in New York together, how she won the heir of Camelot's heart, and what would have been had they not gotten on that plane.
Carolyn was a pretty fascinating figure before she was the queen consort of the Kennedy dynasty, however. She was an All-American girl in the truest sense. Her 29 pre-John John years were filled with love, family, and a keen sense that she was meant for something different. Fame wasn't it, however, as Carolyn's early years allegedly left her disenchanted with the idea of life in a family many are convinced is "cursed."
Carolyn Bessette Kennedy will forever be remembered as JFK Jr.'s soulmate. She was much more than that in her 33 years. Carolyn Jeanne Bessette was born on January 7, 1966, in White Plains, New York, to school administator Ann and cabinet maker William.
Carolyn was the third child, with twin older sisters, Lauren and Lisa. Their parents divorced when she was 8 years old. Her mother soon remarried, and the three girls moved with her to Greenwich, Connecticut.
In 1984, an 18-year-old Carolyn arrived fresh-faced at Boston University, ready to pursue a degree in education. She quickly became popular on campus for her incredible good looks and sensational personality. She appeared in the "Girls of B.U." calendar during her last year at the school.
Carolyn lingered in Boston after graduation. She briefly worked in event management for a nightclub company before she landed a sales assistant role at Calvin Klein. By 1989, she'd moved into a PR position and transferred from Boston to New York City.
JFK Jr. wasn't the first famous face to show interest in Carolyn. She dated Italian clothing heir Alessandro Benetton and future NHL star John Cullen, and she kept model Michael Bergin as her back-burner beau when she met the heir to the Kennedy dynasty. As for how they met, there are different stories, from the two jogging into each other in Central Park rom-com style to them being introduced by a mutual friend.
The two became an item in 1994, and they quickly seemed like a perfect match. Carolyn didn't go easy on John, however.
"Early on, he would be frustrated," attorney Brian Steel, a coworker from the Manhattan District Attorney's office, recalled in the 2018 ABC News special, The Last Days of JFK Jr.
"He would say, 'I called her and she hasn't called me back.' And John did not like that."
The bachelor's assistant, RoseMarie Terenzio, wrote about meeting Carolyn in Fairy Tale Interrupted: A Memoir of Life, Love, and Loss.
"She was exactly the kind of girl I imagined would date someone like John Kennedy Jr.," she recalled.
She went on to explain that Carolyn was "different from the typical gorgeous girls you see around Manhattan. She wasn't trying too hard. She wasn't trying at all."
The more serious things got between the two, the more Carolyn was confronted with what a future with John would mean. She was already drawing parallels to Jacqueline Kennedy, and it wasn't what she wanted for herself.
She grew frustrated and concerned for her safety as she started getting mobbed by paparazzi. John declined to employ security, which made the situation even more nerve-wracking.
"John wasn't sensitive to the fact that this had been his life since he was born, but it was not Carolyn's," RoseMarie told People magazine.
That attention only amplified after it was announced the two were engaged. Carolyn made John wait three weeks for an answer to his proposal, finding herself at a crossroads. He popped the question during a weekend on Martha's Vineyard.
"He went into this thing about how everything's better with a partner, not just fishing but life," RoseMarie recalled.
"He said, 'I want you to be my partner.'"
The two tied the knot in an intimate wedding on Georgia's Cumberland Island on September 21, 1996. The attention surrounding Carolyn only got worse then. She couldn't take a breath without it being photographed, and it was grating on her.
Despite the press writing her off as icy and a killjoy, Carolyn was remembered as being warm and fun by those who truly knew her.
"She had this amazing sense of humor, really sharp and funny," Matt Berman, the creative director of George and a close friend of the couple told Town & Country.
"For the most part no one really knows what she sounded like or talked like or what kind of woman she was. I found her very down to earth, very funny, very supportive of her friends, very caring. All the things that you don't see in a picture."
Carolyn's fear of being hounded by the press was amplified during the summer of 1997. She attended Gianni Versace's funeral and was seated behind Princess Diana. Weeks later, the Princess of Wales died in a car accident that many feel was caused by the paparazzi's incessant pursuit of her.
"I'm not sure what I'm going to do about Carolyn," John reportedly told his friend Billy Noonan. "She's really spooked now."
Carolyn and John fought hard and loved hard. They found themselves in an increasingly complicated place in the summer of 1999, when their lives were cut short in a tragic plane crash.
The couple was allegedly debating whether they were ready to have kids, which would involve a move out of the city. Carolyn was trying to figure out what professional interests she wanted to explore. John was determining whether he could continue on with George.
Carole Radziwill, a close friend of the couple who was married to Anthony Radziwill, John's cousin and best friend, imagined what the couple might be like today.
"I'd like to think John and Carolyn would have lots of kids," she told Town & Country.
"I know they both wanted that. I imagine the tabloids would eventually tire of them and leave them to live in peace. John's magazine, George, would be a spectacular success story. But that's the thing about young deaths: You don’t only mourn what was, you also mourn what could have been."
