Her mother later remarried Richard Freeman, an orthopedic surgeon, and moved to Old Greenwich, Connecticut, while Bessette's father stayed in White Plains.

[8] During her career there, she went from being a saleswoman at the Chestnut Hill Mall in Newton, Massachusetts, to becoming the director of publicity for the company's flagship store in Manhattan.

[8] Sokol, impressed with Bessette's grace and style, later recommended her for a position dealing with Klein's high-profile clients, such as actress Annette Bening and newscaster Diane Sawyer.

[10] Bessette and Kennedy began dating in 1994 and became a popular paparazzi target, and gossip columns detailed where they ate and shopped, and even covered their public disagreements.

[14] The ceremony took place by candlelight on the remote Georgia island of Cumberland, in a tiny wooden chapel, the First African Baptist Church.

The couple were permanently on show, both at fashionable Manhattan events and on their travels to visit celebrities such as Mariuccia Mandelli and Gianni Versace.

The couple were given a White House tour by President Bill Clinton in March 1998,[21] and she acted as the hostess at parties for her husband's political magazine George.

[22] According to some reports published posthumously, the Kennedys were experiencing marital problems and contemplating divorce in the months preceding their deaths.

According to author Edward Klein, Bessette-Kennedy's "insecurity fueled a need to control and manipulate; her frequent use of cocaine made her paranoid".

Moreover, Bessette-Kennedy was jealous of and barely on speaking terms with her sister-in-law Caroline Kennedy, who reportedly criticized the bride for being late to her own wedding and wearing heels on the beach.

Robert Littell, who spent the weekend with John and Carolyn a week before the accident, also rejected the allegation that the couple were living apart at the time of their deaths.

[26][27] Bessette-Kennedy died on July 16, 1999, along with her husband and older sister Lauren, when the light plane John Jr. was piloting crashed into the Atlantic Ocean off the western coast of Martha's Vineyard.

The National Transportation Safety Board (NTSB) determined that the probable cause of the crash was: "The pilot's failure to maintain control of the airplane during a descent over water at night, which was a result of spatial disorientation.

The bodies were recovered from the ocean floor by Navy divers and taken by motorcade to the county medical examiner's office, where autopsies revealed that the crash victims had died upon impact.

[33] In 2004, Kennedy's fellow Brown University alumnus and ex-roommate, Robert T. Littell, published The Men We Became: My Friendship With John F. Kennedy Jr.[34] In 2005, Bessette-Kennedy's close friend Carole Radziwill, wife of John's cousin Anthony Stanislas Radziwill, published a memoir entitled What Remains: A Memoir of Fate, Friendship and Love, that includes her memories of the plane crash that took place just weeks before her own husband's death from cancer.