Carolyn Bessette-Kennedy

According to some reports published after their deaths, the Kennedys were experiencing marital problems and contemplating divorce in the months preceding their deaths. The couple had various disagreements, including her refusal to start a family, John’s work on the George magazine where she felt forsaken, and her dislike of John’s publishing partner Michael Berman. According to Vanity Fair, 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.

In 2015, Wes Gordon, known for disliking discussion about the influences of his collections, admitted Bessette-Kennedy's impact on the clothing for women in that year's collection. Gordon was long interested in Bessette-Kennedy's style prior to production.

In 2012, Kennedy's assistant and publicist, RoseMarie Terenzio, published her experiences and behind-the-scenes observations based on her five years working with Kennedy and, eventually, her friendship with him and his wife in Fairy Tale Interrupted: A Memoir of Life, Love, and Loss.

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.

Before marrying Kennedy, Bessette was in a relationship with Calvin Klein model Michael Bergin, who wrote a memoir titled The Other Man: John F. Kennedy Jr., Carolyn Bessette, and Me, which was published in 2004.

In 2004, Kennedy's fellow Brown University alum and ex-roommate, Robert T. Littell published, The Men We Became: My Friendship With John F. Kennedy Jr.

In his book, The Kennedy Curse: Why Tragedy Has Haunted America's First Family for 150 Years, author Edward Klein claimed that the couple's problems reportedly stemmed from Bessette-Kennedy's difficulty dealing with the media attention surrounding her and the marriage, accusations of infidelity, disagreements about having children, and Bessette-Kennedy's alleged cocaine use. Although Klein is the author of several Kennedy books, John Kennedy Jr. said, when speaking of Klein, "he is a guy who had lunch with my mother twenty years ago and has been dining out on it ever since." Friends of the couple's, including John Perry Barlow and Christiane Amanpour, said that Bessette-Kennedy and Kennedy fought on occasion and that Bessette-Kennedy had trouble adjusting to the intense media coverage, but denied that she used drugs or that the couple was planning to divorce. The couple began seeing a marriage counselor in March 1999 and sought counseling from Cardinal John O'Connor in the summer of 1999. In the summer of June 2019, a video of the secret wedding that took place in the remote Georgian Island was released for public viewing.

Bessette-Kennedy died on July 16, 1999, along with her older sister Lauren and husband, when the light plane he 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. Factors in the accident were haze and the dark night."

While the interest surrounding the couple continued, Bessette-Kennedy refused to give interviews and turned down offers to appear in fashion magazines. Towards the end of her life, Bessette-Kennedy became more involved with charity work and often accompanied her husband to dinners at the White House (the couple were given a tour by President Bill Clinton in March 1998) and acted as the hostess for parties for her husband's political magazine George.

Kennedy and Bessette succeeded in keeping their September 21, 1996, wedding a secret from the press, avoiding media onlookers. The ceremony took place by candlelight on the remote Georgia island of Cumberland, in a tiny wooden chapel, the First African Baptist Church. The bride selected the then-little-known designer Narciso Rodriguez of Cerruti for her wedding dress of pearl-white crepe. The groom's older sister, Caroline Kennedy, was matron of honor, and Anthony Radziwill, the son of his aunt Lee Radziwill-Ross, served as Kennedy's best man. Caroline's two daughters, Tatiana and Rose, were flower girls, and her son Jack was the ring bearer. The couple honeymooned in Turkey.

Bessette was introduced to John's uncle, Senator Ted Kennedy, in the late summer of 1994. Following the marriage, the senator would tell the press: "You could tell right away that there was something special between the two of them." Bessette moved into Kennedy's Tribeca loft in the summer of 1995, and the couple became engaged later that year. She quit her job at Calvin Klein in the spring of 1996.

Bessette first met Kennedy in 1992, while he was dating actress Daryl Hannah. 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 arguments. Paparazzi often waited outside the couple's Tribeca apartment to snap photographs.

After graduating from high school in 1983, Bessette attended Boston University's School of Education, graduating in 1988 with a degree in elementary education. While there, she dated John Cullen, star of the school's ice hockey team, who would later play professional hockey in the NHL.

Carolyn Jeanne Bessette-Kennedy (January 7, 1966 – July 16, 1999) was a publicist for Calvin Klein and the wife of John F. Kennedy Jr. After her marriage, Bessette-Kennedy's relationship with her husband and her fashion sense became the subjects of media scrutiny, drawing comparisons to her mother-in-law Jacqueline Kennedy Onassis. The couple and Bessette-Kennedy's older sister, Lauren, died in a plane crash off the coast of Martha's Vineyard in July 1999.