Our Favorite Photos of Dazzling Couple JFK Jr. & Carolyn Bessette

On July 16, 1999, John F. Kennedy Jr. boarded a small aircraft with wife Carolyn Bessette and her sister Lauren Bessette, intending to fly from New Jersey to Martha’s Vineyard and then on to Cape Cod for his cousin Rory’s wedding; instead, he crashed into the Atlantic Ocean off the coast of Massachusetts, leaving no survivors. Their loss became another in a series of what some call the “Kennedy curse:” the tendency of members of this family to die prematurely, like President John F. Kennedy, assassinated at age 46, or his brother Robert F. Kennedy, assassinated at age 42. The loss of the young, beautiful couple of JFK Jr. and wife Carolyn only intensified comparisons to his illustrious parents JFK and Jackie O., and their legacy has since taken on the same harrowing blend of glamour and tragedy.

Before meeting JFK Jr., Carolyn Bessette went to Boston University and then worked at Calvin Klein, first as a salesperson and then as a publicist. She began dating her future husband in 1994, moved into his Tribeca apartment in 1995, and quit her job in 1996, marrying Kennedy in a small, secret ceremony in September of that year. Their brief marriage was largely characterized by Carolyn’s often-difficult time adjusting to the media frenzy that now surrounded her day-to-day life, an experience longtime friend Carole Radziwill compared to Meghan Markle joining the royal family in early 2021.

“I love how people say Meghan knew what she was getting into,” Radziwill, who was married to JFK Jr.’s best man, the late Anthony Radziwill, tweeted after watching Meghan and Prince Harry’s bombshell Oprah interview. “People said the same thing about Carolyn Bessette when she married into the Kennedy family. You could never know. Meghan said it right the perception is nothing like the reality.”

Read on for our favorite photos of JFK Jr. and Carolyn Bessette, a couple taken from us too soon.

A version of this article was originally published in July 2021.