A short while later, they met again at a fundraiser reportedly called Don’t Bungle the Jungle II. This is when the sparks really began to fly.
May 1992: Kennedy brings Bessette to Sea Song, Long Island, to spend a long weekend with his cousin, Anthony Radziwill. Radziwill’s then-wife, Carole Radziwill (yes, that Carole Radziwill), said in a documentary, “We were sharing a summer house, Anthony and I and John, and he brought [Bessette] for Memorial Day weekend. They had been seeing each other for a few months super on the DL. And that’s when I first met her.”
Per an excerpt from Elizabeth Beller’s book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, published in People, the relationship took a bad turn after this weekend. At dinner, Kennedy confronted Bessette with a letter he’d received from a friend, which claimed that she was a partier out for fame and fortune. He apparently tossed the letter at her and stormed out of the restaurant.
1992-1994: They remain off and on for two years, as Kennedy was also dating Hannah at this time. In the JFK JR: The Final Year documentary, Kennedy’s former assistant, RoseMarie Terenzio, said that Kennedy remained hot and cold with Bessette for a little while. At one point, the New York Daily News ran a photo of Kennedy and Hannah at a movie premiere together. According to Terenzio, Bessette’s own mother sent her a clipping, with the note, “Carolyn, please get on with your life, love mom.”
1994: After Kennedy’s mother, Jackie Kennedy Onassis, dies, he breaks it off with Hannah for good and gets serious with Bessette.
Evan Agostini
July 1995: Kennedy proposes to Bessette.
In his book, Four Friends: Promising Lives Cut Short, excerpted in Vanity Fair, William D. Cohan writes that Kennedy popped the question over Fourth of July weekend in Martha’s Vineyard. “At one point John asked Carolyn to go fishing. While they were out on the water, John asked her to marry him. ‘Fishing is so much better with a partner,’ he said to her. He added that many things in life are better with a partner.”