John F. Kennedy Jr. And Carolyn Bessette Couldn't Dodge Affair Rumors

"Love Story," a limited series by FX, has introduced a new generation to the tragic romance between John F. Kennedy Jr. and Carolyn Bessette. The couple enjoyed a passionate relationship, which was endlessly documented by tabloids, until their untimely deaths on July 16, 1999. Kennedy was flying himself, Bessette, and her sister to a wedding when their plane crashed outside of Martha's Vineyard, claiming all their lives. Unsurprisingly, their tragic ending didn't stop the interest in the couple — including affair rumors.

Both Kennedy and Bessette allegedly entertained other people. In 2010, Sybil Hill spilled the beans about her supposed affair with the president's son, which reportedly started prior to his romance with Bessette, in 1991, but continued into their marriage. After crossing paths with Kennedy during a date with another guy, Hill claims that John gave her his number, and they eventually started dating, per Woman's Day.

Sybil also claimed that they slept together in 1998, while Kennedy and Bessette were navigating marital problems. She also believed that Bessette posed as a reporter and called to inquire about the nature of the bond. "She asked me, 'Are you dating John Kennedy?' I said 'no' and she hung up," Hill shared with Radar Online in February 2026. "Her tone was so angry that I think it was Carolyn." After that, Hill was reportedly unable to reach him again.

Carolyn Bessette was also believed to have cheated on John F. Kennedy Jr. during their relationship. Like Sybil Hill, Bessette's alleged affair partner, model Michael Bergin, has also spoken publicly about their time together.

Bergin supplied quotes about their relationship to Edward Klein for his book, "The Kennedy Curse: Why The Tragedy Has Haunted America's First Family for 50 Years," in 2003. "Carolyn and I had a very intense love for each other. We were inseparable for a couple of years," said Bergin (via New York Post). "And I know deep in my heart that she still loved me even after she married ... Some things just don't end." His manager, Clifford Streit, also claimed that Bergin was the one to eventually end their affair because of her marriage. "There is something strangely decent about Michael, and he was respectful of marriage vows," he said.

In 2004, Bergin published his book "The Other Man: A Love Story," after he realized how unflattering Bessette's life had been framed by Klein. "[Klein's book] just caused this whirlwind of stories saying that she's just a horrible monster, that she's a coke addict, she's this and she's that. And I knew her very well," he shared with "Good Morning America" at the time (via ABC News). "And she's not any of that. The whole book was all lies. I had to do something."