John F. Kennedy Jr.’s Dating History: Daryl Hannah, Carolyn Bessette

The first significant relationship in JFK Jr.’s life began in high school with Jenny Christian. They dated from 1978 to 1979 after meeting at Phillips Academy Andover. After this early romance, he crossed paths with Sally Munro at Brown University, where they began a six-year relationship.

While at Brown, JFK Jr. also met actress Brooke Shields. They rekindled their connection in the 1980s. Brooke later shared her experience on The Howard Stern Show, revealing that JFK Jr. once remarked she resembled his mother.

Shields described their date as memorable and their kiss as the best she had ever experienced.

“I froze though because he was so precious to me,” she expressed.

Following his time with Brooke, JFK Jr. dated Christina Haag, a former classmate. Their five-year relationship would eventually inspire Christina to write a memoir titled Come to the Edge.

In 1989, he met model Julie Baker, and they had an on-again, off-again relationship until 1991.

Julie recounted how surprised she was to receive a call from JFK Jr., inviting her to a poetry reading. Their friendship continued even after their breakup, with Julie noting she saw him just a week before his tragic death.

However, it was his relationship with actress Daryl Hannah that is often remembered as one of his most serious. They dated for five years after reconnecting at his aunt’s wedding in 1988.

Ultimately, JFK Jr. met Carolyn in the early 1990s, and the couple married in 1996.

Their relationship faced intense media scrutiny, but sources noted they worked to nurture their bond. Tragically, they died in a plane crash off the coast of Hyannis Port, Mass., in 1999.

Their love story continues to captivate the public, now the subject of FX’s limited series Love Story.