Inside John F. Kennedy Jr.'s Long Dating History With Notable Women — From Sarah Jessica Parker to Brooke Shields
John F. Kennedy Jr. had many women interested in him.
April 9 2026, Published 8:30 p.m. ET
John F. Kennedy Jr., son of the late President John F. Kennedy, was not only a public figure but also a prominent figure in the dating world. His romantic history includes high-profile relationships that spanned decades.
Before marrying Carolyn Bessette in 1996, JFK Jr. dated several notable women, capturing media attention and public interest, and RadarOnline.com can reveal them all now.
Jenny Christian and Sally Munro
JFK Jr.'s first relationship started way back in high school in 1978.
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.
Brooke Shields
He also went on a date with Brooke Shields.
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.
Christina Haag
One of JFK Jr's former girlfriend wrote a memoir.
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.
Madonna
JFK Jr. was rumored to have dated Madonna.
During a brief break with Haag, JFK Jr. sparked romance rumors with pop icon Madonna, who was separating from actor Sean Penn.
Julie Baker
He also had an on-again, off-again relationship with Julie Baker.
In 1989, he met model Julie Baker, and they had an on-again, off-again relationship until 1991.
Baker 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.
Sarah Jessica Parker and Cindy Crawford
The 'Sex and the City' star had a romance with JFK Jr.
JFK Jr. also dated Sarah Jessica Parker for six months and was rumored to have had a brief romance with supermodel Cindy Crawford in 1995.
Daryl Hannah
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He dated actress Daryl Hannah for five years.
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.
Carolyn Bassette
JFK Jr. and Carolyn Bessette tied the knot in 1996.
Ultimately, JFK Jr. met Bessette 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.
