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Before John F. Kennedy Jr. began dating Carolyn Bessette, retrospective accounts linked him to several women, including Jenny Christian, Sally Munro, Christina Haag and Daryl Hannah. Other names—including Brooke Shields, Madonna, Julie Baker and Sarah Jessica Parker—appear in reports with varying degrees of certainty. The clearest turning point is the timeline: Kennedy met Bessette in 1992 through her work at Calvin Klein, and biographies place the start of their relationship in 1994.
How to read the accounts of Kennedy’s dating history
There is no definitive, verified list of everyone Kennedy dated before Bessette. Retrospective coverage uses different language: some women are described as girlfriends or partners, while others are said to have been linked to him or involved in a rumored romance. The dates and durations below reflect those accounts, not a complete public record.
Reported relationships and connections, in chronological order
Jenny Christian: a high-school relationship
Us Weekly describes Christian as Kennedy’s first serious girlfriend. It reports that they met in high school and dated from 1978 to 1979. Us Weekly’s retrospective account
Sally Munro: reported Brown University relationship
Us Weekly reports that Kennedy met Munro at Brown University in 1979 and that they dated for six years. That duration comes from this retrospective entertainment account; the other reviewed sources do not independently verify the chronology. Us Weekly’s retrospective account
#1 Best Overall
Christina Haag: a relationship recalled by Haag
ABC News says Haag dated Kennedy while he attended NYU Law School. Haag recalled that they performed together in a play in the winter of 1985 and fell in love during the production. Us Weekly describes the relationship as lasting five years and notes Haag’s memoir, Come to the Edge. ABC News Us Weekly
Brooke Shields: a reported link and a remembered date
Us Weekly says Shields and Kennedy were linked in the 1980s and recounts Shields’s memory of a date with him. That supports describing a reported connection, not treating them as a long-term couple. Us Weekly’s retrospective account
Madonna: a rumored romance
ABC News includes Madonna among women Kennedy dated, but Us Weekly characterizes the episode more cautiously as romance rumors during a break in his relationship with Haag. The accounts therefore do not establish Madonna as a confirmed partner. ABC News Us Weekly
Julie Baker: an on-and-off connection reported through her recollection
Us Weekly reports that Kennedy and Baker met in 1989, dated on and off, and ended their relationship in 1991. Its account attributes the recollection to Baker, who was interviewed for the 2024 book JFK Jr.: An Intimate Oral Biography by Liz McNeil and RoseMarie Terenzio. Us Weekly’s retrospective account
Sarah Jessica Parker: a reported six-month relationship
ABC News identifies Parker as one of Kennedy’s well-known dating connections. Us Weekly reports that they dated for six months in 1991–92 and attributes their separation to the public interest in the relationship. ABC News Us Weekly
Daryl Hannah: the major relationship before Bessette
Biography.com describes Hannah and Kennedy’s relationship as an on-again, off-again romance lasting about five years, with an official breakup in 1994. Bessette’s Biography.com entry says Kennedy was still with Hannah when he met Bessette in 1992. Those accounts establish the broad sequence, but do not settle every detail of the timing or any overlap. Biography.com on Daryl Hannah Biography.com on Carolyn Bessette
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When Kennedy met Carolyn Bessette
Bessette worked for Calvin Klein and met Kennedy during a fitting in 1992. Biography.com and ABC News place the beginning of their dating relationship in 1994. ABC News also reports an assistant’s account that they briefly dated in 1993 before reuniting, so the sources leave some nuance between their first meeting and the relationship’s later start. Biography.com ABC News Biography.com on Carolyn Bessette
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Further reading
JFK Jr.: An Intimate Oral Biography (2024), by Liz McNeil and RoseMarie Terenzio, includes Julie Baker’s recollection as reported by Us Weekly. It offers one participant’s perspective rather than a definitive catalogue of Kennedy’s relationships. Us Weekly’s account of the book and Baker’s recollection
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