JFK Jr.'s other women: Unseen trove of photos shows the world's most eligible bachelor with slew of dates who WEREN'T shown in Carolyn Bessette biopic

By LAURA PARNABY, US SENIOR NEWS REPORTER 21:36 26 Mar 2026, updated 21:51 26 Mar 2026

He was hailed as the world's most eligible bachelor... until Carolyn Bessette snared him in a wedding dress considered one of the world's most iconic.

But prior to that fateful union, John F. Kennedy Jr. enjoyed relationships with a slew of other women. Some were famous, others were not - although all of them were beautiful.

As the smash hit FX series Love Story draws to a close with an episode depicting John and Carolyn's deaths in 1999, the Daily Mail has unearthed stunning archive photos detailing JFK Jr's life before Carolyn.

They offer a tantalizing insight into life in 1990s New York and may well trigger thoughts of what might have been for the women who did not get JFK Jr up the aisle.

Many will likely breathe a sigh of relief, knowing they escaped the fatal plane crash which killed 'the world's sexiest man' and his wife Bessette.

LISA SHIELDS

Lisa Shields first met the Kennedy scion while she was a student at the Columbia School of Journalism in the late 1980s.

The two were captured frequently together by paparazzi in the summer of 1991. Although their romance was short-lived, they maintained an enduring friendship.

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Lisa Shields dated JFK Jr around 1991, and photographs like the one above show them in the summer of that year. Shields, an assistant producer and writer for the Arts and Entertainment cable network, is seen with him in New York city on August 19, 1991

Even dressed in casual clothes and with JFK Jr's knee wrapped, the couple cut a glamorous pair. They appeared engrossed in their conversation and completely oblivious to the paparazzi as they were photographed during their brief relationship in the summer of 1991

DARYL HANNAH

Kennedy dated actress Daryl Hannah from 1988 to 1994. The pair were long-term friends whose families vacationed together in the Leeward Islands when they were in their early twenties.

The pair reconnected at the wedding of JFK Jr's aunt Lee Radziwill, and they dated for almost six years including up until Kennedy met his eventual wife Bessette at a party.

Blade Runner actress Daryl Hannah knew JFK Jr since their families vacationed together in the Leeward Islands when they were in their early twenties. They are pictured frolicking in Central Park on March 13, 1993, close to Jackie O's Fifth Avenue home where he grew up

They only had eyes for each other and seemed oblivious to onlookers as they play-fought on the grass in September 1994 in the image shown above - though this was shortly before they broke up. Daryl is now an environmental activist who has been married since 2018

The pair reconnected in 1988 at the wedding of JFK Jr's aunt Lee Radziwill and dated for almost six years until Bessette entered his orbit. They are pictured above in Central Park on March 13, 1993, towards the end of their almost six-year relationship

Hannah and JFK Jr are pictured strolling through New York City close to Jackie O's 5th Ave. home after frolicking in Central Park later on March 13, 1993. They are dressed in their usual casual attire, but still caught the eyes of onlookers as one of the world's most famous couples

JFK Jr and Hannah are shown above in the first photograph snapped of them in Soho, on April 3, 1993. She had just broken up with Jackson Browne and fled to NYC to be with JFK Jr

The photograph above shows a topless JFK Jr. holding hands with Hannah as they played frisbee in Central Park on November 9, 1993, as rumors circled that they were due to wed in the Hamptons that weekend. They never tied the knot, and JFK Jr wed Bessette years later

SALLY MUNRO

Sally Munro entered Kennedy's orbit while both were students at Brown University.

The pair dated from 1979 to 1985 as Munro was said to be one of the few classmates who was not over-awed by JFK Jr.'s star power.

The couple stayed together after graduation and remained amicable even after the relationship broke down.

JFK Jr met one of his first girlfriends, Sally Munro, while they were at Brown University. They dated for around six years and vacationed together in India during 1983. The young couple is pictured close to 86th Street in Manhattan's Upper East Side on October 16, 1983

Munro couldn't keep her hands off JFK Jr and they were spotted several times in New York City. The two were often beaming and looking loved up as they hung out

In the photograph shown above, Munro looks lovingly at JFK Jr as he smiled back at her and they walked in -step down the sidewalk in the Upper East Side in October 1983

The 6'1" JFK Jr placed a protective hand on Munro's shoulders as they were seen strolling down 86th Street

JFK Jr and Munro cut a classy pair even while she wore a casual dress and he lounged in a loose-fitting polo and sneakers as they hung out around Manhattan in 1983

The couple were seen on the same day, October 16, 1983, in a change of clothes as JFK Jr switched his shorts for pants and Munro her dress for a more casual look

Munro, who JFK Jr met while they were both students at Brown University. She often appears attentive in paparazzi photographs of the pair from 1983, while he appears to be animated, caught mid-sentence as he told her a story while they strolled through Manhattan

Munro was also pictured with JFK Jr's family on June 17, 1983. He looked nonchalant in shades with a newspaper tucked beneath his arm, while Munroe wore a cozy over-sized white jumper next to his cousin Willie Smith as they walked between cars down Madison Avenue

CHRISTINA HAAG

Manhattan-born actress Christina Haag dated the Kennedy scion from 1985 until 1990. They were childhood friends, and they both attended Brown University.

JFK Jr dated Christina Haag from 1985 until 1990. They both attended Brown University, and they knew each other as children. They are seen above arriving at his mother's Fifth Avenue apartment in Manhattan after his graduation on January 11, 1989

JFK Jr and Haag are shown the same day looking slick in their leather jackets, wrapped up against the January chill in jumpers, while the political heir also donned a hat and scarf. They had just been to see Pack of Lies at the Royale Theater in New York City

MYSTERY WOMAN

The latest haul of JFK Jr archive pictures also includes the above image of him effortlessly carrying a bike on his shoulder as he strolled down the street with an unidentified woman

ANOTHER MYSTERY WOMAN

On June 16, 1984, JFK Jr was pictured in Manhattan with another mystery woman. She is only visible from behind as they chatted while he stopped on his bike on the sidewalk

JFK Jr pictured with the same unidentified woman who places her hand on his back

1 / 22

Lisa Shields dated JFK Jr around 1991, and photographs like the one above show them in the summer of that year. Shields, an assistant producer and writer for the Arts and Entertainment cable network, is seen with him in New York city on August 19, 1991

2 / 22

Even dressed in casual clothes and with JFK Jr's knee wrapped, the couple cut a glamorous pair. They appeared engrossed in their conversation and completely oblivious to the paparazzi as they were photographed during their brief relationship in the summer of 1991

3 / 22

Blade Runner actress Daryl Hannah knew JFK Jr since their families vacationed together in the Leeward Islands when they were in their early twenties. They are pictured frolicking in Central Park on March 13, 1993, close to Jackie O's Fifth Avenue home where he grew up

4 / 22

They only had eyes for each other and seemed oblivious to onlookers as they play-fought on the grass in September 1994 in the image shown above - though this was shortly before they broke up. Daryl is now an environmental activist who has been married since 2018

5 / 22

The pair reconnected in 1988 at the wedding of JFK Jr's aunt Lee Radziwill and dated for almost six years until Bessette entered his orbit. They are pictured above in Central Park on March 13, 1993, towards the end of their almost six-year relationship

6 / 22

Hannah and JFK Jr are pictured strolling through New York City close to Jackie O's 5th Ave. home after frolicking in Central Park later on March 13, 1993. They are dressed in their usual casual attire, but still caught the eyes of onlookers as one of the world's most famous couples

7 / 22

JFK Jr and Hannah are shown above in the first photograph snapped of them in Soho, on April 3, 1993. She had just broken up with Jackson Browne and fled to NYC to be with JFK Jr

8 / 22

The photograph above shows a topless JFK Jr. holding hands with Hannah as they played frisbee in Central Park on November 9, 1993, as rumors circled that they were due to wed in the Hamptons that weekend. They never tied the knot, and JFK Jr wed Bessette years later

9 / 22

10 / 22

JFK Jr met one of his first girlfriends, Sally Munro, while they were at Brown University. They dated for around six years and vacationed together in India during 1983. The young couple is pictured close to 86th Street in Manhattan's Upper East Side on October 16, 1983

11 / 22

Munro couldn't keep her hands off JFK Jr and they were spotted several times in New York City. The two were often beaming and looking loved up as they hung out

12 / 22

In the photograph shown above, Munro looks lovingly at JFK Jr as he smiled back at her and they walked in -step down the sidewalk in the Upper East Side in October 1983

13 / 22

The 6'1" JFK Jr placed a protective hand on Munro's shoulders as they were seen strolling down 86th Street

14 / 22

JFK Jr and Munro cut a classy pair even while she wore a casual dress and he lounged in a loose-fitting polo and sneakers as they hung out around Manhattan in 1983

15 / 22

The couple were seen on the same day, October 16, 1983, in a change of clothes as JFK Jr switched his shorts for pants and Munro her dress for a more casual look

16 / 22

Munro, who JFK Jr met while they were both students at Brown University. She often appears attentive in paparazzi photographs of the pair from 1983, while he appears to be animated, caught mid-sentence as he told her a story while they strolled through Manhattan

17 / 22

Munro was also pictured with JFK Jr's family on June 17, 1983. He looked nonchalant in shades with a newspaper tucked beneath his arm, while Munroe wore a cozy over-sized white jumper next to his cousin Willie Smith as they walked between cars down Madison Avenue

18 / 22

JFK Jr dated Christina Haag from 1985 until 1990. They both attended Brown University, and they knew each other as children. They are seen above arriving at his mother's Fifth Avenue apartment in Manhattan after his graduation on January 11, 1989

19 / 22

JFK Jr and Haag are shown the same day looking slick in their leather jackets, wrapped up against the January chill in jumpers, while the political heir also donned a hat and scarf. They had just been to see Pack of Lies at the Royale Theater in New York City

20 / 22

The latest haul of JFK Jr archive pictures also includes the above image of him effortlessly carrying a bike on his shoulder as he strolled down the street with an unidentified woman

21 / 22

On June 16, 1984, JFK Jr was pictured in Manhattan with another mystery woman. She is only visible from behind as they chatted while he stopped on his bike on the sidewalk

22 / 22

JFK Jr pictured with the same unidentified woman who places her hand on his back

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