Paparazzi photographers take pictures of John F. Kennedy, Jr. on a New York City street. (Photo by Mitchell Gerber/Corbis/VCG via Getty Images) — Image Credit: Corbis/VCG via Getty Images

Back in the days John F. Kennedy Jr was a catch. Prior to his passing in a plane crash in 1999 alongside his spouse Carolyn Bessett, the son of the late former president of the United States of America had all eyes set on him.

After all, he was named “Sexiest Man Alive” in 1988.

Julie Baker

The politician’s son, who passed away at age 38-years-old, dated Julie Baker for two years after meeting in 1989. The model disclosed to Liz McNeil and RoseMarie Terenzio – who wrote JFK Jr: An Intimate Oral Biography – that she was asked by the charmer to go on a date to a poet reading but declined the offer because she found it too “boring.”

She revealed on The Last Days of JKF Jr., “I just loved that he was kind of silly, quirky, forgetful, fun, and adventurous.” The two ended up going out elsewhere but eventually ended up as friends.

Christina Haag to Madonna

American attorney John F Kennedy Jr (1960 - 1999) (dark jacket, back to camera) and Pop singer Madonna (born Madonna Ciccone) talk together at the MGM Grand Garden Arena, Paradise, Nevada, June 28, 1997. They were there to attend the WBA Heavyweight Championship, a rematch between boxers Mike Tyson & Evander Holyfield. (Photo by Michael Brennan/Getty Images) — American attorney John F Kennedy Jr (1960 – 1999) (dark jacket, back to camera) and Pop singer Madonna (born Madonna Ciccone) talk together at the MGM Grand Garden Arena, Paradise, Nevada, June 28, 1997. They were there to attend the WBA Heavyweight Championship, a rematch between boxers Mike Tyson & Evander Holyfield. (Photo by Michael Brennan/Getty Images)

During the year of 1988 John Fitzgerald Kennedy Jr. was in a five year relatiolnship with actress Christina Haag. Though they were living their busy lives together and seemed to have a strong relationship, that all came to an end when he had a short-lived affair with pop star Madonna.

As per Christopher Anderson who noted in The Good Son: JFK Jr. and the Mother He Loved, the two would love to spend time with one another, but his mother Jackie was not a fan of their relationship which resulted in their breakup.

Sarah Jessica Parker

The Sex and the City star was in a romance with John for about six months – 1991 to 1992. Their relationship was so talked about that the 59-year-old actress felt that people would know her only for dating him – she told The New York Times in 1992.

“We would go places where there wasn’t a soul around, and the next day I’d see pictures of us there in the tabloids…He’s a nice man, but for God’s sake, I feel like I should apologize for dating him. It has become the defining factor in the person I am. It’s pathetic.”

Brooke Shields

The 59-year-old actress revealed during The Howard Stern Show that she once dated the popular lad, and he was her “best kiss”. She mentioned how she was madly in love with him and since she was little her mother hinted at her she would marry him one day.

Brooke recalled, “He kept saying I looked like his mother, which was really interesting and a compliment, [but] I also was like, ‘I don’t know how to feel about this.’ And then we did have a real date. And I wouldn’t sleep with him because I kind of loved him too much.”

Daryl Hannah

The two were romantically linked for a couple years but became exclusive in 1992. They knew each other from their teenage years and after they split from their respective partners they got together. They had a rocky relationship as “she did not get along” with his mother, as per John admitted once which placed a lot of pressure on them.

The list continued with many other women who stole his heart such as Xuxa, Meg Azzoni, and rumored sparks with Cindy Crawford. Ultimately, he tied the knot with his late spouse Carolyn Bessette in 1996.