John F. Kennedy Jr.'s Dating History — From Pop Star Fling to Princess Diana Rumors

Marrying into the Kennedy family is a prize to be won. After all, who wouldn't want to cozy up with one of America's most affluent families? Some people had the chance to snag JFK Jr. up as a husband, but only one could do it.

While Kennedy ended up marrying Carolyn Bessette-Kennedy, he certainly had a lengthy dating history prior to finding the love of his life. Let's take a look:

It was a dream come true for Brooke Shields when she met Kennedy for the first time. She was crushing on him since the time she was three, Brooke confessed on The Howard Stern Show.

So, when they happened to meet in Aspen, C.O. while they were on a skii trip, she immediately had heart eyes. "He kept saying I look like his mother," she explained on the show. "Which is really interesting, and a compliment, but it was also like, 'I don't know how to feel about this.' And then we did have a real date."

Unfortunately, the dream was shattered. While Kennedy was interested, Brooke ended up turning him down because she didn't want to burn her chances in the future. It backfired, though, as they never spoke again.

Sarah Jessica Parker and Kennedy only had a brief six-month situationship. They met at a theater in 1991 where he reportedly asked the actress out, much to everyone's surprise.

"She called me, screaming, 'You're not going to believe who asked me out!'" her close friend Adam Shankman told People. While SJP is totally famous, it all became a bit too much for even her.

"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," she told the New York Times, adding, "I never had any idea what real fame was until I met John."

Model Julie Baker had nothing but nice things to say about her ex. She said she "just loved that he was kind of silly, quirky, forgetful, fun, and adventurous," according to Town & Country.

Kennedy and Madonna's relationship was always kept pretty under wraps. Only the two of them known all the details, and the pop star hasn't been too willing to dish.

A friend of Kennedy told People, "They saw each other a few times and they had a flirty and friendly banter but it wasn't a 'relationship.'" Apparently, the relationship had some logistical issues, but other reports suggest that Jackie Kennedy didn't approve of her son's choice.

"Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn't understand any of that," biographer J. Randy Taraborrelli told People.

The fall of Kennedy and Daryl's relationship allegedly happened because of her dog. While his mother was on her death bed, he was in Los Angeles for Daryl's dog's funeral. Once Jackie died, a similar situation happened again. According to biographer Steven M. Gillon, via Instyle, he told a friend: "Can you believe this? I just lost my mom and all she wants to talk about is her sick dog."

There's been a rumor floating around that Princess Diana and Kennedy actually had a total affair. He reportedly wanted the royal to pose for a cover of his magazine. Matt Berman, George magazine creative director, told People that Kennedy and Diana linked up to discuss the possibility.

Christina Haag and Kennedy dated for five years, but according to the actress, they split because they were too "young," as per her memoir, Come to the Edge. She added: "I felt happy that he was able to find someone that he wanted to spend his life with."