Brooke Shields reminisces about her ‘crazy crazy crush’ on JFK Jr

Brooke Shields is reminiscing about one of the great romantic crushes of her life. Shields has been promoting her new TV show, visiting numerous talk shows and sharing some of the biggest stories of her life. Shields has been famous for most of her life, and has plenty of great stories about Hollywood and celebrity life, including an almost-romance with one of this year’s most notorious figures, the late JFK Jr.

In an appearance on “Watch What Happens Live,” Shields opened up about her almost-romance with JFK Jr. in the ’80s, when the two used to hang around the same social circles. Shields was asked about her romance with him, clarifying some things. “I didn’t have a love story, I had a crazy, crazy crush.”

“We dated, but I never slept with him, so I don’t know if that counts … He was lovely to me,” she concluded. 

Shields also revealed she watched “Love Story,” the TV show that came out this year, depicting the romance between JFK Jr. and Carolyn Bessette. The show has been largely responsible for bringing both figures to the spotlight, sparking a lot of interest in their personal lives and the people they used to know when they were alive. “I watched it from start to finish. I loved it. I thought the acting was amazing,” said Shields. 

© Rick Maiman

In an interview with PEOPLE, Shields revealed that she had an interesting personal connection to the show. Her daughter Rowan served as one of its production assistants. “That was a little weird. I was away, and my daughter called me and she says: ‘Oh my God, you’re mentioned in Love Story,’ and she’s like: ‘Is it true?’ I was like: ‘OK, I’d be happy to tell you all the stories if you want, but yes.'” 

Shields and JFK Jr.’s fateful meeting

Brooke Shields has discussed her relationship with JFK Jr. on different occasions. In 2023, in an appearance on “The Howard Stern Show,” she opened up about their first kiss, describing it as “the best kiss I’ve ever had in my life.” 

“It was beyond not-disappointing. The lips are beautiful, and the face is amazing, and the body and the person, and he was down to earth and funny and irreverent,” she said, sharing that she had a lifelong crush on him, like many women who grew up in that era. 

© Getty Images

Shields and JFK Jr. coincided at a Kennedy family drinking party. After the kiss, Shields revealed that she froze. “He was so previous to me. I was like, ‘Oh my God, you’re falling in love and if you sleep with him, he may not talk to you again. And you can’t handle that.” Shields left and the relationship didn’t progress any further. 

Despite how dreamy the encounter was, Shields reveals that JFK Jr didn’t respond in the most chivalrous way. The two ran into each other again at the ski slopes, with JFK Jr. ignoring her. 

© Ron Galella Collection via Getty