Brooke Shields Reveals John F. Kennedy Jr.'s "Less Than Chivalrous" Reaction to Her Turning Him Down

Brooke Shields once dated the late John F. Kennedy Jr. Find out why, according to her, an evening in Aspen ended abruptly and details about the awkwardness that ensued.

By Corinne Heller Apr 05, 2023 10:21 PMTags

The man who gave Brooke Shields her best kiss turned out to be a less-than-stellar date.

The star of the new Hulu docu-series Pretty Baby: Brooke Shields recalled how an evening in Aspen with her childhood crush, the late John F. Kennedy Jr., ended with a solo ride home for her after she refused to have sex with him. At the time of their date, the son of late President John F. Kennedy and First Lady Jackie Kennedy Onassis was one of the most sought-after bachelors.

"I was invited with the family. He kept saying I looked like his mother, which was really interesting and a compliment, but it was also like, I don't know how to feel about this," Shields, 57, said on The Howard Stern Show April 4. "And then we did have a real date and I wouldn't sleep with him because I just, I kind of loved him too much."

The Suddenly Susan alum said she and Kennedy, often nicknamed John-John, started out the evening by going to a bar with his family.

They Dated? Surprising Star Couples

"Everybody's just drinking at the bar and there's bar fights and drinking and he's like, 'You want to get out of here? and I was like, 'Uh yeah, I do want to get out of here, John Kennedy,'" she remembered. "We had to take cabs around everywhere because he didn't have a car there. And we went back to this chalet hotel that he was in. He like, kissed me and it was like the best kiss I've ever had in my life."

MediaPunch/Shutterstock; Robin Platzer/IMAGES/Getty Images

But the Blue Lagoon actress was not interested in more than that at the time. "I froze though because it was so precious to me," she explained, "and 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 added that she suspected her date wanted to take things further, though "I wasn't playing a game."

"I was so afraid of being really hurt," she continued, "because if I slept with him, I would have given him my entire universe, my heart, my everything."

According to the actress, Kennedy had her find her own transportation back to her hotel. "I had to get a cab home," she said, "which is a little less than chivalrous."

Awkwardness ensued the next day as they saw each other again on the ski slope. "He didn't look at me and he didn't talk to me," Shields said. "And on the one hand, I was like, 'S--t,' and on the other hand, I like, 'Oh, thank God, thank God,' because he still might not have talked to you, even if you had and you would have given something that he wouldn't have like, cared about. He showed his true colors in that."

Their situation got a little more uncomfortable when the snowy weather prohibited Shields from leaving the trip. "We got stranded," Shields recalled. "We were all supposed to leave. We got snowed in and he had to stay in the house my mom was renting. So, then it was my mom and John-John and me in this chalet and it was just like, [This was surreal.'"

Kennedy died in 1999 at age 38 in a plane crash. The attorney and magazine publisher, who piloted the small aircraft, was killed alongside his wife Carolyn Bessette and sister-in-law Lauren Bessette.

Shields has been married to Chris Henchy for 22 years. The two are parents to daughters Grier, 16, and Rowan, 19.

Latest News