Brooke Shields Says JFK Jr. Was ‘Best Kiss’ She’s Had & Reveals Why She Didn’t Sleep With Him

In a new interview, Brooke Shields reflects on going on a date with John F. Kennedy Jr. and opens up about why they didn't do more than kiss.

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Brooke Shields got candid about her dating history in an interview with Howard Stern on April 4. The actress confirmed that she had a tryst with John F. Kennedy Jr. at some point before his death in 1999. She admitted that she had been “madly in love” with “John-John” since she was just a toddler, and she had the chance to meet him when she and her mom were on a ski trip to Aspen, where the Kennedys were also vacationing.

“We went out. I was invited out with the family,” Brooke shared on The Howard Stern Show. “He kept saying I looked like his mother, which was really interesting. It was a compliment, but also…I don’t know how to feel about this.” Brooke confirmed that the two did go on a “real date,” but said she didn’t sleep with him afterward because she “just kind of loved him too much” and didn’t want to ruin it.

brooke shields jfk jr
Brooke Shields and JFK Jr. (Elisa Leonelli/Adam Scull/

The night started out at a bar with John’s family, but the two ended up sneaking off on their own and going back to JFK Jr.’s chalet. “He kissed me,” Brooke dished. “It was, like, the best kiss I 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. He was down to Earth and funny and irreverent.”

When John tried to take things to the next level, Brooke said she “froze” because the possibility of sleeping with him to was too “precious” to her. “It was like, ‘Oh my God, you’re falling in love and if you sleep with him he may never talk to you again and you can’t handle that,” she explained. “I wasn’t playing a game. I really as just so afraid of being hurt. If I slept with him, I would have given him my entire universe, my heart, my everything.”

After the evening together, Brooke said she had to get a cab back to her hotel, which she described as “a little less than chivalrous.” The next day, when she saw JFK on the slopes, he didn’t look at her or talk to her. “On the one hand, I was like, ‘Oh s***,'” she said. “But on the other hand, I was like, ‘Oh, thank God, because he still might not have talked to you even if you had [slept with him], but you wouldn’t given him something he might not have cared about.’ He showed his true colors in that.”

The two came face-to-face again, though, when they both got snowed in in Aspen and John had to stay at Brooke’s mother’s chalet with her. She said JFK never once mentioned what had previously happened between them. “I think I knew enough about myself by then,” she concluded. “I’d been doing work on myself to say, ‘You won’t be able to handle this [if you sleep with him].”