During an appearance on The Howard Stern Show to promote her new documentary, Pretty Baby: Brooke Shields, the actress revealed that she had been in love with Kennedy since she was three years old and that her mom had predicted that they would get married.
Shields went on to describe how she got to spend time with Kennedy in Aspen, Colorado, when her mom took her to a wedding where the Kennedys were skiing.
Shields tried to impress Kennedy by skiing, even though she had never done it before. After catching his attention, Kennedy invited her to spend the evening with his family at a local bar. Shields recalled that there were some bar fights, but that Kennedy asked her if she wanted to leave, and she agreed.
After their date, Shields turned down Kennedy's advances because she loved him too much. She also recounted their first kiss, which she described as the best kiss she had ever had in her life. However, when the possibility of taking things further was suggested, Shields got nervous and backed off, saying that she was afraid of being hurt.
Shields revealed that after she rejected Kennedy, he left her to find her own way back to her chalet, which she felt was not very chivalrous. Despite the disappointing end to their date, Shields has fond memories of her time with Kennedy and the unforgettable experience of being with her childhood crush.
