Brooke Shields Once Went On A Disastrous Date With JFK Jr.

Before John F. Kennedy Jr. let down Brooke Shields in a big way, the actress had high hopes. She told Howard Stern that she was "madly in love" with Kennedy from the time she was three years old. Shields' mother would even say to her, "That's the boy you're gonna marry." Shields initially met Kennedy in Aspen, Colorado, when she went there to attend a wedding and go skiing for the first time. Even though she struggled a lot with skiing and Kennedy did not help her at all, Shields was still charmed by him. 

She recalled during Stern's show that she went to a bar with Kennedy's family one night, and he asked her, "You wanna get out of here?" Shields joked to Stern, "I was like, 'Uh, yeah, I do wanna get outta here, John Kennedy.'" When they went back to his hotel together, things started off really well. "He kissed me, and it was like the best kiss I ever had in my life," the model remembered. "The lips are beautiful, and the face is amazing, and the body, and the person," she gushed. She remembered him as "down to earth," "funny," and "irreverent." Sadly, the romantic moment proved short-lived.