Love Story, John F. Kennedy and Carolyn Bessette
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John F. Kennedy Jr. reportedly liked baring it all, according to author Maureen Callahan. On a recent episode of The Nerve with Maureen Callahan podcast, the author of Ask Not: The Kennedys and the
Brooke Shields was interviewed by Howard Stern in 2024, where she discussed her documentary Pretty Baby: Brooke Shields. While combing through her colorful life, Stern asked a question many '80s kids wanted answered: Did she ever date Kennedy Jr.?