The article explores the enduring fascination with John F. Kennedy Jr., highlighting a CNN documentary and Ryan Murphy's upcoming series that delve into his life, legacy, and the cultural impact of his brief but influential public presence, including his magazine George and his tragic death in 1999.
A new book reveals that John F. Kennedy Jr. had brief romantic encounters with Madonna and Brooke Shields but did not sleep with either. Madonna's relationship with JFK Jr. was purely physical and brief, while Brooke Shields, who was a virgin at the time, chose not to sleep with him to avoid emotional attachment.
Carolyn Bessette, wife of John F. Kennedy Jr., reportedly had a rebellious response to one of JFK Jr.'s party rules. Despite his request for guests not to wear black, Bessette wore black anyway, stating, "F— it, I don't care. I don't work for George. I can wear black." The couple's love story was filled with passion and fights, and they were together until their tragic deaths in 1999.
According to author J. Randy Taraborrelli, John F. Kennedy Jr. would consider the future of his relationships based on his mother Jackie Kennedy's opinion. If Jackie approved, John would become unsure, but if she disapproved, as she did with Daryl Hannah, he became more attached. Jackie reportedly ignored Hannah and would eat in another room when she visited. John and Hannah dated on and off from 1992 until shortly after Jackie's death in 1994. John later married Carolyn Bassette, and they both tragically died in a plane crash in 1999.
Ethel Kennedy, aunt of John F. Kennedy Jr., reportedly gave Carolyn Bessette a blunt pep talk before their wedding, advising her on what it takes to be a Kennedy wife and survive in the public eye. Ethel emphasized the importance of maintaining one's own identity, not letting their husbands influence them into bad behavior, and not fighting in public. She praised Bessette's character and intelligence, stating that she was more powerful than any of the other women JFK Jr. had dated. The couple married in 1996 and tragically died in a plane crash in 1999.
Ethel Kennedy, aunt of John F. Kennedy Jr., reportedly gave Carolyn Bessette a blunt pep talk before their wedding, advising her on what it takes to be a Kennedy wife. Ethel emphasized the need for self-confidence and not letting public scrutiny or her husband's influence lead to bad behavior. She also warned against fighting in public and praised Bessette's intelligence and character. Nine months later, JFK Jr. and Bessette married in a secret ceremony, but tragically died in a plane crash in 1999.
Journalist Legs McNeil claims that Sinéad O'Connor broke John F. Kennedy Jr.'s pencil and told him to "Fuck off!" when he asked for her phone number at a restaurant in New York in 1988. McNeil, who had a brief romance with O'Connor, reflects on their time together and praises her strong will and bravery. O'Connor was found dead in her London home on July 26, 2021, and her death is not being treated as suspicious.
Jackie Kennedy was reportedly unhappy about her son John F. Kennedy Jr.'s brief romance with Madonna in the 1980s due to the singer's marital status and her penchant for attention. Despite attending one of Madonna's plays in disguise, Jackie refused to meet the musician backstage, not wanting to validate their relationship. Madonna and John remained on decent terms after their breakup, with John even asking Madonna to pose on the cover of his magazine years later, though she declined.
Janice Dickinson revealed in an interview with Queerty that she unknowingly stole Donald Trump's limousine during a snowstorm in the 1980s to meet John F. Kennedy Jr. for a date. She said she drove the limo a few blocks down the street, swerving and making fishtails in the street, and didn't discover it belonged to Trump until the next day. Brooke Shields also recently spoke about her date with Kennedy Jr. on "The Howard Stern Show," saying he showed his "true colors" after she refused to have sex with him.
Brooke Shields revealed on "The Howard Stern Show" that she had a real date with John F. Kennedy Jr. in Aspen, Colorado, where he took her to a pub with his family and kissed her, which was the best kiss she ever had. However, the next day, Kennedy ignored her on the slopes, showing his true colors. Shields decided not to sleep with him that night and took a cab home. Kennedy went on to marry Carolyn Bessette-Kennedy, and they died in a plane crash in 1999. Shields is currently promoting a documentary about her life.
Brooke Shields revealed on "The Howard Stern Show" that the best kiss of her life was with John F. Kennedy Jr., whom she had been "madly in love" with since she was a young girl. Shields also shared that she stopped receiving Tom Cruise's exclusive Christmas cake after a 10-year run, which came with a card from Cruise, his then-wife Katie Holmes, and their daughter, Suri. Shields also discussed her postpartum depression and use of antidepressants, which led to a public feud with Cruise over his comments about psychiatric drugs.
Brooke Shields revealed in an interview with Howard Stern that she refused to have sex with John F. Kennedy Jr. on their first and only date in Aspen in the 1980s. Shields said Kennedy was "less than chivalrous" after she rejected his advances, leaving her to call a cab back to her own lodgings. Despite sharing a passionate kiss, Shields turned down sex with Kennedy because she was afraid of being hurt. Kennedy later married publicist Carolyn Bessette, while Shields had a short-lived marriage to tennis ace Andre Agassi.
Brooke Shields revealed on "The Howard Stern Show" that John F. Kennedy Jr. was "less than chivalrous" towards her after she rejected his sexual advances on their first date. Shields said she was left to make her own way back to her chalet after turning down Kennedy's advances. She added that Kennedy ignored her on the slopes the following day, showing his "true colors." Shields and Kennedy had a short-lived romance in the 1980s.
Brooke Shields revealed on "The Howard Stern Show" that John F. Kennedy Jr. was "less than chivalrous" towards her after she refused to sleep with him on their first date. Shields said she was "madly in love" with Kennedy since she was three years old and tried to impress him during a skiing vacation in Aspen. After rejecting his advances, Shields said Kennedy ignored her on the slopes the next day, showing his "true colors."