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In a recent candid interview, Madonna opened up about her most memorable romantic encounter-and it was with a well-known figure from the past. The 67-year-old pop icon revealed that her “best” romance was with none other than John F. Kennedy Jr.
The conversation took place during a discussion sponsored by the hookup app Grindr, promoting her upcoming album, Confessions II, set to release on July 3. Madonna chatted about her past relationships with a variety of notable personalities, including Bob the Drag Queen, dancer Ivy Mugler, designer Raul Lopez, playwright Jeremy O. Harris, and Saturday Night Live star Marcello Gutierrez.
When asked about her top romantic connection, Madonna playfully prefaced her answer by saying, “I’m only going to name dead people,” before whispering, “John F. Kennedy.”
The panel’s reaction was instant and lively, with exclamations of surprise. Raul Lopez chimed in, noting the well-known rumors about JFK Jr.’s romantic prowess, to which Madonna gave a cheeky confirmation.
Madonna and JFK Jr. are believed to have shared a brief relationship in the late 1980s. The son of President John F.
Kennedy and Jacqueline Kennedy Onassis was known for his high-profile romances with actresses like Daryl Hannah, Sarah Jessica Parker, and Brooke Shields before marrying Carolyn Bessette. Their relationship was confirmed in the 2024 book JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, where a close friend described Madonna’s involvement as “totally a fling.”
Further insight comes from one of Madonna’s former backup dancers, who revealed in Christopher Anderson’s biography The Day John Died that JFK Jr. was “totally in awe” of the pop superstar when they first met. Earlier this year, Brooke Shields also praised JFK Jr., calling him “one of the best kissers” she had ever encountered.
JFK Jr.’s romantic life has long fascinated the public, including his relationship with his wife Carolyn, recently portrayed in the FX series *Love Story: John F. Kennedy Jr.
& Carolyn Bessette*, produced by Ryan Murphy. Tragically, JFK Jr., Carolyn, and her sister Lauren all died in a plane crash in 1999.
Meanwhile, Madonna is currently dating 29-year-old soccer player and model Akeem Morris. The two met during a 2022 photo shoot for Paper Magazine and were seen dancing together at Coachella this past April, moments that quickly made the rounds on social media.
Madonna’s revelation not only offers a glimpse into her personal history but also sheds light on a lesser-known chapter in JFK Jr.’s storied life.