Madonna joined Bob the Drag Queen, Jeremy O. Harris, and more for a candid conversation about sex.

Madonna says John F. Kennedy Jr. was ‘best f---’ of her life

Madonna joined Bob the Drag Queen, Jeremy O. Harris, and more for a candid conversation about sex.

Joey Nolfi

Joey Nolfi is a senior writer at *. *Since 2016, his work at EW includes RuPaul’s Drag Race video interviews, Oscars predictions, and more.

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May 29, 2026 9:07 a.m. ET

Madonna and John F. Kennedy Jr. in 1997. Credit:

GTRES/Shutterstock

- Madonna revealed that the "best f---" of her life was former fling John F. Kennedy Jr.

- The pop icon had a wild conversation about sex on the Grindr app's YouTube page.

- Other guests included* RuPaul's Drag Race* winner Bob the Drag Queen, playwright Jeremy O. Harris, and more.

Madonna has officially confirmed which celebrity was the "best f---" of her life in a new, jaw-dropping conversation about sex, love, and intimacy.

The pop icon sat down for a video chat with a group of queer media personalities as part of dating app Grindr's promotional campaign for Madonna's upcoming album, *Confessions II*, which covered topics like the horrors of receiving a "hole pic" to assessing the size of particular bits of anatomy.

At one point, Madonna was asked who was the "best f---" of her life, to which she first replied, "I’m going to only name dead people."

Madonna then put her hand to her mouth and whispered, "John Kennedy Jr."

The "Hung Up" singer's reply elicited a shocked response in the room, with designer Raul Lopez comically exclaiming that "everyone said his dick was crazy."

Madonna and John F. Kennedy Jr., the son of President John F. Kennedy, were widely reported to have dated in the 1980s, while Madonna was also spotted with him years later in public during a Las Vegas event in 1997.

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A new generation of fans have taken an interest in JFK Jr.'s love life thanks to FX's recent (and controversial) *Love Story* TV* *series, which dramatized the relationship between JFK Jr. and Carolyn Bessette before they died in a 1999 plane crash.

Madonna's Grindr video is part of the superstar's rollout for her *Confessions II* album, which serves as a sequel to her 2005 LP *Confessions on a Dance Floor.*

To promote the album, Madonna also appeared on stage at Coachella in April alongside pop star Sabrina Carpenter, who sang *Confessions II* single "Bring Your Love" with the Queen of Pop at the California music festival.

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In addition to "Bring Your Love," Madonna released the buzz single "I Feel So Free" to rave reviews ahead of *Confessions II'*s July 3 release date.

Watch Madonna, Bob, Harris, and more discuss their love lives in the — warning —NSFW video above.

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