Madonna Brought Confessions Back To Times Square, Then Named Her Best Sex Ever
Madonna opened Pride Month by turning Times Square into a free, open-air nightclub. On 4 June she played a surprise pop-up concert with Grindr. The set ran from 6pm to 7pm and gave fans a first listen to new songs from her upcoming album Confessions II. Thousands packed the intersection on a Thursday evening to watch it happen.
A free concert in the middle of New York
Four days into Pride, the Queen of Pop did what she does best. She showed up unannounced and owned the room, even when the room was a city block. The 67-year-old leaned back into the dance music that built her career, mixing older material with fresh tracks from the new record.
The album is her 15th, and a proper sequel to 2005’s Confessions on a Dance Floor. It arrives on 3 July through Warner Records, with longtime collaborator Stuart Price producing again. The lead single, Bring Your Love, features Sabrina Carpenter.
The Grindr “Confessions” and the Romantic Bombshell
While the Times Square concert brought the stadium-level energy, it was the accompanying promotional video partnership with the LGBTQ+ dating app Grindr that delivered the ultimate media shockwave.
In a raw, unfiltered roundtable interview titled Grindr Presents: Confessions with… Madonna, the singer sat down with a panel of prominent queer cultural figures, including fashion designer Raul Lopez, Bob the Drag Queen, and playwright Jeremy O. Harris. The conversation quickly shifted from her decades of AIDS activism to a completely unhinged “kiki” about her legendary romantic past.
The definitive standout moment of the entire campaign arrived when Raul Lopez asked her to name the single greatest physical encounter of her life:
“What was your best f**? Who was your best d***-down?”*
Pausing briefly to respect her living exes, Madonna drew a firm boundary before dropping a historic bombshell:
“I’m going to only name dead people… John Kennedy Junior.”
As the room erupted in gasps, Lopez validated the pop star’s claim, adding, “Everyone said his d*** was crazy and he was a good f***. You’re the third person to say that.” Madonna simply smiled and confirmed the legacy with a knowing, definitive, “Mm-hmm.”
Watch the full set
We’ll be replaying this one for a while. Catch Madonna’s full Times Square performance on the official livestream.
