Madonna and her towering toyboy Akeem Morris bundled up for an outing in New York City on Saturday not far from her $32.5M Upper West Side abode (three Georgian townhouses).

At 66, the Queen of Pop is 38 years older than the Jamaican-born soccer coach, but they’ve been going strong as far back as the Fourth of July.

Akeem happens to be the same exact age – 28 – as the eldest of Madonna’s six children, daughter Lourdes Leon.

The two-time divorcée was still hot and heavy with her prior toyboy – boxer Joshua Popper – when she featured the former Oyster Bay United FC forward in her Paper Magazine spread in 2022.

Madonna and Akeem sparked engagement rumors on New Year’s Eve when she flashed a curious diamond bauble on her left ring finger as they rang in 2025 at the Louise Bourgeois exhibition in Tokyo.

Madonna and her towering toyboy Akeem Morris bundled up for an outing in New York City on Saturday not far from her $32.5M Upper West Side abode

At 66, the Queen of Pop is 38 years older than the Jamaican-born soccer coach, but they’ve been going strong as far back as the Fourth of July

Before meeting the seven-time Grammy winner – Morris was employed as a Loomis armed guard driver, ELEMENT Complex doorman, and Old Field Club banquet server following his 2018 graduation from Stony Brook University.

Michigan-born Madge famously loved and left men like Warren Beatty, Tupac, Jean-Michel Basquiat, Vanilla Ice, and Dennis Rodman as well as being married to her Shanghai Surprise leading man Sean Penn from 1985-1989 and her Swept Away director Guy Ritchie from 2000-2008.

The self-made superstar will ‘soon’ re-release her sixth studio album Bedtime Stories, which was nominated for best pop album at the Grammys and scored two No. 3 singles on the Billboard Hot 100 chart, Secret and Take a Bow back in 1994.

And Madonna isn’t just feeling nostalgic over past glory as she is ‘putting my heart and soul into my new music’ for an upcoming sequel to her 2005 dance album, Confessions on a Dance Floor, with musical director Stuart Price.

‘I can’t wait to share it with you!’ the Material Girl wrote on February 13.

Madonna – who gets 37.1M monthly listeners on Spotify – impressively concluded her $225.3M-grossing, 81-date Celebration Tour on May 4.

And over a year after Universal shelved her self-directed biopic starring Julia Garner, the Desperately Seeking Susan alum revealed last July that she and screenwriter Erin Cressida Wilson were rewriting the script now called Who’s That Girl.

Madonna previously helmed two dismally-reviewed box office bombs – Filth and Wisdom in 2008, and W.E. in 2011.

Akeem happens to be the same exact age – 28 – as the eldest of Madonna’s six children, daughter Lourdes Leon (pictured January 28)

The two-time divorcée was still hot and heavy with her prior toyboy – boxer Joshua Popper – when she featured the former Oyster Bay United FC forward (R, pictured on February 13) in her Paper Magazine spread in 2022

Madonna and Akeem sparked engagement rumors on New Year’s Eve when she flashed a curious diamond bauble on her left ring finger as they rang in 2025 at the Louise Bourgeois exhibition in Tokyo

The seven-time Grammy winner will ‘soon’ re-release her sixth studio album Bedtime Stories from 1994

And Michigan-born Madge isn’t just feeling nostalgic over past glory as she is ‘putting my heart and soul into my new music’ for an upcoming sequel to her 2005 dance album, Confessions on a Dance Floor, with musical director Stuart Price (pictured February 13)

And over a year after Universal shelved her self-directed biopic starring Julia Garner (L, pictured in 2023), the self-made superstar revealed last July that she and screenwriter Erin Cressida Wilson were rewriting the script now called Who’s That Girl