Madonna Spotted in NYC with 28-Year-Old Toyboy: Engagement Rumors Heat Up!

On a chilly Saturday in New York City, Madonna and her tall companion Akeem Morris ventured out nearby their $32.5M Upper West Side mansion (consisting of three Georgian townhouses) wrapped up against the cold.

The Pop Queen, who is 66 years old, is 38 years senior to the Jamaican soccer coach in age, yet their bond dates back to Independence Day celebrations.

Coincidentally, both Akeem and Lourdes Leon share the same age – 28 years old. They are, in fact, the same age.

The twice-divorced woman was still passionately involved with her ex-boxer boyfriend, Joshua Popper, at the time she showcased him in a feature for Paper Magazine in 2022, when he was previously a forward for Oyster Bay United FC.

On New Year’s Eve in 2025, speculations about an engagement arose when Madonna and Akeem were spotted at the Louise Bourgeois exhibition in Tokyo, with Madonna showing off a mysterious diamond ring on her left hand while welcoming the new year together.

After my triumphant graduation from Stony Brook University in 2018, I found myself embarking on a unique journey, working as an armed guard driver for Loomis, doorman at the ELEMENT Complex, and banquet server at Old Field Club. Little did I know that my life was about to take an extraordinary turn when I crossed paths with a seven-time Grammy winner.

Born in Michigan, Madge is well-known for having relationships with numerous men such as Warren Beatty, Tupac Shakur, Jean-Michel Basquiat, Vanilla Ice, and Dennis Rodman, in addition to marrying her Shanghai Surprise co-star Sean Penn from 1985 to 1989 and her Swept Away director Guy Ritchie for the years 2000 to 2008.

The renowned artist who built her success from scratch is about to bring back her sixth studio album, titled Bedtime Stories, which was once nominated for the Best Pop Album at the Grammys and produced two top-charting singles on the Billboard Hot 100 in 1994 – Secret and Take a Bow.

Instead of simply reminiscing about old successes, Madonna is pouring her heart and spirit into her fresh tunes for the follow-up to her 2005 dance album, Confessions on a Dance Floor, collaborating once more with musical director Stuart Price.

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

As a devoted admirer, I’m proud to share that I, too, have been captivated by the remarkable journey of Madonna, whose music resonates with an astounding 37.1 million monthly listeners on Spotify. Her grand Celebration Tour, grossing an impressive $225.3M across its 81 dates, came to a triumphant close on May 4th.

Approximately one year following Universal’s decision to put on hold a self-directed biopic starring Julia Garner, the actress previously known for Desperately Seeking Susan disclosed in July that she and screenwriter Erin Cressida Wilson were currently reworking the script, now titled Who’s That Girl.

As a die-hard admirer, I can’t help but reflect on Madonna’s journey as a director, a path that has seen her tackle two films met with less than favorable criticism – “Filth and Wisdom” from 2008 and “W.E.” in 2011. These cinematic endeavors didn’t exactly set the box office alight, but they surely added another layer to the enigma that is Madonna.