GLAMOROUS NIGHT OUT! Madonna Suits Up for a Stunning Rooftop Date with Boyfriend Akeem Morris

They sparked engagement rumors in January

Madonna is in love and unbothered. The 66-year-old pop icon was seen heading into a rooftop dinner at Broadwick Soho in London with boyfriend Akeem Morris, rocking a full suit and tie, black shades, and her signature “icon walking” attitude.

Madonna and Akeem Morris © The Grosby Group
The couple is unbothered by there 38 year age gap

As the couple left the restaurant, the 66-year-old flipped off the cameras—strategically, of course—pressing her middle finger against her sunglasses in what might’ve been the most Madonna way to exit a date night.

The rooftop and Madonna have some history. It’s the location of her first photoshoot in 1983, when the building was the Warner Music HQ.

The dinner follows months of engagement speculation after Madonna posted a giant diamond ring on that finger in a New Year’s photo carousel. In the photos from her night out in the UK, the “Like a Virgin” singer pulled a Hailey Bieber, keeping her left hand in her pocket as photographers snapped images.

Akeem and Madonna rang in 2025 together with four of her six kids at Tokyo’s 1 Oak nightclub, and it seems like he has the family’s approval.

The 28-year-old joined her for her 66th birthday in Italy, the twins’ birthday party, and Christmas/Hanukkah festivities last year.

If they do tie the knot, it would be Madonna’s third marriage, following Sean Penn in the ’80s and Guy Ritchie in the 2000s. But whether she’s engaged or not, Madonna seems unbothered by the rumors and firmly in her “doing whatever I want” era.

Madonna: A girl’s girl

Following her London outing, the “Like A Virgin” singer shared a snap of her walking down the street in her brown suit. She wrote on the photo, “‘Did you see so-and-so copied you?’” Making it clear she’s not one to shame another woman, she wrote, “God forbid a woman takes inspiration.” “I see you, I love you,” she wrote in the caption. “You’re doing great sweeties.”

Naturally, fans dove straight into the comments trying to decode who she was talking about. Most landed on Lady Gaga, whose recent Coachella performance channeled some very Madonna-esque energy.

And while the two have had a famously rocky relationship over the years, especially after comparisons between “Born This Way” and “Express Yourself,” this felt like a full-circle moment.

Madonna showing love to Gaga (or any woman who dares take a page from her playbook) feels like a shift, encouraging a girl’s girl energy.