Madonna’s love life has always been nearly as famous as her music. At 65, the “Material Girl” is still making headlines – not just for her chart-topping hits or boundary-pushing performances, but for her romantic life, which the public follows with endless curiosity and opinions.
Most recently, Madonna has been seen with Josh Popper, a boxing coach who’s about 40 years younger than her. They reportedly met when Popper began training one of Madonna’s sons in early 2023. Since then, the two have been photographed together at various events, looking cozy, but neither has felt the need to spell out exactly what’s going on. True to form, Madonna seems content to keep people guessing.
Madonna’s Romantic History
Looking back, Madonna’s relationships read like a who’s who of creative and sometimes rebellious personalities. Her marriage to Sean Penn in the 1980s was dramatic enough to fill a tabloid on its own. In the early 2000s, she married British director Guy Ritchie, and together they had a son, Rocco, while also adopting David Banda from Malawi. Before, after, and in between, Madonna’s love life included actor Warren Beatty, rapper Vanilla Ice, basketball star Dennis Rodman, and Carlos Leon – the father of her first child, Lourdes.
What’s striking is how Madonna so often goes her own way in love. After her split from Ritchie, her partners tended to be significantly younger men, including dancer Brahim Zaibat, dancer Timor Steffens, model Kevin Sampaio, and dancer Ahlamalik Williams. Her relationship with Williams reportedly ended in 2022, just before she was linked to Popper.
Despite living so much in the public eye, Madonna tends to hold the real details close to the vest. She’s never shied away from expressing her sexuality and her independence through her art, but in interviews and public comments, she rarely volunteers the inside story about her personal relationships.
Public Perception vs. Private Reality
There’s a funny contrast between Madonna’s larger-than-life, fearless persona on stage and what those close to her say about her private life. Friends and former collaborators have hinted that, away from the spotlight, she’s actually much more traditional than people expect – hoping for genuine connections rather than just attention or tabloid fodder.
Madonna herself hinted at this in her documentary “Madame X,” admitting she’s “just looking for someone who can handle me, who isn’t intimidated by who I am and what I do.” And if her decades-long career has proved anything, it’s that she’s determined to do things her way, romance included.
While other celebrities stage public announcements or share intimate details on social media, Madonna prefers to let photos, rumors, and the occasional blink-and-you-miss-it Instagram post set the narrative. She’s never been one to confirm or deny what the world thinks is going on, a move that keeps both the press and her fans endlessly intrigued.
Approaching 70, Madonna hasn’t started following anyone else’s rules. Criticism about the age gaps in her relationships simply doesn’t faze her. If anything, she seems amused by society’s hang-ups, continuing to write her own story and ignore the noise.
Past Relationships
Akeem Morris
Pabllo Vittar
Anitta
Josh Popper
Andrew Darnell
Ahlamalik Williams
Kevin Sampaio
Idris Elba
Aboubakar Soumahoro
Diplo
Timor Steffens
Brahim Zaibat
Adam Senn
Gerard Butler
Amber Rose
Gabriel Byrne
Jesus Luz
Alex Rodriguez
Guy Ritchie
David Blaine
In the end, Madonna’s approach to love looks a lot like her artistic legacy: bold, unapologetic, and entirely her own.