Madonna’s love life

Sean Penn

Taking on the position of Madonna’s first husband was Sean Penn. The actor, now 62, and the singer tied the knot on 16 August 1985 after meeting the year before on a studio lot while she filmed the music video for Like A Virgin. In 1986, Madonna dedicated her album True Blue to him, writing, “This is dedicated to my husband, the coolest guy in the universe.” In 1986, they appeared together in movie Shanghai Surprise, but the couple eventually split in 1989.

Michael Jackson

In 1991, Madonna brought Michael Jackson as her date to the Academy Awards, where her film Dick Tracy, which also starred Warren Beatty and Al Pacino, was nominated for seven awards. Since then, the singer has called the moment her “best date ever” and admitted that Michael had taken her back to his afterwards.

Vanilla Ice

Madonna and Vanilla Ice, born Robert Van Winkle, dated for eight months in the early ’90s after the singer made her move at one of his shows in New York. Speaking about how their relationship started, Vanilla Ice, 54, said, “She’s aggressive. She wanted me. She was much older, so I was like ‘Whoa, what’s going on with this?’ She came into my dressing room right after the show. She grabbed me and we were having cocktails that night.”

Carlos Leon

The Queen of Pop’s romance with personal trainer Carlos Leon started in 1994, after he approached her while she was jogging in Central Park. Carlos, now 56, and Madonna ended up dating for nearly three years, and were even rumoured to be engaged at one point. But they called things off in 1996, shortly after the Material Girl hitmaker gave birth to their daughter Lourdes, 25, in October.

Tupac Shakur

Actress Rosie Perez reportedly introduced Madonna to the rapper at the Soul Train Awards in 1993. The details surrounding their relationship have always been a mystery, but in July 2017, a letter Tupac wrote while serving time in prison for sexual abuse was sold at auction and shed light on why the California Love hitmaker ended their romance. He wrote, “For you to be seen with a black man wouldn’t jeopardise your career. But for me… I felt due to my ‘image’, I would be letting down half the people who made me.”

Guy Ritchie

Madonna met director Guy Ritchie, now 53, in 1999, after they were introduced by the musician Sting. After a whirlwind romance, they married on 22 December 2000 at Skibo Castle in Scotland. After eight years together and the birth of their son Rocco Ritchie, 22, and adoption of son David Banda, 16, the pair divorced. Madonna regularly discusses her time with him, and in 2015 ref lected, “There were times I felt incarcerated. I wasn’t allowed to be myself.”

Jesus Luz

Yes, Madonna and Jesus. The pair dated on and off following her split from Guy in 2008. They met on the set of a shoot for magazine W, where she quickly became enamoured with the Brazilian model, who was 28 years younger than her. Jesus broke up with her in early 2010, with a source saying many were surprised it lasted at all as they had nothing in common.

Ahlamalik Williams

Most recently, Madonna has been linked to 28-year-old dancer Ahlamalik, who she met in 2015 during her Rebel Heart tour. The couple eventually got together in 2019, but split earlier this year after Madonna found it “hard to keep the romance alight”. At the time, a source revealed, “Things have been on and off with Ahlamalik for a while. There’s a lot of love there, but for now, they have decided to separate.”