In August 2022, Madonna turned 64 and proved the “Material Girl” is still down for a good time. The “Like A Virgin” songstress celebrated her big day with her loved ones in Italy. At some point in the night, Madonna provided a callback to her legendary VMAs performance with Britney Spears and Christina Aguilera by kissing two friends in a taxi.
Of course, Madonna’s PDA moment isn’t the first time her romantic endeavors have made headlines. Throughout her fame, Madonna’s relationship history has involved bizarre rumors and some confirmed relationships that were even more shocking. Let’s look at some of Madonna’s famous suitors.
In 1985, Madonna met actor Sean Penn on the set of her “Material Girl” music video, and six months later, they were married on her 27th birthday on Aug. 16, 1985. Although Madonna and Sean loved each other and moved their relationship quickly, the young couple had their own issues.
According to People, Sean accused Madonna of cheating on him with singer Nick Kamen after they collaborated on her song, “Each Time You Break My Heart.” The actor’s 1987 arrest also reportedly strained their marriage. In January 1989, Madonna filed for divorce from Sean after four years.
As we mentioned earlier, Madonna has been in multiple rumored relationships that turned out not to be true. However, in 2017, TMZ unearthed a letter detailing her former romance with Tupac Shakur. In 1995, Tupac wrote to Madonna in prison and said they could no longer sleep together because of her race.
"For you to be seen with a black man wouldn't in any way jeopardize your career, if anything, it would make you seem that much more open and exciting,” Tupac said in the letter. "But for me, at least in my previous perception, I felt due to my 'image' I would be letting down half of the people who made me what I thought I was."
Madonna and Tupac kept their relationship to themselves, so no one knew they dated until after the rap legend died in 1996. In 2019, his breakup letter to Madonna was auctioned for $100,000.
Dennis and Madonna dated for two months in 1994. While they didn't last long, the NBA legend eventually cashed in on the relationship. In his 1996 memoir Bad As I Want to Be, Dennis claimed Madonna wanted him to have a baby with her during their relationship.
"Madonna talked all the time about having a baby," the former San Antonio Spurs player said. “I think she wanted every bit of Dennis Rodman— marriage, kids, everything."
Dennis has also insisted Madonna offered to pay him millions to conceive a child with her, which she reportedly denies, per Marie Claire. Although Dennis discussed their relationship in the 2020 docuseries, The Last Dance, Madonna hasn’t said much about her ex.
This relationship was also one of Madge’s shorter ones. The “Ice Ice Baby” performer stated in an episode with The Dan Patrick Show that a “much older” Madonna approached him after one of his concerts. According to InStyle, Ice and Madonna had a seemingly ordinary relationship as two pop icons. On several occasions, they snuck into movie theaters wearing disguises.
As “exciting” as the relationship was, Ice admitted he broke up with her after eight months. The rapper told News World in 2011 that the decision came when he saw Madonna’s controversial erotic coffee-table book, Sex. Ice referred to the book as “disgusting and cheap” and didn’t like how it made his girlfriend look.
“We were in a relationship, yet it looked like she was screwing all these other people,” he explained. “I thought she was taking pictures and running round naked because she was like that. Then when the book came out, I was so embarrassed and ashamed. It was a porno.”
Madonna and Guy Ritchie met in 1998 when they sat next to each other at a dinner party. At the time, she was a single mom to her and Carlos Leon’s daughter, Lourdes. After two years of dating, Madonna and the renowned film director married in Scotland, and Madonna gave birth to their son, Rocco, in August 2000. Before the couple divorced in 2008, they also adopted their son, David, in 2006.