Madonna Dating History
Complete list of Madonna dates, listed in chronological order.
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Married
Relationship
"Encounter"
On-Screen
Jean Michel Basquiat
Capricorn
1982
Andy Warhol writes in his diary November 7, 1984 - "Madonna was on the platform and since Jean Michel had been involved with her, we started to go up. And Madonna kissed Jean Michel on the mouth, but she was with Jellybean. And Jean Michel was moody because Madonna got so big and he'd lost her."
Sandra Bernhard
Gemini
1985 - 1988
Were friends in 1988; although they appeared publicly on dates they never confirmed a relationship with the press, although in his biography, Andrew Morton asserts that Madonna privately acknowledged a sexual relationship with Bernhard
Sean Penn
Leo
August 1985 - September 1989
This couple`s relationship was infamously contentious, with Penn at point being arrested for assaulting a photographer on a film set while married to Madonna. Madonna dedicated her third studio album "True Blue" to Penn, writing in the liner notes that Penn was "the coolest guy in the un ...
John Kennedy Jr.
Sagittarius
1987
1987: In between her separation and legal divorce from Sean, Madonna passed time dating Hollywood and political royalty John F. Kennedy, Jr. for about a year.
Michael Jackson
Virgo
1990
They met just a few of times because they were planning of singing a duet together. In some biographies of both of them (one is the book written by Christopher Andersen) it was reported that Madonna tried to seduce Michael but that she never succeded. It was reported that they had a dinner together ...
Vanilla Ice
Scorpio
February 1992
Robert Van Winkle aka Vanilla Ice dated Madonna in 1992. According to the Ice Ice Baby rapper, he was the one to end it with Madonna when she published her 1992 book Sex, which featured revealing photographs of the couple as well as images of her with other men. "I broke up with her after she printed ...
Dennis Rodman
Taurus
1994
The two spent a very public two-month period together. Some complained that their affair took away from Rodman`s focus while he competed with the San Antonio Spurs in the 1994 NBA Playoffs.
Jenny Shimizu
Gemini
1994
Jenny revealed in her memoir that she had dated Madonna (at the same time she was dating Angelina Jolie), and that Madonna would fly her around the world for romantic liaisons.
Carlos Leon
Cancer
September 1994 - September 1997
The couple have one daughter together, Lourdes Maria Ciccone Leon, born on October 14, 1996.
Guy Ritchie
Virgo
August 1999 - October 2008
The two were married in a lavish ceremony in Scotland on December 22, 2000. They have one son, Rocco, born on August 11, 2000, and adopted a child named David.
Alex Rodríguez
Leo
2008
Madonna and Alex Rodriguez were both spotted in Mexico City last weekend. The two have not confirmed their romance. But they reportedly had their public "coming out" Nov. 26, when, according to E!, the Yankees third baseman handed Madonna a water bottle during her Miami concert. They also ...
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