Madonna » Dating History

Historical look at Madonna relationships, listed in date order.

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Mark McGrath
Madonna Ciccone and Mark McGrath unknown date RUMOR
David Blaine
David Blaine and Madonna unknown date RUMOR
Dan Gilroy
Madonna and Dan Gilroy 1980 - 1981
Jean Michel Basquiat
Jean-Michel Basquiat and Madonna 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." [more]
Sandra Bernhard
Madonna and Sandra Bernhard 1985 - 1988 RUMOR
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 [more]
Sean Penn
Madonna and Sean Penn 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 ... [more]
John Kennedy Jr.
Madonna ciccone and John Kennedy, Jr. 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. [more]
Warren Beatty
Madonna and Warren Beatty January 1989 - August 1990
Michael Jackson
Michael Jackson and Madonna 1990 - 1991 RUMOR
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 and then she tried to have sex with him, but unsuccessfully. Some time later, his ... [more]
Tony Ward
Madonna and Tony Ward 1990 - 1991 RUMOR
Vanilla Ice
Madonna and Vanilla Ice 1991 - 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 ... [more]
Jim Albright
Madonna and Jim Albright 1992 - 1993
John Enos III
John Enos III and Madonna October 1992 RUMOR
Ingrid Casares
Madonna and Ingrid Casares 1994
1994: Madonna dated sexy nightclub owner Ingrid Casares and the two were even photographed together at the Golden Globes at the Beverly Hilton Hotel. Coincidentally, it was Madonna's ex, Sandra Bernhard, who introduced the two years back. [more]
Dennis Rodman
Dennis Rodman and Madonna 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. [more]
Jenny Shimizu
Jenny Shimizu and Madonna 1994 RUMOR
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. [more]
Carlos Leon
Madonna and Carlos Leon September 1994 - September 1997
The couple have one daughter together, Lourdes Maria Ciccone Leon, born on October 14, 1996. [more]
Andy Bird
Madonna and Andy Bird 1997 - 1998
Chris Paciello
Chris Paciello and Madonna 1998 RUMOR
Guy Ritchie
Guy Ritchie and Madonna 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. [more]
Alex Rodríguez
Alex Rodriguez and Madonna 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 ... [more]
Jesus Luz
Madonna and Jesus Luz December 2008 - 2010
Brahim Zaibat
Madonna and Brahim Zaibat September 2010 - December 2013
Timor Steffens
Madonna and Timor Steffens 2014
January 7, 2014 The 55-year-old’s new man, 26-year-old Dutch backup dancer Timor Steffens. Madonna debuted her latest plaything at designer Rudolph Valentino‘s private New Year’s Eve Party in Gstaad, Switzerland. According to a party guest, “The chemistry between Madonna and ... [more]

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