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Who Has Madonna Dated, Married, and Divorced?

By

'W.E.' Premiere - 2011 Toronto International Film Festival
Jason Merritt / Staff/Getty Images Entertainment/Getty Images

Singer Madonna was born in Bay City, Michigan in fairly humble surroundings. Who would have thought that she would grow up to become Madonna known to all simply by her first name. Miss Madonna has also become known for another thing - her vast relationship history. The list of people that this pop star has hooked up with, dated, married, and divorced is far from short.

Late 1970s: She dated Dan Gilroy and they went on to form a band together called Breakfast Club.

Early 1980s: She had a busy couple of years here as she dated music collaborator Stephen Bray, painter Jean-Michel Basquiat, record producer Mark Kamins, and musician John "Jellybean" Benitez.

1985: While filming the video for Material Girl, Madonna, then 26, ran into actor Sean Penn, who just so happened to be on the lot at the time. He certainly wasn't a superstar at that point, more like a young kid starting out in Hollywood. Sean, 24 at the time, was instantly attracted to the singer and after a super brief courtship, the two were married in August of 1985. Just two years later, Sean and Madonna filed for divorce. They quickly withdrew the paperwork and claimed that all was well with them. In December 1988, they decided to legally separate. By September of 1989, the short lived marriage between Madonna and Sean Penn was over.

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.

1988: Perhaps in attempt to be controversial, Madonna began dating wildly outspoken comedian Sandra Bernhard. The public romance proved to be too much and after a year, they called it quits.

1989: Warren Beatty romanced Madonna but they broke up after a year when Warren's suspicious and accusatory nature destroyed any chance for a future.

1990: Madonna briefly dated Latin actor Antonio Banderas, bad boy singer Lenny Kravitz, and bisexual model Tony Ward, who starred in the videos for Cherish and Justify My Love.

Early 1991: She dated rapper Vanilla Ice for about 8 months, and he famously made a cameo in her very scandalous (and now impossible to find in stores thank to Madonna herself trying to buy out the stash) Sex Book.

1992: She has brief romances with actor Willem Dafoe, rapper Big Daddy Kane, and legendary baseball player Jose Canseco.

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.

1994: Madonna had a tumultuous but brief romance with basketball star and super outrageous guy Dennis Rodman. In an interview, Madonna once said that she wanted Dennis to father her children.

September 1994: Madonna met and fell hard for her fitness trainer, Carlos Leon, and the two began a steamy affair. In early 1996, Madonna became pregnant by Carlos and in October of that same year, she gave birth their baby girl named Lourdes Maria Ciccone Leon. Just a few months later, Madonna dumped her trainer/lover/baby daddy.

1998: Madonna began quietly dating aspiring screenwriter Andy Bird. Three months into the relationship, the rumor mills went wild at the time claiming that she was pregnant with his child. The gossip mongers went on to claim that Madonna decided to have an abortion. After just 18 months, the relationship was over and he sold their story to a local tabloid.

1999: Madonna was introduced to film producer Guy Ritchie via power couple Sting and his influential wife Trudie Styler. In August of 2000, Madonna and Guy welcomed a son together named Rocco. In December of that year, just days before Christmas, Madonna and Guy were married at a castle in Scotland. Eight years later, in October 2008, they officially separated. Rumors swirled that an alleged affair with baseball player Alex Rodriguez was behind the split. Just two months later, the marriage was formally over and Guy Ritchie supposedly walked away a very rich man.

2009: Madonna, 52 at the time, met model Jesus Luz, 22 at the time, at a photo shoot and the two dated on and off for about a year.

2011: Madonna was spotted hooking up with French dancer Brahim Zaibat, 24.

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