Just in the extremely rare case you haven't heard before of the Queen of Pop, Madonna, Madonna is an American singer, songwriter, actress, director, dancer and entrepreneur. According to Guinness World Records, Madonna is recognized as the best-selling female recording artist of all time. Wanna know who dated the Queen of Pop? Let us examine Madonna's dating history below... 
Madonna dated American screenwriter Dan Gilroy. In fact, Gilroy was an early boyfriend of Madonna and was the first person to teach her guitar. Madonna later joined Gilroy's early band "The Breakfast Club".
Madonna dated American artist Jean Michel Basquiat. 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."
Madonna dated American drummer, guitarist, songwriter, DJ, remixer and music producer Jellybean Benitez.
Madonna and American comedienne, singer, actress and author Sandra Bernhard were pals 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 affair with Bernhard.
Madonna was married to American actor, screenwriter and film director Sean Penn. This pair'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 universe." Penn was later charged with felony domestic assault, after allegedly hitting her with a baseball bat.
In between her separation and legal divorce from Sean Penn, Madonna spent time dating Hollywood and political royalty John F. Kennedy, Jr. for about a year.
Madonna dated American actor, producer, screenwriter and director Warren Beatty. They worked together on the set of "Dick Tracy," with Madonna portraying the role of gangster moll "Breathless" Mahoney. They sang together on the duet "Now I'm Following You" for the Dick Tracy-themed album "I'm Breathless."
Lenny Kravitz reportedly dated Madonna back in 1990, which made later romantic triangles even more complex. Madonna was linked to Alex Rodriguez over a decade later, while Alex Rodriguez's ex-wife Cynthia was linked to Kravitz.
Madonna dated American model and actor Tony Ward (real name: Anthony Borden Ward)
Madonna had a fling with American rapper Vanilla Ice (real name: Robert Matthew Van Winkle). While the two never seemed to become serious, the evidence of their time together lives on, thanks to intimate pictures of the two that were released on Madonna's photography book "Sex." According to the Ice Ice Baby rapper, he was the one to end it. "I broke up with her after she printed it…" Vanilla Ice revealed then.
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 them years back.
Madonna had a fling with Dennis Rodman.The two spent a very public two-month period together. Some complained that their romance took away from Rodman's focus while he competed with the San Antonio Spurs in the 1994 NBA Playoffs.
Madonna dated American model and actress Jenny Shimizu. 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. "I was her secret "booty call" available any time of the day or night for secret sex sessions," Shimizu was quoted as saying.
Madonna dated Cuban personal trainer, comedian and actor Carlos Leon. The two have one daughter together, Lourdes Maria Ciccone Leon, born on October 14, 1996.
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.
Madonna and Guy Ritchie 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.
Madonna was rumored to be dating Alex Rodriguez in 2008, after reports claimed the athlete visited Madonna at night. Madonna denied any romantic relationship.
Madonna dated Brazilian underwear model Jesus Luz. The two had a significant age gap (Madonna is 28 years older than the Brazilian model). Their relationship was short lived, only for a year, and it looks like both were unable to bridge the relationship and age gap as well. According to reports, it was Jesus who initiated the break up as he understood the fact that their love is not strong enough to conquer the sizeable age difference.
Madonna became romantically involved with French dancer Brahim Zaibat in 2010. In 2012 rumors emerged that Zaibat had popped the question to Madonna, but neither has confirmed the rumors. The two are often photographed together.
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