A Chronology of Madonna’s Exes

We all know that Madonna is the Material Girl, but what some of us might not know is that she is a serial dater also. Madonna has dated a lot of celebrities and some non-celebrities.

The trend seems to be that early in her career, Madonna would date men (and women) that would help out in her career. As she became more famous, she started dating celebrities that were hot at that moment (Vanilla Ice, Dennis Rodman, etc.).

Once Madonna got older, she started settling down and having kids (Carlos Leon and Guy Ritchie). However, true to herself, Madonna cannot say settled for long. Her latest catch is baseball superstar Alex Rodriguez.

– Andy

For a brief history of Madonna’s dating life, follow the JUMP:

Picture and list courtesy of thefrisky.com

• Late 1970s: Dated Dan Gilroy; Formed the band Breakfast Club together.
• Early 1980s: Dated her collaborator Stephen Bray, who still
  holds master recordings to many unreleased Madonna songs; Dated painter
  Jean-Michel Basquiat; Dated DJ and record producer Mark Kamins, who
  helped launch her career by presenting a demo of “Everybody” to Seymour
  Stein of Sire Records; Dated Musician John “Jellybean” Benitez, who
  produced “Holiday.”
• 1985: Met and married Sean Penn.
• December 1987: Penn and Madonna filed and then withdrew divorce papers.
• 1987-1988: Dated John F. Kennedy, Jr.
• December 31, 1988: Madonna and Penn separate.
• 1988-1989: Dated Sandra Bernhard.
• September 1989: Madonna and Penn divorce.
• 1989-1990: Dated Warren Beatty, who was notoriously jealous and suspicious that she was cheating.
• 1990: Dated Antonio Banderas and Lenny Kravitz.
• Late 1990: Dated Tony Ward, a bisexual model and porn star who starred in the videos for “Cherish” and “Justify My Love.”
• Early 1991: Madonna broke up with Ward and started an eight-month relationship with Vanilla Ice, who appeared in her “Sex” book.
• 1992: Dated Willam Dafoe, rapper Big Daddy Kane, and baseball player Jose Canseco.
• 1992-1994: Dated James Albright and nightclub owner Ingrid Casares.
• Mid-1990s: Dated basketball player Dennis Rodman, who said that she wanted him to be the father of her children.
• September 1994: Madonna met fitness trainer Carlos Leon, who became her trainer and lover.
• October 14, 1996: Madonna gave birth to their daughter, Lourdes Maria Ciccone Leon, in Los Angeles.
• 1997: Madonna broke up with Leon.
• 1998: Dated Andy Bird, a penniless aspiring screenwriter; was supposedly pregnant with his child after dating for three months. She later supposedly aborted the baby and they broke up after 18 months—he then sold the story of their romance to a tabloid.
• 1999: Madonna met Guy Ritchie through Sting and Trudie Styler.
• August 11, 2000: Madonna gave birth to their son Rocco in Los Angeles.
• December 22, 2000: Madonna and Ritchie married in Scotland.
• October 15, 2008: Madonna and Ritchie confirm their split
  because they “can’t bear to live with the pretense any longer.” Madonna
  is rumored to be entangled in a romantic relationship with baseball
  player Alex Rodriguez.