Madonna’s Many, Many, Many Romantic Entanglements

Annika Harris | August 16, 2010 - 6:30 pm

Happy 52nd Birthday, Madonna! In honor of the Material Girl, we’ve decided to take a look back at her romantic relationships. And, lordy, have there been a lot.It seems the Material Girl collects partners just as much as she collects wealth and music awards. When she was just starting out as a singer, Madonna dated men who could help her career. Once she was established, only of-the-moment celebs would suffice. Why else would she have dated Vanilla Ice and Dennis Rodman? As Madge got older, she settled down in Britain with Guy Ritchie, but even that relationship didn’t last. After reading through our timeline below detailing the ton of men — and a couple of women — that Madonna has dated, try to come up with who she should — or could — date next.

  • Late 1970s: Dates Dan Gilroy; they form the band Breakfast Club together.
  • Early 1980s: Dates her collaborator Stephen Bray, who still holds master recordings to many unreleased Madonna songs; dates painter Jean-Michel Basquiat; dates DJ and record producer Mark Kamins, who helped launch her career by presenting a demo of “Everybody” to Seymour Stein of Sire Records; dates musician John “Jellybean” Benitez, who produced “Holiday.”
  • 1985: Meets and marries Sean Penn.
  • December 1987: Penn and Madonna file and then withdraw divorce papers.
  • 1987-1988: Dates John F. Kennedy, Jr.
  • December 31, 1988: Madonna and Penn separate.
  • 1988-1989: Dates Sandra Bernhard.
  • September 1989: Madonna and Penn divorce.
  • 1989-1990: Dates Warren Beatty, who is notoriously jealous and suspicious that she’s cheating.
  • 1990: Dates Antonio Banderas and Lenny Kravitz.
  • Late 1990: Dates Tony Ward, a bisexual model and porn star who starred in the videos for “Cherish” and “Justify My Love.”
  • Early 1991: Madonna breaks up with Ward and starts an eight-month relationship with Vanilla Ice, who appears in her Sex book.
  • 1992: Dates Willem Dafoe, rapper Big Daddy Kane, and baseball player Jose Canseco.
  • 1992-1994: Dates James Albright and nightclub owner Ingrid Casares.
  • Mid-1990s: Dates basketball player Dennis Rodman, who later says that she wanted him to be the father of her children.
  • September 1994: Madonna meets fitness trainer Carlos Leon, who becomes her trainer and lover.
  • October 14, 1996: Madonna gives birth to their daughter, Lourdes Maria Ciccone Leon, in Los Angeles.
  • 1997: Madonna breaks up with Leon.
  • 1998: Dates Andy Bird, a penniless and aspiring screenwriter. She was supposedly pregnant with his child after dating for three months and aborted the baby. They broke up after 18 months; he then sold the story of their romance to a tabloid.
  • 1999: Madonna meets Guy Ritchie through Sting and Trudie Styler.
  • August 11, 2000: Madonna gives birth to their son Rocco in Los Angeles.
  • December 22, 2000: Madonna and Ritchie marry 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 — and then confirmed — to be entangled in a romantic relationship with baseball player Alex Rodriguez.
  • December 2008/January 2009-Present: Madonna begins dating model Jesus Luz after meeting him at a photo shoot and the two have been virtually inseparable ever since.