Madonna’s Many, Many, Many Romantic Entanglements

Madonna has dated A LOT of people. 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 that 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 has not lasted. 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 date next. BTW, A-Rod is too easy.

• 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.