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2024 Emmy Nominee for Outstanding Entertainment News Program

Madonna started dating Jesus Luz, a 22-year-old Brazilian model, at the end of 2008 -- fresh from her divorce from Guy Ritchie.

In the ‘90s, Madonna scored with eccentric Chicago Bulls forward Dennis Rodman. It’s reported she said she wanted him to father her children. (AFP/Getty Images: Doug Collier)

Actor Warren Beatty and Madonna hooked up while working on “Dick Tracy.” The couple had a 21-year age difference, and broke up in 1990. (Getty Images: Brenda Chase)

Rocker Lenny Kravitz rocked Madonna’s world in 1990. (Getty Images: Frank Micelotta)

Madonna and famous bachelor John F. Kennedy, Jr. dated in 1987 while she was separated from Sean Penn. (AFP/Getty Images: Vin Cataani)

Madonna and Vanilla Ice (aka Rob Van Winkle) dated for eight months in 1991. Ice appeared in Madonna’s controversial coffee table "Sex" book. (Getty Images: Kevin Winter)

In 1992, Madonna dated future Oscar-nominated actor Willem Dafoe and baseball slugger Jose Canseco. (Getty Images/Extra composite)

In 1985, Madonna married reclusive actor Sean Penn. The rocky relationship ended in 1989. (Getty Images: Brenda Chase)

Madonna and fitness trainer Carlos Leon were romantically linked in 1994. Two years later, Madonna gave birth to Lourdes Maria Ciccone Leon. (AFP/Getty Images: Chris Pizzello)

In 1999, Madge met director Guy Ritchie. A year later, they welcomed son Rocco. In Dec. 2000, they were married in a lavish ceremony in Scotland. (AFP/Getty Images: Lucy Nicholson)

Crude comic Sandra Bernhard was linked to Madonna in 1988. (Newsmakers)

In the mid-Nineties, nightclub owner and lesbian icon Ingrid Casares and Madonna are spotted together on numerous occasions. (Getty Images: Brenda Chase)

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Madonna and fitness trainer Carlos Leon were romantically linked in 1994. Two years later, Madonna gave birth to Lourdes Maria Ciccone Leon. (AFP/Getty Images: Chris Pizzello)

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