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It's hard to believe that Madonna turns 54 on Aug. 16, because she's rarely acted -- or dated! -- her age. The Material Girl has always had younger men falling at her feet, from second hubby Guy Ritchie (10 years younger) to current boyfriend Brahim Zaibat (30 years younger). Even before she established her cougar cred, Madge had a famously wild love life. Here are some highlights from the pop legend's impressive dating history.
John "Jellybean" Benitez (Dated 1983-1985)
Relationship highlight: Club deejay Benitez met Madonna in 1982, when she was just starting to make a name for herself in the downtown New York scene. Not only did Jellybean date the singer for two years, but he also produced her breakout hit, "Holiday."
How it ended: Following the release of her first album, Madonna, she dumped Benitez as a producer -- and as a boyfriend. They continued to work together from time to time, though: He produced her 1985 single "Crazy for You," which went to No. 1.
Sean Penn (Began Dating February 1985; Married August 1985; Separated December 1987; Reconciled January 1988; Divorced January 1989)
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Relationship highlight: Six months after meeting on the set of her "Material Girl" video, Sean Penn and Madonna were married in a surprisingly classy Malibu ceremony. Guests, including Tom Cruise, Cher, Christopher Walken, Carrie Fisher and Andy Warhol, danced to Madonna's own music and filled an entire room with wedding gifts.
How it ended: It's surprising that it lasted as long as it did, seeing as Penn was allegedly an abusive alcoholic. Madonna filed for divorce after a horrific incident, during which Penn reportedly held her hostage for nine hours. Looking back, however, Madonna says she has no regrets. "I learned a lot [from the marriage]," she told Larry King in 1999. "He's an incredible human being. He's intelligent; he's talented. Even though things didn't work out for us in terms of our marriage, I don't regret marrying him for a moment."
Warren Beatty (Dated 1989-1990)
Relationship highlight: Madonna, then 30, fell for her director and co-star Beatty, 52, while making the hit film Dick Tracy. "She's always walking up behind him and putting her arms around his chest and squeezing him. That's when we know the work day is about over," a source on the set told People.
How it ended: The cinematic relationship fell apart during Madonna's 1990 Blonde Ambition tour. The tension was on full display in her documentary Truth or Dare, in which Beatty argued with her on the phone and mocked her attention-seeking ways. ("Why would you say something if it's off camera?" he joked. "What point is there existing?")
Tony Ward (Dated September-December 1990)
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Relationship highlight: Madonna dated the bisexual fashion model one year after casting him in her "Cherish" video. During their brief relationship, he starred in her banned-by-MTV "Justify My Love" video.
How it ended: There were lots of unconfirmed rumors (Tony secretly eloped with another woman, Madonna had an abortion) but the pair obviously stayed in touch -- he appeared in her kinky 1992 photo book SEX. "We fell hard immediately. Too much, too soon for the both of us," Ward later told Attitude magazine. "In the end when you love something, let it go."
Dennis Rodman (Dated 1994)
Relationship highlight: Both Rodman and Madonna love attention, and they got plenty of it during their brief affair. "I love Dennis Rodman. He's hot. I adore him," Madonna told USA Today. "He's a rebel, the Madonna of the NBA."
How it ended: In his autobiography Bad As I Wanna Be, Rodman claimed that Madonna desperately wanted to have a baby and the relationship floundered when they couldn't get pregnant. But when Oprah Winfrey asked Madonna for confirmation, the singer said flat-out, "Well, he's lying."
Carlos Leon (Dated September 1994-May 1997)
Children: Lourdes, born October 1996
Relationship highlight: Madonna, then 37, met personal trainer Leon, then 29, while jogging in Central Park. She kept their relationship uncharacteristically quiet until the birth of their daughter. "This is it," the new mom told People, "the greatest miracle of my life."
How it ended: Madonna and Leon parted ways less than a year after Lourdes was born. The split seemed totally amicable; Madonna threw him a birthday party just weeks after the break-up, and they share parenting duties to this day. "I'm forever grateful to [Madonna]. I have no regrets. I wouldn't change anything," Leon told People in 2011. "I got the best thing out of that relationship, and that's my daughter."
Guy Ritchie (Began Dating 1998; Married December 2000; Separated October 2008; Divorced January 2009)
Children: Rocco, born August 2000; David, adopted May 2008
Relationship highlight: British filmmaker Ritchie directed his wife in the 2002 romantic comedy Swept Away. The film was a flop, but from behind-the-scenes footage, it's obvious that the couple had a blast making it. "If our relationship couldn't have handled the failure of that movie, what would have been the basis of it?" Madonna reflected in 2003.
How it ended: There were rumors of an affair with New York Yankee Alex "A-Rod" Rodriguez, which Madonna denied. Other reports blamed Madonna's obsessive workouts, her devotion to Kabbalah, or her desire to adopt more children. Madonna says the relationship simply ran its course. "It’s not as romantic as it used to be," she told Newsweek in 2012. "You think, 'This isn’t what I thought it was going to be,' and 'How much am I willing to sacrifice?'"
Jesus Luz (Dated January 2009-February 2010)
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Relationship highlight: Two months after separating from Ritchie, Madonna did a W magazine photo shoot with Luz, then an unknown Brazilian model. "Madonna is beautiful, a person full of positive energy, with no visible faults. I found her marvelous," he told a Brazilian TV station. By the time the divorce was finalized, Madonna and Luz, 26 years her junior, were an item.
How it ended: Luz reportedly broke up with Madonna after a year because they didn't have enough in common -- and Madonna, apparently, agreed. "It's really pushing it for us to have common ground these days," the singer reportedly told a friend. "We have Kabbalah, that's about it." It probably didn't help matters that Luz's mother -- who is 14 years younger than Madonna -- disapproved of the relationship.
Brahim Zaibat (Dated September 2010-present)
Relationship highlight: To celebrate her 53rd birthday, Madonna spent a romantic day at the beach with French breakdancer Zaibat, then 24. The paparazzi caught them kissing while son David and youngest daughter Mercy, whom Madonna adopted in 2009, played in the sand nearby.