Madonna has been the undisputed Queen of Pop for four decades, and during her legendarily shapeshifting and influential reign, she’s earned much attention for her bold sexuality. Given the singer’s dedication to provocation, it’s no surprise that her personal affairs—from her two marriages to her many flings—have long been a source of gossip. Here’s a deep dive into the highs and lows of the Material Girl’s fascinating love life.
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Madonna’s early romances in the NYC club scene
Before Madonna became a household name, she was a fixture of New York City’s ultra-cool club scene, and this was where she made her earliest musical and romantic connections.
In 1979, shortly after Madonna arrived in the city, she met musician Dan Gilroy at a party and they began dating. At the time, she hoped to make it as a dancer, but her focus changed to music when Gilroy taught her to play guitar and encouraged her to write songs. They soon formed a band together, Breakfast Club, but Madonna left the group in 1980. In a Rolling Stone interview, Madonna called her early years with Gilroy, “one of the happiest times of my life.”
Madonna’s involvement in the downtown art scene led her to strike up a relationship with artist Jean-Michel Basquiat in 1982. Madonna found Basquiat’s artistic dedication deeply inspiring, saying, “Basquiat was my boyfriend for a while, and I remember getting up in the middle of the night and he wouldn’t be in bed lying next to me; he’d be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that, that he worked when he felt moved.”
Madonna and Basquiat’s relationship didn’t last due to the painter’s battle with drug addiction, and he sadly died at just 27 in 1988. Their brief romance took on a mythical aura, given the fact that they became two of the most famous figures in their respective fields.
Madonna then met DJ John “Jellybean” Benitez through the club scene, and they began a relationship that proved highly influential in her career, as he helped to shape her 1983 debut album and produced many of her earliest hits. Looking back at the relationship in an exclusive First for Women interview, Benitez said, “We connected right away, both romantically and in the studio. There was a lot of magic that happened, and the stars aligned.”
Madonna and Sean Penn’s turbulent marriage
Madonna met actor Sean Penn on the set of her “Material Girl” music video in 1985, and they married that year. She dedicated her hit 1986 album True Blue to him, and they costarred in the film Shanghai Surprise, which notoriously flopped at the box office.
Madonna and Penn were one of the most famous couples of their day, but their union didn’t last, as Penn was known for his erratic and often violent behavior toward the press and men Madonna was working with, and he was alleged to have physically abused her—though she ended up denying those allegations years later.
Madonna filed for divorce in 1989, and at a 2016 charity event she hosted, she told him, “I’m still in love with you,” and joked that she’d be willing to remarry him if he donated enough money to the cause.
Madonna’s high-profile ’90s relationships
In 1990, Madonna had a highly publicized relationship with one of Hollywood’s most legendary ladies’ men, Warren Beatty. She played his saucy lounge singer love interest in Dick Tracy, which he directed and starred in that year, and sang a number of songs on the soundtrack, including the Oscar-winning “Sooner or Later.” Beatty could also be seen in the 1991 documentary Truth or Dare, which followed the pop star on her Blond Ambition tour.
Madonna and Beatty’s relationship fizzled out after Dick Tracy premiered, she looked back fondly at their time together, and in a Howard Stern interview, she admitted that his long history of dating famous women piqued her interest and said he was an incredible lover.
After breaking up with Beatty, Madonna dated Tony Ward, a model who appeared in her scandalous “Justify My Love” music video. Their relationship was short-lived, and Ward recalled, “My world changed quite a bit once I met her.” She then had an affair with her bodyguard, Jim Albright, who set off tabloid drama by saying, “She’d never been faithful to one man—period. She told me that. She is only loyal to herself.”
As the ’90s continued, Madonna was rumored to be dating David Fincher, the director of many of her most famous music videos, including “Express Yourself” and “Vogue.” She was then briefly linked to an eclectic variety of fellow stars, including rappers Vanilla Ice and Tupac Shakur, basketball player Dennis Rodman and political scion John F. Kennedy Jr.
Madonna becomes a mom
In 1994, Madonna met trainer and actor Carlos Leon by chance while jogging in New York’s Central Park. Their daughter, Lourdes, now a singer and model, was born in 1996, and becoming a mother inspired Madonna’s acclaimed 1998 album Ray of Light.
While Madonna said, “My daughter’s birth was like a rebirth for me,” her relationship with Lourdes’ father didn’t last, and they split up in 1997. A decade after they broke up, Leon said, “I have a great relationship with all my ex-girlfriends, but especially Madonna. There was a friendship and there still is a friendship. If she needs to talk to me I’m there and if I need to talk to her she’s there. That’s the way it goes.”
Madonna’s ’00s marriage to Guy Ritchie
Madonna met her second husband, British director Guy Ritchie, at a party hosted by Sting and his wife, Trudie Styler, in 1999. Their son, Rocco, now an artist, was born in 2000, and they married that year. They adopted their son David, now a musician, from Malawi in 2006.
In 2002, Ritchie directed Madonna in a remake of the ’70s Italian film Swept Away. The movie was a critical and commercial failure. Ritchie and Madonna divorced in 2008, and a messy custody battle ensued.
Madonna was initially drawn to Ritchie because she recognized him as a kindred spirit, saying, “He’s a risk taker and he’s got a hungry mind,” but once the marriage ended, she revealed, “I think when you get married you have to be willing to make a lot of compromises and that’s fair enough. I think that’s the way it goes in relationships. However, you know, I did find myself sometimes in a state of conflict. There were many times when I wanted to express myself as an artist in ways that I don’t think my ex-husband felt comfortable with.”
In 2022, when asked about decisions she’s regretted during her time in the spotlight, Madonna quipped, “Getting married. Both times.”
Madonna’s recent affairs with younger men
In 2009, Madonna adopted her daughter, Mercy, from Malawi. Following her divorce from Ritchie, Madonna was rumored to be dating baseball player Alex Rodriguez, though she claimed they were just friends.
In 2010, Madonna started dating dancer Brahim Zaibat, who performed during her 2012 MDNA tour and said, “She was just a woman almost like the others. An exceptional artist and world-famous, of course, but a woman first. I was just happy to meet her.”
In 2014, Madonna was linked to another much younger dancer, Timor Steffens, who said, “There is an age gap between me and Madonna but I don’t notice it. My girlfriends have always been older than me and that’s how I like it. I learn a lot.” A relationship with Ahlamalik Williams, a dancer on her 2015 Rebel Heart tour, followed, and she adopted her twin daughters, Stella and Estere, from Malawi, in 2017.
Madonna dated boxing trainer Josh Popper in 2023, and the pair kissed onstage during her Celebration tour. Currently, the singer is dating Akeem Morris, a Jamaican soccer player nearly four decades her junior.
When asked about her age-gap relationships, Madonna was characteristically blunt, saying, “I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable.”
Madonna also said she’s learned a lot about romance over the years, revealing, “The older I get, the more I understand about the nature of relationships and how to have a successful one. The more I realize that it has to do with compromise and sacrifice and that’s just the way it goes. And unless you want to be alone for the rest of your life you have to realize that.” It’s sound advice even for those of us who aren’t pop divas, and it’s clear that Madonna has always been unapologetic about the highs and lows of her many relationships.
