Madonna’s A-List Dating History: All of Her Boyfriends, Husbands & Forgotten Flings

1979-1981: Dan Gilroy

Before becoming a household name, Madonna met musician and comedian Dan Gilroy at a party in New York in 1979. At the time, Gilroy was living in an abandoned synagogue in Queens, where Madonna crashed for a few nights and discovered her love for making music.

“He stuck a guitar in my hand and tuned it to an open chord so that I could strum,” she told Rolling Stone in 1984. “That really clicked something off in my brain.” 

After a brief stint in Paris, Madonna returned to New York to join Gilroy’s band Breakfast Club, taking on the role of the drummer while Gilroy sang and his brother played guitar. Eventually, Madonna’s desire to sing and find commercial success drove a wedge between the couple. Madonna split with Gilroy and left the band in 1981.

“I knew that with that kind of drive and devotion to getting ahead something had to happen,” Gilroy told Rolling Stone but admitted, “I missed her very much.” Gilroy went on to date Shelley Duvall from 1989 until her death in 2024.

1982: Jean-Michel Basquiat

Madonna dated artist Jean-Michel Basquiat, a protégé of Andy Warhol, when they were both rising stars in 1982. 

“Basquiat was my boyfriend for a while,” Madonna told Interview magazine in 2014. “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.”

In 2015, Madonna told The Howard SternShow, according to Rolling Stone, that their romance ended because of Basquiat’s drug use.”He wouldn’t stop doing heroin. He was an amazing man and deeply talented, I loved him,” said the singer.

“When I broke up with him, he made me give [the paintings he gave me] back to him. And then he painted over them black.” Basquiat died of an overdose in 1988. 

1983-1985: John ‘Jellybean’ Benitez

After meeting and collaborating on her hit song “Holiday,” Madonna dated DJ and producer John “Jellybean” Benitez. According to a 2001 cover story inPeople, the couple even briefly got engaged while living together in Soho. 

“He was in love with her,” a friend of Benitez’s told People. “They were a great team. But she was the one in charge. She’s a diva—man, they like to command attention.” They split in early 1985.

1985-1989: Sean Penn

Madonna and actor Sean Penn’s relationship began in February 1985 after meeting on the set of her “Material Girl” music video before later starring in 1986’s Shanghai Surprise. Within six months of meeting, they were married on August 16, 1985 — Madonna’s 27th birthday. 

Trouble in their marriage first became clear in 1986 when Penn was charged with battery after allegedly assaulting musician David Wolinski after he saw him talking to Madonna.   

Reports accused Penn of hitting his then-wife with a baseball bat in 1987 and physically assaulting her in 1989 which the singer denied while testifying on Penn’s behalf in a 2015 defamation lawsuit.

“While we certainly had more than one heated argument during our marriage, Sean has never struck me, ‘tied me up,’ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false,'” Madonna’s statement read, according to The Guardian.

In December 1987, Madonna filed for divorce from the Oscar winner, citing “irreconcilable differences” but, according to the Los Angeles Times, withdrew the filing two weeks later. They divorced for good in 1989.

In her 1991 documentary, Truth or Dare, Madonna called Penn the love of her life.

In 2016, the pair appeared together at a charity auction to auction their wedding photos. There, Madonna said that she was “still in love” with Penn and offered to remarry him if he bid $150,000. 

In 2024, Penn also revealed his affections for his ex-wife, calling her “someone I love.”

1988: John F. Kennedy Jr.

While separated from Penn, Madonna allegedly had a six-month romance with JFK Jr., who was still with his girlfriend Christina Haag at the time. The pop star and the Camelot heir kept their love on the down low.

The fling allegedly didn’t have the blessing of JFK Jr.’s devoutly Catholic mom, Jackie Kennedy Onassis, who found Madonna’s wardrobe and accessorizing with crosses “sacrilegious,” according to Christopher Anderson’s book, The Good Son: JFK Jr. and the Mother He Loved.

1990: Tony Ward

In 1990, Madonna briefly dated model Tony Ward, who costarred in her “Justify My Love” music video and appeared in her controversial photography book, Sex.

1990-1991: Warren Beatty

Madonna met Warren Beatty, who was 21 years her senior, on the set of Dick Tracy in 1989 and went on to date him for around 15 months beginning in 1990.

Beatty and Madonna split shortly after promoting their movie, seemingly because of their conflicting views on publicity, which was evident when Beatty appeared in Madonna’s Truth or Dare documentary.

“She doesn’t want to live off-camera, much less talk,” Beatty says when Madonna refuses to talk to her doctor off-camera. “There’s nothing to say off-camera. Why would you say something if it’s off-camera? What point is there existing?”

In 2016, Beatty reflected on the relationship and spoke highly of his former girlfriend’s public persona. “She’s a huge personality, diligent and disciplined and a spectacular dancer and performer,” he told People. “She’s a phenomenon.”

1991: Michael Jackson

Madonna and Michael Jackson never officially dated but their date night at the 1991 Oscars will go down in pop culture history.

The duo, who met years earlier, attended the award show together but it was primarily for publicity. That didn’t stop Madonna from teasing fans with details.

“Michael [Jackson] was like, ‘Well, who are you going to go with?'” Madonna said in a VH1 interview. “I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’ … And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.”

In a 2016 appearance on James Corden’s Carpool Karaoke, the singer was asked if she kissed the Prince of Pop and responded: “Of course. I mean, baby, I’ve been around.” 

Jackson and Madonna were seen out together on a couple of occasions after the Oscars but things seemingly turned south quickly. In The Michael Jackson Tapes: A Tragic Icon Reveals His Soul in Intimate Conversation, the “Thriller” singer said Madonna was “not a nice person.” He claimed that, after their split, Madonna “wrote some mean things about me in the press.”

“I wrote that she is a nasty witch, after I was so kind to her,” Jackson said. However, Madonna seemed to bury the hatchet after Jackson’s death when she gave a heartfelt speech at the 2009 VMAs. “I can’t say we were great friends,” she said, according to Rolling Stone, before reflecting on one of their dates.

“It felt like he was looking for more of a friend than a romance, and I was happy to oblige. In that moment, he didn’t feel like a superstar. He felt like a human being.”

1991-1992: Vanilla Ice

Vanilla Ice briefly dated Madonna for about 8 months from 1991 until 1992. In a 2013 interview, Vanilla Ice called the “Material Girl” singer a “sweetheart” and reflected on their romance. “We would go to movies. We had disguises. I had a mustache and a hat with hair coming down and she would go as an old lady,” he said. “We’d do dinner that way and nobody would ever recognize us. It was the greatest.”

In a 2023 interview, the rapper claimed Madonna, who is nine years his senior, even proposed to him. “Things were going so crazy and fast, man. I was just like, ‘What? I thought the guy was supposed to do that,'” he said. “‘I’m just getting started here and I’m way too young for this.'”

He claimed things took a turn when he was featured in her controversial book Sex without his consent.

“I said, ‘How could you do that to me?'” he recalled. “I could’ve sued her. I didn’t want to. I was like, ‘I don’t need that controversy. Let’s just let it go and you go your way, I go mine.'”

In Morton’s 2001 biography, Ice also hinted that Madonna’s heartbreak over her split from Penn might have played a role too. 

“I felt that she still loved him. In fact, I know she did because she told me,” he said.

1991-1994: Jim Albright

Biographer Andrew Morton revealed in his 2001 biography of the pop icon that she had a secret, “hot and heavy” 3-year affair with her bodyguard, Jim Albright, beginning in 1991. “It was like I was making a pact with the devil,” Albright told Morton of falling in love with Madonna.

Albright even left his longtime girlfriend for the singer and says their intense romance consisted of endless phonecalls and accusations of infidelity on both ends. Their relationship ended in 1994 and Albright even went on to sell letters and faxes from the singer in 2009. 

1992: Chris Paciello

During Madonna’s Miami club days in the early ’90s, she was linked mobster Chris Paciello, who turned into a nightlife impresario with her former friend Ingrid Casares.

1993: Tupac Shakur

After Madonna revealed in 2015 that she briefly dated Tupac Shakur, actress Rosie Perez admitted she was the one who introduced them at the Soul Train Awards in 1993. “[I told Tupac], ‘she wants to meet you’ and he goes ‘hook that up,'” Perez said, according to HuffPost. “And I hooked it up and I was very happy about it.”

Their private romance didn’t last long and, in 2017, fans got insight into why they split when a letter the rapper sent his ex from prison was sold at an auction.

“For you to be seen with a Black man wouldn’t in any way jeopardize your career – if anything it would make you seem that much more open and exciting,” Shakur wrote.

“But for me, at least in my previous perception, I felt due to my ‘image,’ I would be letting down half of the people who made me what I thought I was. I never meant to hurt you.” 

1993-1994: Ingrid Casares

In his 2008 book, Madonna’s estranged brother Christopher Ciccone claimed the singer had a secret fling with her best friend Ingrid Casares from 1993 until 1994, according to an excerpt in Daily Mail. 

Her ex, Jim Albright, also claimed the same thing in Morton’s biography. 

1993-1994: Jenny Shimizu

According to Daily Mail, via Pink Times, model Jenny Shimizu once claimed she had a fling with the singer. The model, who was also attached to Angelina Jolie for a few years, said: “I was [Madonna’s] secret ‘booty call’ available any time of the day or night for secret sex sessions.” 

1994: Dennis Rodman

Madonna and Dennis Rodman dated briefly in 1994. The basketball star dished on the relationship in a 2019 interview on The Breakfast Club, claiming that the “Like A Virgin” singer once sent a private plane to Las Vegas, where he was gambling, and flew him to New York City because she was ovulating and wanted to have a child with him.

After the deed was done, he claims he went straight back to the casino in Nevada. 

“I tried,” the former basketball player said, alleging that Madonna also allegedly offered him $20 million to get her pregnant.

1994-1997: Carlos Leon

Madonna started dating fitness instructor Carlos Leon after reportedly meeting him on a jog in Central Park, allegedly mistaking him for Albright briefly. 

According to Morton’s biography, Leon and Madonna revealed their plans to have a baby to family and friends at her 37th birthday party.

On Oct. 14, 1996, they welcomed daughter Lourdes Leon. However, seven months later, the couple split for good. “It was a real relationship,” Madonna’s friend Rosie O’Donnell told Morton. “They made a valiant effort to stay together.”

The parents have reportedly kept a healthy relationship after their split with Leon revealing in a 2008 interview that they maintain a friendship for the sake of their daughter.

“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,” he said at the time, according to People. “Parents can learn from us in that way.” 

1998: David Blaine

David Blaine and Madonna reportedly had a short-lived fling in 1998, according to The Mirror. They did, however, remain friends and Blaine even interviewed the singer in a 2014 story in Interview Magazine.

He also reportedly played a role in helping her reconcile with her son, Rocco, after her custody battle with his ex-husband Guy Ritchie.

1999-2008: Guy Ritchie

Madonna met her second husband, Guy Ritchie, through Sting in 1999. “I had a whole premonition of my life fast-forward,” she later recalled in Morton’s biography. “My head didn’t just turn, my head spun round on my body. I was taken by his confidence. He was sort of cocky but in a self-aware way.”

The pop star and the British director moved quickly and, in March 2000, announced they were expecting a baby. Ritchie and Madonna’s son Rocco Ritchie was born on August 11, 2000. Their wedding followed on December 22 at Skibo Castle in Scotland. 

In 2006, they adopted son David Banda from Malawi, but their marriage only survived another two years. They announced their divorce in October 2008, with sources alleging that Madonna’s devotion to Kabbalah, lifestyle differences and an alleged emotional affair with Alex Rodriguez played a role.

Madonna later reflected on their marriage in a 2017 interview with Newsweek. “When you start off, everything’s great and lovely, and the person you’ve married is flawless, and you’re flawless,” she said. “Then time goes by, and you share a life, you have children, and there are cracks in the veneer. It’s not as romantic as it used to be.”

In 2011, Ritchie also looked back on the marriage in an interview with Details magazine. “It’s definitely not something I regret. The experience was ultimately very positive. I love the kids that came out of it,” he said, per E! News. 

“But you move on, don’t you? You’re right, I stepped into a soap opera, and I lived in it for quite a long period of my life.”

In 2015, the couple entered into a bitter custody war over their son, Rocco, who allegedly wanted to live primarily with his father in the UK. After over a year of back and forth, the dispute appeared to be settled with both parents choosing a school for Rocco in the UK. 

2008: Alex Rodriguez

In July 2008, Madonna was accused of having an emotional affair with Alex Rodriguez. The claims came after his wife, Cynthia Scurtis filed for divorce, accusing her husband of six years of “extramarital affairs” and her attorney told People that Rodriguez and Madonna had an “affair of the heart” with no “sexual infidelity.”

“Cynthia is a strong person,” a source told People. “But a wife with two young children can only take so much.” Another insider added, “The embarrassment over Madonna was the last straw.” 

Madonna, still married to Richie, issued her own denial to People three months before announcing her divorce, saying: “My husband and I are not planning on getting a divorce. I know Alex Rodriguez through Guy Oseary, who manages both of us. I brought my kids to a Yankee game. I am not romantically involved in any way with Alex Rodriguez.”

In 2020, Rodriguez’s then-fiancée Jennifer Lopez seemed to confirm the rumors in an interview with Andy Cohen after he asked about her choice to dress up as Madonna a few months earlier. “Was that not odd given that Alex maybe dated Madonna for two seconds?” Cohen asked Lopez.

“That was so long ago,” Lopez replied. “It wasn’t weird at all. He loved it.”

2009-2010: Jesus Luz

Madonna started Brazilian model/DJ Jesus Luz in December 2009 after meeting on a photoshoot for WMagazine, beginning her string of dating younger men. Their 28-year age gap made plenty of headlines at the time before they inevitably split in February 2010.

At the time the Daily Mail reported that Luz felt he had nothing in common with the then-51-year-old star who adopted her fourth child, Mercy, just over six months before meeting Luz. 

2010-2013: Brahim Zaibat

Madonna dated dancer Brahim Zaibat from September 2010 until December 2013. They met after Zaibat performed at the launch of Madonna’s clothing line “Material Girl” before he then joined her on her MDNA tour. 

The singer defended their 29-year age gap in a January 2019 interview on Nightline. “I didn’t choose to, you know, I didn’t, like, write down on a piece of paper I’m now going to have a relationship with a younger man,” she explained. “That’s just what happened. You see, that’s the romantic in me. I just met someone that I cared for, and this happened to be his age.”

Brahim also addressed their romance and recalled their first meeting in an interview with OK! that same month. “She was just a woman almost like the others,” Brahim recalled. “An exceptional artist and world-famous, of course, but a woman first. I was just happy to meet her.”

“I will not say the romance is going too fast, but things take their course,” he added. Despite appearing together at the 2013 Met Gala, pictured here (Zaibat is on the right), their relationship did run its course and the couple broke up in December 2013.

2014: Timor Steffens

Six months after her split from Brahim Zaibat, Madonna started dating dancer and choreographer Timor Steffens.

Two months into their fling Steffens spoke about Madonna, and their 30-year age difference, in an August 2014 interview with The Mirror. “There is an age gap between me and Madonna, but I don’t notice it,” he explained. “My girlfriends have always been older than me and that’s how I like it. I learn a lot.”

However, not long after the interview, Madonna and Steffens were reported to have broken up.

2017: Kevin Sampaio

In 2017, Madonna was briefly linked to Portugese model Kevin Sampaio (pictured here on the right with twin brother Jonathan).

Sampaio met the singer when he starred in her “B-tch I’m Madonna” music video in 2015. It was a friendship that developed into a brief relationship before they split.

2019-2022: Ahlamalik Williams

Though they didn’t start dating until 2019, Madonna met dancer and choreographer, Ahlamalik Williams in 2015 when he worked on her Rebel Heart Tour before joining her again on her 2019 Madame X Tour.

Ahlamalik’s dad, Drue Williams, defended the couple’s 36-year age gap in a 2019 interview. “Love has no age,” he told TMZ. “My son is livin’ la vida loca, and I’m just happy for him.” 

The low-key couple weren’t seen out and about too much but Williams did occasionally feature on Madonna’s Instagram, including on a vacation with her kids for her 62nd birthday in 2020. 

2023-2024: Josh Popper

In early 2023, it was reported that Madonna was dating Josh Popper, her son’s boxing coach. The couple were not shy about their romance, with Popper even joining her on stage during her Celebration tour in December 2023. 

However, in May 2024, a source told The US Sun that the couple had broken up. “Madonna has barely seen Josh for months because her schedule was so hectic. Things just fizzled out,” the source claimed. “There is genuinely no bad blood — they’re still fond of each other.” 

July 2024-now: Akeem Morris

Madonna debuted a new romance in July 2024 when she posted a series of Instagram photos cuddling up to Akeem Morris over July 4 weekend.

Around that time, the Jamaican-born soccer player’s ex-girlfriend Regan Rice posted an image of Morris and Madonna on TikTok, writing: “Put a finger down if your boyfriend of 3 years is now dating Madonna.”

In August, the two were photographed celebrating Madonna’s 66th birthday in Italy. 

Morris and Madonna seemingly met back in 2022 when he appeared in her Paper Magazine cover shoot.