Madonna's Dating History: From Sean Penn to Guy Ritchie

Mar. 15, 2025

Photo: Jason Merritt/Getty

Madonnahas been in the spotlight for decades and has had a handful of high-profile relationships over the years.

The Queen of Pop has been married twice — first toSean Pennfrom 1985 to 1989, then toGuy Ritchiefrom 2000 to 2008. She has also had a slew of relationships and flings with several other Hollywood stars, includingTupac,Dennis RodmanandWarren Beatty, among others. Most recently, she has been linked to former soccer playerAkeem Morris.

While Madonna is famous for being unapologetically herself, it doesn’t mean she has “absolutely no regrets” about her past. During a 2022Q&A on YouTube, a fan asked the “Take a Bow” singer about a life decision that “wasn’t the best idea,” to which she quickly replied, “Getting married. Both times!”

In October 2022, the “Ray of Light” hitmaker sent fans into a tizzy with a TikTok video in which she appeared tocome out as gay, though she has not yet directly discussed her sexuality.

Here is a look back at Madonna’s romances through the years.

Dan Gilroy

Madonna; Dan Gilroy.Vinnie Zuffante/Getty; Ron Galella, Ltd./Ron Galella Collection via Getty

Vinnie Zuffante/Getty; Ron Galella, Ltd./Ron Galella Collection via Getty

Madonna credits her ex-boyfriend Dan Gilroy with changing her focus from dance to music. As she toldRolling Stoneduring a 1984 interview, she met Gilroy at a party in 1979 and spent a few nights at an abandoned synagogue in Queens, New York, where he and his brother lived. “He stuck a guitar in my hand and tuned it to an open chord so that I could strum,” she told the outlet. “That really clicked something off in my brain.” She then cut back her dance classes to concentrate on singing.

Not long after, she was invited to travel to Paris to be a background singer and dancer for Patrick Hernandez. While abroad, she was lonely and felt unseen. She and Gilroy exchanged letters, which kept her going.

“He was my saving grace. His letters were so funny,” she said. “He’d paint a picture of an American flag and write over it, like it was from the president, ‘We miss you. You must return to America.’ He really made me feel good.”

When a bout with pneumonia forced Madonna to return to the states, she immediately got back in touch with Gilroy and worked with him for what she called a period of “intensive musical training.”

“It was one of the happiest times of my life. I really felt loved. Sometimes I’d write sad songs and he’d sit there and cry,” she said. “Very sweet.”

Over the course of about a year, Madonna and Gilroy collaborated, and she eventually began to play drums for his and his brother Ed’s band the Breakfast Club.

“I stayed there so much, but I hadn’t really moved there yet, and I remember when I said, ‘Can I just live here, Dan?’ " she recalled. “And he said, ‘Well, we have to ask Ed.’ And I said, ‘Ed! You have to askEd?’ "

Eventually, Madonna’s drive to sing in the band drove a wedge between her and Gilroy, as well as Gilroy and his brother, and she left both the group and the relationship so she could pursue singing full-time.

“I was just a lot more goal-oriented and commercial-minded than they were. I just took over in the sense that I said, ‘What do you know? Teach it to me,’ " she toldRolling Stone. “I took advantage of the situation. I wanted to know everything they knew because I knew I could make it work to my benefit.”

Jean-Michel Basquiat

Vinnie Zuffante/Michael Ochs Archives/Getty ; Rose Hartman/Getty

In aMarch 2015 interviewwithHoward Stern, Madonna said that her relationship with Basquiat was short-lived because of the painter’s struggle with addiction, which ultimately took his life in August 1988 when he was just 27 years old.

“He was an amazing man and deeply talented. I loved him,” she said. “When I broke up with him, he made me give all [his paintings] back to him. And then he painted over them black.”

Madonna has since takenher childrento see Basquiat’s paintings, as she shared in a since-deleted Instagram, perW Magazine.

John “Jellybean” Benitez

Ron Galella/Ron Galella Collection

In 1983, Madonna met DJ John “Jellybean” Benitez, who would later produce her song “Holiday.” The pair hit it off and began dating, and friends of Benitez believed thattheir romance was serious. The couple even reportedly got engaged and began living together, however, they hit a rough patch when Madonna reportedly hooked up with journalist Steve Neumann, who was dating her friend Erika Belle at the time.

“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.”

Benitez and Madonna’s romance ended in 1985, right around the time that she met Sean Penn.

Sean Penn

Vinnie Zuffante/Michael Ochs Archives/Getty

Madonna andSean Pennbegan dating in February 1985 after meeting on the set of her iconic “Material Girl” music video. Theygot marriedon Madonna’s 27th birthday, which was also the day before Penn’s 25th birthday, just six months after they first met.

“We haveso much in commonthat he’s almost like my brother,” she said of Penn in July 1985. “His temperament is also similar to mine. That doesn’t always make for ideal relationships, but I don’t know what will happen.”

Their professional lives merged as well: The pair costarred in the 1986 filmShanghai Surprise.

Madonna and Penn’smarriage was a tumultuous one, and the cracks began to show as early as April 1986, when theI Am Samactor reportedly attacked songwriter David Wolinski when he spotted Wolinski speaking to Madonna. Penn was fined $1,000 and sentenced to a year of probation for the incident. A source close to the singer told PEOPLE: “The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for her. Wolinski was someone she knew, and it really shook her up.”

Four months later, Penn got into scuffles with two photographers in New York. Around this time, Penn was reportedly jealous of model and singerNick Kamen, who was working on a track called “Each Time You Break My Heart” with Madonna, and was convinced they were having an affair, despite Madonna’s denial.

On Dec. 4, 1987, Madonna filed for divorce from Penn. “There was no one direct incident leading up to this,” her rep told PEOPLE. “It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation — that they weren’t happy together.”

TheLos Angeles Timesreported that Madonna requested to withdraw her divorce filing within less than two weeks, but the pop star later filed for divorce for good in January 1989.

The pair have since remained friendly, and in December 2016, Madonna said she was “still in love” with Penn, evenoffering to remarry himif he bid $150,000 in a charity auction.

Tony Ward

Warren Beatty

Madonna metWarren Beattyon the set of the filmDick Tracyin 1989, and the pair dated for about 15 months beginning in 1990. “She’s a huge personality, diligent and disciplined and a spectacular dancer and performer,” Beatty later told PEOPLE in 2016. “She’s a phenomenon.”

In the film, Beatty, who is 21 years Madonna’s senior, starred as the title detective, while Madonna played lounge singer Breathless Mahoney.

During their relationship, they initiallybutted headson whether Beatty would appear in the documentaryMadonna: Truth or Dare.

“When we were going [out] and she was making the documentaryTruth or Dare, I said, ‘I don’t want to be in it,’ " Beatty recalled. “And she said, ‘Why would I want you in it?’ " Eventually, Beatty agreed to appear in the film if he could have approval over what footage they used of him. Madonna and Beatty split not long afterDick Tracyhit theaters due to their overall disagreements about fame and publicity.

Michael Jackson

The Queen of Pop took the King of Pop as her dateto the Oscarsin 1991 — but it wasn’t what it seemed. Observers told PEOPLE that Madonna andMichael Jackson’s legendary outing to the Academy Awards was little more than a publicity stunt, and once away from the cameras, Madonna spent time with then-beau Beatty.

Jim Albright

Steve Granitz Archive/WireImage

Jim Albright started as Madonna’s bodyguard. In 2001, he recalled that they became more than colleagues in February 1991,embarking on a secret three-year affair. Albright had a girlfriend when he and Madonna first became lovers, and Madonna seemed to grow distant once Albright split with his girlfriend to be with the “Like a Virgin” singer. When he stepped down as her security guard in 1993, it actually made them closer, with Albright noting that Madonna spoke to him every single day.

The pair grew serious enough, Albright alleged, that they considered marrying, but Madonna insisted on a prenup that he refused.

Albright claimed that Madonna became more and more “insecure” and jealous throughout their relationship and that the singer had affairs with athletes and other celebrities, including Ingrid Casares and comedianSandra Bernhard. Despite Madonna’s alleged infidelity, Albright said it wasn’t until he admitted to hooking up with someone else on the side that Madonna called it quits with him.

“She’d never been faithful to one man — period,” Albright alleged. “She told me that. She is only loyal to herself.”

Vanilla Ice

Ron Galella, Ltd./Ron Galella Collection

In a2013 interviewwith George Stroumboulopoulos, Vanilla Ice (born Robert Van Winkle) said Madonna was “a sweetheart” and recalled that they frequently wore disguises when they went on dates. “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. “And we could walk in and the bodyguards would be like 20 feet behind, kinda looking like we’re nobody. And just walk in and go and see our movie and just have a good, normal … we’d do dinner that way and nobody would ever recognize us. It was the greatest.”

Vanilla Ice said he and the Queen of Pop split up, in part, because shewanted to get more seriouswith him despite still pining for her ex Penn. “I was digging her,” he said in Andrew Morton’s bookMadonna. “But there was a desperate neediness about her, an impatience to get married.” He added of Madonna’s torch for Penn, “I felt that she still loved him. In fact, I know she did because she told me.”

Tupac Shakur

Patrick McMullan/Patrick McMullan

Madonna dated another famous rapper,Tupac Shakur, after actressRosie Perezintroduced them at the 1993 Soul Train Awards, but the romance didn’t last long. Shakur broke down exactlywhy he ended the relationshipin a letter written to Madonna from January 1995. The handwritten note was made public when TMZpublished a redacted version of it in 2017.

“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,” Tupac wrote in the candid note, sent to Madonna from prison. “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.”

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” Shakur wrote. “It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things. … Can you feel me?”

He also apologized several times to Madonna for not being more clear with her at the time of their split.

“In the time since, as you can see, I have grown both spiritually and mentally,” he wrote. “It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”

Dennis Rodman

Andrew D. Bernstein/NBAE

Those “basketball players” Madonna mentioned? One of them wasDennis Rodman. The twobriefly datedin 1994, and although the relationship didn’t last, Rodman looked back on it fondly in his 1996 memoirBad as I Wanna Be. “We never had any problems. It was one of the easiest relationships I’d ever been in,” he wrote.

As short as Rodman and Madonna’s romance was, Madonna took it seriously, according to the NBA star: In a September 2019 interview onThe Breakfast Club, Rodman alleged that Madonna offered him $20 million to get her pregnant. Though he claimed they tried, she and Rodman never had a child together.

John F. Kennedy Jr.

Philip Ramey/Corbis/Getty

Madonna reportedlyhad a flirtationwithJohn F. Kennedy Jr., in the ’90s, though it didn’t go much further than flirty faxes and phone calls.

The pair were drawn to each other, but the spark eventually fizzled out. “I think she gave it right back to him and she teased him and she was irreverent and he liked it,” the friend added. “The flirtation kind of continued and they would try to get together but it was hard because she was on tour and he was working. They saw each other a few times and they had a flirty and friendly banter but it wasn’t a ‘relationship.’ "

Carlos Leon

S. Granitz/WireImage

Madonna met personal trainerCarlos Leonin 1994 after a chance encounterjogging past himin Central Park. She reportedly sent a member of her team to ask him who he was, thinking it was her former flame Albright. She and Leon hit it off, though he reportedly had a hard time with the media attention that came with dating the famed songstress.

At Madonna’s 37th birthday party in August 1995, the couple told their loved ones that they’d planned to have a child together after she finished filmingEvita. Madonna was surprised to learn that she was 11 weeks pregnant during filming and was reportedly nervous that her pregnancy would negatively impact the shoot.

On Oct. 14, 1996, Madonna gave birth to her first and only child with Leon, daughterLourdes “Lola” Maria Ciccone Leon. However, the pair split up the next year in May 1997. Madonna’s close friend,Rosie O’Donnell, later told biographer Andrew Morton, “It was a real relationship. They made a valiant effort to stay together.”

Guy Ritchie

Mike Marsland/WireImage

Even her longtime pal Rupert Everett approved, noting of Ritchie, “Guy works almost as hard as Madonna does. He’s definitely not a boy toy.”

But it wasn’t love at first sight for Ritchie, however, who had an on-again, off-again relationship with Madonna for months. By January 2000, Madonna told PEOPLE she wasin lovewith Ritchie and that their romance was “excellent.” That March, the couple announced they were expecting a child together, and their sonRocco Ritchiewas born on Aug. 11, 2000.

Madonna married Ritchie on Dec. 22, 2000, at Skibo Castle near Dornoch, Scotland, in a private ceremony with their families, Sting, Styler,Gwyneth Paltrow,Donatella Versaceand a few other pals in tow. Madonna explained of the remote locale, “We wanted to find a place that was really hard to get to, because when people have to work hard to get somewhere, you know they really want to be there.”

While initially enamored with each other, Madonna and Ritchie’s relationship has its fair share of issues, and theyannounced their divorcein October 2008. One insider told PEOPLE that theirproblems grew more severearound 2007 — and that Madonna’s alleged emotional affair with baseball playerAlex Rodriguezdidn’t help matters.

“It wasn’t just one thing,” a source told PEOPLE. “They just lost their connection … [Rodriguez] was a factor in a long list of problems that they had been having over the past year or two. But it wasn’t the reason. If she wanted to move past that she would have, and Guy would have too.”

The source added: “It was unraveling throughout the last year. They were living separate lives and coming together every now and then for the cameras.”

Lifestyle differences, including Madonna’s devotion to Kabbalah and love of the spotlight, neither of which Guy shared with her, also played a role in the split.

“She would try to get him to come to things, and he resisted,” the insider said. “She was more about being a celebrity and he was more low-key. He wanted to live in London and live a normal life but that’s impossible when you’re married to Madonna.”

A friend of Madonna concurred: “She was always first when it came to her husband or herself, and that really took a toll on Guy. There was only so much he could put up with.”

In 2011, Ritchie spoke toDetailsmagazine about their marriage. “It’s definitely not something I regret,” he said, according toE! News. “The experience was ultimately very positive. I love the kids that came out of it, and I could see no other route to take.”

Though the split seemed relatively amicable at first, Madonna and Ritchie would later have abitter custody warover Rocco that last from December 2015 until June 2016.

Alex Rodriguez

Richard Corkery/NY Daily News Archive/Getty ; Joe Corrigan/Getty

Prior to her divorce from Ritchie, Madonna was linked to Yankees playerAlex Rodriguez, who divorced his then-wifeCynthia Scurtisin September 2008. Scurtis' attorney accused A-Rod of having “an affair of the heart” with the “Material Girl” singer, causing their split. In a statement before her own divorce announcement, Madonna told PEOPLE: “I know Alex Rodriguez through Guy Oseary, who manages both of us. I brought my kids to a Yankee game. I amnot romantically involvedin any way with Alex Rodriguez. I have nothing to do with the state of his marriage or what spiritual path he may choose to study.”

Though insiders told PEOPLE that Madonna and A-Rod shared a “spiritual, emotional and romantic bond,” Rodriguezinsisted he and Madonna were just friends.

Brahim Zaibat

Raymond Hall/FilmMagic

Madonna began dating French model and dancer Brahim Zaibat in September 2010 after he performed at the launch of her Macy’s clothing line, Material Girl. During their three-year romance, the pair enjoyed a trip to Paris, and he performed during her 2012MDNAtour.

The couple walked the red carpet together at the 2013 Met Gala but split that December.E! Newsreported that it was due to “busy and conflicting schedules.”

Timor Steffens

Kevin Mazur/WireImage ; Anthony Harvey/Getty

Though the couple weren’t together for very long, Steffens, who is 30 years younger than Madonna, was happy to talk about the romance withTheMirror. “There is an age gap between me and Madonna but I don’t notice it,” he said. “My girlfriends have always been older than me and that’s how I like it. I learn a lot.”

He added of Madonna, “She always looks for new ­challenges in life. When everyone walks the right path, she will walk the left path to show that she has a vision and her own way of expressing. She is a very strong woman and doesn’t need to follow the mainstream. That’s what makes her an artist.”

The pair reportedly split not long after Steffens spoke to the tabloid.

Ahlamalik Williams

Jamie McCarthy/Getty

Madonna first sparked speculation that she was dating dancer and choreographerAhlamalik Williams, who is 36 years her junior, in June 2019, when she posted a since-deleted Instagram video dancing with him to celebrate her albumMadame Xtopping the Billboard charts. The couple reportedly first met in 2015 when Williams was a dancer on herRebel Hearttour.

Madonna and Williams were relatively low-key over the course of their relationship, but he was a fixture in her life and Instagram feed through 2021: The pairspent Thanksgivingtogether with her children anddressed up as elveswith her family that December. The couple alsorang in Madonna’s 62ndand63rd birthdaystogether. They reportedly split in April 2022, after three years of dating.

Josh Popper

Madonna and Josh Popper.Josh Popper/Instagram

In early 2023, Madonna was seen spending time with boxing trainer andSummer HousestarJosh Popper,sparking rumorsthat the two were an item. The pair reportedly met while Popper was training the singer’s son David Banda at Bredwinners gym in N.Y.C., which he owns.

Shortly after, Madonna was spotted attending another one of Popper’s boxing matches at the Classic Car Club in N.Y.C. on March 3.

In December 2023, Popper and the “Vogue” singer shared a kiss on stage during herCelebration Tourstop in Brooklyn.

It’s unclear when the rumored couple went their separate ways in 2024.

Akeem Morris

Madonna/Instagram

Madonna andAkeem Morrisfirst met on the set of herPaper Magazinecover shoot in August 2022. However, the pair didn’t spark romance rumors until July 2024 when they were seen cuddled up in New York City on the Fourth of July.

A month later, Morris joined the “Like a Prayer” singer in Italy for her66th birthday bash.

source: people.com