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

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Madonna has 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 to Sean Penn from 1985 to 1989, then to Guy Ritchie from 2000 to 2008. She has also had a slew of relationships and flings with several other Hollywood stars, including Tupac, Dennis Rodman and Warren Beatty, among others. Most recently, she has been linked to Summer House star Josh Popper.

While Madonna is famous for being unapologetically herself, it doesn't mean she has "absolutely no regrets" about her past. During a 2022 Q&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 to come 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

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Madonna credits her ex-boyfriend Dan Gilroy with changing her focus from dance to music. As she  told Rolling Stone during 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 ask Ed?' "

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 told Rolling 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

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Madonna dated artist Jean-Michel Basquiat in 1982 and was in awe at his dedication to painting. In 2014, she told Interview magazine: "I mean, 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."

In a March 2015 interview with Howard 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 taken her children to see Basquiat's paintings, as she shared in a since-deleted Instagram, per W Magazine.

John "Jellybean" Benitez

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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 that their 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

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Madonna and Sean Penn began dating in February 1985 after meeting on the set of her iconic "Material Girl" music video. They got married on Madonna's 27th birthday, which was also the day before Penn's 25th birthday, just six months after they first met.

"We have so much in common that 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 film Shanghai Surprise.

Madonna and Penn's marriage was a tumultuous one, and the cracks began to show as early as April 1986, when the I Am Sam actor 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 singer Nick 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."

The Los Angeles Times reported 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, even offering to remarry him if he bid $150,000 in a charity auction.

Tony Ward

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In 1990, Madonna dated model and actor Tony Ward, who costarred in her "Justify My Love" music video — which MTV banned for being too racy. Their romance was short-lived, however. PEOPLE reported in 1991: "It may be a coincidence, but [Ward] seems to have dropped from [Madonna's] arm at about the same time tabloids revealed that he had married an old flame, Amalia Papadimos, 23, in a quickie ceremony in Las Vegas on Aug. 21, 1990 — after he had begun dating Madonna."

Warren Beatty

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Madonna met Warren Beatty on the set of the film Dick Tracy in 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 initially butted heads on whether Beatty would appear in the documentary Madonna: Truth or Dare.

"When we were going [out] and she was making the documentary Truth 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 after Dick Tracy hit theaters due to their overall disagreements about fame and publicity.

Michael Jackson

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The Queen of Pop took the King of Pop as her date to the Oscars in 1991 — but it wasn't what it seemed. Observers told PEOPLE that Madonna and Michael 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

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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 comedian Sandra 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

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In 1991, Madonna began dating Vanilla Ice, who was nine years her junior. She dated the "Ice Ice Baby" rapper for eight months until splitting in 1992.

In a 2013 interview with 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 she wanted to get more serious with him despite still pining for her ex Penn. "I was digging her," he said in Andrew Morton's book Madonna. "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

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Madonna dated another famous rapper, Tupac Shakur, after actress Rosie Perez introduced them at the 1993 Soul Train Awards, but the romance didn't last long. Shakur broke down exactly why he ended the relationship in a letter written to Madonna from January 1995. The handwritten note was made public when TMZ published 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."

He added that he was hurt by a remark Madonna allegedly made in an interview in which she said, "I'm off to rehabilitate all the rappers & basketball players."

"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

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Those "basketball players" Madonna mentioned? One of them was Dennis Rodman. The two briefly dated in 1994, and although the relationship didn't last, Rodman looked back on it fondly in his 1996 memoir Bad 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 on The 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.

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Madonna reportedly had a flirtation with John F. Kennedy Jr., in the '90s, though it didn't go much further than flirty faxes and phone calls.

A friend of JFK Jr. later told PEOPLE, "It was a flirtation, and when other people referred to her as M around that time, just by her first initial, he would say, 'I started that.' He called her M when he wrote or faxed her. There were no cell phones then and he was always very territorial that he started that moniker for her."

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

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Madonna met personal trainer Carlos Leon in 1994 after a chance encounter jogging past him in 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 filming Evita. 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, daughter Lourdes "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."

The breakup was amicable, and by his own account, Madonna and Leon stayed "good friends" after their split as they co-parented Lourdes.

Guy Ritchie

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Madonna met director Guy Ritchie at a party hosted by mutual pals Sting and Trudie Styler in 1999. "I had a whole premonition of my life fast-forward," she recalled. "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. … He's a risk taker and he's got a hungry mind."

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 was in love with Ritchie and that their romance was "excellent." That March, the couple announced they were expecting a child together, and their son Rocco Ritchie was born on Aug. 11, 2000.

Six days later, on Madonna's 42nd birthday, she found a crumpled paper bag near her bed that she almost threw out, mistaking it for garbage. "Then I noticed something in it, a little box," she recalled, adding that the box contained a ring and a card. "It was a really sweet letter that he wrote to me about everything we've been through, my birthday and the baby and how happy he was."

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 Versace and 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 they announced their divorce in October 2008. One insider told PEOPLE that their problems grew more severe around 2007 — and that Madonna's alleged emotional affair with baseball player Alex Rodriguez didn'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 to Details magazine about their marriage. "It's definitely not something I regret," he said, according to E! 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 a bitter custody war over Rocco that last from December 2015 until June 2016.

Alex Rodriguez

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Prior to her divorce from Ritchie, Madonna was linked to Yankees player Alex Rodriguez, who divorced his then-wife Cynthia Scurtis in 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 am not romantically involved in 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," Rodriguez insisted he and Madonna were just friends.

Brahim Zaibat

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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 2012 MDNA tour.

In January 2012, Zaibat told OK! Magazine that he wasn't intimidated by Madonna when they first met. "She was just a woman almost like the others," he said. "An exceptional artist and world-famous, of course, but a woman first. I was just happy to meet her. But not particularly stressed!" Zaibat added the pair initially connected over their love of dance: "I will not say the romance is going too fast, but things take their course."

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

Timor Steffens

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Following her split from Zaibat, Madonna had a "fling" with choreographer Timor Steffens in 2014. The pair reportedly met in Switzerland through their mutual friend, designer Valentino Garavani, per E! News.

Though the couple weren't together for very long, Steffens, who is 30 years younger than Madonna, was happy to talk about the romance with The Mirror. "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

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Madonna first sparked speculation that she was dating dancer and choreographer Ahlamalik Williams, who is 36 years her junior, in June 2019, when she posted a since-deleted Instagram video dancing with him to celebrate her album Madame X topping the Billboard charts. The couple reportedly first met in 2015 when Williams was a dancer on her Rebel Heart tour.

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 pair spent Thanksgiving together with her children and dressed up as elves with her family that December. The couple also rang in Madonna's 62nd and 63rd birthdays together. They reportedly split in April 2022, after three years of dating.

Josh Popper

Josh Popper/Instagram Madonna and Josh Popper

In early 2023, Madonna was seen spending time with boxing trainer and Summer House star Josh Popper, sparking rumors that the two are 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.

On Feb. 12, 2023, Madonna appeared in photos posted by Popper on Instagram. In one picture, the pop star poses with the boxer and his coaches after he won a match at Gleason's Gym. In another, the pair pose together, with Madonna holding onto Popper's arm.

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. She later shared photos from the event on her Instagram Story.

Both Madonna and Popper have yet to discuss their rumored relationship publicly.