Inside Madonna's Relationship History

Madonna needs no introduction. The reigning Queen of Pop has been steadily churning out hits and amazing looks since the '80s, and has legions of fans of all ages. Madonna came from humble beginnings, and her dedication and drive helped her rise to superstardom. She has reinvented herself time and time again, through fashion, different genres of music, and successful acting roles. She is undoubtedly an icon whose career is the very definition of success. But what of her love life?

The pop legend has not always had it easy in that department, with tumultuous marriages, salacious rumors, and a habit of dating the bad boy type. Plus, constantly being in the spotlight cannot possibly be easy when it comes to dating. Having had high-profile relationships for over 30 years, has Madonna finally found a love that will last? Read on to find out more about the megastar's relationship history and who she's (maybe) dating now.

Dan Gilroy helped Madonna make music

When Madonna moved to New York City from her native Michigan in the late '70s, her main focus was on dance. She studied at the prestigious Alvin Ailey American Dance Theater but had aspirations to sing as well. When Madonna met musician Dan Gilroy at a party, she found a love that led her on the path to stardom. Gilroy encouraged Madonna to make her own music, which was a revelatory experience for her. "He stuck a guitar in my hand and tuned it to an open chord so that I could strum," she told Rolling Stone. "That really clicked something off in my brain."

When Madonna took a gig in Paris as a backup dancer, she felt lonely and alienated, but Gilroy's letters from home kept her going. "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,'" she remembered. "He really made me feel good." When Madonna returned to New York, she and Gilroy, along with his brother and a fellow dancer, formed a band called the Breakfast Club, featuring Madonna on drums.

Her ambition eventually propelled her to move on to bigger endeavors, but Madonna recalled her relationship with Gilroy fondly. "I really felt loved. Sometimes I'd write sad songs and he'd sit there and cry. Very sweet," she shared.

Madonna loved Jean-Michel Basquiat but his addiction got in the way

In 1982 Madonna began dating famed artist Jean-Michel Basquiat. Basquiat was a graffiti artist who rose to success in the early '80s contemporary art scene. Madonna recalled being inspired by her boyfriend, telling Interview, "I remember getting up in the middle of the night and ... he'd be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that." But Basquiat's substance use was a dealbreaker for Madonna. She put it bluntly during an interview on The Howard Stern Show, "He wouldn't stop doing heroin" (via YouTube).

The couple's breakup seemed to be a tough one, and Basquiat wouldn't let Madonna keep the paintings he'd gifted her while they'd been together. "He made me give them all back to him ... and then he painted over them black," Madonna told Howard Stern.

Basquiat died at the of 27 due to a drug overdose, but his art lives on. In 2017 Madonna took two of her children to see an exhibit featuring his paintings. "My Past meets My Present!! JMB #legend," she captioned a since-deleted Instagram picture of daughters Stella and Estere in front of one of her ex-bf's iconic works (via W).

Madonna and Sean Penn had a rocky marriage

In 1985, as Madonna's star was on the rise, she met actor Sean Penn. The couple were introduced when Penn stopped by Madonna's "Material Girl" video shoot and the two became inseparable, marrying months later. But the whirlwind romance was plagued by problems.

Penn had a reputation for losing his temper, especially with the paparazzi. The couple's fame only led to more media attention, which led to Penn punching, throwing rocks at, and spitting on paparazzi. "His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen," Madonna said (via People). Jealousy seemed to be an issue as well, with a source telling People in 1987, "Sean has a lot of insecurities." But Madonna had issues of her own, admitting, "I have my insecure moments and that puts a lot of strain on people. You take things out on the person you love, and that causes fights, alienation, grief ..."

The couple divorced in 1989, but it seems as though the love they once shared is still intact. Madonna and Penn appeared together in 2016 at a charity benefitting Raising Malawi. On stage, Madonna offered to remarry her ex, telling him, "I'm still in love with you," in front of a star-studded audience (via ET). In 2018, Stephen Colbert asked Penn on "The Late Show" to choose between Madonna and Britney Spears, Penn replied, "I love my first wife very much."

Madonna and Warren Beatty were often at odds

In 1990, Madonna began yet another high-profile relationship with an actor. Madonna and Warren Beatty met while filming "Dick Tracy," and dated for a little over a year. Beatty was 21 years older than the pop superstar and had a playboy reputation in Hollywood, but the two seemed to make a great couple. However, disagreements over fame and privacy eventually broke up their glamorous union.

The relationship coincided with the filming of the documentary, "Madonna: Truth or Dare," and the couple were at odds when it came to what should be captured on camera. There is a scene in the documentary where Beatty is commenting on Madonna's decision to be filmed during a doctor's examination. "She doesn't want to live off-camera, much less talk," the actor retorted (via People). Beatty also admitted to having had reservations about being included in the film himself. "I said, 'I don't want to be in it.' And she said, 'Why would I want you in it?'" he shared with People.

But years later, Beatty had nothing but praise for his ex. "She's a huge personality, diligent and disciplined and a spectacular dancer and performer," the actor expressed.

Madonna and Vanilla Ice had fun while it lasted

In 1991, Madonna dated rapper Vanilla Ice of "Ice Ice Baby" fame. The two were even photographed together as part of Madonna's coffee table book titled "Sex," which would prove to be the eventual downfall of their relationship. "That's what ruined it between me and her, because she put me in that book without my consent, without my knowledge, without anything," Vanilla Ice, whose real name is Robert Van Winkle, alleged on a 2023 podcast episode of "Just Jenny" with Jenny Hutt.

He also claimed that Madonna proposed to him at one point during their relationship and that freaked him out. "Wait a minute, this is too fast ... I'm way too young for this," the rapper recalled.

But it sounds like the couple had a good thing going while it lasted. On an episode of "George Stroumboulopoulos Tonight" in 2013, Vanilla Ice described going to the movies with Madonna while wearing disguises. "She was a sweetheart, we had great times ... you take away the fame and everything and you got two people who just basically had a normal relationship," he said of his megastar ex.

Madonna and Tupac Shakur broke up for a surprising reason

In 1993 Madonna began dating yet another rapper, the late Tupac Shakur, after being set up by mutual friend Rosie Perez. On an episode of "The View" in 2015, Perez said she was with Tupac at the Soul Train Awards as friends when Madonna showed interest. "I said [to Tupac] she wants to meet you and he goes, 'hook that up.' And I hooked it up and I was very happy about it."

However, the relationship was not built to last and its ending was somewhat surprising. In 2017, TMZ published portions of a letter Tupac had written to Madonna while incarcerated in 1995. In it, he explained why he ended things with the singer, citing race as an issue. "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," the rapper 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."

The letter contained multiple apologies, with Tupac saying he never meant to hurt the pop star. He also brought up the time Madonna allegedly told an interviewer, "I'm off to rehabilitate all the rappers & basketball players" which vexed the rapper (via People).

Madonna wanted to settle down with Dennis Rodman

In 1994, Madonna went on to date basketball player, Dennis Rodman. Although the relationship didn't stand the test of time, it seemed there was a point when Madonna hoped to settle down with Rodman. In his 1996 memoir, "Bad As I Wanna Be," Rodman wrote, "She wanted me to calm down a little and be happier just hanging with her and living a slower lifestyle ... but I couldn't just drop everything. I was still having fun, still looking for new challenges." He also commented on the intensity of Madonna's fame and how it was difficult for her to do normal things like go out to dinner without being mobbed.

In 2019, Rodman dropped a bombshell when he went on "The Breakfast Club" and spilled more details about his relationship with the superstar. Rodman claimed that Madonna had offered to pay him $20 million to get her pregnant, even flying him to New York from Las Vegas during the times she was ovulating.

Madonna and Carlos Leon have a child together

Madonna eventually did get pregnant, and the way she met her child's father was something out of a rom-com. Personal trainer Carlos Leon caught Madonna's eye as she jogged past him in Central Park one day. She had a member of her team introduce them, and they actually hit it off quite well despite being perfect strangers. The two went on to date and announced they would be starting a family together in 1995.

Madonna was filming "Evita" at the time she found out she was pregnant and worried that her pregnancy would interfere with filming. But everything went well, and Lourdes "Lola" Maria Ciccone Leon was born on October 14, 1996. Madonna and Carlos Leon stayed together for nearly a year after Lourdes was born, but eventually, their union came to an amicable end. Madonna's pal Rosie O'Donnell said of the pair, "It was a real relationship. They made a valiant effort to stay together" (via People).

In a 2008 interview with People, Leon spoke lovingly of his daughter with Madonna saying, "She's my princess. I spoil her with love — and American Apparel and Urban Outfitters."

Madonna fell hard for Guy Ritchie

By Madonna's own account, it was love at first sight when she met director Guy Ritchie at a party in 1999. "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," Madonna said (via People). The couple kept things casual at first but then in 2000, they announced they were expecting their first child together. Madonna gave birth to Rocco Ritchie in August 2000, and the couple got married in December that same year.

While the marriage lasted longer than Madonna's former relationships, it had its fair share of issues. In 2008, it was rumored that Madonna was having an affair with Yankees star Alex Rodriguez. Although A-Rod's then-wife allegedly left him because of his dalliance with Madonna, the baseball phenom and the superstar both denied the affair. A rep for Madonna told People, "Madonna and Alex have the same manager, Guy Oseary. They have met. They know each other and Madonna took her kids to a Yankees game last week. There's really not anything to comment on beyond that."

But other sources have said there was no external reason for Madonna and Ritchie's split, and that the two simply grew apart. A source told People, "It was unraveling throughout the last year. They were living separate lives and coming together every now and then for the cameras." Madonna and Ritchie divorced in 2008.

Brahim Zaibat was not intimidated by Madonna

In 2010, Madonna began a relationship with French model and dancer Brahim Zaibat. The couple met when Zaibat performed at the launch of Madonna's Material Girl clothing line and went on to date for three years. Zaibat, who is 30 years younger than Madonna, even joined her on her "MDNA" tour in 2012 as a backup dancer.

Zaibat opened up about his relationship with the legendary songstress during an interview with OK!, revealing that he was not intimidated by her star power. "She was just a woman almost like the others," Brahim said. "An exceptional artist and world-famous, of course, but a woman first. I was just happy to meet her. But not particularly stressed!"

In fact, Zaibat even admitted he wasn't that big of a fan of Madonna's music, telling OK!, "It is not the kind of music I prioritize in [sic] my iPod. But like everyone else, I know her hit songs." The couple attended the Met Gala together in May 2013 but called it quits later that year.

Madonna had a fling with Timor Steffens

In 2014, Madonna was seen out and about with dancer and choreographer Timor Steffens. Steffens, like Madonna's ex-flame Brahim Zaibat, is also 30 years younger than the pop superstar, but he admitted that he preferred it that way. "There is an age gap between me and Madonna but I don't notice it," he told The Mirror, adding, "My girlfriends have always been older than me and that's how I like it. I learn a lot."

Sources said that the relationship, which reportedly began when the couple met at designer Valentino's Switzerland chateau, was just a fling. And perhaps that's why it ended as quickly as it did. Steffens, who worked as a backup dancer for Beyoncé, Michael Jackson, and Chris Brown, revealed to The Mirror, "I want to be a dad, it's my goal to have my own family, that's there in the back of my mind all the time." He and Madonna parted ways not long after that interview.

Madonna and Ahlamalik Williams had a fun relationship

Madonna first met Ahlamalik Williams in 2015 when he performed as a backup dancer during her Rebel Heart tour. But the two didn't appear to be romantically involved until they were spotted getting cozy together during a Miami vacation in 2019. The relationship seemed pretty low-key, but the two clearly got closer and Williams was often seen spending time with Madonna and her family. Williams partied with Madonna and her friends and family for the singer's 63rd birthday, and the couple even dressed up as elves for an adorable holiday photo with Madonna's kids in 2021 (via People).

Williams is 27 years younger than Madonna, but apparently, the legendary performer thinks age is nothing but a number. She opened up to Harper's Bazaar in 2017 about her love life and being judged for her choices, saying, "I refuse to live a conventional life. I've created a very unconventional family. I have lovers who are three decades younger than me. This makes people very uncomfortable."

While the couple seemed happy, they reportedly went their separate ways in April 2022.

Madonna and Josh Popper have sparked rumors

Although they have yet to go public with their romance as of November 2023, Madonna is rumored to be dating Josh Popper. Popper is a boxing coach and a model who appeared on Season 7 of Bravo's "Summer House." He is also an active boxer who was named the NYC Ring Masters Heavyweight Champion at Madison Square Garden in 2023.

Madonna's son David Banda reportedly trained at Popper's New York City gym, Bredwinners, which is how the two most likely became connected. In February 2023, Popper posted a photo on Instagram, decked out in his boxing gear with Madonna by his side.

In April 2023, Madonna posted an Instagram video featuring her family and Popper around the dinner table, in which she announced Madonna: The Celebration Tour would be heading to Mexico. Whether or not this relationship has what it takes to stand the test of time remains to be seen, but Madonna and Popper appear to be having a good time for now. And isn't that what the Queen of Pop deserves?