Madonna’s Boyfriend: Ahlamalik Williams & Men She’s Loved Before – Hollywood Life

Madonna’s Boyfriend: Her Most Recent Ex Andrew Darnell & More From Her Romantic History

Here we break down the pop icon's current and past relationships from Sean Penn to Guy Ritchie to her most recent relationship with Andrew Darnell, who she split up with in Feb. 2023.

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  • Madonna is a legendary pop singer known for her hits “Material Girl”, “Hung Up”, and more.
  • She is not known to be dating anyone as of Feb. 24, 2023.
  • The songstress was once married to actor Sean Penn from 1985 to 1989.
  • Most recently, she was linked to 23-year-old Andrew Darnell, who she has reportedly split from, as of Feb. 24, 2023.

Madonna, 64, is a woman of the world. As such, the “Queen of Pop” has had many relationships, including two ex-husbands and numerous lovers. Ever since her star took off in the early ’80s, she’s enjoyed a series of lovers, flings, long-term relationships, and marriages, and often with a star-studded cast of men.

In 2004, the famed singer opened up to Oprah magazine about her outlook on love. “I’ve learned to make it work for me. I’ve taken that longing, that searching, that yearning for answers, and I’ve turned it out to the world,” she said at the time. “That’s one reason I’m as insatiable for knowledge as I am. I’m looking to fill myself up.” Amid her recent split from Andrew Darnell, 23, learn all about Madonna’s love life here! It’s a long list, but one definitely worth diving into!

Andrew Darnell

Following her split from Ahlamalik Williams in spring 2022, it wasn’t long until Madonna found romance once more. The blonde beauty was first linked to model and skateboarder, Andrew Darnell, who is 41 year her junior, in the summer of 2022. Not only were the now-exes spotted getting cozy, but they also posed on his Instagram on Aug. 11, 2022. “M!”, he captioned the post inside of a night club in New York City at the time. And on Sept. 9, 2022, a source close to the star told HollywoodLife that they were dating “casually” and that she didn’t factor in their age difference as an issue.

“Madonna is casually dating Andrew Darnell and although some of her friends think the fact that he is 23 is a bit strange, Madonna does not seem to care at all,” the insider dished at the time. “She has never really let age affect her decision on who to date and who not to date and it is not like Madonna is going to settle down, nor does she want to.”

Finally, Andrew and M’s brief romance came to a halt in Feb. 2023, just six months after they were first linked to each other. “It was only a very casual thing [with Andrew] so she’s not broken-hearted. It’s just that it has come at a bad time,” the insider claimed to Page Six on Feb. 24. “She had a lot of fun with Andrew but it was never love or anything like that.” Interestingly, Andrew has since moved on and is seeing someone closer to his age range, per the outlet’s source.

Ahlamalik Williams

Madonna began dating her backup dancer, Ahlamalik Williams, in 2018 after first meeting in 2015. Although many people pointed out how the dancer was almost 40 years her junior, Madge was never bothered.

Born in Sacramento, California, Ahlamalik is a professional dancer and choreographer who’s worked on various shows, including Madonna’s 2019 Madame X tour. The two aren’t super public with their relationship, although Madonna shared an intimate video of the two to her Instagram in March 2021 with them making out!

After almost four years of dating, however, the pair decided to call it quits in spring 2022. “Madonna has thrown herself into a busy social life and has been seeing her friends and family after the split,” a source claimed to The Sun on April 26, 2022. “She has a packed schedule, working on her upcoming biopic, new music and looking after her family.” The source added that things were “on and off” with Ahlamalik “for a while” and that there was “a lot of love” still between them, but they ultimately “decided to separate.”

Brahim Zaibat

Madonna and Brahim ZaibatCostume Institute Gala Benefit celebrating the Punk: Chaos To Couture exhibition, Metropolitan Museum of Art, New York, America - 06 May 2013
Madonna and Brahim Zaibat attend the Met Gala, 2013. (Matt Baron/BEI/Shutterstock)

Brahim Zaibat, 35, joins a list of young models and backup dancers with whom Madonna shared intimacy, but he’s perhaps the one Madonna has dated the longest so far. Born in 1986 in Lyon, France, Brahim is a dancer and choreographer of Algerian origin and was linked to the singer from 2010 to 2013. Madonna first met the dancer when he was chosen to dance for promoting her Material Girl Collection clothing line at Macy’s in Sept. 2010 and he went on to tour with her in her MDNA world tour in 2012. Although the couple broke up in December 2013, they made a memorable public appearance together at the 2013 Met Gala.

Jesus Luz

Madonna and boyfriend Jesus LuzMadonna and boyfriend Jesus Luz out and about in Knightsbridge, London, Britain - 31 Mar 2010 Madonna pictured showing a rather wrinkled skin on one side of her neck, on leaving a private address in Knightsbridge with brazilian toy-boyfriend Jesus Luz, at around 1am. At the private party were also present italian fashion designer Valentino, actress Gwyneth Paltrow and Stella MacCartney.
Madonna & Jesus Luz at a private party, 2010. (Copetti/Photofab/Mcp/Shutterstock)

Another in Madonna’s string of what several outlets called “toyboy” lovers, Jesus Luz, 35, is a Brazilian model Madonna dated from around 2008 to 2010. The former couple met at a magazine photoshoot in 2008 and quickly began a romance shortly after her divorce from Guy Ritchie was finalized. According to the Daily Mail, the “Material Girl” singer was said to have been “on edge” when she visited Jesus’ mother, hairdresser Cristiane Regina da Silva, who is 14 years her junior, while visiting Rio de Janeiro, due to the mother not approving of the relationship.

According to a source who spoke with the Chicago Sun-Times, ‘It was not only totally amicable, but it was Luz who initiated the split,” adding that the pair didn’t have many mutual interests that bonded them.

Alex Rodriguez

New York Yankees Third Baseman Alex Rodriguez Waits in the On Deck Circle As Fans Hold Photos of Madonna in the Second Inning Against the Boston Red Sox at Fenway Park in Boston Massachusetts Usa 25 July 2008Usa Baseball Mlb - Jul 2008
New York Yankees Third Baseman Alex Rodriguez Waits in the On Deck, 2008. (Gunther/EPA/Shutterstock)

Although short-lived, Madonna and former New York Yankees star, Alex Rodriguez, 47, were rumored to have briefly dated in 2008. In December 2020, Alex’s ex, Jennifer Lopez, seemed to have confirmed those rumors as Andy Cohen pressed her on his Radio Andy show about dressing up as Madonna for Halloween since her then-fiancé “dated Madonna for two seconds.” Jennifer laughed and then replied, “No. I mean, it was so long ago.”

Guy Ritchie

Guy RitchieChelsea Flower Show, Press Day, London, UK - 20 Sep 2021
Guy Ritchie
Chelsea Flower Show, Press Day, London, UK – 20 Sep 2021. (James Veysey/Shutterstock)

Perhaps one of Madonna’s well-known suitors is film director Guy Ritchie, 53, to whom she was married for eight years between 2000-2008. The former couple reportedly met at the home of Trudie Styler (musician Sting‘s wife) in 1999 at a dinner party. After Trudie played matchmaker with the pair, they quickly fell in love and the “Like a Virgin” singer gave up life in the U.S. to live in England and start a family with her beau. Madonna shares her son, Rocco, 22, with Guy and the former couple also adopted David Banda, 16, while she funded an orphanage in Malawi.

“[I was] certainly asking a kind of existential question that I think people ask when they’ve been married that long: what is the perfect love?’” Madonna told the Daily Mail after her divorce. “Because when you start off, everything’s great and lovely, and the person you’ve married is flawless, and you’re flawless. 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. You think, ‘This isn’t what I thought it was going to be,’ and ‘How much am I willing to sacrifice?’”

Andy Bird

During Madonna’s Ray of Light era, she briefly dated Andy Bird, a British executive who was chairman of Walt Disney International until 2018 and is now CEO of Pearson Education. Around 1997, the now executive was a wannabe screenwriter who met Madonna at a director friend’s Los Angeles dinner party and the two hit it off quickly.

Unfortunately, after things fizzled out, Madonna phoned Andy multiple times and left desperate voicemails, which ended up being obtained by the British press. “We have something special together, we love each other,” she stated, in a transcript of the tape published in the Daily Mail. “I’ve written a song called ‘Beautiful Stranger’ and it’s all about you. I hope you’ll hear it one day because I’ll never forget you or stop loving you.”

Carlos Leon

CARLOS LEON MADONNA Evita" star Madonna and Carlos Leon, father of their infant daughter, arrive for the film's premiere, at the Shrine Auditorium in Los AngelesEVITA OPENING, LOS ANGELES, USA
Madonna & Carlos Leon at ‘Evita’ premiere. (Chris Pizzello/AP/Shutterstock)

Madonna dated personal trainer Carlos Leon, 56, from 1994 to 1997 and the two share a daughter, Lourdes Leon, 25, together. Although the former couple ended things after three years, Carols noted that he still maintains a “great relationship” with the “Like a Virgin” singer. “There was a friendship and there still is a friendship,” Billy Bush Show in 2008. 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. Parents can learn from us in that way. Any parents that stay friends, it’s really good for the children.”

Dennis Rodman

Dennis Rodman
Dennis Rodman, 2005. (Shutterstock / Featureflash Photo)

Perhaps both at the peak of their fame, Madonna and former Chicago Bulls basketball star Dennis Rodman, 61, were an item in 1994 for only two months. Although their relationship was short-lived, it was definitely wild and highly publicized. In his memoir, Bad As I Wanna Be, Dennis talked about he and Madonna’s sexual practices and also claimed that the “Hung Up” songstress wanted him to impregnate her. “Madonna talked all the time about having a baby. I think she wanted every bit of Dennis Rodman—marriage, kids, everything,” Vulture reported.

Dennis also shared that one time when he was gambling in Las Vegas, “I picked up the phone and Madonna was like, ‘I’m ovulating, I’m ovulating. Get your ass up here.’ So I left my chips on the table, flew five hours to New York and did my thing.” He added, “We got done and she was standing on her head in an attempt to promote conception—just like any girl trying to get pregnant. I flew back to Las Vegas and picked up my game where I left off.”

Tupac Shakur

Tupac Shakur
Tupac Shakur. (Moviestore/Shutterstock)

Madonna and the late rapper Tupac Shakur were rumored to have dated in the ’90s, and Madonna confirmed the rumors on a 2015 appearance on Howard Stern‘s Sirius XM radio show in 2015. When the radio host pressed Madonna about her seemingly hostile interviews on David Letterman‘s late night show in the ’90s, she explained,  “I was mad at David Letterman and I said the f-word a lot. I was in a weird mood that day.” She continued, “I was dating Tupac Shakur at the time and the thing was he got me all riled up about life in general. So when I went on the show I was feeling very gangsta.” 

Rolling Stone also reported on a handwritten apology letter from the rapper to the pop star that went up for auction starting at $100,000. The letter, written about a year before the rapper was fatally shot, reveals him apologizing for not being “the kind of friend I know I am capable of being.” Tupac revealed that he felt uncomfortable being seen dating a white woman because he “would be letting down half of the people who made [him] what [he] thought [he] was.” 

Vanilla Ice

Madonna and Vanilla Ice
Madonna and Vanilla Ice
‘Truth Or Dare’ party. (Bei/Shutterstock)

Madonna dated rapper Vanilla Ice, 54, in the early ’90s when he broke out with his smash hit, “Ice Ice Baby.” Although the pair were an item for eight months, the rapper broke things off with Madonna due to her controversial Sex book. “I broke up with her after she printed [the explicit book, “Sex”] because I was hurt to be an unwitting part of this slutty package,” the rapper told News of the World, according to Digital Spy. “We were in a relationship, yet it looked like she was screwing all these other people. I thought she was taking pictures and running around naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno.”

Michael Jackson

Madonna & Michael Jackson
Madonna and Michael Jackson at the 1991 Academy Awards. (Joyce Silverstein/Shutterstock)

The King and Queen of Pop were rumored to have been something of an item in the early ’90s, and Madonna claimed that the late Michael Jackson was the “best date ever” after they showed up together to the 1991 Academy Awards. Although the two were never public or serious about being linked, she did admit in a 2016 episode of The Late Late Show With James Corden that she and the “Thriller” singer at least kissed. According to Madonna, she made the first move and offered Michael some chardonnay which apparently “worked wonders.”

Warren Beatty

Madonna & Warren Beatty
Madonna & Warren Beatty. (John Barrett/Shutterstock)

Movie star Warren Beatty, 85, and Madonna got heated both on and off screen in 1991 after co-starring in his comic book movie Dick Tracy. In the flick, Madonna played the sexy lounge singer, Breathless Mahoney, and her sultry ways ended up seducing the actor-director off set as well. “She’s a huge personality, diligent and disciplined and a spectacular dancer and performer,” Warren said of the singer in 2016 to People. “She’s a phenomenon.” The two ended up splitting due to their conflicting views of living in the public eye, as fans could witness in her documentary at the time, Truth or Dare, which Warren did not want to be a part of at first.

“When we were going [out] and she was making the documentary Truth or Dare, I said, ‘I don’t want to be in it.’ And she said, ‘Why would I want you in it?’” But Warren ended up conceding: “I said if I can have approval, I don’t want to inhibit you.”

John F. Kennedy Jr.

John F. Kennedy Jr.
John F. Kennedy Jr. in Washington, 1995. (Shutterstock / mark reinstein)

Madonna dated the late John F. Kennedy Jr. for six months in the ’80s and was reportedly not a big hit with the political heir’s mother, Jackie Kennedy. Apparently the heiress didn’t love Madonna’s adoption of Catholic imagery into her style and image and didn’t approve of her son dating the “Like a Prayer” singer. The Kennedy Heirs, biographer J. Randy Taraborrell also noted that Madonna actually spoke of John’s temper to her friends, saying that he frightened her more than her ex-husband, Sean Penn.

“Whereas Sean would act out, perhaps give a photographer a body shot just to vent, somehow John’s way seemed more personal,” the biographer wrote, per InStyle. “Madonna said that he would get up in her face, maybe an inch away, and scream at her at the top of his lungs when they were in a fight.”

Sean Penn

Sean Penn & Madonna
Sean Penn & Madonna at the Mike Tyson vs. Michael Spinks Boxing Match, 1998. (Shutterstock)

Actor Sean Penn, 61, met Madonna on the set of her “Material Girl” music video, and the two were married from 1985 to 1989 after an illustrious and often tumultuous relationship. People magazine reported in 1987 about Sean’s unpredictable behavior that led to his issues with Madonna and the ultimate dissolution of their marriage. The outlet cited a 1986 incident when Sean attacked songwriter David Wolinski at a nightclub after he thought David had kissed Madonna. “The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for [Madonna],” a source told the magazine at the time. “Wolinski was someone she knew, and it really shook her up.”

In 2017, Madonna responded to rumors that Penn was abusive toward her during their marriage. “I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me,” she said at the time, according to The Daily Beast. “Specifically, I am aware of the allegations concerning an alleged incident that occurred in June 1987, whereby (according to tabloid reports), Sean allegedly struck me with ‘a baseball bat.’ I know the allegations in those and other reports to be completely outrageous, malicious, reckless, and false.”

Jean-Michel Basquiat

In her early New York City club scene days, it was only in the stars that Madonna would be linked to then-rising artist Jean-Michel Basquiat. The pair enjoyed a brief affair between 1982-83, during the time when both were on the brink of international stardom — her as a definitive American pop star and him as a wunderkind of the neo-expressionist movement of the downtown SoHo scene. During an interview with Howard Stern, Madonna shared, “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.”