Inside Madonna's Relationship With Ahlamalik Williams

Every aspect of Madonna's life has been intensely scrutinized from the moment she burst onto the music scene in the early '80s with her hit debut album, "Madonna." The superstar is famous for constantly reinventing herself, pushing boundaries, and taking career risks that many would shy away from. One of the more fascinating aspects of her life is the long list of much younger men she's dated over the years. Madonna has been with her current boyfriend, Ahlamalik Williams, since the end of 2019 (per Page Six). The decades separating them represents the largest age gap between the "Material Girl" singer and anyone she's dated publicly (per Daily Mail).

Originally from Sacramento, Williams moved to Las Vegas in 2013 with plans of becoming a street performer but ended up snagging a role in Cirque du Soleil's homage to Michael Jackson, "One" (per Dance Track). Williams, who is a dancer, choreographer, and aspiring rapper, met Madonna in 2015 and went on to tour the world with her. In 2019, some candid photos of them behaving affectionately on the balcony of a hotel in Miami provided ample confirmation of their romance (per Daily Mail).

The dance phenom, who once sold hip-hop lessons on line for five dollars and aspired to "change the world through art," is now performing regularly on some of the world's largest stages with his superstar girlfriend.  

Madonna told Harper's Bazaar, "I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable." Though she made this statement in 2017, her trend has continued with Ahlamalik Williams, who is 36 years her junior. According to the Daily Mail, with the exception of Warren Beatty, who was 21 years her senior, all of the men she's dated over the years have been younger than her. 

During that '80s, Madonna dated artist Jean-Michel Basquiet and political scion John F. Kennedy Jr. and married actor Sean Penn, all of whom were two years her junior. She later dated Brahim Zaibat, who is 29 years younger than her. Two more boyfriends, who were 30 and 33 years younger than her, filled the years until Williams entered the picture. 

During a guest spot on "The Ellen DeGeneres Show," host Ellen DeGeneres brought up the singer's love life and penchant for younger men, to which she responded, "Why is everyone so obsessed? Age is a number," noting, "People just don't like it when I have fun."

Madonna's "Rebel Heart" tour was successful for her in many ways. According to Forbes, at the conclusion of the tour, she had totaled up $1.31 billion in ticket sales, which was the most that any solo artist had ever sold up to that point. The concert received great reviews, including one from Rolling Stone that asserted, "The whole night was a tour of everything only Madonna can do. She's not the same. She has no shame. She's on fire." Vulture's review was markedly less enthusiastic, but it gave a glowing shout-out to Madonna's cast of dancers, saying, "Madonna gave us human spectacle: a double-jointed man doing a mesmerizing dance with a billowing sheet, pairs of dancers writhing on gravity-defying beds to the subtle tune of 'Sex.'" 

A closer review of the concert footage reveals that, in fact, the "double-jointed man" the writer referred to was none other than Ahlamalik Williams. Evidently he caught Madonna's eye from day one, as TMZ reported that she personally picked him during the audition process. The spectacle of that concert was heightened by Williams' solo interlude during which Madonna appeared in video form as he performed center stage. Review after review pointed out the talents of the dancers, with The Hollywood Reporter saying, "Madonna's dancers served impressive spectacles that left the crowd gasping in awe," and The Guardian declaring, "Madonna's interludes are as good as the main event." 

Madonna and Williams clearly work well together.

Though Madonna and Ahlamalik Williams have known each other since 2015 (when he became one of her dancers), the couple appears to have waited a few years before embarking on a personal relationship. Some candid photos that were taken at the end of 2019, however, seemed to confirm that romance was afoot (per Daily Mail). The couple, who was in Miami for some shows, was spotted on a hotel balcony, where Williams gave Madonna a shoulder massage and embraced her affectionately from behind. The intimate nature of the interaction led to speculation that the two, who were rumored to be in a relationship, were finally putting an end to the suspicion.

Williams subsequently appeared in some Instagram posts on Madonna's feed, according to Today, though they were still keeping a low profile. No official proclamations accompanied any of Madge's posts, but Williams was definitely participating in family activities by that point. In addition to joining Madonna and her clan on a trip to Jamaica in 2020 to celebrate her 62nd birthday, he showed up again in one of her photo carousels around Thanksgiving of the same year. 

In 2021, Madonna traveled with Ahlamalik Williams and all six of her children to Italy to celebrate her 63rd birthday. The group flew private to the country and spent the vacation enjoying the sights and the culture. She announced the start of the trip with an Instagram post that was captioned, "Let the Birthday Games Begin." The "Borderline" singer made time to indulge in outings geared both toward romance and family. During the getaway, she made lots of Instagram posts documenting time with her boyfriend, most of which were fairly tame compared to some of her more risqué offerings. In one, Madonna carries a glass of rosé. In another, the couple licks the same ice cream cone. Photos taken by paparazzi featured the couple strolling the streets hand-in-hand, occasionally stopping to smooch (via Page Six).

The group enjoyed one particularly festive dinner where everyone sang, danced, and shook tambourines, as noted by the Daily Mail. The couple also shared some sweet moments in the backseat of a car as they were being chauffeured. In an affectionate post shared by Williams, the duo is seen from behind as they walk and hold hands. He posted the sweet caption, "Happy circle round the galaxy day Home skillet."

Madonna's history of dating much younger men is legendary, and she continued her streak when she became romantically involved with back-up dancer Ahlamalik Williams. In this case, however, not only is she older than the object of her affection, but she is also older than both of his parents. When Williams' parents met his lady in 2019, Madonna was 61, Williams' dad Drue was 59, and his mom Laurie was 55. His parents were unbothered by the decades separating the two, however, and Drue told The Mirror, "We know there's a huge age gap between the two — 36 years. Madonna is two years older than me." He also said, "But I have told my son love doesn't have an age range when you're consenting adults."

Interestingly, Drue reported to TMZ that by the end of 2019 the couple had actually been dating for over a year, which differs from most outlets' reporting that the couple only got together at the end of that year. Drue also revealed in his interview with The Mirror that they had been introduced to Madonna in New York after one of her shows. He also told TMZ, "Love has no age," and, "My son is livin' la vida loca, and I'm just happy for him."

Madonna has enjoyed lots of youthful arm candy over the years, but Ahlamalik Williams might just be the last one. According to his parents, their son's relationship with "Her Madgesty" may go the distance. TMZ reported that dad Drue told them that Madonna had told Williams she loved him. The dancer's parents also spoke with The Mirror and shared their thoughts about the relationship. Drue said, "Madonna went on and on about how much she cares about our son. She said he's intelligent and very talented." He also said, "She told us she is so much in love with him and that we didn't have anything to worry about as she was going to take care of him." 

In that same interview, mom Laurie was also enthusiastic, revealing that they were "big fans of Madonna," and that the star had gushed about their son to them. Laurie said, "We met her after a show and it was incredible. The first thing she said to me was, 'Wasn't he fantastic?' You never know, they could get married." 

Notably, in 2004, Madonna told O, The Oprah Magazine, "To be brave is to love someone unconditionally, without expecting anything in return. To just give. That takes courage, because we don't want to fall on our faces or leave ourselves open to hurt." Then again, she also told Oprah Winfrey, "My husband [Guy Ritchie] is my soul mate." That comment didn't exactly age well. 

Regarding COVID-19, Madonna was predictably controversial. Forced to cancel some of her "Madame X" shows in Paris because of the virus (per Daily Mail), the artist took to making videos she shared on Instagram called "Quarantine Diaries" (per CNN). In the videos, Madonna shared her musings about the pandemic and the state of the world. The posts not only fell flat for many (per The Washington Post), but she was also accused of spreading misinformation about the virus. Some of her comments about coronavirus did not land well with her audience including the statement: "It doesn't care about how rich you are, how famous you are, how funny you are, how smart you are, where you live, how old you are, what amazing stories you can tell. It's the great equalizer, and what's terrible about it is what's great about it."

She seemed to find firmer ground with her followers in a playful post that featured her in the kitchen with boyfriend Ahlamalik Williams and some of her children (per Daily Mail). Williams fawned over her lovingly as she stirred the contents of a mixing bowl while the kids hung out nearby. She also shared an affectionate birthday post for Williams on Instagram that consisted of several pics of them together along with an illustration of them in masks. She added a sweet sentiment, writing, "Happy Birthday My Love. I Could not think of a better person to be in Quarantine with!"

On the trip she called a "homecoming" (per Daily Mail), Madonna, boyfriend Ahlamalik Williams, and four of her children visited several sites in Africa, where they connected with tribes and local citizens. The family spent time with the Pokot Tribe in Kenya's the Baringo Valley, where they joined in on the group's dancing, singing, and praying. She also spent time with the Samburu Tribe (per The Standard), describing the scene by saying, "Men are singing, dancing and telling stories to attract the attention of the females." Boyfriend Williams' dance performance figured prominently in one of the videos, as he jumped up to share some of his own moves. 

Madonna adopted four of her children from the country of Malawi and her charity, Raising Malawi, was responsible for setting up the Mercy James Institute for Pediatric Surgery and Intensive Care, which is named for one of her adopted daughters. The singer and her entourage also toured the Jacaranda School for Orphans and cut the ribbon for the newly established Madame X Dance Studio there, where she gave a passionate speech about following one's dreams to its residents. 

The family appeared to be "glamping" in several of the photos she shared and enjoying recreational activities like riding ATVs and learning to shoot arrows (per Us Weekly). No doubt that the trip was meaningful for the whole family.

Back in 2020, The U.S. Sun shared a very intriguing video of Madonna's man, Ahlamalik Williams, grooving to a track that provided no further explanation. As the dancer and aspiring rapper was feeling the music, commenters quickly began chiming in when they recognized Madonna's vocals on the track. Though there had been speculation that the duo had planned to release a song together (per Daily Mail), there is no evidence of a finished product to be easily found. So far, it appears that he has released three songs, but none of them are a collaboration with the pop star. 

Williams, who is presumably providing the lead vocals on the track, sings lyrics like, "It's beautiful above the clouds," while Madonna croons in the background. She samples lyrics from "La Vie En Rose," an Edith Piaf classic that she's been known to cover in the past. She sings, "Je voie la vie en rose," which translated to English means, "I see life through rose-tinted glasses." People praised the effort, though a final version of the collaboration doesn't appear to have been released.