Fans have been fascinated with Madonna‘s boyfriend and love life for a while. In her 40-plus years in Hollywood, Madonna has been married twice and shares several kids with her exes. As fans know, Madonna came onto the music scene in August 1968 with her first single, “Everybody.”

After that, it didn’t take long for Madonna to earn her title as the “Queen of Pop” with historic hits such as “Like a Virgin”, “La Isla Bonita”, “Like a Prayer”, “Vogue” and “Music.” In an interview with Oprah Winfrey for O magazine in 2004, Madonna opened up about her outlook on love.

“Each of us is responsible for everything that happens in our lives. When good things happen—we win an award, meet the love of our lives, or get a promotion—we take ownership of that,” she said at the time. “But when bad things happen—we get fired or we divorce—we often don’t take responsibility. We call it something that just happened. I now understand that just as we can draw the positive, we can draw the negative.”

Madonna also told Oprah about what she’s learned from her past relationships. “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.”

Ahead is what to know about Madonna’s boyfriend, Ahlamalik Williams, and who her past relationships have been with. Read on for a look into Madonna’s dating history.

Ahlamalik Williams (2018 – Present)

Madonna started dating her backup dancer, Ahlamalik Williams, around 2018. Williams’ father, Drue Williams, confirmed their relationship in 2019, telling TMZ that the two had been dating for more than a year. “Love has no age,” he said. “My son is livin’ la vida loca, and I’m just happy for him.”

Williams, who is 36 years younger than Madonna, is a professional dancer and choreographer from Sacramento, California, who has performed in shows like Cirque du Soleil and Michael Jackson ONE. He was also a part of the dance crew Raw by Nature. According to TMZ, Ahlamalik was “personally picked” to be one of Madonna’s backup dancers for her Rebel Heart Tour in 2015. He also worked on her Madame X Tour in 2019.

In March 2021, Madonna shared a rare video of her making out with Williams on her Instagram. The video, which was captioned “after party,” showed Williams blowing smoke into Madonna’s mouth he leaned in for a tongue-filled kiss.

Source: Instagram

Guy Ritchie (2000 – 2008)

Madonna married director Guy Ritchie in 2000. The two share sons Rocco, as well as David Banda, who they adopted together. After eight years of marriage, the couple split in 2008. In an interview with Newsweek in 2012, Madonna revealed that she knew her relationship was over as she was writing her movie W.E., which is about an affair between Wallis Simpson and Edward VIII.

“[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?’” she said at the time. “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?’” Ritchie, for his part, has said that he doesn’t regret his relationship with Madonna but called their romance a “soap opera,” according to The Daily Mail.

Carlos Leon (1994 – 1997)

Madonna dated personal trainer Carlos Leon from 1994 to 1997. The two share daughter Lourdes. Split their split, the two have had an amicable relationship. “I have a great relationship with all my ex-girlfriends, but especially Madonna,” Leon said on the Billy Bush Show in 2008. “There was a friendship and there still is a friendship. 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.” He continued, “Parents can learn from us in that way. Any parents that stay friends, it’s really good for the children.”

Sean Penn (1985 – 1989)

Madonna was married to actor Sean Penn from 1985 to 1989. The two met in 1985 on the set of Madonna’s music video for “Material Girl.” People reported in 1987 that Penn’s unpredictable behavior led to issues in his marriage to Madonna. The magazine cited an incident in April 1986 when Penn attacked songwriter David Wolinski at a nightclub after he thought that Wolinski 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 People 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.”

from StyleCaster