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Madonna’s Relationship History Includes Industry Names: From Guy Ritchie to Ahlamalik Williams

Musical artist Madonna has dated and married a few noteworthy men throughout her highly successful singing career. Though her past relationships didn’t work out, the Queen of Pop doesn’t let it affect her.

The “Like a Prayer” pop star debuted her latest relationship with boxer Josh Popper nearly one year after her April 2022 split from choreographer Ahlamalik Williams. Madonna and Ahlamalik – who is more than 30 years her junior – dated for three years before she “called it quits,” an insider exclusively told In Touch at the time.

“Madonna and Ahlamalik are dunzo,” the source added. “They haven’t been together for months … Stella and Estere are now 9 [years old], and Madonna is putting all of her love into them,” She’s beyond protective over the twins.”

Madonna adopted her twin daughters from Malawi in 2017, in addition to her other adopted daughter Mercy James in 2009. She shares daughter Lourdes Leon with ex Carlos Leon and children Rocco Ritchie and David Banda with ex-husband Guy Ritchie.

The insider also told In Touch in April 2022 that Madonna and Ahlamalik’s “relationship ended amicably.”

However, the “Borderline” artist shared a cryptic message via her Instagram Stories following the news of their breakup. “Karma said: when somebody in your life is not right for you, God will continuously use them to hurt you until you become strong enough to let them go,” the quote read.

She also spoke candidly about her sex life following the split, noting in an August 2022 YouTube video that her favorite thing to make is “wait for it … love.” The singer also revealed that “getting married” to “both” Guy Ritchie and Sean Penn “wasn’t the best idea.”

Aside from Ahlamalik, Madonna has dated a few other men who were noticeably younger than she was, such as ex-boyfriend Brahim Zaibat. Nevertheless, the Michigan native pays no mind to the criticism she has received about the age difference.

“I didn’t choose to, you know, I didn’t, like, write down on a piece of paper, ‘I’m now going to have a relationship with a younger man,’” she said on ABC News in January 2012. “That’s just what happened. You see, that’s the romantic in me. I just met someone that I cared for, and this happened to be his age.”

In a separate interview, the MTV Video Music Award winner also opened up about common perceptions and expectations surrounding love.

“Unfortunately, we are raised on those fairytales, and even if we are sophisticated, educated, intellectually evolved human beings, we still, in the back of our mind, think that Mr. Right is going to come along, and we are going to live happily ever after,” Madonna said on the Graham Norton Show in January 2012. “In the front of our minds, we keep getting reminded it’s not true, and in the back of our minds, we keep thinking it’s true, so we keep getting disappointed. It’s a paradox — you want it, but if you have half a brain, you know it doesn’t really exist.”

Scroll through the gallery to see Madonna’s ex-husbands and boyfriends.