Madonna's Always 'Hung Up' On Love: Inside The Queen Of Pop's Complete Dating History

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Source: mega;@madonna/instagram

Mar. 11 2023, Published 12:05 p.m. ET

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Give Me All Your Luvin'! Madonna has been searching for a forever flame to "Justify My Love" since she ignited her famous career at the young age of 24-years-old.

While the earlier days of her career sparked a brief relationship with Breakfast Club frontman Dan Gilroy from 1979-1981, followed by a fling with late artist Jean-Michel Basquiat, there would be many other loves to cross the Queen of Pop's path.

Keep scrolling to see a list of all the fellas lucky enough to date Madonna!

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Sean Penn

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Source: mega

Sean Penn was the first man to claim Madonna's heart with the words, "I Do," after they met on the set of her legendary "Material Girl" music video. The former spouses tied the knot in 1985 before officially divorcing in 1989.


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Source: mega

Tupac and the "Like a Virgin" singer were involved in a relationship for roughly a year before he left her in 1994 due to societal pressures at the time.

In a letter from prison released by TMZ in 2017, the late rapper wrote a lengthy message to Madonna confessing the reasoning behind their romantic demise.

"Can u understand that? 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. 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. I never meant to hurt you," Tupac explained in January 1995 before he was fatally shot in September 1996.

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Dennis Rodman

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Source: mega

Following her and Tupac's split, Madonna engaged in a two-month relationship with retired Chicago Bulls star Dennis Rodman. The NBA legend revealed in his Bad As I Wanna Be memoir that the mother-of-six wanted to conceive a child with him.

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Carlos Leon

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Source: mega

And here comes baby No. 1! Madonna and her personal trainer, Carlos Leon, dated for three years and welcomed her eldest child, Lourdes Leon, 26, in 1996.

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Vanilla Ice

madonna vanilla ice
Source: mega

Vanilla Ice may have brought the spice to the award-winning artist's life, however, he wasn't ready to commit with a ring.

"She even proposed to me," the rapper confessed during a podcast appearance at the end of January. "I mean things were going so crazy and fast man," he noted of the couple's 8-month relationship in 1992.

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Guy Ritchie

madonna guyritchie
Source: mega

Fans thought Guy Ritchie would have Madonna's heart for good.

The lovebirds exchanged vows in 2000 and seemed inseparable until their marriage ultimately ended in 2008. They share a biological son, Rocco Ritchie, 22, and adopted son David Banda, 17, together.

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Alex Rodriguez

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Source: mega

Alex Rodriguez was rumored to have had an affair with the pop star in 2008 following his split from ex-wife Cynthia Scurtis.

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Brahim Zaibat

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Source: mega

Madonna appeared to enter her much-younger-model phase when she was linked to French dancer and choreographer Brahim Zaibat, then 24, from 2010-2013. They even arrived at the 2013 Met Gala side by side.

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Ahlamalik Williams

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Source: mega

Madonna's passionate romance with Ahlamalik Williams convinced fans they were in it for the long hall. The couple first started dating in 2018 and called it quits during the spring of 2022.

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Andrew Darnell

Source: @madonna/Instagram

Madonna's relationship with Andrew Darnell caused quite the controversy, as the 23-year-old model's young age left a 40-year gap between the two. The couple's fling was exposed in September 2022 after the lovebirds were seen cuddled up for Labor Day weekend.

It was revealed in February that the duo has parted ways — which left Madonna suffering a "crisis of confidence," as OK! previously reported.

"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," a source explained to a news publication on Thursday, February 23.

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Josh Popper

madonna joshpopper ig
Source: @madonna/instagram

Madonna has most recently been linked to her son's boxing coach, Josh Popper, 29.

The duo first sparked romance rumors on Wednesday, March 1, as she seemed to confirm their relationship with a steamy smooch shared just one week later.


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