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During the height of her fame in the ’80s and ’90s (and to some extent, to this very day), Madonna enjoyed a run at the top as America’s leading sex symbol.
There was a time when America as a whole collectively became obsessed with not just Madonna, but each and every man in her life who served as a romantic partner, many of which had quite the age gap. Considering the queen of pop herself has managed to remain on everyone’s radar, it’s no surprise she’s attracted some big names. Here is everyone Madonna has dated over the years.
Updated November 30th, 2022: Around September 2022, rumors swirled that Madonna had split from her boyfriend Ahlamalik Williams and was dating a new — and even younger — beau.
14/14 Tony Ward
During the early ’90s, model Tony Ward served as Madonna’s boyfriend and muse.
Not only did he cameo in a number of music videos for her, but he also made an appearance in her highly controversial coffee table photography book she titled simply Sex. Ward, among others, was featured in erotic photos.
13/14 Sean Penn
The two-time Oscar winner and two-time husband were able to claim Madonna as his first wife. However, their marriage only lasted between 1985 and 1989.
Despite their marriage being marred in controversy, Sean Penn confirmed in a Late Show interview with Stephen Colbert that after 30 years, he’s still in love with his ex.
12/14 Lenny Kravitz
Occasional music collaborators (most notably on the song “Justify My Love”), Lenny Kravitz and Madonna were also reported to have been lovers at one point back in 1990.
The duo was said to have fallen for one another during their recording session.
11/14 Tupac
In perhaps the most surprising and oft-forgotten addition to the list, Madonna dated world-renowned late rapper Tupac Shakur after Rosie Perez introduced them at the Soul Train Awards in 1993.
While in prison, as revealed in an excerpt of said letter released by TMZ, Pac broke up with Madonna in a 1995 letter.
10/14 Dennis Rodman
Before he was chasing rings with Michael Jordan as a Chicago Bull, Dennis Rodman was chasing Madonna in 1993 as a San Antonio Spur.
As was detailed in his 2019 ESPN documentary, Madonna fell in love with Rodman enough to want to have his baby, which is exactly why Rodman dumped her.
9/14 Carlos Leon
Although not many people will remember the name Carlos Leon, he was one of Madonna’s greatest loves.
Their relationship only lasted between the years 1995 and 1997, but in that time frame, the two had a child, Lourdes Leon, before they decided they were better off as best friends instead of lovers.
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8/14 David Blaine
In another unlikely and surprising choice of partner, Madonna dated David Blaine. While they wound up opting to be friends instead of staying as lovers, he did help her reconcile with her estranged son Rocco back in 2016.
7/14 Vanilla Ice
The romantic tale of the singer and the rapper circa 1991 was perhaps one of Madonna’s most controversial relationships to date up until this point.
Fans and critics alike often pegged this pairing as merely a publicity stunt.
6/14 Guy Ritchie
In the year 2000, Madonna married the Gentleman movie director, two years before Guy Ritchie directed his then-wife in Swept Away. During their time together, they had a son together the same year they married before adopting another child in 2006.
They ended up divorcing over irreconcilable differences in 2008. Their split cost Madonna a whopping $92 million in what became one of the biggest divorce settlements, ever!
5/14 Alex Rodriguez
Everyone remembers back in 2008 during the summer for a game at Fenway Park, heckling Red Sox fans in attendance heckled A-Rod with pics of him and Madonna during their rumored affair.
The former MLB player moved on from Madonna to actress Kate Hudson and later dated (and got engaged to) Jennifer Lopez.
4/14 Brahim Zaibat
One of her choreographers and backup dancers, Madonna dated Brahim Zaibat after he hired her in 2010 to dance to help promote her new Material Girl clothing line collection.
Chemistry sparked from there to the point that a romance with the much younger man blossomed that lasted all the way until 2013.
3/14 Timor Steffens
A year after the breakup, in 2014, Madonna found herself another young boy toy in the form of a personal trainer named Timor Steffens.
Fans learned about their relationship at the top of that summer, but by the end of the season in August, they were reported to have fallen out while on holiday.
2/14 Ahlamalik Williams
Madonna and her much-younger beau Ahlamalik Williams dated from 2019 to 2022. Madge celebrated her 63rd birthday with Ahlamalik in 2021; he was 27 at the time.
1/14 Andrew Darnell
In late 2022, Madonna was linked to Andrew Darnell, a model even younger than her most recent ex; he was 23 when they met.
Sources told Hollywood Life that Madge is “living her best life” and “does not seem to care at all” about her new beau’s age. However, Madonna doesn’t seem to have confirmed the romance.
