You’re in for a treat if you’re a die-hard Madonna fan or are simply interested in her romantic history! A complete list of every man Madonna has ever been with is available here.
This list includes everyone, from famous couples with singers and actresses to more discreet love affairs. Prepare for a trip down memory lane as we examine the pop icon’s previous romances to see who cut!
America as a whole once developed a communal obsession with not just Madonna but with every man who acted as her romantic partner, many of whom had a significant age difference.
It’s hardly surprising that the pop queen herself has drawn several notable figures given how she has managed to stay on everyone’s radar. Anyone Madonna has dated over the years is listed below.
Rumors that Madonna had broken up with her boyfriend Ahlamalik Williams and was dating a new, even younger man began to circulate in September 2022.
1. Andrew Darnell
Madonna was rumored to have dated 23-year-old model Andrew Darnell in late 2022, who was even more recent than her most recent ex.
According to sources, Madge is “living her best life” and “does not appear to care at all” about the age of her new boyfriend, according to Hollywood Life. The romance doesn’t appear to have been confirmed by Madonna, though.
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2. Ahlamalik Williams
From 2019 until 2022, Madonna was romantically involved with Ahlamalik Williams, a significantly younger man. In 2021, Madge and Ahlamalik celebrated their 63rd birthday together. Ahlamalik was 27 years old at the time.
3. 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. Timor Steffens was Madonna’s second young boy toy following Sean Penn.
Fans found out about their romance at the beginning of that summer, but by the time the season came to a close in August, it was claimed that they had broken up while they were on vacation.
4. Brahim Zaibat
To promote her new Material Girl clothing line collection, Brahim Zaibat hired Madonna’s backup dancer and choreographer, and Madonna soon started dating Brahim Zaibat. One of Madonna’s choreographers was Zaibat.
From that point on, chemistry began to develop, and as a result, a relationship with the much younger man began and continued up until 2013.
5. Alex Rodriguez
Everyone recalls how, in the summer of 2008, Red Sox fans in attendance heckled A-Rod with images of them together during their rumored romance during a game at Fenway Park.
The former Baseball star later dated (and got engaged to) Jennifer Lopez after moving on from Madonna.
6. Guy Ritchie
Two years before Guy Ritchie directed his then-wife in Swept Away, Madonna wed the Gentleman movie director in the year 2000. Before adopting a second child in 2006, they had a boy as a couple in the same year they were married.
In the end, they divorced in 2008 due to irreconcilable disagreements. One of the largest divorce settlements in history cost Madonna a stunning $92 million as a result of their breakup.
7. Vanilla Ice
One of Madonna’s most contentious relationships to this time may have been her romance with the rapper in the year 1991. Both supporters and detractors viewed this combination as little more than a marketing gimmick.
8. David Blaine
One such improbable and unexpected choice of a spouse was Madonna’s relationship with magician David Blaine. Even though they eventually decided to keep their relationship platonic rather than romantic, he was instrumental in her making up with her estranged son Rocco in 2016.
9. Carlos Leon
Carlos Leon was one of Madonna’s greatest loves, even though few people will remember his name.
Just lasting from 1995 to 1997, their union resulted in the birth of Lourdes Leon before they realized they would be better off as best friends rather than lovers.
10. Dennis Rodman
Dennis Rodman chased Madonna in 1993 as a San Antonio Spur before chasing championships with Michael Jordan as a Chicago Bull.
Rodman dumped Madonna because she wanted to become pregnant with his child, as was explained in his 2019 ESPN documentary.
After Rosie Perez introduced them at the 1993 Soul Train Awards, Madonna began a relationship with the legendary late rapper Tupac Shakur, which is probably the most unexpected and frequently overlooked addition to the list.
Pac broke up with Madonna in a 1995 letter while he was incarcerated, as was revealed in a portion of the letter that was made public by TMZ.
12. Lenny Kravitz
Lenny Kravitz and Madonna, who occasionally work together in the music industry (most notably on the song “Justify My Love”), were rumored to have been romantically involved in the past, specifically in the year 1990.
Throughout their recording session, it is stated that the two artists developed feelings for one another.
13. Sean Penn
Although having been married twice before, the two-time Oscar winner and two-time husband were allowed to claim Madonna as his first wife. Despite this, they were only wed from 1985 to 1989, a little period.
Sean Penn said during a guest appearance on The Late Show with Stephen Colbert that he has been in love with his ex-wife for 30 years even though their marriage was dogged by scandals for the duration of their relationship.
14. Tony Ward
Model Tony Ward was Madonna’s beau and muse in the early 1990s.
He not only made appearances in a lot of her music videos, but he also appeared in her hotly contested coffee table photography book, Sex. Among others, Ward was shown in sexy pictures.