Summary
- Madonna has dated a variety of high-profile men throughout her career, including Tony Ward, Sean Penn and Lenny Kravitz.
- Madonna's relationships have often been marked by controversy and intense media scrutiny, but she has remained a prominent figure in the public eye.
- Madonna's current boyfriend, Josh Popper, is a boxing trainer who initially met her while training her son, and the couple has been going strong since early 2023.
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 whom 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 October 2023: While critics were not sure how long the romance would last, it appears that Madonna and her latest beau, Josh Popper are very happy together. Popper has been spotted on vacations with Madonna and even at family birthday parties. However, this does not mean that Madonna is going to be planning on jumping into anything too serious too soon or moving in with Popper in the near future. But for now, the two appear to be happy with the direction their relationship is headed, title or no.
15 Tony Ward
Age: 27-Years Old When Dating Madonna; 60-Years Old Now
- Dated: Late 1990 to Early 1991
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.
14 Sean Penn
Age: 25-Years Old When Married To Madonna; 63-Years Old Now
- Married: July 1985 to January 1989
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.
13 Lenny Kravitz
Age: 26-Years Old When He Had A Fling With Madonna; 59-Years Old Now
- Dated: Had brief affair in 1990
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.
12 Tupac
Age: 23-Years Old When Dating Madonna; Died In 1996 At 25-Years Old
- Dated: March 1993 to January 1995
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.
11 Dennis Rodman
Age: 32-Years Old When Dating Madonna; 62-Years Old Now
- Dated: Unknown time in 1994
Before he was chasing rings with Michael Jordan as a Chicago Bull, Dennis Rodman was chasing Madonna in 1993 as a San Antonio Spur in his 30s.
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 reportedly dumped her.
10 Carlos Leon
Age: 27-Years Old When Dating Madonna; 57-Years Old Now
- Dated: From 1994 to 1997
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 short time frame, the two had a child, Lourdes Leon, before they decided they were better off as best friends instead of lovers.
9 David Blaine
Age: 25-Years Old When Dating Madonna; 50-Years Old Now
- Dated: Unknown time during 1998
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.
8 Vanilla Ice
Age: 24-Years Old When Dating Madonna; 55-Years Old Now
- Dated: 1991 to 1992 for eight months
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.
7 Guy Ritchie
Age: 32-Years Old When Married To Madonna; 55-Years Old Now
- Married: December 2000 to October 2008
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!
6 Alex Rodriguez
Age: 35-Years Old When Dating Madonna; 48-Years Old Now
- Dated: Briefly in 2008
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. Lopez and Rodriguez broke up and in 2022, Rodriguez was linked to his current girlfriend, Jaclyn Cordeiro.
