Jean-Michel Basquiat (1982-1983)
Rising Stars: Madonna and the late Jean-Michel Basquiat dated back to the ’90s
Madonna briefly dated the late painter Jean-Michel Basquiat when they were both rising stars in New York City.
Sean Penn (1985-1989)
Rocky Marriage: Madonna was married to Sean Penn from 1985 until 1989. The couple is photographed attending an AIDS scholarship November 11, 1987 in Los Angeles
The singer is best known for marrying actor Sean Penn, after the duo met on the set of her Material Girl music video.
Their often turbulent relationship ended in 1989, with reports citing Ben’s unexpected behavior as one of the main contributing reasons.
John F. Kennedy Jr. (1997)
Mingling with the Kennedy Family: During the breakup with Ben, Madonna reportedly dated the late John F. Kennedy Jr. for six months. Pictured in 1997 in Las Vegas
During the split from Ben, Madonna reportedly dated the late John F. Kennedy Jr. for six months.
The romance with the political heir did not last long, as his mother, Jackie Kennedy, reportedly did not approve of the controversial singer. Madonna also reportedly objected to John’s temper.
Warren Beatty (1991)
Movie Romance Star: She then dated movie star Warren Beatty, after they co-starred in the comic book movie Dick Tracy; Pictured June 24, 1990, in New York City
The singer dated Warren Beatty after co-starring in the comic book film Dick Tracy, starring as Breathless Mahoney.
The two ended up splitting due to their conflicting views on living in the public eye.
Vanilla Ice (1992)
Ice ice baby! Madonna dated Vanilla Ice for eight months before they split in 1992
Madonna dated Vanilla Ice for eight months before they split in 1992.
The Like A Virgin singer dated rapper Ice Ice Baby when he was 23 and she was 32.
He reportedly broke up with the star after she published her infamous coffee table book called Sex, in which he appeared, saying he was ‘hurt’ to be a part of it.
Tupac Shakur (1994)
In love with a rapper: Madonna dated late rapper Tupac Shakur in the 1990s but they broke up due to societal restrictions; Pictured 1994 in New York
Madonna and late rapper Tupac Shakur date back to the ’90s. The duo reportedly broke up due to societal restrictions.
Tupac told Madonna that he’s uncomfortable with the picture of dating a white woman because he’d “let down half of the people who made [him] what or what [he] Think [he] It was ‘as he explained in a handwritten letter, the pop star wrote a year before he was fatally shot.
Dennis Rodman (1994)
From rapper to ballerina: After her romance with Tupac, the singer was briefly engaged to former Chicago Bulls basketball star Dennis Rodman for two months
After her romance with Tupac, the singer was briefly engaged to former Chicago Bulls basketball star Dennis Rodman for two months.
Although they were only together for a short time, the athlete revealed that Madonna wanted to have a baby with him in his memoir, Bad As I Wanna Be.
Carlos Leon (1994-1997)
First child: Madonna had her first child – daughter Lourdes Leon, 25 – with personal trainer Carlos Leon, whom she dated for three years.
Despite being unable to have a child with Rodman, Madonna continued the pregnancy with personal trainer Carlos Leon, whom she dated for three years.
The two share a daughter, Lourdes Leon, 25, together and have maintained a good friendship.
Guy Ritchie (2000-2008)
Married: She married director Guy Ritchie. The two have been together for eight years and share a son, Rocco, 22, and adopted son David Banda, 16; Pictured in 2007
One of Madonna’s longest relationships is with film director Guy Ritchie, to whom she has been married for eight years.
It is said that the former couple met at the house of Trudie Styler (musician’s wife Sting) in 1999 at a party.
They share son Rocco, 22, and adopted son David Banda, 16, together.
Jesus Luz (2008-2010)
A series of boy games: After her divorce was finalized, the star started dating 24-year-old Brazilian model Jesus Luz; Pictured 2009
Shortly after her divorce was finalized, the star started dating 24-year-old Brazilian model Jesus Luz.
The former couple met on a photo shoot for W magazine, but eventually broke up due to not having many interests in common.
Ibrahim Zibat (2010-2013)
Love for younger men: joining the list of younger models and dancers, the star Brahim Zibat – a French dancer – was 24 years old at the time; Pictured 2013
Joining the list of younger models and dancers, the star Brahim Zibat – a French dancer and choreographer – was 24 years old at the time.
He went on the MDNA World Tour with her in 2012. The duo also appeared together at the 2013 Met Gala, where they made a trendy pair in punk-inspired outfits.
Ahlamalik Williams (2018 – 2022)
Recent Romance: Madonna began dating her 28-year-old backup dancer, Ahlamalec Williams—who was nearly 40 years her junior—in 2018; Pictured 2021
Madonna started dating her 28-year-old backup dancer Ahlamalec Williams – who was nearly 40 years her junior – in 2018.
The couple called on her to quit smoking after four years of dating in the spring of 2022.
Andrew Darnell (2022–present)
New romance? Madonna is currently rumored to be dating 23-year-old model Andrew Darnell
Madonna is currently rumored to be dating 23-year-old model Andrew Darnell.
The duo was first photographed kissing on the cover of Paper magazine in August, and They were recently spotted “cuddling and cuddling” during the Labor Day weekend at the REMA concert in New York City.