Jean-Michel Basquiat (1982 – 1983)
Rising stars: Madonna and the late Jean-Michel Basquiat dated in the 1990s
Madonna briefly dated the late painter Jean-Michel Basquiat when they were both rising stars in New York.
Sean Penn (1985 – 1989)
Rocky marriage: Madonna was married to Sean Penn from 1985 to 1989. The couple are pictured attending an AIDS charity event on November 11, 1987 in Los Angeles
The singer was famously dating actor Sean Penn after the duo met on the set of her Material Girl music video.
Their often tumultuous relationship ended in 1989, with reports citing Penn’s erratic behavior as one of the main reasons.
John F. Kennedy Jr. (1997)
Mingling with the Kennedys: During a split with Penn, Madonna dated the late John F. Kennedy Jr. for six months; Pictured in 1997 in Las Vegas
During her split from Penn, Madonna 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 was rumored to disapprove of the scandalous singer. Madonna is also reported to have picked on John’s temper.
Warren Beatty (1991)
Movie Star Romance: She then dated movie star Warren Beatty after the two starred in his comic film Dick Tracy; Pictured on June 24, 1990 in New York
The singer dated movie star Warren Beatty after they starred in his comic book movie Dick Tracy, where she played singer Breathless Mahoney
The two separated due to their conflicting views on life 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 split with the star after she published her infamous coffee table book called Sex, which featured him, saying he was “hurt” to be a part of it.
Tupac Shakur (1994)
Rapper crush: Madonna dated the late rapper Tupac Shakur in the 1990s, but broke up due to societal restrictions; Pictured in 1994 in New York
Madonna and the late rapper Tupac Shakur dated in the 90s. The duo reportedly split due to societal restrictions.
Tupac told Madonna that he was uncomfortable with the image of dating a white woman because “it would disappoint half the people that did [him] What [he] a thought [he] was,” as he explained in a handwritten letter he wrote to the pop star a year before he was fatally shot.
Dennis Rodman (1994)
From rapper to ball player: After her romance with Tupac, the singer briefly dated former Chicago Bulls basketball star Dennis Rodman for two months
After her romance with Tupac, the singer was briefly linked to former Chicago Bulls basketball star Dennis Rodman for two months.
Although only for a short period of time, the athlete revealed that Madonna wanted to have a child with him in her memoir Bad As I Wanna Be.
Carlos Leon (1994 – 1997)
First baby: Madonna gave birth to her first child – daughter Lourdes Leon, 25 – with personal trainer Carlos Leon, whom she dated for three years
Although she was unable to have a child with Rodman, Madonna became pregnant with personal trainer Carlos Leon, whom she dated for three years.
The two have a daughter, Lourdes Leon, 25, together and maintain a good friendship.
Guy Ritchie (2000 – 2008)
Married: She married director Guy Ritchie. The two were together for eight years and share a son, Rocco, 22, and an adopted son, David Banda, 16; Pictured in 2007
One of Madonna’s longest relationships was with director Guy Ritchie, to whom she was married for eight years.
The former couple are said to have met at the home of Trudy Styler (wife of musician Sting) in 1999 at a party.
They share son Rocco, 22, and adopted son David Banda, 16, together.
Jesus Luz (2008 – 2010)
A string of boy toys: After her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz; Pictured 2009
Shortly after her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz.
The former couple met at a W magazine photo shoot, but eventually broke up due to not having much in common.
Brahim Zaibat (2010 – 2013)
Love for younger men: Joining the list of younger models and dancers the star has dated is Brahim Zaibat – a French dancer – who was 24 at the time; Pictured 2013
Joining the list of younger models and dancers the star has dated is Brahim Zaibat – a French dancer and choreographer – who was 24 at the time.
He went on the MDNA World Tour with her in 2012. The duo also appeared together at the Met Gala in 2013, where they made a fashionable pair in punk-inspired outfits.
Ahlamalik Williams (2018 – 2022)
Recent romance: Madonna began dating her 28-year-old backup dancer Ahlamalik Williams – who was almost 40 years her junior – in 2018; 2021 is pictured
Madonna began dating her 28-year-old backup dancer Ahlamalik Williams – who was almost 40 years her junior – in 2018.
The couple split after four years of dating in the spring of 2022.
Andrew Darnell (2022 – Present)
A 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 two were first photographed kissing on the cover of Paper magazine in August and were most recently spotted “hugging and cuddling” over Labor Day weekend at musician REMA’s concert in New York City.