Madonna suggests she is gay in playful TikTok video


Jean-Michel Basquiat (1982 – 1983)

Rising stars: Madonna and the late Jean-Michel Basquiat dated in the 90s

Rising stars: Madonna and the late Jean-Michel Basquiat dated in the 90s

Madonna briefly dated the late painter Jean-Michel Basquiat when both were rising stars in New York City. 

Sean Penn (1985 – 1989) 

Rocky marriage: Madonna was married to Sean Penn from 1985 until 1989. The couple are pictured attending an AIDS benefit November 11, 1987 in Los Angeles

Rocky marriage: Madonna was married to Sean Penn from 1985 until 1989. The couple are pictured attending an AIDS benefit November 11, 1987 in Los Angeles

The singer was famously married to actor Sean Penn, after the duo met on the set of her Material Girl music video. 

Their often tumultuous relationship came to an end in 1989, with reports citing Penn’s unpredictable behavior as one of the major contributing causes.

John F. Kennedy Jr. (1997)

Mingling with the Kennedy's: During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months; Pictured 1997 in Las Vegas

Mingling with the Kennedy’s: During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months; Pictured 1997 in Las Vegas

During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months.

The romance with the political heir didn’t last long, as his mother, Jackie Kennedy, was said to not approve of the controversial singer. Madonna also reportedly took issue with John’s temper. 

Warren Beatty (1991) 

Movie star romance: She then dated movie star Warren Beatty, after they co-starred in his comic book movie Dick Tracy; Pictured June 24, 1990, in New York City

Movie star romance: She then dated movie star Warren Beatty, after they co-starred in his comic book movie Dick Tracy; Pictured June 24, 1990, in New York City

The singer dated movie star Warren Beatty after they co-starred in his comic book movie Dick Tracy, where she starred as singer Breathless Mahoney

The two ended up splitting due to their conflicting views of living in the public eye. 

Vanilla Ice (1992) 

Ice, Ice baby! Madonna dated Vanilla Ice for eight months before splitting in 1992

Ice, Ice baby! Madonna dated Vanilla Ice for eight months before splitting in 1992

Madonna dated Vanilla Ice for eight months before splitting in 1992. 

The Like A Virgin singer dated the Ice Ice Baby rapper 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 was featured, saying he was ‘hurt’ to be part of it. 

Tupac Shakur (1994)

In love with a rapper: Madonna dated late rapper Tupac Shakur in the ’90s but they split up due to societal constraints; Pictured 1994 in New York

In love with a rapper: Madonna dated late rapper Tupac Shakur in the ’90s but they split up due to societal constraints; Pictured 1994 in New York

Madonna and the late rapper Tupac Shakur dated in the ’90s. The duo reportedly split up due to societal constraints.

Tupac told Madonna that he was uncomfortable with the image of dating a white woman because he ‘would be letting down half of the people who made [him] what [he] thought [he] was’ as he explained in a handwritten letter he wrote the pop star a year before he was fatally shot. 

Dennis Rodman (1994)

From rapper to baller: Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months

From rapper to baller: Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months 

Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months.

Though only together for a short period of time, the athlete revealed Madonna wanted to have a child with him in his memoir, Bad As I Wanna Be.

Carlos Leon (1994 – 1997) 

First baby: Madonna had her first child - daughter, Lourdes Leon, 25 - with personal trainer Carlos Leon, whom she dated for three years

First baby: Madonna had her first child – daughter, Lourdes Leon, 25 – with personal trainer Carlos Leon, whom she dated for three years

Despite not being able to have a child with Rodman, Madonna went on to get pregnant 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 went on to marry director Guy Ritchie. The two were together for eight years and share son, Rocco, 22, and adopted son David Banda, 16; Pictured in 2007

Married: She went on to marry director Guy Ritchie. The two were together for eight years and share son, Rocco, 22, and adopted son David Banda, 16; Pictured in 2007

One of Madonna’s longest relationship is that with film director Guy Ritchie, whom she was married to for eight years.

The former couple reportedly met at the home of Trudie Styler (musician Sting‘s wife) in 1999 at a party.

They share son, Rocco, 22, and adopted son David Banda, 16, together. 

Jesus Luz (2008 – 2010) 

String of boy toys: After her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz; Pictured 2009

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 photoshoot, but eventually split up due to not having many interests in common.

Brahim Zaibat (2010 – 2013)

A love for younger men: Joining the list of younger models and dancers the star dated is Brahim Zaibat - a French dancer - who was 24-years-old at the time; Pictured 2013

A love for younger men: Joining the list of younger models and dancers the star dated is Brahim Zaibat – a French dancer – who was 24-years-old at the time; Pictured 2013

Joining the list of younger models and dancers the star dated is Brahim Zaibat – a French dancer and choreographer – who was 24-years-old at the time.

He went on the MDNA world tour with her in 2012. The duo also showed up together to the 2013 Met Gala, 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; Pictured 2021

Recent romance: Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams – who was almost 40 years her junior – in 2018; Pictured 2021

Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams – who was almost 40 years her junior – in 2018. 

The pair called it quits 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

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 were first pictured kissing on the cover of Paper magazine in August, and were most recently spotted ‘snuggling and cuddling’ over Labor Day weekend at musician REMA’s concert in NYC.



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