Entertainment

Vanilla Ice reflects on the time his ex-girlfriend Madonna proposed to him in the 1990s

Vanilla Ice displays on the time his ex-girlfriend Madonna proposed to him within the Nineties

Jean Michel Basquiat (1982 – 1983)

Rising Stars: Madonna and the late '90s Jean-Michel Basquiat

Rising Stars: Madonna and the late ’90s Jean-Michel Basquiat

Madonna briefly dated the late painter Jean-Michel Basquiat when each have been rising stars in New York Metropolis.

Sean Penn (1985 – 1989)

Rocky Marriage: Madonna was married to Sean Penn from 1985 to 1989.  The couple is pictured attending an AIDS charity on November 11, 1987 in Los Angeles

Rocky Marriage: Madonna was married to Sean Penn from 1985 to 1989. The couple is pictured attending an AIDS charity on November 11, 1987 in Los Angeles

The singer was famously married to actor Sean Penn after the duo met on the set of their music video Materials Woman.

Their usually tumultuous relationship led to 1989, with reviews citing Penn’s unpredictable conduct as a significant trigger.

John F Kennedy Jr (1997)

Mixing with the Kennedys: During a breakup with Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months;  Pictured in Las Vegas in 1997

Mixing with the Kennedys: Throughout a breakup with Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months; Pictured in Las Vegas in 1997

Throughout a break up from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months.

The romance with the political inheritor did not final lengthy as his mom Jackie Kennedy is claimed to not approve of the controversial singer. Madonna additionally reportedly had points with John’s mood.

Warren Beatty (1991)

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

Film Star Romance: She then dated film star Warren Beatty after they starred in his comedian guide movie Dick Tracy; Pictured June 24, 1990 in New York Metropolis

The singer met film star Warren Beatty after they starred in his comedian guide movie Dick Tracy, through which she starred as singer Breathless Mahoney

The 2 ultimately broke up as a consequence of their conflicting views on public life.

Vanilla Ice Cream (1992)

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

ice cream child! Madonna dated Vanilla Ice for eight months earlier than splitting in 1992

Madonna dated Vanilla Ice for eight months earlier than splitting in 1992.

The “Like A Virgin” singer dated rapper “Ice Ice Child” when he was 23 and he or she was 32.

He reportedly break up from the star after she launched her notorious photograph guide referred to as Intercourse, through which he appeared, and stated he was “damage” to be part of it.

Tupac Shakur (1994)

In love with a rapper: Madonna dated the late rapper Tupac Shakur in the '90s, but they broke up due to societal pressures;  Pictured in New York in 1994

In love with a rapper: Madonna dated the late rapper Tupac Shakur within the ’90s, however they broke up as a consequence of societal pressures; Pictured in New York in 1994

Madonna and the late rapper Tupac Shakur dated within the ’90s. The duo reportedly break up as a consequence of societal pressures.

Tupac advised Madonna that he was uncomfortable with the image of courting a white lady as a result of it “would let down half the individuals who did it.” [him] What [he] thought [he] was,’ as he defined in a handwritten letter he wrote to the pop star a 12 months earlier than he was fatally shot.

Dennis Rodman (1994)

From rapper to baller, the singer briefly dated former Chicago Bulls basketball star Dennis Rodman for two months following her romance with Tupac

From rapper to baller, the singer briefly dated former Chicago Bulls basketball star Dennis Rodman for 2 months following her romance with Tupac

After her romance with Tupac, the singer briefly dated former Chicago Bulls basketball star Dennis Rodman for 2 months.

Though the athlete solely dated for a short while, the athlete revealed in his memoir Dangerous As I Wanna Be that Madonna needed to have a toddler with him.

Carlos Leon (1994 – 1997)

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

First child: Madonna had her first baby – daughter Lourdes Leon, 25 – with private coach Carlos Leon, with whom she dated for 3 years

Regardless of not having the ability to have a toddler with Rodman, Madonna grew to become pregnant with private coach Carlos Leon, whom she dated for 3 years.

The 2 have a daughter collectively, Lourdes Leon, 25, and preserve an excellent friendship.

Man Ritchie (2000 – 2008)

Married: She married director Guy Ritchie.  The two dated for eight years and share son Rocco, 22, and adopted son David Banda, 16;  Pictured in 2007

Married: She married director Man Ritchie. The 2 dated for eight years and share son Rocco, 22, and adopted son David Banda, 16; Pictured in 2007

Certainly one of Madonna’s longest relationships is with movie director Man Ritchie, to whom she was married for eight years.

The previous couple reportedly met at a celebration in 1999 on the house of Trudie Styler (spouse of musician Sting).

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

Jesus Luz (2008 – 2010)

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

A spread of boy toys: After her divorce was finalized, the star started courting 24-year-old Brazilian mannequin Jesus Luz; Pictured 2009

Shortly after their divorce was finalized, the star started courting 24-year-old Brazilian mannequin Jesus Luz.

The previous couple met at a photoshoot for W journal, however ultimately break up as a result of they did not have many pursuits in frequent.

Brahim Zaibat (2010 – 2013)

A 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

A love for youthful males: Becoming a member of the checklist of youthful fashions and dancers the star has dated is Brahim Zaibat – a French dancer – who was 24 on the time; Pictured 2013

Becoming a member of the checklist of youthful fashions and dancers the star dated is Brahim Zaibat – a French dancer and choreographer – who was 24 on the time.

He went on the MDNA world tour together with her in 2012. The duo additionally confirmed up collectively on the 2013 Met Gala, the place they made a modern couple in punk-inspired outfits.

Ahlamalik Williams (2018 – 2022)

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

Current romance: Madonna started courting her backup dancer, 28-year-old Ahlamalik Williams, who was virtually 40 years her junior, in 2018; Pictured 2021

Madonna started courting her 28-year-old backup dancer, Ahlamalik Williams, who was virtually 40 years her junior, in 2018.

The couple referred to as it quits in spring 2022 after 4 years of courting.

Andrew Darnell (2022–current)

New romance?  Madonna is currently reported to be dating 23-year-old model Andrew Darnell

New romance? Madonna is at the moment reported to be courting 23-year-old mannequin Andrew Darnell

Madonna is at the moment reported to be courting 23-year-old mannequin Andrew Darnell.

The duo have been first kissed and kissed on the quilt of Paper journal in August have been final seen “cuddling and cuddling” at musician REMA’s live performance in NYC over Labor Day weekend.

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