8. Carlos Leon

Fitness trainer Carlos Leon used to have a passionate love with Madonna in mid-1990s. Carlos was 8 years old younger than her. They met each other in New York and had a daughter Lourdes in 1997. Although they broke up soon when their daughter was only 7 months, Carlos has still considered Madonna as the love of his life and has never regretted of loving her.

 

7. Dennis Rodman

Madonna dated with basketball player Dennis Rodman who was less than her 3 years old in 1993. This relationship just lasted 2 months but Dennis revealed that Madonna had expected to have a child with him. She even promised to give him 20 million USD if she were pregnant with him. However, she was not lucky enough to have a baby with Dennis that time.  

 

6. Tupac

In 1993, Madonna had a romantic relationship with rapper Tupac who 13-year-old younger than her. In love letter of Tupac revealed in 2007, he admitted the reason of their breakup in 1995 was because he felt complexed of his skin color. “I must apologize to you,” he wrote. “Because like you said I haven’t been the kind of friend I know I am capable of being. Not because I am evil or because you weren’t worthy but at the risk of sounding over dramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman.” Tupac also expressed his passion for her and his heartbroken when he had to tell breakup words. In 1996, Tupac was murdered when being in a car in Las Vegas.  

 

5. Vanilla Ice 

From 1991 to 1992, Madonna dated with rapper Vanilla Ice who was 9-year-old younger than her. In 2011, Vanilla recalled his old relationship: “She was older than me in terms of age and was a great lover”. He also revealed the reason why they broke up. After 8 months together, Madonna released the book “Sex” which he was mentioned together with many other lovers of her, which made him hurt.

 

4. John Kennedy Jr

In 1988, Madonna used to make journalist lawyer John Kennedy Jr infatuated with her. He was the son of former president John F. Kennedy and the First Lady Jacqueline Kennedy. However, Mrs. Jacqueline didn’t like Madonna because she took photos like Marilyn Monroe who was her husband’s ex-lover on cover of Life magazine. 

 

3. Sandra Bernhard

Madonna was rumoured to be in a lesbian relationship with comedian Sandra Bernhard who less than her 3 years old. However, Sandra affirmed that she has never slept with Madonna.  

 

2. Jean-Michel Basquiat

Madonna used to be a lover of artist Jean-Michel Basquiat who was less than her 2 years old. This relationship didn’t last long becuase Jean-Michel Basquiat passed away in 1988 at his 27 due to overdose.

 

1. Sean Penn

First marriage of Madonna was with actor Sean Penn. They got married in 1985 when Madonna 27 years old while Sean was 25. This famous couple of Hollywood had been together for only 4 years. Up to now, Sean Penn has still admitted that Madonna always stays a special place in his heart and he still loves her very much. 

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