Inside Madonna’s relationships – from toyboy lovers to rock legends

MADONNA has dominated headlines for three decades with her personal life getting just as much attention as her record-breaking music career.

The most powerful woman in music has never been without a long line of adoring men – from Hollywood heartthrobs to future reality TV stars.

Madonna and Guy Ritchie divorced in 2008 after an eight-year marriage
PA:Press Association

PRINCE – rumoured fling (mid 1980s)

Madonna is thought to have enjoyed a fling with Prince after they collaborated on her Like A Prayer album

J. Randy Taraborrelli’s biography of Madonna claims that the couple met at one of Prince’s concerts and that he had to “fight her off” on their way to the gig so he could “preserve his energy.”

The biographer claims that it was Madonna who called time on the fling when she refused to commit after Prince asked her to make their romance official. But Prince’s camp claims that Madonna “pestered” the singer for weeks after he “stopped acting interested in her.” 

The pair later collaborated on her Like A Prayer album in 1989 where Prince played guitar on three songs, including the title track.

SEAN PENN – first husband (1985 – 1989)

Madonna and Sean Penn during their 80s romance
Getty – Contributor

Madonna met first Hollywood actor and first husband Sean Penn in 1984 while on a studio lot filming the music video for Like A Virgin.

Tying the knot just six months after they first met, the couple’s romance played out in front of the world’s tabloids with Madonna dedicating her 1986 True Blue album to him, writing: “This is dedicated to my husband, the coolest guy in the universe.”

But there was trouble in paradise with Sean and Madge’s film Shanghai Surprise flopping at the Box Office and Sean becoming jealous  of Madonna’s male friends and paranoid of losing her affections.

Madonna and Sean Penn have remained friends and appeared in public together several times since their divorce
Getty – Contributor

After their divorce in 1989, Madonna and Sean continued to support each other’s careers.

In 1991, she released documentary In Bed With Madonna, where the singer was asked to name the love of her life. She coyly whispered back one single word: “Sean.”

Sean was spotted attending two nights of Madonna’s Rebel Heart tour in 2015.

She even teased that they could marry again after vowing to tie the knot with Sean for a second time if he donated 150,000 dollars to her charity.

CARLOS LEON – rumoured fiance (1994 – 1997)

Madonna shares daughter Lourdes with Carlos Leon

Madonna struck up a romance with personal trainer Carlos Leon after meeting in New York City back in 1994.

With the relationship lasting nearly three years, the pair were long-rumoured to have been engaged.

They called off their romance just months after welcoming daughter Lourdes in October 1996.

Madonna and Leon continue to co-parent Lourdes, but the Queen of Pop didn’t attend his wedding to designer Betina Holte in 2013.

Carlos supported Madonna at the premiere of Evita in 1996

Guy Ritchie – second husband (2000 – 2008)

Guy and Madonna attended several red carpet events while together
Corbis – Getty

Madonna met film director Guy Ritchie in 1999 after being introduced by musician Sting.

After striking up a romance, they married on December 22, 2000 at Skibo Castle in Scotland.

Randy J Taraborrelli’s biography on Madonna notes that one of Guy’s friends claimed the relationship was “one scene of emasculation after another.”

The mystery pal went on to claim that being seen as “Mr Madonna” greatly upset the movie director.

Madonna supported Guy Ritchie at a movie premiere just weeks before their divorce
Getty – Contributor

The Mirror reported in 2008 that Guy longed for a “regular husband and wife” arrangement.

Guy is also alleged to have said that his former wife was “obsessed with her own public image.”

More recently, Madonna and Guy battled over custody for their son Rocco.

The teen was travelling with his mum during her Rebel Heart tour, but rising tensions forced him to seek solace with father Guy.

Madonna has since made amends with son Rocco and recently wished him a happy 18th birthday.

JESUS LUZ – toyboy romance (2008 – 2010)

Madonna’s ex Jesus Luz has gone on to participate in Italy’s Strictly Come Dancing
Rex Features

After calling time on her marriage to Guy Ritchie, Madonna made headlines when she swapped him for 21-year-old Jesus. 

They met on a cover shoot for W magazine and their relationship lasted just over 12 months, ending in February 2010. 

Jesus has since turned his hand to DJ’ing and put his footwork to the test in 2013 as a contestant on Italy’s version of Strictly Come Dancing.

Kevin Sampaio – rumoured boyfriend (2017 – present)

Kevin Sampaio, pictured on Instagram is rumoured to have been dating Madonna
Kevin Sampaio, pictured on Instagram is rumoured to have been dating Madonna since starring in her video

Recent reports suggest that Madonna has found love again with hunky model Kevin Sampaio.

Madonna met Kevin after he appeared in the music video for her single, B***h I’m Madonna.

After they struck up a romance, Madonna was reportedly “impressed” that Kevin didn’t sell their love life secrets.

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