Madonna Dating History: A Look Back at Madonna, Guy Ritchie and Sean Penn’s Most Famous Relationships | Explain

Madonna has dated several celebrities, especially in the early years of her career. The pop star was linked to Tupac, Warren Beatty, Jean-Michel Basquiat, and Dennis Rodman, among others.

But no one made more of a lasting impression on the star than the two most famous romances of her life: Sean Penn and Guy Ritchie.

Let’s take a look back at these two special relationships for the Queen of Pop.

Read more: Madonna’s life and career through the years

Sean Penn: A rocky relationship

Madonna met actor Sean Penn in 1985 when she was 26 years old, while filming the music video for Girl items. The pair hit it off immediately, and soon they were hanging out every day.

Things started slowly: they both had just gotten out of relationships and wanted to stick to being friends with benefits. The plan didn’t quite work, however, and they married just six months after meeting, on the pop star’s 27th birthday.

“We have so much in common that he’s almost like my brother,” she said People a month before their wedding. “His temperament is also similar to mine. That doesn’t always make for good relationships, but I don’t know what will happen.”

They lived their lives in the spotlight, always facing the scrutiny of the media and fans. In 1986, they both starred in the film Shanghai wonder. Later that year, Madonna released an album true blue, dedicated to Penn.

Although they appeared to be the picture of love and happiness, reports were swirling that there was trouble in paradise behind closed doors. Penn was reportedly very jealous, accusing Madonna of cheating several times. Allegations of infidelity, domestic violence, and constant arguing between the two made headlines in the late 1980s.

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In April 1986, Penn was charged after attacking songwriter David Wolinski in a nightclub, because he thought he saw him kissing his wife.

“The marriage had been under stress all along, but this was the first big stress, the first really difficult event for him. [Madonna]”, said a source People at the time. “It was someone she knew, Wolinski, and she was very surprised.

Despite widespread reports of Penn’s jealousy and anger, Madonna supported her husband.

“I have my uncertain moments,” Madonna admitted at one point during the relationship, “and that puts a lot of pressure on people. You take things out on the person you love, and that causes fights, alienation, sadness, sessions decline and lots of ca-ca.”

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In December 1987, Madonna filed for divorce, but withdrew the papers just two weeks later. She applied them again a year later, in January 1989.

The couple remained friends, however.

In 1991, in her documentary In bed with Madonna, the star named Penn as “the love of her life”. He has been seen attending her concerts over the years, and in 2017, he told Stephen Colbert says he still loves his ex-wife “a lot”.

At an Art Basel gala in 2016, Madonna said she was “still in love” with Penn, even offers would remarry if he contributed $150,000 in a charity auction.

Although there were many rumours after the divorce that Penn was violent towards Madonna, but the singer dismissed these allegations.

“While we certainly had more than one heated argument during our marriage, Sean has never hit me, ‘tied me up,’ or physically assaulted me, and any statement to the contrary is absolutely outrageous, malicious, reckless and deceitful,” Madonna said in 2015.

Guy Ritchie

Madonna met Guy Ritchie, an English film director, in 1999 at a party hosted by their mutual friend Sting.

It was attraction at first sight for the pop star. “I had a whole rehearsal of my life on fast forward,” she said People. “My head wasn’t just spinning, my head was spinning on my body. I was taken by his confidence. He was a bit silly but in a self-aware way… He’s a risk taker and he has a hungry mind.”

The media mentioned her toy boy, because he was, at the age of 29, ten years younger than her.

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But Ritchie had made a name for himself. “Guy works almost as hard as Madonna,” her friend and actor Rupert Everett said of the couple. “It’s definitely not a boy’s toy.”

It took a while for the relationship to get off the ground, as they were all so focused on their own careers and unwilling to compromise. He was also seeing TV presenter Tania Strecker at the time, while also hanging out with Madonna on the side.

But by the end of 1999, the singer gave in, agreeing to move to London with her beau. Their son Rocco was born in August 2000, after a complicated pregnancy and birth.

Ritchie proposed to his girlfriend shortly after Rocco’s birth, and they married in a secret ceremony at Christmas time at a castle in Scotland.

“We wanted to find a place that was really hard to get to, because when people have to work hard to get somewhere, you know they really want to be there,” said Madonna. said of the place. Gwyneth Paltrow and Donatella Versace among the guests. Yes

The couple adopted a son, David, from Malawi in 2006, but just a few months later, reports revealed that the couple’s relationship was on the rocks. there were rumours that Madonna had an emotional affair with soccer player (and J.Lo’s future boyfriend) Alex Rodriguez.

Insiders told reporters that the couple had just been drifting apart for a while. “It wasn’t just one thing,” a source said People. “It was a solution for the last year. They lived separately and got together from time to time for the cameras.”

“She was more about being a celebrity and he was more important. He wanted to stay in London and have a normal life but that’s impossible when you’re married to Madonna.”

At first, the couple’s split was amicable. In 2011, Ritchie said Details magazine: “The experience was very positive in the end. I love the children that came out of it, and I didn’t see any other way to take it.”

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But in 2015 the couple got involved in a bitter battle for their son Rocco. At first, the 15-year-old was traveling with his mother on the Rebel Hearts tour, before choosing to live full-time with his father in the UK.

A judge ordered Rocco to return to Madonna’s home in NYC, but he refused. Eventually, the couple settled the dispute.

The same year, Madonna spoke openly about her husband. “I sometimes found myself in a state of conflict,” she told the lawyer sun. “There were times when I wanted to express myself as an artist in ways that I don’t think my ex was comfortable with.

She said, “There were times I felt like I was in prison. I wasn’t allowed to be myself.”

In 2022, in a YouTube quiz, Madonna was asked if she had ever made any decision that she now believes wasn’t the best idea, the star kept it simple : “Marrying,” she said. “Both times.”

Guy Ritchie is now married to model Jacqui Ainsley; the couple have three children.